This is a classic chicken-and-egg problem that executives often grapple with when it comes to running planning cycles that run on top of day-to-day work for companies that are growing and innovating. How do I keep the current work going, yet plan for the next steps, which may not be closely related to the current work, with the same group of people?

Let’s say I run a simple product organization with 3 online retail businesses in the US: Dogs, Cats, and Other Pets. If I keep the existing teams and ask the team to plan bottom-up, then I’ll get plans that mirror the current distribution of projects. But perhaps I want to invest more in Capybaras and Goats next year, and need less planning from the Dogs and Cats team. Or, the future direction might require input from someone on another team who has a different skill set (e.g. mobile and web teams need to work together with the creative team to design in-store digital experiences for new physical stores). Or it could be such a new topic that the current team doesn’t have enough context to plan well for it (e.g. you want to enter a non-US market).

If I try to shuffle the teams first based on high-level strategic direction, then everyone gets pulled into a different set of contexts and problems, and the current work gets disrupted. In addition, I will likely make the wrong calls on how the future team should look, because there are no official execution-level plans yet. This means there will likely be another reorg after the detailed planning, and more churn for weeks on the teams.

When a company is 1) mature enough to have standing areas of investment and 2) has enough teams to cover the whole surface area of the product, then this dilemma comes up less frequently. Teams can generally plan for similar areas and scope year over year, and the small adjustments are easier to make.

However, at fast-paced, rapidly scaling startups, this issue comes up almost every quarter. Teams don’t cover the full surface area of the product, so it’s necessary to shift the same team from one area to another. If the business is also changing, then there is always a new bet to scope, or an investment that didn’t work out to defund. Changing official org lines at the strategic direction level within detailed resource plans can cause resourcing to not actually follow stated priorities, or follow-up reorgs after the plans are finalized.

The Magic of Planning Teams

To solve this dilemma, I frequently rely on a concept called planning teams. I iterated on this concept at Thumbtack and Meta, and successfully introduced it to Fuzzy Pet Health’s team of ~150 across engineering, PM, and design as we quickly iterated through multiple different strategies over 2 years.

Planning teams are temporary teams assembled for planning purposes. A planning team is formed for each important area of investment for the next year. Each team has a planning lead and includes critical members from each function that needs to be involved in the planning (e.g., marketing, sales, customer support, operations, finance, engineering, design). This team meets according to the planning cycle, coming together for brainstorming sessions, prioritization, resource planning, and executive reviews.

The planning team model solves for a few important challenges:

• A scarce resource could help on multiple planning teams. Let’s say you have one AEO expert, yet two areas require AEO support. That person could join both planning teams, even if they will not officially work on one of the areas.

• Existing work and team cadences can continue in parallel to the planning team work. Planning teams are not official teams with reporting lines or component ownership. They remain lightweight and distinct from performance management cycles.

• Planning teams do not have to have continuity beyond the planning period (though some may). This gives executives a chance to rebalance resources after the detailed planning is complete without touching official org lines.

• There can be more people on the planning team and in the planning discussions than in day-to-day team execution. The planning team allows for more cross-functional input early on, without slowing the core execution team down later.

• It allows executives to see how someone performs in a new area or extended scope in the planning process before formalizing new leadership roles. It also gives executives a chance to see the dynamics of a team for a few weeks before formalizing the new team structures.

Planning teams often do become official teams after some adjustment, particularly for brand new areas of investment. Therefore, as a leader, it is important to choose the teams with some care and thought. It sets up future leaders to lead and is often the beginning of new group dynamics. However, without the additional stress of official org line changes, planning teams can remain flexible and shift based on where business cases and priorities fall after detailed planning.

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

Yue

Hi everyone,

It’s been quite a while since I last published a fresh newsletter consistently. I was very proud of my two-year streak of publishing weekly and am sad to lose it. But it has been hard to bring myself to write. Two things happened at the same time that led to this:

First, I source much of my content from the challenges my clients face. Their questions and our work together inspire my writing. Starting around May this year, a majority of tech companies began measuring token usage in earnest, pursuing thoughtless layoffs or role changes, and setting unrealistic goals for the remaining team.

