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Client: I saw an issue with a process on my team recently and brought it up directly in a team meeting a few days later. I was very direct about the problem, gave all the details, and explained how it impacted everyone. To my surprise, my manager shut it down completely, and now I cannot get any buy-in from anyone. What happened? Where did I do wrong?

Being thoughtful and strategic in how you communicate has a bad reputation. Many high-performers think of it as being inauthentic, calculating, and manipulative. This trap comes in three different flavors.

• If my idea is good, it should speak for itself. I shouldn’t have to manage how it lands. This is how a lot of strong technical people end up stuck.

• I don’t want to tell people what they want to hear instead of the truth.

• If I don’t just tell it as it is, then I'm being manipulative.

Being manipulative or telling people what they want to hear includes an element of deception. You are intentionally leaving out certain context in order to mislead or exaggerate the reality.

When you’re about to give a close friend difficult feedback, you think about how she’s doing that day, whether she’s already stressed, what she needs to hear first to know you’re on her side. We call that empathy and caring, not manipulation.

Being thoughtful about when, how, and with what framing you have a conversation is not deception. It’s best practice for communication excellence. The best leadership teams have a communication plan that has been carefully thought through for any major organizational change or product launch. Before any high-stakes or controversial conversation, it’s best practice to ask yourself: “How should I best communicate this?”

How To Be Direct And Strategic

Being strategic in communication starts with empathy. It is grounded in knowing the context of the other person and caring about how it will impact them. Being direct means getting to the point or core of the issue quickly, without too much setup.

Here is what to strategize around for any high-stakes conversation:

1. What does this person already believe? Not what they should believe, or what the data says they should believe. Understanding their current mental model of the situation tells you where the friction points are before you walk in.

2. What emotion is this conversation likely to trigger? Conversations about performance, strategy, resources, or change almost always carry an emotional charge. This is information.

3. What needs to be said first? Knowing how to best open a conversation, particularly in a group setting, is a skill. Consider where the audience needs to be sold further, certain egos need to be appeased, or it’s appreciated to jump straight in.

Starting with these three points allows you to avoid triggering defenses so high that the conversation ends before anything real gets said. In being strategic, you’ll more effectively facilitate the conversation and move conversations forward.

My Client’s Next Steps

My client went back to her manager a few days after our conversation. Same problem. Same recommendation. But she started differently, by asking what her manager was hearing about the cross-team dynamic, why she thought it was happening, and what she was worried about. And then introduced her feedback in a way that added on to what she was hearing, and avoided triggering her worries.

“Yes, I think you’re right.” Her manager said with a big sigh. “It’s time to fix this.”

The truth didn’t change. The conversation did.

Strategic communication isn’t about compromising your integrity or authenticity. Done right, it’s what makes your integrity and authenticity shine to others.

That’s all folks! See you next week at 3:14 pm.

Yue

For most of the last century, knowledge was power. Education was the golden ticket to upward mobility. Business valued intellectual horsepower: the ability to access and gather information, analyze it, spot patterns, and produce recommendations. This created high-paying jobs in law, finance, engineering, and medicine.

That era is ending.

AI is smart. It has read more medical literature than any physician. More case law than any attorney. More financial filings than any analyst. It can look at what has been done, said, written, and published across the known world and produce a synthesis that is comprehensive and fast. It operates at a scale and speed that no single individual human can match.

AI is democratizing knowledge. Being “head smart” is becoming a baseline rather than a differentiator for the top roles.

The Three Centers of Wisdom

There’s a framework I return to often in my coaching work, drawn from spiritual traditions and increasingly validated by neuroscience: humans have three centers of intelligence, not one.

The Head is the center we know best. Logic, analysis, synthesis, pattern recognition. It operates through facts and reason.

The Heart is the center of connection, creativity, and curiosity. It operates through emotions, not reason. When the heart leads, it brings people together and helps them connect.

The Gut is the center of discernment and ethical judgment. We call it the “gut instinct”, a knowing that something is right or wrong when you can’t fully articulate why. It tells us the right way when no one else knows, and the data is incomplete.

Most high-performing professionals (myself included) have spent our lives growing the wisdom of the Head. In school, we learned critical thinking and built our information database. In early careers, we got in the room by having the best analysis or project report.

Unfortunately (or fortunately), AI just became the most capable, smartest kid in the room. And it’s available to everyone.

Where Humans Excel

AI can only generate from what already exists. It cannot truly create. The creative leap that comes from caring deeply about a problem and having the courage to propose something with no precedent is not a capability that AI possesses. This type of wisdom lives in the Heart.

AI can model empathy, but it cannot feel it. It is like that weird friend who can logically explain emotions in a way that feels removed. When a team is demoralized after a reorg, when opinionated people disagree, when someone needs to be told a hard truth, those moments require a human being. It requires someone who is in touch with their wisdom of the heart and skilled in managing emotions.

AI has no ethics. It can reflect the ethical frameworks that humans have published. But the judgment of what is right, especially in novel situations where existing rules don’t quite fit. When someone has to stand for something important, that is Gut. And it is required at every level of senior leadership.

Evolving The Type of Wisdom We Invest In

Most of the leaders I coach haven’t developed these two centers because they have been overlooked for a long time in business. Saying like “don’t get emotional” or “let’s just stick to the facts” minimizes the wisdom of emotions. Organizations historically rewarded analytical rigor, not “feelings”.

With AI “winning” the wisdom of the brain, the leaders who will matter in the next decade are those who can create, connect, and influence not just with data and logic, but also with emotions and a strong sense of ethics.

Here’s how to build up your other two centers of wisdom:

For the Heart:

• Pay attention to what genuinely interests you, not just what you’re good at. Do more of those what increases your curiosity.

• Invest in your ability to read what’s happening emotionally in a room, and then manage it in a way that serves a positive outcome

• Let yourself be moved by things and name the emotion. Show others that you dare to lead in the face of fear, not in the absence of fear. Show others your passion and excitement about a new idea.

For the Gut:

• Slow down before high-stakes decisions and give a moment to hear your gut instinct. Physically try to feel and sense what’s going on in your stomach area. Is it butterflies and uneasy? Is it calm and grounded?

• Notice when your body registers discomfort when your mind can’t really explain it. We often can sense danger before it appears. Or we “know” something might happen.

• When something bad happens, notice how your body feels. Remember that feeling instead of resisting it.

The era of getting ahead by getting the best grades, memorizing more information than others, or having access to obscure information is ending. Instead, the truly hard work of building trust and relationships and bringing disparate opinions together is what will become a differentiator. I believe that when knowledge is so easily accessible, the most important leadership skill may be knowing when to let feelings override logic.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

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The Signals That Hold You Back

As much as you think you are ready for that next level, certain behaviors and actions signal to leadership that you are mostly executing, not leading. This can get frustrating because noone really clarifies the difference.

Here are four that I come across frequently:

1. Your “Strategy” Is Really Just Prioritization

Some leaders call it strategy when they rank tasks, sequence projects, and make trade-offs within their team. While it is a form of strategy, it is not a leadership-level strategy. It feels more like organizing a box.

Leadership-level strategy is about framing and making tradeoffs that impact multiple teams and functions. The impact magnitude can be measured with company-level metrics, and execution time is on the time horizon of quarters and years.

It’s not what your team (or close partner teams) work on in the next few weeks. Real strategic work pulls you out of your domain.

2. Your Influence Stops at Your Job Description

Many people think they have leadership-level influence when they are only playing in their lane. Their influence mostly comes from being responsible for a particular project or task. People listen to you about your team’s work because you’re the person accountable for it. This is only table stakes.

True leadership level influence is when people seek out your perspective on things that aren’t in your domain. When you’re invited into conversations because of what you think, not what you own.

Directors and VPs who are genuinely operating at a leadership level spend a meaningful portion of their time helping others outside their teams. They’re shaping conversations about areas they don’t formally own.

If your influence lives mostly “within my team’s scope,” you’re not there yet.

3. You Start With Execution Updates

Think about your last few 1:1s with your manager or skip-level. What did you lead with? If the answer is “what shipped, what’s in progress, and where things stand”, then you are leading with execution.

A leader leads with strategy and ideas:

Here’s an idea I’ve been thinking about for how we could address this market differently

I’ve noticed this unhealthy pattern across three teams that I think we need to fix.

I want to talk through how we can grow our team’s scope next year.

Execution updates can usually be written and read. When it comes to airtime with leadership, lead with perspectives, ideas, and problems to solve.

4. You’re Still the Answer

As a high performer, you may pride yourself on being the person who solves problems. When the team comes to you with a question, you dive in, triage, and give answers.

Leaders don’t default to solving a problem themselves. They ask questions that help their team find the answer. Or they let problems simmer…so that someone on the team can rise to solve it. They don’t step in unless absolutely necessary.

Many managers know this intellectually. But it’s hard because when you’re watching something go sideways and you have the answer in your head, sitting on your hands feels irresponsible.

As a leader, your job is no longer to have the answer. Your job is to build the rooms where the answer can emerge. This is why leaders spend time on forums, processes, and people.

What Marcus Did

Six months after that conversation, Marcus was promoted to Director.

