# Leading a team, from your first reports to your next reorg — Full Chat Transcript The Executive Coaching work group coaches managers in group chats, from leading a first team to running the business week to week. It also helps with the harder parts of the job, such as strategic thinking, a difficult coworker or a reorg that shrinks your scope. Updated: 2026-10-13 HTML page: [Leading a team, from your first reports to your next reorg]() Summary: [Summary]() Work group: [Executive Coaching]() ## Participants - [Julie Zhuo]() — Co-founder of Sundial. Author of The Making of a Manager and former VP of Product Design at Facebook - [Cat Lee]() — Founder and executive coach at Real & Kind. Former Head of Growth at Pinterest - [Nikhyl Singhal]() — Founder of the Skip community. Former VP of Product at Meta and CPO at Credit Karma - [Yue Zhao]() — Executive coach and author of The Uncommon Executive. Former Chief Product & Technology Officer at Fuzzy - [Christina Wodtke]() — Lecturer at Stanford University and author of Radical Focus. Former General Manager at Zynga - [Elena Luneva]() — Chief Product & Technology Officer at Madison Reed. Former Chief Product Officer at Braintrust - [Diana Stepner]() — Product leadership coach. Former VP of Product at SimplePractice and Head of Product, Education at the Chan Zuckerberg Initiative ## Full Chat Transcript #### [Where a first-time manager should put their attention]() **Question:** What should a first-time manager focus on to lead a team well? ##### [Cat Lee]() Start by deciding which "you" shows up in each conversation. The hardest part of the first manager role is relational. Yesterday you were a peer, and today you might be a peer in one meeting, a coach in a 1:1, and the person making the call in a planning review. When new managers don't name that stance, their team can't tell whether "what do you think?" is an invitation or a decision already made. I coach leaders to pick the stance on purpose before each interaction. Second, make yourself easy to work with. Write a short manager "user manual" that covers how you like to communicate, how you give feedback, and what you need from people. It removes a lot of guessing from day one, and you update it as your style changes. For each new report, define what success looks like over the first 90 days and use that same window to check how well you're managing them. Third, run the team on learning instead of status. Move updates to async reading and spend meeting time on what you learned from recent work. Start with low-stakes topics so people get used to speaking openly. Less experienced teams need more structure, with clear next steps toward the level you expect. Expect coaching to be part of the job, since you won't find a plug-and-play hire. Finally, pay attention to your own discomfort. Moving from doing the work to leading people feels awkward, sometimes physically. Name what makes you hesitate and practice in small, real moments, like owning a meeting agenda, so you aren't relying on theory alone. Leadership looks different on everyone, so the goal is to find your own version instead of copying someone else's. ✨ ##### [Julie Zhuo]() Start by changing what you measure yourself on. As a new manager, your job is to get better outcomes from a group of people working together. Your own output stops being the scorecard. In my book I break that into three levers: purpose (does the team know what success looks like and why it matters), people (are the right people in the right roles, growing), and process (how the team works together day to day). Three practical things I wish I'd done sooner: 1) Be honest about being new. When I became a manager at 25, my peers were suddenly my reports, and I acted like I thought a manager should: confident, authoritative, with all the answers. People could tell it was an act. I wish I'd sat down with each person and said, "I'm new to this, and I'm going to need your help." [Citation: https://www.youtube.com/watch?v=XFxsTGSnhbQ] "I don't know, but let's figure it out together" builds more trust than bluffing. [Citation: https://www.linkedin.com/feed/update/urn:li:activity:7107800229151719424/] 2) Give work to people's strengths. You won't be the best designer, presenter, or organizer on the team (I was none of these). Let the best visual designer set the type guidelines and have the best presenter show off the team's work. [Citation: https://www.linkedin.com/feed/update/urn:li:activity:7107800229151719424/] 3) Model the behavior you want. If you want the team focused on top priorities, don't schedule a wall of recurring meetings. If you want excellence, be the first to call out sloppy work. If you want growth, be the first to share what you learned. [Citation: https://lg.substack.com/p/the-looking-glass-the-loudest-way] Cat's 90-day success definition for each report works upward too. Your first three months are when naive questions are welcome, so ask your own manager what success looks like for you at three and six months. [Citation: https://medium.com/p/9f2713bdd68c] One check before any of this: imagine a full day of back-to-back 1:1s. If that sounds awful, management will be an uphill slog, because most of the job is people. [Citation: https://medium.com/p/f2c42d68604b] ##### [Yue Zhao]() Most first-time managers set up one routine for everyone: a weekly team meeting, a few stand-ups, and weekly 1:1s for every report, because it feels fair and simple. That setup breaks fast. The weekly meeting gets too in the weeds for your senior people, and a standing 1:1 is too high level for someone stuck on a messy 0-to-1 project. Cat's point that less experienced teams need more structure goes further than that. Match how you manage to the person and the kind of work. [Citation: https://news.theuncommonexecutive.com/p/why-one-size-fits-all-team-routines] ✅ Run well-defined, repeatable tasks (shipping features, triaging tickets) through group check-ins once or twice a week. Early-career folks get quick redirects that way, and they learn from each other. ✅ For strategy or cross-org work that runs over weeks or months, use 1:1s and leadership reviews. Your job there is to guide, coach, and unblock. Dictating tasks to that work slows it down. ✅ Get out of execution yourself. Being in the weeds feels like helping, but your real job is to find the biggest opportunities for your team's impact and protect time for that thinking. Strategic time is required from day one. You don't earn it after the operational work is done. [Citation: https://news.theuncommonexecutive.com/p/time-for-strategic-work-is-not-optional/comments] ✅ Give your team agency. At Meta and Fuzzy I learned that when I asked teams to follow the rules without question, I got incremental wins and more of the status quo. So in 1:1s I started asking, "Is this a good case for an