The deep conversations about leadership and careers disappeared. Instead, I spent most of my time with very stressed-out leaders who were either ready to quit due to AI or extremely worried about AI taking over their jobs. Most of the conversations happened in a high-anxiety “we must solve this now”, making it super difficult to go deeper and be open to longer-than-a-day possibilities. There was so much fear: about how to fit learning AI into their already crazy workloads, about all their years of education and experience becoming irrelevant, or about whether they were still “on the right path.” Everyone was scrambling to get an AI degree (what is that), take an AI course on Evals, or read 20 articles on “how to adopt AI in X”.

It was a great business opportunity for coaches and educators. My inbox filled with subject lines that featured AI prominently. Everyone had a hot take. Demand for AI courses was at an all-time high. Many around me built thriving businesses off this unprecedented demand.

Unfortunately for me, fulfillment with my work was at an all-time low. I get fulfillment when I can slow down with a client, connect with them at a deeper, more emotional level, and help them build confidence, curiosity, and courage. But as the stress around AI increased, the conversations got shorter, more tactical, and more “what can I do now immediately?” And I lost much of my own motivation for the work. And that made it hard to coach others.

Second, I started to use AI for drafting my newsletters. I leaned into a writing process where I would take a walk, talk to Claude, and then have it do the first draft. I would then edit, tweak, and publish. It was faster, but much less enjoyable over time. I tried to persist. I pushed myself to keep it up. And after a few weeks, the joy of writing disappeared entirely. I found myself creating posts for the sake of creating them, perhaps because my business needed it, rather than writing from the heart as a way to help others or distill my own thoughts on a topic.

And so I stopped. One Monday, I decided that I was just going to hit pause. I stopped writing (and pressuring myself to get something out there). I cut back on accepting new clients to referrals only. I ended some client engagements that were draining me and refunded them in full.

I took a break.

A much longer-than-expected break.

I thought my break would be for around 2 weeks, coinciding with some family vacation time in August. But then came September, back to school, and now we’re basically at the end of October. And finally, I’m feeling more energized again.

Now, it’s hard to say anything is normal right now, with all the geopolitical challenges, volatile markets, and AI end-of-world prophecies. However, I’ve found that leaders and executives are back to asking more grounded questions about their life and career, and more open to me creating the space for slower conversation. The strategy is less “use AI at all costs” and more “let’s see what we’re getting out of it. Is it speed? higher quality?” There’s less “I need to do this because A\ or OpenAI or some $1B funded AI native startup is doing it” and more “This is what’s right for my team and organization.” It feels less "grasping at a straw” and more “let’s go on a difficult journey together”.

And at the same time, I feel my creative energy finally returning. I will avoid using AI for writing this newsletter for a while, at least the first draft. It has its uses in our home (e.g., meal planning, finances, and budgeting) and my work (e.g., my course content, social posts, AEO). But I’ve realized that I need to go through the work of writing, not just talking, to truly let creativity flow. It’s like how I love making a bowl in my ceramics studio. While I could get a machine to produce a bowl that is perhaps even of higher “quality”, it’s about the process, not the outcome.

So, this is a very long-winded way to say: I’m back. I look forward to sharing more leadership and career learnings with you through this newsletter. Anyone considering executive coaching with me, please say hello through a free intro call.

See you next week at 3:14 pm!

Yue

And previously, I was advised not to invest time in NPTs. So should I be doing these tasks or not?

Non-Promotable Tasks vs Influence Building

Non-promotable tasks are work that doesn’t show up in promotion packets. Examples include taking notes in a group review meeting, planning the team offsite, or mentoring the new hire. NPTs don’t have direct or clear business impact. It’s hard to make the connection to increasing revenue or decreasing costs. Instead, NPTs come up because teams want to collaborate better or level up the skills of the overall team. As I’ve written about in this past post, women and high performers are more frequently asked to do these tasks. So the advice is to say no, protect your calendar, and prioritize the stuff that counts.

It turns out this is only half correct.

Let’s take the influence-building lens. To build influence, we want to rely on the very human tendency to reciprocate ( What we get wrong about influence). When you help someone, they are likely to return the favor in the future. When you help someone, you have gained (some) influence over that person. Trust and influence are built through repeat interactions where someone seeks your support, and you live up to their expectations. Therefore, through the lens of helping another person and triggering reciprocity, we may decide to prioritize non-promotable tasks.

How To Prioritize Your Work

Here, we have a standard two-by-two. On the X-axis, we consider whether the task is a non-promotable task (refresh rules on how to decide if it’s a NPT). On the Y-axis, we consider whether this task allows us to help a stakeholder with whom we need to build more influence.