He didn’t work harder. He stopped solving his team’s problems and started asking questions to help them find the answers. This freed up time for him to meet with leaders outside his org to hear their problems. He stopped opening his 1:1s with a rundown of the sprint and started with problems and ideas he was thinking through. This generated introductions to other senior leaders and airtime during the monthly all-hands.

If you feel stuck at your level, take a look at your strategy, influence, and execution patterns. Are you going broad enough? Do you influence beyond your scope? Are you still giving out answers?

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

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Jenny was filtering out all the signals that she was already at the VP level. Instead, she was noticing the areas where she was not there yet, and telling herself and others that she is not ready.

Why We Rationalize

Jenny was working from the idea that the title comes after you’ve earned it. And when you have earned it, it’ll be given to you in the form of a promotion. This belief is prominent in our school days: put in the work, nail the tests, and then they hand you a diploma. Early career is similar: do a good job, get recognized by your manager, and get a promotion. But at the senior levels, you have to shift your behavior first to act at the next level, and this is a nuanced step many people miss.

I’ve seen many clients already operating at the next level: they have the opportunity to make the calls; they are being asked to lead those complex projects. Yet they keep looking for evidence that they are not yet good enough. It is how they rationalize their reality.

Then, this belief becomes a self-fulfilling prophecy. When you don’t believe you are there (yet), you hedge your arguments, you defer to others to make the final call, or you go with the group’s opinion rather than standing firm on yours. You might even tell others that you don’t think you’re quite ready for the next level yet. This behavior keeps others from looking to you for support or direction. And your skip level will look at this and think: “She’s not ready for VP yet.”

Change Your Lens For Yourself

In order to “operate at the next level”, we first have to notice and give ourselves credit for when we already do this. we can do it. This means updating your internal narrative of yourself to reflect the evidence that’s already in front of you. The question to ask yourself isn’t “am I ready?” It is: “What evidence is there that I am already at the next level?”

Jenny didn’t notice that her work was already VP ready until I pointed it out. And from then on, she noticed when other senior leaders deferred to her perspectives. Or came to her for support on an idea. Or wanted her input on their work. Noticing these events gave her confidence and courage, and she showed up differently to meetings and conversations. Jenny was more direct, opininated, and confident in herself. Within six month, the CEO endorsed her VP promotion.

That’s all folks! See you next week at 3:14pm.

Yue
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The Uncommon Executive is a newsletter for senior managers and directors navigating the transition to the next level. If this resonated, forward it to someone who's still gathering evidence.

When Nuance Becomes Noise

When we are in the weeds doing the work, we are praised for being thorough. When you’re leading a team, thoroughly talking through both sides feels like you’re covering your bases and not making a call. When we are influencing our peers, rigor builds confidence and influence. At the executive level, people look for someone who has synthesized all the complexity and is willing to take a stand.

What people look to you for changes as you move up the ranks. In the more junior levels, your ability to influence and persuade depends on your expertise. And rigor increases expertise. As an executive, people want clarity, simplicity, and direction. They want a vision and direction that gives them the room to run, not step-by-step instructions that run 20 pages. The nuance that was appreciated becomes noise in clear decision-making.

The difference is not in how much you might prepare or how thorough you are in your work. It is in how you then show up in front of others and what you visibly communicate. It often comes down to trusting in your instincts and showing up with confidence in yourself.

How To Show Up At the Next Level

At the executive level, people want to know what you think. They care much less about you getting their input. They’ve been struggling with the confusing trade-offs or dealing with combative colleagues. They are scared that the competitors will win or worried the company is not innovating. They want a clear, decisive answer, not a debate. That is why the nuance does not matter. If nuance and details could have solved their concerns, then their concerns would not have come to you. They want you to make a call.

Here’s how to show up differently at VP+:

Before: Bring all the data, then encourage others to draw their own conclusions.
Executive: Absorb all the data, lead the conversation with your conclusion.

Before: Show your work, because the work is what earns trust from peers.
Executive: Lead with the call. Assume trust is there.

Before: Be comprehensive in showing your work. Articulate both sides and all the different options.
Executive: Voicing both sides signals that you aren’t sure. Pick one, and state why.

This way of leading does not mean be shallow or overly confident. On the contrary, it require the same level of thoroughtfulness and rigot that got you to the VP level position. However, rather than starting with all the nuance, you now start with the summary, the pitch, or your take. The best leaders then can dive deep as needed in different directions with different functions and stakeholders.

That’s all folks! See you next week at 3:14 pm.

Yue

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The Uncommon Executive is a newsletter for senior managers and directors navigating the transition to the next level. If you found this useful, forward it to someone who's still doing the previous job exceptionally well.

Yue’s Coaching Corner

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I had been at Thumbtack for three years. In those years, the company grew from 20 to 250. I had launched major product features for the marketplace and built functions including customer support, analytics, and user research. I coached and mentored many new director-level hires, and quietly absorbed extra scope when a team was short-staffed.

My manager noticed. I knew this because I received an ongoing stream of praise. A quick “great job on the presentation” after an important meeting. A shout-out in the team channel for mentorship. A “we couldn’t do this without you” from during a one-on-one.

And yet, nothing else changed.

No new title. No meaningful compensation increases. No formal acknowledgment that my scope had grown with the company.

Three years in, I almost quit. It would not have been a graceful exit, letting the CEO know how much I appreciated his support and why I could not pass up this opportunity. Instead, the conversation was heated, tense, and tearful. “I feel completely undervalued and invisible, and I’ve done more and more, and yet it’s still the same.” My manager was blindsided and angry.

Nobody had seen it coming. It had been silently building within me for months.

The Slow, Silent Build

Here’s what happened in the silence when I did not speak up about what I wanted and proactively advocated for my growth:

First, I rationalized. They’re busy. They’ll notice eventually. We’re a startup. It’s too early to talk about compensation philosophy. It would be awkward to bring it up. I don’t want to seem entitled.

Then I see someone get hired at a higher salary. And someone else who’s done less gets an equity refresh.

The rationalization becomes a question: Do they even see me?

I start to look for signs that they don’t value my work to validate my feelings. They didn’t give me extra resources for this new project. They didn’t seem happy about my latest strategy document.

Slowly, the question becomes a belief: They don’t actually value what I do. They don’t actually value me.

Resentment begins to build. At first, it’s barely noticeable, a fleeting thought here or there that quickly goes away. I keep showing up and delivering.

Inevitably, the resentment starts to accumulate. I start to think about it daily, and it starts to affect my work quality. The motivation fades.

By the time The Conversation finally happens, it’s no longer about dollars and titles. It is about whether my work matters. Whether I matter.

That is no longer a performance conversation.

The Deadly Silence

I see this trend across the clients I teach, often across seniority levels and experience. We don’t raise our needs for a few reasons:

• The work should speak for itself: Great work gets noticed. But in many imperfect organizations, it does not automatically translate into a promotion conversation in the timeframe you want.

• I don’t want to seem demanding or entitled: There’s a fear, particularly among women and underrepresented groups, that asking for what you need will be read as aggressive or ungrateful.

• I am waiting for certainty: We’re looking for the “right time” when we can make a bulletproof case. Perhaps a company-wide compensation review or formal compensation reevaluation.

All of these reasons are excuses that hold you back. The root of it is that it is uncomfortable and scary to ask for what you want, especially when it’s related to title and compensation.

However, these inner narratives erode the trust between you and your senior leadership. Leaders are often caught off guard by the intensity of these conversations. Most leaders in fast-moving organizations are very busy handling multiple competing priorities a day, not sitting around thinking about specific employees and whether they are valued. They assume that no news is good news. If you haven’t told them what you need and want, there’s a reasonable chance they genuinely don’t know.

How to start the conversation

Speaking up doesn’t guarantee you get what you want. But it lets the steam off the boiling pot, and keeps the conversation out of identity and values. Here are a few starting points:

• Name it early, not at the breaking point. Don’t wait until you’re already resentful to raise compensation or title. The best time to have this conversation is when things are going well, and you are also in high spirits.

• Avoid ultimatums: Adopt a collaborative tone. “I want to talk to you about my growth trajectory at the company and what I need to feel like I’m progressing.” Avoid being combative, “give me a raise or I’m leaving,” type messages.

• Get tangible and specific. Avoid vague statements like “I’d like to grow”. Instead, give them specific titles, dollar numbers, and/or timelines. “I’m targeting a Director level promotion in the next 12 months, and I’d like us to align on what that path looks like.”

Speaking up about what you need is not an act of entitlement. It is a signal of trust. It gives your manager the information they need to do their job. It keeps you from becoming a flight risk they never saw coming.

If Sarah had said, eight months earlier, “I want you to know that I’m not happy with my compensation and my title, and I’d love to have a conversation about what the path forward looks like for me here”, her manager might have gone to bat for her.

Or she might have learned that there wasn’t a clear path at her current company, which would have been useful to know before she spent another eight months building resentment that results in burning bridges in a highly networked professional world.

If this resonated, I’d love to hear where you are in this pattern. Are you the one who waited too long, the one who’s in the middle of it now, or the one who finally had the conversation and is glad they did?

That’s all folks! See you next week at 3:14 pm.

Yue

When I was at Instagram, I worked with many amazing PMs. However, once in a while, I would encounter a Product or Engineering leader who was overtly hostile. They did not want to hear my ideas on how we could work together towards a shared goal. If I tried to talk to anyone on their team, they got protective and angry. If I proposed a different option in a meeting, they got defensive and combative. They were often loud and overly confident, focusing their attention on getting on the good side of senior leadership.

Working with this type of coworker is draining, mentally and emotionally. However, they are able to behave this way because they are in the good graces of senior leadership. This makes collaboration with them an unfortunate necessity. Here are some ways to tackle this situation.

Sidestep and Redirect

Colleagues who are overly confident often dominate the room in group meetings and loudly proclaim their opinions as facts. One tactic to manage this is to lean into and redirect this energy rather than go against it. This throws them off balance and allows you to be heard.

This idea of using their momentum against them is popular in martial arts. In Judo and Aikido, an attacker who is fully committed to a direction can be momentarily off-balance when you move with that direction rather than against it. In Sumo, a lighter wrestler can use a heavier opponent's charging momentum against them by sidestepping at a critical moment, causing the opponent to lurch forward and out of the ring.

Tactically, doing this involves three simple steps:

1. Ground yourself with some deep breaths. We are often filled with annoyance and frustration with these types of comments, and this should not show in your tone when you speak.

2. Follow up on their comment and reframe it: Rather than ignoring or invalidating their comment, counterintuitively build on top. Use sentence structures like

   1. “That’s a great idea for the future. And in the short term [insert your idea].”

   2. “That’s an inspiring vision. Tactically, we should consider [insert your idea] in the short term.”

   3. “Those are good options. Building on it, here’s another…”

3. Rinse and repeat: Every time to bring up their overly confident proposal, view it as a chance to add to it your proposal or viewpoint. Be consistent. It’s okay if it’s not taken up the first time. Keep trying.

By not putting up a defense, you are sidestepping a battle of influence and ego. Instead, you are using their ability to interrupt and gain attention to get yourself heard. And by proposing a truly more practical idea consistently in the framing of building on top, you’ll see conversations shift over time and get the credit for collaboration.

Reframe And Add

This second strategy involves anchoring in the subjective, not objective, and opening up possibilities. We want to avoid arguing who is right or wrong, or what the facts are. These logic-based debates sound like this:

“Based on the data, this is the right approach.”

“We should do this because xyz.”

“No, you are wrong. We saw this in the data. And therefore…”

These types of phrases trigger defensiveness quickly. Both parties anchor their arguments in logic and data, and each is now invested in proving the other person wrong.

To reframe this conversation, use language that is subjective and anchored in beliefs.

“That’s very possible. What I’ve seen in past situations like this is…”

“It’s interesting you believe that. I believe…”

“Yes, that’s one way to approach it. What do we think of this other option…”

This strategy does a few things simultaneously. First, it reframes their comment as a subjective opinion, not a fact. Second, it frames it as one of many possibilities, giving you room to add your proposal. Finally, by putting their option in a positive frame, you also anchor your follow-up in a similarly positive backdrop.

To use these strategies effectively, practice, practice, practice. Reflect on a past situation where you had a combative debate, and take your time in reframing or redirecting. Write down your reframed response. Then say those words out loud. This individual practice will help you remember the words when a similar situation arises the next time.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

• I’m in the process of revamping my AI Leadership Accelerator into an AI-oriented leadership program that prepares mid-level leaders for the AI age. While the foundations stay the same (influence, relationships, storytelling), I’ll be adding conversations on developing taste and jugement, handling change management, and how to rethink org structures.

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I am a coach to senior leaders and executives at top Silicon Valley companies like OpenAI, Google, Amazon, and Instacart, who manage teams of 50+ to 2000+ people. This performance review season, they all used AI to supplement their work. Some use it to draft written feedback for their team. Some use it to suggest an improvement plan. Some use it to stress test an on-the-border rating. Others use it to find teams with ratings that deviate from an expected average. It’s no longer a question whether AI models are influencing performance conversations and evaluations. It does. And it is also a reality you need to get ahead of.

Where AI Strengthens Performance Reviews

Humans are biased, forgetful, and emotional. There are some areas where AI does better than humans when it comes to measuring value delivery and identifying areas for growth:

• Humans have recency bias: we tend to forget easily and overindex on recent events. We remember the last product launch or the latest exchange we had with someone. We are not great at remembering what happened 12 months ago when the strategy was first decided, or those wins that came early in the quarter.

• Humans have negativity bias: we tend over-emphasize negative events and generalize them. That one time you forgot to send meeting notes? Now you’re someone who’s not good at following up.

• Humans have similarity bias: we overvalue the work of people who we see as similar to us. Two of your team members each had successful product launches. One reminds you of yourself when you were younger. As a manager, you are likely to give more credit to that person.

AI has the advantage in that it can process a large amount of context and store it over time. It doesn’t treat two people differently if the data is the same. And it can quickly analyze patterns and spot variations.

Where AI Can Hurt Fairness And Adverse Incentives

What’s also important to know is that AI has its own set of biases, most of it arising from imperfect context. Here are some areas where AI tends to be more biased than humans:

• AI overemphasizes measurable activity: Since the AI is not (yet) a person who wanders the halls, catching nuanced conversations and interactions, it tends to overemphasize what is logged and written down (and accessible to it). Small gestures and relationship-building work tend to get overlooked.

• AI may decontextualize a signal: A teammate who goes against the rules in an exceptional situation may get dinged for not following protocol. A team effort on a project may be falsely attributed to the person who wrote up the final report. AI currently isn’t great at judgment calls that require human interpretation.

• AI can amplify existing bias in the system: If the company has 5 performance metrics related to short-term revenue and 1 metric on long-term investment, AI will over-value short-term gains in performance analyses. If the AI doesn’t measure team members helping each other, it will reward the lone-wolf mentality.

Similar to choosing a metric for a company goal, any AI (metric) is an imperfect measurement of reality. Any AI (metric) can and will be gamed. Knowing how an AI (metric) might be gamed and staying focused on the intention behind the AI (metric) is critical to staying on the winning path.

How To Set Yourself Up For Success

With AI as a core part of performance reviews, the key to managing it effectively is giving it context and data that accurately measure your performance. More than ever, what is tracked, measured, and written will influence the outcome.

• Keep a log of tasks completed in your AI tool: use a combination of daily voice note dumps, meeting notes, and dumps from calendar and email. If you keep timesheets or track work in another software, do regular exports. You want to avoid your manager getting an AI summary that doesn’t include a project she thought you did, and doubting whether she remembered it correctly.

• Make it measurable.

  • Know what proxy metrics the AI in your organization uses for performance, and focus on how you are being measured for those. If you’re not sure, start by just asking it. For example, some companies use Slack or email response time for “engagement.” Other track “token used” or “app run time” for AI expertise. Figure out what matters.

  • Figure out what you’re doing that’s not measured. Then get it measured, or consider dropping it. If it’s not tracked or visible, it didn’t happen.

• Complement AI with People: Have AI do your own review from your manager’s and skip’s perspectives. Know where it says your weak spots will be based on the data and context it has access to. Then, proactively address this through storytelling and influence with critical stakeholders at the company. This way, the human judgment with AI support will provide the complete picture.

• Just get started: This is one of those the sooner you do it, the more helpful it’ll be scenarios. The log is more valuable the longer it is kept. The proxy metrics will be more improved the longer you work at it. The new metrics will gain more credibility the sooner they are implemented. Perfection is the enemy.

AI brings a lot of benefits to the performance review process: time savings, context retention over time, processing large amounts of information quickly, and being blind to organizational politics. However, without careful management, AI will amplify its own bias, at times to your detriment. It’s no longer a question of whether you need to account for AI as a stakeholder in your promotion process: the question is how to do it in a way that helps you and your organization succeed.

That’s all folks! See you next week at 3:14 pm.

Yue

The challenge with only focusing on productivity gains is that while each function becomes more efficient within its own boundaries, the boundaries remain. A new learning from a sales call does not naturally affect marketing and product prioritization. A win in paid marketing does not change how sales prioritizes leads. The coordination and context transfer between marketing, sales, product, and customer success remains manual. There is time spent reconciling data between systems, reinterpreting insights across functions, and re-explaining context in recurring meetings. As teams grow, this drag compounds nonlinearly.

Context built into the system

Sustainable competitive advantage will come from reducing and eliminating coordination costs across functions and teams. This requires fundamental structural changes to how information is gathered and stored, and then pushed out into the organization. Leaders must evolve their data infrastructure, tooling, and processes such that context is embedded in the system and pushed to the AI agents and teams when relevant. When context is at the fingertips of the user, and not hidden in the minds of select individuals, coordination cost decreases and acceleration compounds.

In the pre-AI days, teams that embedded context into their documentation moved faster than those who struggled to propagate context. Engineers who comment the logic and dependencies of the code in line. PMs who kept a running list of decisions made at the top of their requirements documents. Project managers who kept versions of project plans in the same spreadsheet for historical context. Sales teams that auto-updated a Slack channel with every new deal and comments from the rep who closed it. All of these are mechanisms where context lived with the artifact, and was easy discoverable and spread across organizational lines and across time. This accelerated decisions and reduced coordination cost.