In the top right, we have work that has clear business impact and builds influence with those who matter. This is a no-regrets P0 for your to-do list. These tasks allow you to nail two birds with one stone, building towards your career progress and increasing your influence at the same time. For example, as a PM, you prioritize a feature your team wants to build that also unblocks the team whose VP you need in your corner.

Then, in the bottom right, we have your core project work for your role. Doing well at these tasks is the foundation for building influence. It’s unlikely that others will seek help from someone who isn’t good at their core job.

Now, let’s look at the work that’s considered non-promotable tasks. In the top left, we have tasks where the “impact” is in building influence. For this work, the core question to ask is whether you want to increase influence with the person asking. For example, if your team is asking you to take notes, and you already have their trust, then it’s likely best to say no. However, taking and sending next steps in a cross-functional forum where you want to get your name in front of the executive sponsoring the project is likely a yes. The key is to be deliberate about mapping out and knowing where you want to invest.

And finally, if it doesn’t help you build influence and it’s a NPT, then practice saying no kindly. (Related read: How To Say No to NPTs).

The tldr? Adding the influence-building lens makes some NPTs worthwhile. But be intentional about who you need to build influence with and why you’re taking on a NPT.

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

Yue

Yue’s Coaching Corner

• Hey guys, I’m back! It’s been a while since I’ve regularly new content on Substack. I’ve been in a sort of writing block and needed to take some time away. Thanks for hanging in there. In the meantime, we’ve crossed the 30,000 subscribers mark!! Woot! =)

• On 7/21, I’m doing a free talk on “what executives really mean”. Basically, I’ll share some common translations of what executives are really looking for when they ask certain questions. I’ll also be staying longer for Q&A. Come join the conversation or get the recording here.

• Want to up-level your influence & executive communication? Join the Sept cohort of my course, Outsmart the Room: AI-Powered Executive Communication & Influence (Rated 9+/10 stars, Top 100 Maven course!).

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• 1 spot left! My AI Amplified Leadership Accelerator starts next Monday! I am pumped after a great group that just finished a few weeks ago. The 6-week group coaching program brings together mid-career leaders who want to adapt and accelerate their careers in the age of AI.

• My course, Outsmart the Room: AI-powered Executive Communication & Influence was ranked #8 in Leadership and a Top 100 Maven course! =)

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    https://practice.theuncommonexecutive.com/ (built with love with Claude)

• I have 2 coaching spots opening up in the summer. If you’re interested in working with me 1:1, hop on a free intro call here to see if we’re a good fit.

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Super IC teams are the popular new kid on the block, growing at the same clip as AI-native company valuations. Every startup and scale-up wants to spin up 3-person cross-functional teams led by experienced individual contributors. The problem is, few know how to do it well and set it up for success. Many companies simply make the change, throwing groups of people together without much strategy. Others take their best, most expensive people to spearhead the effort. It turns out the key here is not just the people but, more importantly, the structure and environment created to help super ICs thrive.

There is precedence (and learnings to look to). For a few years, I was a part of one at Instagram for the Instagram consumer teams. We tackled projects like hiding the Like count in the feed, the COVID-19 response, and more. These types of teams have existed at companies like Meta and Google for years. There have been many iterations on how the teams were set up. Here’s what works.

What Has to Be True

Four conditions separate the Super IC teams that generate outsized impact from the ones that quietly dissolve.

1. They must report to someone at the executive level who has outsized influence across the entire company.

At Meta, these teams reported directly to the CTO. The CTO influenced not just the tech teams, but also sales, finance, legal, marketing, and operations. Super IC teams need direct access to the latest information in real time. They need to be in the loop and up to date on the latest business strategy, competitive signals, and customer feedback. And they need a senior sponsor who can open doors that wouldn’t open based on their own seniority alone: code reviews from partner teams, a slot in someone’s roadmap, a conversation with busy teams, or data that lives in another team.

The team operates outside normal org structures. Without an involved and proactive executive sponsor, these teams spend half their time negotiating access and managing politics instead of building or moving fast in the wrong direction.

2. The team must be fully self-sufficient.

From ideation to launch to post-launch learning, every required function needs to be dedicated to the team. No borrowed engineers who are “mostly” committed. No designer supporting three other teams. Everyone is in the room, together. This generates speed. In some cases, leaders go as far as to exempt them from interviews, recruiting, mentorship, and more. The goal is to build as much focused time as possible.