AI unlocks an entirely new set of possibilities to continously refine and recalibrate across teams. The learnings from one sales call could immediately be translated into a shift in a paid marketing campaign and a new prototype for a product feature. A customer support complaint can automatically trigger a bug fix in the code. Sales strategies can get updated regularly based on live trends hitting a certain threshold of volume, rather than follow a quarterly process.

Enabling these trigger-based actions with AI rather than time-based actions (e.g. quarterly planning cycles, weekly team meetings), starts with ensuring context and information is trascribed, extracted, and stored as much as possible. Transforming the organization’s data flow and infrastructure is the priority. For every day you do not store sales calls and product decisions, you lose a day of advantage to your AI-native competitor startup.

Feed your webinar transcripts, product documentation, CRM notes, meeting transcripts, behavioral engagement data, social signals, and win-loss data from paid campaigns into well structured AI accessible repositories. If it requires collaboration, avoid being the owner of orphaned documents and conversations. Leaders should no longer be worrying about valuable context leaving with departures or “only one person knows how this works.” Write it down.

Then, build on top of these continuously updating repositories AI agents and automations. Teach AI to continously learn from these repositories, auto-alerting people as a trend emergies, or automatically evolving messaging in an outreach email as it learns what is effective. Create workflows around triggers based on trends and signals, not time passed.

That’s all folks! See you next week at 3:14pm.

Yue

Yue’s Coaching Corner

• Earlier this week, I delivered a talk on How To Prep For High Stakes Leadership Conversations with AI to 2200+ attendees. Watch the recording here.

• The next cohort of Master Executive Presence & Communication with AI starts in less than two weeks on March 9th. If you’re interested in accelerating your path to leadership, this is a great course for learning how to influence without authority, develop presence and calm in tough situations, and refining your executive level communications. Learn more.

  • P.S. Get 20% by becoming a paid subscriber to this news letter!

• I’m looking to take on a few corporate clients in 2026 who are interested in transforming how their teams operate with AI (and their data infrastructure) to compete with AI-native teams. If this is a priority for you, let’s talk!

Why Did We Need Middle Management?

Before AI, to get into executive leadership, landing a team management role was mandatory. It was not enough to show that you can build and ship impactful work on your own. It was also critical to demonstrate the ability to lead and work through others. Why? One person can only accomplish so much on their own. Building billion-dollar companies requires teams to work closely together.

As a result, influential leaders spiked in bringing people together behind a bold vision. The top 1% leaders were among the best at bringing people together and resolving conflict. With AI, the bottleneck is moving from execution coordination to creativity and distribution, and changing the type of people-work to be done.

10X Efficiency with AI

With the rise of AI, the constraint of a person’s capacity is greatly loosened. Increasingly, very small teams are doing work that previously required hundreds of people. Pre-AI, the standard team size to hit $100M ARR was 1000 employees. Salesforce had 700 employees and took 5 years. Cursor hit $100M ARR with a team of 20 people in 12 months. Lovable took 45 people about 8 months. As a whole, the new breed of AI-native SaaS companies runs at 7-10X the efficiency of pre-AI SaaS companies.

This incredible step-change in efficiency is achieved through the use of AI agents and AI-first operations. In the AI-first world, humans are no longer executing on task at a time for 40 hours a week. Instead, they are directing, orchestrating, and reviewing multiple AI agents running in parallel around the clock. For example, engineers at OpenAI manage 10-20 threads (source) to support their work. The AI agents run in their own cloud sandboxes, documenting new code, writing new test cases, cleaning up feature flags, and resolving dependencies. 100% of the code at OpenAI for 95% of engineers is code reviewed and maintained by Codex.

This means that ambitious builders no longer need to manage people to deliver outsized impact. Sam Altman talked about the billion-dollar startup with a team of 1 (Forbes), with some putting the time estimate as early as 2028. People leaders will manager larger scope than ever before. The result? More smaller teams, more senior people leaders. The “middle-management” layers will be drastically reduced. Eleven Labs, for example, runs 20 micro-teams of 5 to 10 people, delivering $200M+ ARR.

I believe that the workplace structure will recalibrate to this new reality over the next few years. Increasingly, senior experienced individual contributors will manage teams with the scope of the current Directors. Directors and VPs will either be pushed out or switch to senior IC roles. The executives who adopt AI-first mentalities and skillsets will run ever-larger scopes of work. And those who don’t will get replaced.

Prepping for the Future of Middle Management

Going back to the original question, I would encourage those looking to advance their careers to hone their AI skillset and develop company-level strategic mindsets:

• Build AI agents to support your daily work: if you have a repetitive task, build an AI agent to do or start it for you.

• Understand business strategy: think and strategize at the company and business level, not at the feature or part of a business level.

• Dream big: Don’t wait for permission to dream big and broad, and make your ideas known to your skip-level or skip-skip-level leaders.

I believe the “worst case” here is to sit and wait. If you’re one to two years away from a “middle-management” role, it’s time to pick a side. Either grow your seniority and impact as an AI-first Senior individual contributor, or try to make the hop to the top of a function. It’ll be increasingly difficult to find and land middle management roles as companies orient towards highly empowered microteams.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

• My free talk on How To Prep for High Stakes Leadership Meetings with AI has 1000+ attendees! Join us next Monday live or get the recording. Sign up here.

  

• On the note of executive leadership, my next cohort on Master Executive Presence & Communication with AI is now enrolling for a March 9th start. Get 20% off as a paid subscriber to this newsletter!

Client: I am stepping into managing a larger team for the first time. There are a mix of seniorities. Some are early career, needing regular hand holding and direction. Some have 10-15 years of experience and are mostly independent. In addition, I get a mix of asks and requests from my manager and across the organization. Some are asking for a specific project. Others are asking for my 5 year visions. How do I create a system that helps my team and I succeed?

One-Size-Fits-Fall Falls Short

When we first step into the role of a manager, our inclination is to set up one set of meetings and routines for the entire team’s work. Commonly, there is a weekly team check-in, perhaps a few quick stand-ups, and weekly one-on-ones. We establish the same cadence for every team member, perhaps out of fairness or simplicity. However, this one-size-fits-all model breaks down quickly.

The weekly meeting is too in the weeds or takes too much time for the senior team members. A regular one-on-ones is too high level for zero-to-one projects or not frequent enough for high-stakes strategy conversations.

It turns out that different people, different projects, even the same project at different phases, necessitate different working models. This is where the concept of time horizons is a helpful framework for setting up different rituals based on project and people needs. Here’s how it works.

The short term: concrete tasks

In the short time horizon, there are the daily and weekly tasks. Every team has a set of tasks that are well-defined, lower risk, and contain an element of repetition. Engineers build and launch new product features. Customer support teams triage tickets. Sales team make outbound calls. For those early in their career, these are the tasks they start with and make up most of their time.

Preferred format: These short-term tactical tasks are best managed together as a team. Regular group check-ins like weekly team meetings are great for efficient context sharing and timely redirects. It also creates a way for team members can learn from each other and provide support when unexpected challenges arise. When it comes to short term tasks, weekly or twice-a-week group check-ins are preferred.

The medium term: strategy creation

Then, there are projects that have a time horizon on the order of weeks to months. These include building team strategies or cross-org projects. For this type of work, weekly team meetings are too frequent yet don’t provide enough time to go in depth. In addition, there are often an evolving set of stakeholders, making it difficult to maintain a constant list of attendees. Finally, this type of work is frequently handled by more senior team members who do not want to lead and be visible for the work.

Preferred formats: To tackle these medium term projects, a combination of leadership reviews and one-on-ones work best. Regular leadership reviews give accountability and goalposts for progress, and can be adapte per session for changing decision-makers The role of a manager here is less to dictate regular task and more to guide, coach, and unblock. Therefore, one-on-ones are more needed to give space and time for deeper conversation and addressing higher complexity challenges.

The long term - Big bets, 5-year vision

One of the first things you get asked as an executive is for a 5-year vision and strategy. People want to know: where are we going? What are our big bets for winning? This work requires some tactical input, but is anchored in high level, long term thinking. It is also often driven primarily by the executive. Weekly team meetings fail for this type of work because it is too in the weeds and do no include the wide range of stakeholders required for vision work to land.

Preferred format: Half to full day workshops, two-week sprints, and offsites tend to lend themselves well to work that requires broader, longer term thinking. It bring people out of their day to day to focus on a more creative exercise. A shift in environment can spur creativity. Sharing meals and working on the same challenges increases belonging and consequently, alignment.

Manage These Horizons Simultaneously

As an executive, you’ll need to work across the short, medium, and long term horizons simultaneously. It’s important to clearly identify which projects and people are working in which time horizon, so that you are supporting them effectively. It may be tempting to combine conversations or projects into similar meetings for “efficiency”, but in reality it’ll slow the work down. The ability to hop between a 5-year-vision workshop, a one-on-one about team strategy, and a weekly task planning session is what makes for effective senior leaders.

Interestingly, this combination of time horizons is also common in big zero-to-one-bets. It is one of the reasons these projects are notoriously difficult to do well. The leader of zero-to-one projects must be able to move between short term tasks and long term strategy, and influence a broad range of stakeholders of varying seniority and function. For anyone interested in becoming an executive, getting experience in one of these projects can be invaluable.

That’s all folks! See you next week at 3:14pm.

Yue

Yue’s Coaching Corner

• I completed my year-long Integral Coaching certification with New Ventures West this week. In addition to learning a set of proven methdologies, I also am walking away a more anchored, creative, and confident person. I am so thankful for the experience and look forward to being a part of this community for time to come.

• Now enrolling for my April cohort of The Uncommon Executive Leadership Accelerator. This 8-week group coaching program helps mid-career leaders clarify their career path and boost their influence, executive presence, and self-advocacy. Learn more here.

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• Interested in 1:1 executive coaching with me? Schedule an intro call here to see if there’s a fit. Minimum 6 months commitment.

As an executive coach who helps women and minorities move up the career ladder, one mistake I notice often is that people narrowly focus their promotion pitch on their past accomplishments. Here’s what I’ve done, and here’s the impact it had. They falsely believe that because they did a great job, they deserve the promotion.

Unfortunately, past performance is necessary but insufficient. Past performance can indicate capability. However, what is missing is timing and the potential to deliver at the next level. A great promotion case requires these two additional components.

Timing: Why should we promote you now? Why not in 6 months? What do we gain by paying you more now?

Potential: Will you succeed at the next level? What does that mean for business impact? How critical is the success of your next role or project to the business?

Businesses don’t do promotions at senior levels because you “deserve” it. They promote those who have the highest potential to deliver outsized impact and value. While past performance is an indicator of future success, it’s important to make the case that yours is the most impactful promotion to the business to make happen now.

Make Your Case For Timing = Now

You’ve done great work (and will likely keep doing great work). So why promote you now?

The key here is to articulate what the business will additionally gain from your promotion compared with if you continued at your current level. Ironically, this is where people who work harder after missing out on a promotion shoot themselves in the foot. By showing you can do the work without the promotion, you are giving the business less incentive to promote.

When making the case for “why now”, consider these aspects:

1. How does your success necessitate a more senior role? Consider this from the perspective of writing a job description for your replacement. What would be the mandatory requirements? Some common factors that up-level a role include:

   1. Hire and lead more senior team members

   2. Peer leveling and default invitations to small-group leadership forums

   3. Need to represent the company externally at conferences and workshops with a higher title. For those VP-level roles, building an external brand can help make the case for internal promotions.

2. Do you have attractive alternatives? Whether you think it’s fair or not, promotion as a tool for retention is the business reality. Intentionally or not, managers sometimes delay promotions until it is essential to retain you. In some ways, if they give the promotion, you may be more likely to leave if you are not fully satisfied. Make it clear you don’t plan to leave, but that there are attractive alternatives should the company not allow you to operate at your highest potential.

Address the Why Your Role?

In any company with more than 50 people, there are multiple people up for promotion in a review cycle. Unless you’re at a high-flying AI-native startup, the promotion budget is likely capped. With the on margins and profitability, VPs and executives are more frequently fighting to get their people promoted. In addition to addressing your past accomplishments and timing, it is important to articulate why your specific promotion is essential for business success.

This process looks a bit like writing your future performance review for the new role:

1. Articulate the criticality of the new role: How does it connect with critical business metrics? How does it impact the success of other core teams? What might be at risk if you’re slowed down by unnecessary politics?

2. Show the business gain: How does the promotion accelerate your impact? How does it free up your capacity through increased delegation? How does it increase your effectiveness and speed up your work?

3. Compared to other roles, why is your promotion potentially more critical? Is your role more closely tied to revenue and top-line growth? To a higher priority company goal? This is one of the primary reasons high-visibility projects create faster promotion paths. Or why certain functions see faster promotions than others.

The three components of a great promotion story will include past performance to demonstrate capability and potential, timing criticality, and relative importance to other roles. Having strong arguments on all three fronts will help your leadership pound the table for your promotion to go through.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

• High-stakes meetings break down because we misunderstand incentives, pressures, and fears. On Feb 11, I’m teaching a free lesson on how to use simple AI workflows to anticipate conflicts and communicate with confidence. Register here.

• Wondering what might be stopping you from that next promotion? Check out my The Uncommon Executive Leadership Accelerator made for mid-career leaders looking to transition from a do-er to a lead-er. Over 8 weeks, we cover the core leadership skills you need to become a top 1% leader.

By dictating each action, I triggered defensiveness and frustration. By doing things for them, I rob them of a chance to learn and set myself up for ongoing work. By rushing into getting something done, we fell further behind.

Imagine instead I paused in the moment and took a deep breath. Instead of rushing them further, I calmly let them know that school starts soon. I find a sand timer to visualize the remaining time. I bring in a bit of competition by giving whoever gets out the door first the right to decide what is for dinner. I don’t tell them what needs to be done (they already know) and instead gently remind my kid who forgets to pack his water bottle.

In the work context, we also often rush to “move fast.” Startups and Silicon Valley in particular tend to be extreme in moving with urgency. When a new issue comes up, we jump into solutioning without getting more context. When other teams push back, we tell them that they “must” allow us to move forward and step aside without much explanation. Without investing time upfront in planning or context sharing, we run straight into high coordination costs, disconnected teams, and burnout.

Step Back To Open Up Possibilities

In 2020, I led the COVID-19 response efforts for Instagram’s consumer product team. Our goal was to ship features quickly that helped 1 Billion+ Instagram users to feel connected during shelter-in-place. Time was of the essence, and everyone was working around the clock.

A senior engineer had an idea of creating group stories that collected all the stories related to COVID-19 in one location. It would help users quickly see that others are in the same boat. However, the idea was difficult to implement and created unfair ranking precedents in the system. The more others challenged the idea, the more he became adamant that it was the best way.

Rather than meeting him where he was or dismissing his idea, I took a step back and broadened the scope of the conversation: What are we trying to achieve? Who are we serving? How important is speed to launch? What other lighterweight possibilities might there be that serve the same goal? By opening up the conversation, I helped him see different paths. And he became instrumental in shipping a new COVID-19 feature in record time.

Step Back To Go Forward

In Chinese, there is a saying: “退一步，海阔天空.” Directly translated, it says, “Take a step back, you’ll see the vastness of the oceans and sky.” It reminds one to take a step back when faced with difficulty, rather than push forward with brute force or without a plan. In personal disagreements, a step back allows us to better regulate our emotions and proceed more calmly. In business contexts, the step back broadens our view, leading to different, often more creative, outcomes.

In practice, stepping back looks like disengaging or slowing down. And it is, for the short term. Thinking and planning aren’t always visible actions, but they are critical steps in the process. The next time you feel rushed into action, try the following:

1. Give yourself permission to slow down: Schedule time on your calendar for thinking. Push out meetings you are not ready for. Let others know that you need some space to strategize and plan before taking action, so you can all move faster.

2. Disengage with the chaos: Turn off your notifications. Walk out of unhelpful, anxiety-driven conversations. Find a place you feel safe, and breathe.

3. Broaden the discussion with questions: What is the true challenge here? What else might be affected? Who else needs to be involved? What are three or four ways this could be resolved? What are some short-term and long-term actions?

When you are ready to re-engage, do so strategically and slowly as well. Avoid jumping into large group meetings. Don’t rush the discussions because you feel “behind”. Remember, if things get heated again, it’s never too urgent to take a step back.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

• I’m two weeks away from getting my PPC Integral Coaching Certification from New Ventures West. It’s been such a rewarding year adding to my toolkit as a coach and learning about myself. If you’re interested in 1:1 executive coaching with me, let’s chat via a free Intro Call here!

• Join me later today for a free talk for Maven on what great CPO level communications looks like. Sign up here.

  • This is a part of the promotion for my highly rated course, Master Executive Presence & Communication with AI. The next cohort starts March 9th!

The challenge isn’t having ideas. Most people have interesting ideas about their work, their teams’ work, or other people’s work. Some have entire brainstorming docs, data points, and written documents. Yet they hold back their ideas. They stay quiet through the entire planning off-site. It doesn’t get raised at team meetings. It just sits in the mind or on their computer.

The main concern? I’m not confident yet that it’s a good idea. I don’t think there is enough data backing it. I don’t want to put something out there and get told it is dumb by my colleagues.

This is ego and fear of judgment holding us back. New ideas are, well, new and different. Fear keeps us in the realm of certainty, where we are comfortable.

And it’s a self-fulfilling prophecy. If you rarely share ideas, then more scrutiny is placed on the ones you do share. And when you only have one or two shots on goal, there is a higher bar for it to be good.

Reframe The Goal

When our goal is to share good ideas and get positive feedback, we’ve set the bar very high. How many people can come up with amazing ideas in a vacuum? Setting such a high bar prevents us from taking any action.

Instead, reframe the goal as “Let me put something out there so you can show me why it won’t work.”

When you focus on learning and feedback, the bar to share is much lower. It is implied that the idea isn’t perfect, so it’s ready earlier. I know it might not be good yet. It’s a strawman, a starting point. This framing is a safety cushion for the ego.