It doesn’t require five days in the office for everyone. But it does require enough co-located time that the team develops the shorthand and trust that small, fast teams run on. A Super IC team operating asynchronously across fragmented schedules does not work.

3. Mandate a large customer problem and a grounded hypothesis for impact.

This is where Meta took years to get to the right level of rigor. The team’s operating style isn’t “test 100 things and see what sticks”. It is critical to hone in on a customer problem that, when solved, has a clear line of sight to business impact. Without it, the team will likely build something that is only delightful or interesting. The question isn’t “what could we build?” It’s “if this hypothesis is correct, does it become the next significant line of business for the company?” The bar for greenlighting a project is very high, often higher than for more mature products.

Not every company needs this. Early-stage startups where everyone is already working on growth don’t have the coordination problem Super IC teams are designed to solve. But for mature organizations trying to start a new business line, revamp an existing experience for a new use case, or shift how internal operations work across functions, this is one of the few proven approaches that actually gets past the innovator’s dilemma.

4. Plan for scale, before the need arises

As a project begins to show promise, the team needs to start finding its home in the larger organization before it gets to that level of scale. Incubation teams are not built to scale products. The decision criteria for handoff to another ongoing team that can scale the product need to be aligned in advance. When this is done late, the project stalls. New priorities arrive, the original team moves on, and the impact is lost.

The Added Bonus

The best of Super ICs do more than deliver on their projects. They modeled what great looks like at each step of the process: how to run a brainstorming session or product review, how to sell a business case, how to get buy-in from xfn teams, or how to navigate a tricky political situation. They set the bar for high performance, and are looked up to as leaders in the company through their expertise, and their influence traveled across org lines in ways that managers rarely can. In a time when AI adoption and shifting operating models are the priorities du jour, the people in these roles will leave a lasting impact on the future of the organizations they are in.

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

Yue

I’m so proud! Woohoo!!! <3 I think it’s a great course. ;) https://practice.theuncommonexecutive.com/

• I recently sat down with to discuss the new Super IC path to leadership and whether it’s a YAY or NAY. Watch the recording here.

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• Want to become irreplaceable in the age of AI? Accelerate your path to leadership? Consider working with me 1:1. Schedule a free intro call here.

As you progress in your career, how your peers view your performance takes on increasing weight relative to what your manager (or even sometimes skip level) thinks. Your manager’s view of your performance is critical, but insufficient at senior levels in securing a specific rating. What becomes more important is that your performance is well understood by all the broader organization and teams you don’t regularly collaborate with, especially those who might hold outsized influence in the business.

Calibrations: where “informal feedback” influences the outcome

Formal reviews generally include feedback from your team, your peers, and your managers. However, once you get into the promotion conversations, the people who may comment on your performance are far more wide-reaching.

At bigger companies, the exposure happens during “calibration sessions”, where managers meet to ensure that the reviews are “calibrated” across teams and functions, so the same bar is held by function and seniority. This process tries to avoid the bias that a person doing well on one team could just be average in another, resulting in unfair promotions specific to certain teams. It also ensures that managers don’t miss any feedback from other teams. Calibration sessions open up your performance for discussion and comparison across tens to hundreds of people. At this point, it is no longer just about the people you interact with regularly; it becomes about your brand and reputation.

Many small or early-stage companies don’t have official performance reviews. However, even though your company claims they do not have performance reviews, they still review performance. At smaller companies, reputation is even more critical as there are more casual conversations for senior leader performance, and it can be very “obvious” who holds the influence in a smaller team.

Common surprises during calibrations

People who believe they are ready for promotion and have heard similarly from their manager can be unpleasantly surprised when the official performance review is delivered. The conversation sounds like this:

VP: Hey everyone, I’m Jane’s manager. Jane’s been doing a great job and has been performing at the VP level for more than a year. She successfully launched a multi-team, multi-quarter project and has shown that she can handle more scope. Jane has been delivering a great consistently, and I would like to put her up for promotion to VP.

Peer VP: Jane took an original idea from my PM director, Joe. Joe was working on the project, but she stepped in midway and ran with it. They collaborated on the project, but she ended up in multiple conflicts with Joe. I don’t think she handled the collaboration well or deserves full credit.

SVP 2: My PM director is managing multiple cross-team projects and has consistently delivered double-digit increases in revenue. He has not yet been promoted. Perhaps we should consider him first?

Peer VP 3: When I look at this project and the measured impact, was it calculated correctly and over the right time horizon? Didn’t this other initiative help inflate the numbers?