When you want to know all the ways it won’t work, you’ll also more naturally start conversations with different types of people. You want to gather all the ways it might fail, not just the ones that those with whom you work regularly or are close to the topic can come up with.

More Direct, Supportive Responses

This reverse framing also tends to create more direct, supportive responses from others. When another person comes to you with, “I’ve got this great idea!” Our natural inclination is to critique and find fault. We want to give them all the reasons why it might not work. In the reverse, when someone says “I don’t think this will work, but I do like the concept”, we are more likely to help them find ways to make it work. Not only does the framing lower the bar to share, it also increases the probability of receiving a positive response.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

• I’m joining , , and for a free talk on what great CPO level communications look like. Join us on Jan 22 live or get the recording emailed to you!

• I’m actively booking workshops, fireside chats, and corporate events for 2026. If you’d like me to speak or run your next leadership event, DM me! My go-to topics include executive presence & communication, influence and power, delegation, and AI-powered management.

• Interested in 1:1 executive coaching with me? I have 1-2 spots left for a Feb start. Book a free Intro Call here!

Highlights of 2025

• Started my year-long certification program on Integral Coaching with New Ventures West in Feb. Easily the best personal growth decision I’ve made.

• Got on stage to speak for some of my favorite organizations in Q1’25: ProductTank Barcelona, Chief, Sidebar, Women in Product, and SASE

• May: Joined Asian Leadership Center, a collective of executive coaches who combine Western and Eastern philosophy. Proud to collaborate with Mike Takagawa, Mo, Peter (a high school classmate!), and Wes Kao. Started with a first corporate client in November.

• Converted to an official (part-time) employee at Perk as a leadership coach, supporting C-level and VP-level executives at the $2.7B B2B SaaS startup. Really enjoying coaching in person and leading leadership off-sites!

• In June, I met , who invited me to speak on her podcast, Badass Women. It turns out she is the author of one of my favorite books, The Politics of Promotion.

• In September, I did a repeat collaboration with on How To Manage A Peer-To-Manager Transition. Ethan has graciously been a supporter of my writing and coaching since the beginning!

• My Master Executive Presence & Communication with AI course had a viral moment in December, becoming a best seller on Maven and bringing in a highly engaged group of students that I’ve loved teaching.

• Also in December, finally shipped a guest post with for on Failure Is A Feature, Not A Bug. Ironically, I failed to write this post well at least three times.

Goals Review

From my 2024 Year In Review, my goals for 2025 were to lean into what is working well, experiment with new offerings, and improve running the business. Here’s how it went.

Lean into what is working well

• 🟢 Expand 1:1 executive coaching clients: This is by far what I am most proud of this year. My 1:1 coaching roster grew by so much that I started to maintain a waitlist in October. I was able to get more selective about the topics I coach (e.g. no interview-only coaching), seniority (got my first L10 client from FAANG!), and style (ambitious, vulnerable, curious). A large portion of my previous clients also renewed their 6 or 12-month engagements.

• 🟢 Write consistently for this newsletter: I published weekly posts throughout 2025, taking only 1 week off so far. The newsletter has grown substantially as well, tripling from ~7k to 21k followers.

• 🔴 More corporate workshops and team coaching: Delivered corporate workshops for Thumbtack, Instacart Women’s Month, and Kahilla. While I put effort into this in Q1, as my 1:1 coaching, course, and accelerator program took off, I did not invest much time into new leads, and it was deprioritized.

Iterate on new offerings

• 🟡 The Uncommon Executive Leadership Accelerator: I ran 3 cohorts of The Uncommon Executive Leadership Accelerator program this year. The next cohort starting January 2026 is fully booked. I love group coaching, and the sessions are always impactful. However, it’s always a stressful run-up to the application deadline on whether the spots will fill, and I don’t enjoy that.

• 🔴 Yue’s Coaching Corner: While people continued to join the Slack community in 2025, I lost steam here. It felt like just another advertising channel rather than a true community. I tried a few times to revive it, and even considered bringing someone on to run it, but nothing worked out so far.

• 🟢 (new!) Master Executive Presence & Communication with AI: I did not have this as a goal in 2024, but it ended up taking a large portion of my time in 2025. I ran 4 cohorts, updated the curriculum regularly, did 4 popular free lighting lessons (5000+ attendees!), and hired help with marketing for two cohorts.

Running the business

• 🟡 Repeatable Marketing & Sales: I signed on two different people to help on the marketing front (LinkedIn and Maven). While neither is ongoing, they both helped me set strong foundations. I would say that the process is still very manual and one-off.

• 🟡 Add AI for efficiency: I moved my website to Gamma App (AI-native website builder), and absolutely love it. I also created Claude projects for repurposing my content to LinkedIn and Substac Notes, as well as a writing partner for my Newsletter.

I exceeded expectations in 1:1 executive coaching from all aspects in 2025. My funnel of LinkedIn → Newsletter & website → Free Intro Call → Client worked well. To date, I’ve coached 40+ clients in 6-month+ engagements this year. That’s more than 300+ hours in 1:1 executive coaching conversations!

My Maven course and accelerator program both met expectations. I do not love these offerings as much as 1:1 executive coaching, but it offers a more accessible option for those who are financially constrained or earlier in their career. So, while I have honestly considered quitting after each cohort, there was always a good reason to do the next cohort.

Finally, I did not invest in corporate workshops, podcasts, or newsletter guest posts as much as last year. Perhaps it’s because I now have a significant corporate client that takes up 15+ hours a month of my time, I did not want to do the business development that was needed to keep up these channels.

What Brought Me Energy and What Drained Me

What Brought Me Energy

• Each and every 1:1 coaching conversation, particularly those with people who are open, vulnerable, and thoughtful. I also enjoyed many of the intro calls!!

• Researching and writing my newsletters

• Editing my LinkedIn posts after my AI helps with a first draft. Big change from last year, when I really didn’t find energy in this part of marketing

• Group coaching conversations, podcasts, and fireside chats

What Drained Me

• Hiring and letting go of people in my business. It was a lot of work to ramp up someone and then to take over when they leave. And somehow, in many cases, I did not end up saving time or seeing a significant increase in impact

• Scheduling, calendaring, following up. I have known that logistics is not my strength, and it shows in how much I dislike playing calendar Tetris and following up on reschedules

• Following up with people for reviews for my offerings

• Trying to figure out if I’d have a well-rounded cohort for group coaching as a part of the accelerator

• Cold outreach for corporate workshops

2026 Goals

Looking forward to 2026, my vision is to keep following my energy and do more of the work I find fulfilling. Everything else will come. Here are some directions that speak to my heart:

1:1 executive coaching

• Continue to have this as the core service and focus. Maintain a list of high caliber clients and create career-changing breakthroughs with them

• Automate and professionalize more the operations: scheduling, payments, summaries, outreach

• Create a system for getting reviews and testimonials

• Bring more integral coaching philosophy and practice into regular coaching

Maven Course & Accelerator program

• Incorporate new learnings and update the course each quarter. Put more operations pieces on automation where possible (e.g. reviews, lightening lessons, etc). Aim to run 4 cohorts in 2026.

• Consider stopping the accelerator program after Jan given time limitations with my corporate client commitments.

Corporate Clients

• Continue corporate engagement with a few select companies (less than 5). These take up a significant chunk of time, so be conscious of spreading too thin.

• Continue to work with and support Asian Leadership Center

Business Development

• Do lightweight outreach for corporate workshops, particularly with past and current clients.

• Try for an ongoing cadence of podcasts and guest posts.

• Stretch goal: update my book: The Uncommon Executive: Breakthrough to the C-suite as a Minority

If you have the chance, do sit down and write your own personal look back and look forward this holiday season. Do steak this framework to reflect and then set your intentions for the new year.

That’s all folks! See you in 2026!

Yue

P.S. If you’re curious, read my full 2024 Year In Review here.

As I rose through the ranks in product, I realized that what made the difference between a top performer and an average one was how I did my work. My technical skills got me a seat at the table, but they did not put me on the path to high performance and leadership. A critical and valuable part of the job was how I kept everyone in the loop and made sure that all the teams the project touched were aligned.

In the age of AI, the value of these soft skills is even more pronounced. As AI can now prototype, design, and perform data analysis, technical skills are increasingly a commodity. Your edge at work is the visibility, alignment, and agency you bring to the work being done.

Visibility and Alignment Create Trust

For many of us, we develop the desire to “put our head down and work” in school. For many of our formative years, getting alone time to focus meant we were more likely to do well. Our parents checking in if we did our homework is, at best, very annoying. However, unlike school, where homework assignments and test questions are set months in advance, work projects are ever-changing.

The business environment and goals shift. Partner teams discover previously unknown challenges and change course. As a result, your tasks change as well. Collaboration towards a collective goal is actually one of the most important competitive advantages of mankind. If everyone worked in a black box without talking to each other, it would tend towards chaos. This is the role of managers and leaders: to ensure large teams are working towards a common goal, and to constantly align and realign teams as changes arise.