In this case, Jane’s promotion was blocked due to objections she’d never heard and that may or may not be fully accurate. Sometimes, promotion conversations can take unexpected dives for the worse simply based on the room dynamics at the time. At the core of it, this happens for a few reasons:

• There are unexpected vocal detractors in the room

• The overall team is underperforming

• The manager is viewed as too subjective or not confident enough in their evaluation

• One small comment of hesitation from someone with a large amount of influence in the room

To combat this, it’s important to find advocates and ensure critical decision-makers are on board ahead of formal performance conversations.

How to manage your performance review

Like product reviews or business reviews, performance conversations require influence strategies and pre-meetings.

First, keep an ear to the ground to gather information about how your team and organization are doing. Make sure when you talk about your wins that others are buying into the narrative.

Then, a few months from promotion time, you and your manager should talk to other leaders and teammates in the organization to proactively ask for feedback. This way, you’ll know who will or will not advocate for you, avoiding surprises during promotion time. Knowing whom you must win over early gives you time to invest in building trust and strengthening relationships.

Finally, enlist other advocates for your promotion. Because your manager is your manager, she may be perceived as biased in presenting the case for promotion. You and your manager should try to find another influential advocate who will be in the room. Ask that person to mentor you and help them get to know you over time. Then, during promotion conversations, another person in the room can speak to your capabilities more objectively.

Did you receive your performance review back recently? How did it go? Was it as expected?

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

Yue

Also, I have 2 spots open for executive coaching clients looking to accelerate their careers starting in June (L6+ only). Connect via a free Intro Call to learn more!

“But I had the right answer” is a common retort I hear among high performers. Like them, I believed that if I had the data and did the analysis, then I would surely be able to influence others to “see it my way.” However, at the senior levels, more data doesn’t make the argument stronger. It dilutes clarity.

Our instinct to bring more data comes from our school days. In our early years, we were taught to back up our arguments with research and cite our sources. We showed up to carefully curated forums where we were asked to argue our logic and defend our thesis. At leadership levels, no one is sitting around waiting for you to give your arguments in long speeches. Business decisions need to be made with time as a key constraint. And so, rather than defaulting to getting yet another analysis done, consider these three other approaches instead.

Option 1: Create more trust (through others)

When I can’t get someone to agree with me, my instinct is to get more data to back up my logic. “Here are reasons A, B, and C why my method is better. Don’t you agree?” However, if the other person doesn’t trust me enough to trust the data or my arguments, then I can get 3 more data points or repeat the current arguments until I’m blue, and it will not make a difference.

Here’s what to do instead: Come up with 3-5 other ways of influencing this person without adding more information by default. Try going through another person whom they trust more than you. Let someone else try to make the case. Try a different way of having the conversation, leading with curiosity and questions instead of facts. Try creating a different forum, where they can listen to the debates from a safe place without having to give their two cents (yet).

Option 2: Lead with the conclusion

When preparing for executive reviews, we like to build up the context, talk about the risks and caveats, and then arrive at the conclusion. It sounds like this:

“If we launch on schedule and the next two tests hold and nothing changes with the macro environment and the team executes the roadmap... we should be able to meet our 2026 revenue targets.”

You’ve already lost the person halfway through. They probably won’t agree with your next step, because they didn’t really follow all the details.

Instead, lead with the conclusion, then add the caveats and risks.

“We are on track to meet our 2026 revenue targets. And here are three projects we need to continue to execute well on...”

Same information. Different perceptions of confidence and seniority. Write the conclusion first.

Option 3: Narrow down to ONE point

When we are pitching ourselves for a stretch project or new role, the impulse is to prove you’re qualified by listing everything you’ve accomplished. When someone asks, “Why are you qualified to lead this project (for this role)?” you launch into a 5-minute monologue of your accomplishments. Again, you’ll lose the decision-maker quickly. They don’t want to do the filtering to see what is truly relevant for the task at hand.

Instead, figure out what problem the decision-maker truly wants solved. What is the objective of the project? What is the main challenge or primary goal of the job? The person who lands the project isn’t necessarily the one who has the most accomplishments. They are the ones who walk in and say: here’s the problem you’re trying to solve, here’s the one thing in my background that’s most relevant, and here’s how I’d approach it.

When you’re preparing for an important conversation, stop asking “What do I need to include? Is this enough information?” and start asking “What does this person need to believe, and what’s the single most direct path to that belief?”

Find out what problem they’re trying to solve. Then filter your entire experience through that one lens to increase the relevance and quality of your response.

One of my clients summarized it well after trying the different approaches: “The information was the same and always there,” she told me. “I just kept thinking that if I organized it better, it would land. But really, it was just too much detail. What I was missing was the high-level point that is relevant to each person. The thing that gets their attention.”

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

Yue

Everyone I talk to these days tells me they feel behind.

The Head of AI at a Fortune 50 company is trying to get her 1000-person org to adopt AI tools that are constantly evolving. The Director at a growth-stage startup is caught between the SaaS apocalypse and board mandates to increase shipping velocity. The senior PM at Google is wondering whether the next step is still management.

Those working at the bleeding edge are no different. This week, I coached a researcher at one of the major AI companies. Her team builds tools for next-generation foundational models. She lives and breathes every day AI through demos, research, and working sessions with the brightest minds in tech. And she said this week: “I feel so behind even though I’m always working. There’s always a new eval to build, a new way to work, a new use case. What do I do?”

And the truth is, you are behind. We are behind. If it is a race about book smarts and logical reasoning, humanity is being beaten by AI at rocket speed.

Why This Transition Is Different

There was a time when working at a top-tier tech company meant you were at the frontier of innovation. Google, Meta, and Amazon are the places where ideas and businesses that had never existed are being invented. These companies set the pace. If you worked there, you knew where you stood relative to everyone else. If you stayed sharp enough and worked hard enough, you stayed ahead.

Now, with AI, the race has changed entirely.

Let’s take an analogy. Imagine an elite greyhound racing track. They’re chasing that fake rabbit decoy that runs along the rail just ahead of the pack.

That rabbit is AI. It moves at a speed no horse was built to match.

The frontier of what’s possible with AI is now advancing faster than any individual can consciously integrate. The implications of each new release will take months to fully understand. The secondary effects on roles, on structures, and on geopolitics will take lifetimes to play out. Yet each release is weeks apart. This is why we all feel constantly behind.

Change The Measuring Stick

The shift I keep coming back to with clients is this: stop trying to keep up with the squirrel. Start asking what you can do well, regardless of where the squirrel is.

Here’s what it looks like in practice:

• What are your leadership superpowers in the age of AI? The skills that compound over time in this environment are not related to book smarts. The ones that hold are: providing clarity in ambiguity, building trust with people, quick judgment during uncertainty, and the willingness to make a call when no one else will. (Read more on this here.) Invest in the skills that don’t depreciate when the next model drops. (Check out my accelerator program for this!)

• Set a learning pace that works for you: We’re in a long haul here. It’s a marathon, not a sprint. Create a schedule of learning that works for you on the order of months and years. The leaders I see thriving are the ones who’ve stopped trying to know everything and gotten disciplined about what matters to their specific context.

Change How You Measure Progress

At the end of the day, technology is built to better lives. If it is not bettering lives, then we are not running on the right track. Amidst the frantic need to “stay relevant” and “stay ahead”, it’s helpful to remember why we are here and why we build. And change our own measuring stick of progress. The broader mission of learning and building with AI is to enable humans to live more fulfilling lives. Any other Northstar, be it profitability, power, or simply keeping up with the Joneses, will lead us astray.

When there is a quiet moment, ask yourself: What do I hope AI will enable me to do to better those around me? My community? How do I want to use this technology to contribute to the well-being of the world?

And then, take action from there. When you broaden the lens of what matters, there’s suddenly room to breathe.

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

Yue

Discover your durable leadership superpower and how to get noticed by joining the June cohort of my AI Amplified Leadership Accelerator. Stop feeling behind and start running your own race. Learn more.

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

• I am giving a free talk on Managing Up Effectively on May 6. Sign up here to attend live or get the recording emailed to you.

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• I work with Director+ leaders 1:1 to help them reinvent themselves in the AI era. If you’re interested, set up a free intro call!

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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• The April cohort of Yue’s AI Amplified Leadership Accelerator is wait-list only now. I’m super excited for a new format with more live interactions, live coaching, and a focus on soft skills that are critical in the age of AI. Now enrolling for the next cohort in June!

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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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Now Enrolling for the April cohort of my leadership accelerator program for mid-career professionals who want to double down on the soft skills that get them ahead in the age of AI. Proven curriculum and well loved by past students. We have 2 spots left! Learn more here.

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.

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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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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!