Therefore, when you work on your own island, your manager has to do extra work on your behalf. They spend cycles chasing updates from you, checking with other teams on whether it aligns with their work, and calling meetings to keep everyone aligned. In fact, I often see this in engineering, where managers and PMs will ask to take on communication and alignment tasks such that a critical engineer can stay 100% focused on writing code. This extra work adds up quickly, particularly if your manager has six people on their team and needs to do this for everyone.

Now, imagine your leaders have a large, risky project to assign. Would they assign it to someone who will keep them and others informed along the way, or someone who will go away and then come back when it’s done? As the work gets more complex, risky, and involves close coordination with more teams, the value of proactive visibility and communication grows exponentially.

Remove Friction For Others

The person who will land that next career opportunity proactively removes uncertainty and friction for their leaders and partners. To do this, put yourself in the position of someone who needs to collaborate with you and consider what they would not want. For example, imagine working with someone who:

• Communicates sporadically about what is happening on their projects when you have a dependency on their work

• Let deadlines pass without comments, causing you to have to follow up to see what happened and what to expect

• Individually decides the best way to solve unexpected challenges without consulting you or anyone else. And you don’t find out until the work is done.

Sounds stressful? Now imagine the opposite, someone who:

• Works against a visible timeline. Sets up checkpoint meetings at critical times for leaders and partner teams. Sends updates before they are asked.

• Immediately communicates delays and changes to work priorities broadly. Send out completed work for feedback with time set aside for adjustments.

• Raises unforeseen challenges early with key stakeholders. Explicitly states assumptions and lays out potential options logically and clearly for decisions.

The first person will likely be in performance conversations due to a lack of visibility into their work. The second person is the one that I would want to delegate more important projects to. Proactive visibility and communication are how you build trust with your partners and leaders.

Finally, proactive communication allows you to gain back time. I’ve seen too many junior PMs get randomized and overwhelmed by all the updates. When you have ten people randomly pinging at random times for updates, questions every decision that was made (and then needs to be remade), it introduces quite a bit of work. You feel like you spend all your time giving updates, rather than doing actual work. Investing in a communication system that answers those questions in a scalable way before they are asked. This gives you the ability to control what gets communicated and when, and on the whole, time back.

As we approach the end of the year, take a look at your communication system with your leaders and teams. How can it be improved to be more efficient? What can you adjust to get ahead of asks and give yourself time back?

That’s all folks! See you next week at 3:14 pm.

Yue

When I started working at Instagram, I made it a point to meet senior leaders across different functions and teams. I wanted to build my relationships and visibility from the start. Frequently, the leader would invite me to “reach out for help.” For years, I did not take advantage of these offers. I didn’t really know how. I chalked it up to one of those nice gestures that one offered but did not expect to be taken up.

It turns out that senior leaders do truly want to help. One VP asked me during a subsequent one-on-one a few months later why I hadn’t reached out with any asks. It took my managers at Meta working with me for weeks on why I wasn’t explicitly asking for help for me to finally learn to take advantage of these offers. And when I became a Chief Product Officer, I finally realized how much I had made it harder for myself along the way.

First, The Mindset Shift

The first thing I had to unlearn was the idea that I needed to get everything done myself. That asking for help was a sign of failure. And that asking for help from a senior leader was the same as walking myself out of the company.

I feared others knowing I was struggling with a project. I feared being taken advantage of or being perceived as lacking capability. As a result, I worked long hours trying to figure it out myself. Progress was often glacially slow, and conversations seemed to go in circles. I grew increasingly frustrated at myself, and it showed up in being short-tempered, impatient, or unnecessarily pessimistic.

It turns out that knowing when, who, and how to ask for help is an essential leadership skill. Without it, projects and decisions drag on unnecessarily or balloon into bigger problems that are harder to address. Instead of trying to solve everything myself, I needed to figure out how to bring visibility to my challenges and effectively bring others in to help with a resolution. It was not a judgment on my lack of ability. The challenges I needed to ask for help on were decisions and situations outside my ability to control or influence.

When To Ask For Help

While it’s important to ask for help, knowing when to ask for help is a judgment call. If the challenge is too simple, you risk others (or your inner critic) questioning your capabilities. If you wait too long, you let a problem grow disproportionate and harder to resolve, even for the leaders. Here’s how to think about this balance:

1. Is the challenge in an area where you are the expert? The more the challenge is outside your area of expertise, the earlier the ask should be made.

2. Does the challenge require coordination across multiple teams outside your span of control? The more cross-functional or cross-team the challenge, the better it is to ask for help early. Don’t try to wrangle all the cats yourself.

3. Does it require an exception from a leader outside your line of command? If you’re trying to accomplish something that goes outside business as usual, ask for support early.

When in doubt, err on the side of asking for help earlier. Quite frequently, your ego and fears prevent you from reaching out. When you do reach out, take the time to strategize on the type of help you need.

Types of Asks For Help

In the beginning, I thought that when I asked for help, it meant that the other person had to do the work for me, which I often did not want. It turns out that there are many types of help a leader can provide, some of which play really well to their position and strengths.

The way to think of the type of ask is how involved the other person needs to be:

1. Be A Sounding Board: This is the lightest touch for the leader. You are asking them to simply listen and give you guidance from their perspective.

2. Give Air Cover: You are asking that they back up what you’re saying in a group setting or support you when others raise concerns about your actions. The leader is agreeing with you publicly, and as a result, sharing their power and influence with you.

3. Be A Messenger: In this scenario, the leader helps you deliver an uncontroversial message to others. This ask is made when they have access to people and conversations that you do not have, or when you need help getting many people to align in a short amount of time.

4. Fight With Me: This is the most involved scenario where the leader needs to go and convince others with you. They are actively creating new arguments and taking on a part of the work. This requires much more work from them and for them to actively put their credibility on the line.

I believe that one of the best default asks for leaders is to give you air cover. It is low effort and reactive. It is a type of help that you can ask for in advance of knowing exactly when it’ll be needed. “I’m going to go do X. Can you support with air cover if needed?” It also allows you to maintain the initiative and control while the leader plays a supporting role. This makes it easier to make the ask as well.

That’s all folks! See you next week at 3:14 pm.

Yue

Yue’s Coaching Corner

1 spot left (!) for the Jan cohort of The Uncommon Executive Leadership Accelerator. Join 4 other leaders in mastering critical soft skills in leadership. Rated 5/5 by past students. Apply here!

Now, more so than other times of the year, managers and leaders are being asked:

“Who are your top performers we need to retain and invest in?”

“Who might not have what it takes for the next phase of growth?”

“Who is a good fit for this new role that we are creating? Do we hire externally or promote from within?”

“This team is underperforming. Who can we shift over to reinvigorate the team?”

We all have recency bias. So you want to be top of mind now. This is when all that work you’ve put into building relationships and crafting a narrative pays off. This week, I will share three actions to take in the next two weeks to set yourself up well to be top of mind for career-accelerating projects.

Why is the End of Year A Special Time?

Annual planning and performance reviews dovetail in this special time of the year for many organizations. Executives are reflecting on performance in 2025 and planning for 2026. In closed rooms and off-sites, leaders are implicitly and explicitly solidifying their perceptions of the growth potential of each team member.

Some assessments are explicit as part of official processes. Performance reviews and org planning require leaders to get together to draw org charts and defend their latest conclusions on individual performance. At Meta, managers get together to talk through what each person on their team has accomplished, and “calibrate” with each other on what is considered meeting expectations or not. At smaller companies, managers are asked to put a stake in the ground on who their high-potential high performers are, and who are simply solid but lack potential.

Some perception formations are implicit. Executives are asking who should lead new investments. Leaders are assessing how projects are going, and whether there needs to be people changes to accelerate progress. Senior leaders are creating new roles and looking for people to step up to a bigger scope. These questions implicitly prompt leaders to gauge a person’s cross-functional leadership potential, agency, and creativity.

This is the time of year I see the most instances of leaders whiteboarding org charts, fierce debates between leaders to get “their people” considered for growth roles, and doughling out of career-defining opportunities. Take the time to ensure your sponsors have the fuel they need to throw your name in the hat and pitch your case.

3 Actions To Get Top of Mind

Throughout the year, we are slowly shaping perception through our regular interactions with leaders. Some may be positive when you deliver on high-impact projects or stand up for your beliefs. Some may be more negative. However, it is this time of the year that they’re really putting it together and connecting the dots. Here’s how to influence it to your advantage:

1. Get on a positive note: go their extra mile to ensure their latest interaction with you is positive. Recency bias is very real. Don’t throw away a year of amazing work because the last thing they heard about you is a conflict with another coworker or a small mistake. While bringing gifts might feel cliché and too obvious, it is an example of an attempt to leave a positive impression. Other tactics include going for a coffee or walk, scheduling a time to review a launch or deliverable, or simply sending a “update email”.

2. Give them the highlight reel: Executives have a horrible memory. Most of the time, it is sufficient that they have a vague perception that “I feel like Yue is good and has high potential.” However, this is the time when they need specifics. They need to defend your performance ratings or pitch you for new projects with their managers and peers. Give them a highlight reel of your accomplishments and leadership strengths. Make them quick stories so that they are memorable. This way, when someone asks, “What’s Yue good at?”, they have quick examples on hand.

3. Say Thank You: We rarely express appreciation and gratitude for our leaders, and it goes a long way. They are human too, and seek validation. Find the opportunity to sincerely express your thanks for their support (and use it as a way to remind them of why they love working with you).

If there is one time to get out of your comfort zone to talk about your accomplishments, be helpful, and show appreciation, it is now. Make it a to-do in the next two weeks, and let serendipity to its magic for months to come.

That’s all folks! See you next week at 3:14 pm.

Yue

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• My leadership course, Master Executive Presence & Communication with AI, is a best seller on Maven (woohoo)! The last cohort of the year starts next Monday, December 1st. Get 20% off as a paid subscriber to this newsletter!

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Affinity, Confirmation, and Negativity Biases

The three types of bias that stand out in terms of the highest impact on minorities trying to advance their career are affinity bias, confirmation bias, and negativity bias. These three combined create a self-fulfilling loop that promotes more of the in-group (e.g., white males with roughly 80 percent representation) and further excludes the out-group (e.g., non-white males or females).

Affinity bias is the very human tendency to trust and favor people whom you view as more similar, often based on common experiences, backgrounds, or interests. Affinity bias leads executives to give their “mini-me” more opportunities, less critical feedback, or more benefit of the doubt when it comes to mistakes.

It was in my first job out of college that I saw the affinity bias based on gender and race at play in the workplace at play in the workplace. I landed a business analyst role at McKinsey & Company, where I was the only person not from an Ivy League school to be accepted that year. Shortly after starting, I noticed that although half of my interviewers had been women, most of the partners at the firm were white men. Often, a white male partner would ask a white male associate to take on a part of the presentation and introduce them to the clients. They would go off and plan for future meetings, leaving the rest of the team to do follow-up work. Over time, I noticed that non-minority managers were more frequently given opportunities to work closely with senior clients. This is what affinity bias looks like.

The second is confirmation bias, which is the tendency to interpret new evidence as confirmation of one’s existing beliefs or theories. This means that when we receive new information that does not fit our current beliefs, rather than altering our beliefs to

incorporate the new information, we do the opposite. We alternate our interpretation of the information to fit our beliefs. This is why two very smart people looking at the same set of data or observing the same set of events can come to two very different conclusions. From a career perspective, this shows up in many different places. When hiring, a CEO may interpret interview results in a way that confirms their preexisting beliefs (subject to affinity bias) about a candidate. During performance reviews, managers may subconsciously inflate the performance rating of those who are more like them or be more willing to overlook mistakes. In decision-making, leaders may prefer to hear and pay more attention to information or perspectives that match their own. It’s easy to see how this leads to a disadvantage for minorities, who are more likely to have a different perspective and a different approach than their (usually) white male leaders.

Third is negativity bias. This is where executives over-index on negative actions of people who are unlike them and more readily perceive a mistake as a repeat pattern. For example, I would receive feedback for being “intimidating” or “aggressive” if I spoke harshly in just one meeting, while my male peers were considered “persistent” and “confident” in similar scenarios. If I missed a launch date once, it was considered a pattern of missing

timelines; whereas, for my white male peer, it was viewed as an exception for someone who generally delivered on time. This tendency to over-index on negative action was the reason one small failure of the team would damage my performance review but not that of my white male peer.

Together, these three biases hold minorities and women back from competitive leadership roles. And the mechanism is often not overtly biased actions, but opportunities not given.

Bias Shows Up in Actions Not Taken

Sometimes bias is explicit and easy to recognize, but it also often presents itself in actions not taken or skills not taught. It may not be an action someone takes against you or something someone tells you directly. Rather, it shows up as opportunities given to someone else, an implicit discount on your work impact, or a lack of progress over time. Rarely will someone tell you that they gave an assignment to another person because he is a white male.

This makes the bias more difficult to identify for both the person with the bias and the recipient. Here is a small example: There’s a large group meeting, and the organizer, a white male, is trying to limit the number of attendees. He leaves a minority manager off the invite to “save her time.” At the same time, he invites another white male manager who is his friend and is a go-getter, because he knows his friend would appreciate being in the room. The minority manager will likely not notice that she was left out of the meeting. If she does notice, the organizer could easily explain it away by saying that they had to keep the invite list to the most relevant people. This decision of whom to invite took probably 10 seconds and didn’t even truly register in the organizer’s mind as a bias. However, these types of reflexive biases add up over a person’s career to meaningful differences in opportunity and rate of promotion.

Small Biases Compound

Schelling’s model of segregation, developed in 1971, analyzes the creation of racially segregated neighborhoods. It shows that trivial preferences for same-group people in a neighborhood lead in aggregate to segregation over time. For instance, if white people in a neighborhood prefer diversity with Black people at a 80% white, 20% black ratio, it will lead the neighborhood to be 100% white over time.

Similarly, small, often implicit biases can lead to an executive team that lacks any diversity. In most cases, no one is intentionally trying to hold minorities back. Most people hiring executives are simply looking for the best person for the role and the business.

However, the further you climb up the career ladder, the more competitive it becomes. At the director level and above, most of your peers are well-spoken, intelligent, and ambitious. This high level of competition means that tiny biases that were previously easy to ignore now have an outsized impact on who can break through and get promoted.

…

To continue reading, check out my book on Amazon or borrow it at your nearest library.

That’s all folks! See you next week at 3:14 pm.

Yue

Connect with Yue

• I gave a free talk with Elena Luneva to 2000+ attendees yesterday on building executive presence and leading with calm next Wednesday. Watch here.

• My course, Master Executive Presence & Communication with AI was selected to be a part of Maven’s Fast Track Program. Get 25% with code FAST25 until Monday!

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Some people could draw brilliant insights from research and data. Some were always three steps ahead in thinking through risks and complexity. Some could get a crazy amount of work done and deliver project after project.

But they were not always the people getting promoted.

It turns out that being amazing at execution is a trap that keeps you in execution. Getting into leadership required a different set of skills entirely.

Is there a business need?

As high-performers, we tend to over-index on the amount of control and influence we have over our environment and future. Unlike early career promotions, leadership promotions only occur if there is a business need for someone to operate at the next level.

Senior manager or L6 roles are known as terminal levels. There is no mandate to promote further. It stops being like school and early career, where doing the work you’re given means you graduate to the next grade. You have to seek and create opportunities for yourself where there is a business need for your promotion.

Here are examples of business needs:

• A position has just been vacated (e.g., retirement, reorg, leaders leaving)

• Your area of work is growing rapidly (> 20% year over year), and your area and team are growing alongside.

• The company invests in a new strategic initiative

• There is an opportunity on an adjacent team

• The executives want to reorg in order to realign priorities

From working with hundreds of aspiring executives and years of experience as a product executive promoting others, the environment accounts for at least 50% of whether a leadership promotion occurs. Take a look at your current setup and ask yourself the following:

• Is the team size and resourcing for my skip-level manager’s scope growing?

• Is there a need for a leader at my desired level in the next 6 months? Do we like to keep teams lean?

• What is the culture around promoting new leaders in my organization? Do the executives prefer to hire into senior roles rather than promote from within?

• Has there been a promotion from my current level to the next in the last 6 to 12 months? What was the case that was made?

• Where are the areas of investment for the company, and how close is it to the work I am currently doing?

If your answer is unclear or negative for more than two of the questions, then you’re in a place where it’s an uphill battle for that promotion. Regardless of how well you’re performing, the business case isn’t there.

After a year at Instagram, I wanted to get back into managing a team. I had been given more scope after a peer left the company and was leading the work of two PMs. From a scope perspective, I was set. However, Instagram had a philosophy of keeping PM teams lean with very senior people in each role. There was little room to move into management, and very few internal promotions. Even though I was exceeding expectations for my level, there was simply no business need for the career progression I wanted. To get back into management, I need to transition to other parts of Meta where teams were larger and had more layers of management.

When you are a high performer, it is not uncommon that you outperform your organization’s ability to promote. It’s critical to notice this and make a strategy for your next steps. Some common options include:

• Moving to adjacent teams with higher growth, more scope, or bigger teams

• Taking on higher visibility, higher-risk projects that will get additional investment if successful

• Seeking out external opportunities

Sometimes, it is better to take a step back in terms of title, compensation, or even scope if it allows you to move into a place with higher potential for growth. When we acknowledge that it’s not about working harder and then expecting a reward, we move to paths that accelerate our path towards leadership.

That’s all folks! See you next week at 3:14 pm.

Yue

Connect with Yue

• I’m super excited to be doing a free talk with on executive presence and leading with calm next Wednesday. Register here to join live or get it emailed afterwards.

  • Go further with my associated course: Master Executive Presence & Communication with AI. Dec 1-21, 2025.

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More on Getting Promoted

• Why Being Collaborative May Hurt Your Chances For Promotion

• 3 Reasons Your Manager Will Fail You During Promotions

• Why Performance Reviews Don’t Go As Expected

• How To Say No to Non-Promotable Tasks

• Why Mentoring Doesn’t Get You Into Management

• The art of securing sponsorship in the workplace

• How to anticipate and come out ahead in reorgs

• How can I boost my performance rating?