exception?" I also told the team how I had pushed for exceptions and won them. On Cat's discomfort point, letting go was the hardest part for me. I didn't really learn to delegate until I had a kid and physically couldn't do everything myself. [Citation: https://podcasts.apple.com/us/podcast/breaking-through-to-the-c-suite/id1339384886?i=1000648012722] Bottom line? You'll feel less productive for a while because you're no longer the one doing the work. Plan for that dip in month one. ##### [Cat Lee]() Julie's "I'm new to this, and I'm going to need your help" only works if you set up a way for that help to reach you. Before frustrations pile up, agree with each person on how and when you'll trade feedback in real time. In my coaching work, the relationships that sour fastest are the ones where small irritations go unspoken for months and then come out all at once. Opening with your own development work, including what you're struggling with, makes it easier for the other person to do the same. Second, track energy along with output. I use a simple "battery level" check with leaders: which tasks drain you, which give you energy, and the same questions for each person on your team. New managers often hold onto the IC work that energizes them and push the draining work to the end of the day, and the team picks up on that. Seeing it written down tells you what to delegate, what to protect, and who is running low before it turns into burnout. Julie's back-to-back 1:1s test is a good gut check, and the battery check tells you which parts of the job to build support around. 🙏 ##### [Christina Wodtke]() Your first job is to accept that you have a new job. Most new managers think management means telling people what to do. They're afraid that if they stop, nothing will happen. So they micromanage. Managing is a different job from individual contribution. You're a coach, a facilitator, and the person holding the vision, and all of that starts with trusting your people. [Citation: https://youtube.com/watch?v=_lJ0eMEZAbo] In practice, when someone brings you a problem, resist solving it. Solving it makes you the bottleneck. I walk them through questions instead: 1. What's the reality? What do you know, and what have the tests shown? 2. What options do you see? 3. What are the pros and cons of each? 4. So what are you going to try next? Let me know how it turns out. Over time they get better and more resilient at working through problems without you. [Citation: https://open.spotify.com/episode/39icRpzICl9e3XzwDZTroP] Second, set team norms together. Then check them every week with a five-minute retro: "How did our experiment go, and what's next week's experiment?" Because the retro is so lightweight, small tensions like "can we start on time?" get raised before they turn into conflicts. Review the whole list each quarter. [Citation: https://www.mindtheproduct.com/christina-wodtke-working-with-mindfulness-and-compassion/] Third, write real role descriptions and keep using them after the hire. A job description grabbed off the internet leads to bad interviews and fuzzy expectations later. If you only do one thing, have your team write its own norms. Once people get used to having some control, they start acting differently. And hold a Friday celebration where everyone brags about what they shipped that week, with beer or cake. Sometimes just treating people like humans is the first step toward a high-performing team. [Citation: https://youtube.com/watch?v=nZmE6E6aOEU] ##### [Julie Zhuo]() Yue's productivity dip is real, and it gets worse if the new manager quietly sets up the team as hub and spoke, with every decision and every critique routed through them. That was one of my early lessons. A team works when the designer on the ground can get critique and partnership from another designer directly, without me in the middle. So part of the job is to deliberately build the relationships between your reports, and then ask each person how those cross relationships are going, since you won't see most of them yourself. [Citation: https://www.youtube.com/watch?v=xQIa1sjYBD8] Molly Graham, who was also a leader at Facebook, calls this "giving away your Legos." The work you were great at as an IC is exactly what's hardest to hand off, and handing it off is what frees you for the purpose work Yue describes. [Citation: https://www.youtube.com/watch?v=xQIa1sjYBD8] Delegation only works if the "why" is clear. I push teams to define absolutely unambiguous outcomes: after the work ships, everyone would agree on whether it succeeded. "Users will have a clearer mental model" fails that test (I have said those exact words about many a redesign). "People will use the product more frequently" passes. [Citation: https://www.linkedin.com/feed/update/urn:li:activity:7102380130102099968/] A first-time manager who gets this right can hand off the "how" with confidence, because the team and the manager will judge the result the same way. ##### [Yue Zhao]() Most new managers copy the one manager they remember. On a podcast, Andrew described how it usually goes: either you loved a hands-off boss and promise to be just like them, or a micromanager burned you and you swing to the opposite extreme. The catch is that you only ever saw one side of that manager, with one version of yourself at one point in time. I was lucky to have amazing managers at Meta. Still, when I ask people who worked for those same managers, they describe a very different leader, and that surprises me every time. [Citation: https://podcasts.apple.com/us/podcast/this-chief-product-officer-was-stuck-until-she-learned/id1676766133?i=1000701698152] So don't pick a style ahead of time. Christina's question sequence gives you a middle ground between hands-off and micromanaging. Sue Bethanis adds a useful point: the questions you choose to ask also show what you think is important. Ask coaching questions about a priority and the person learns it matters. You get accountability and urgency without hovering. [Citation: https://www.linkedin.com/feed/update/urn:li:activity:7321544788367822848/] Watch your altitude too. One of my clients, a VP running hundreds of people, hit every team goal and still got passed over for promotion twice in two years. He put his team's needs ahead of the company's. He also took other functions' needs into account without ever building them into his plans. First-time managers develop this habit early because protecting your team feels like good leadership. Start asking what the company needs from your team, then work back to what your team needs. ##### [Cat Lee]() Christina's four questions are the right default, and I'd pair them with one habit: say which mode you're in before you start. Sometimes a new manager does need to be directive, for example with a launch deadline tomorrow or a call only you can make. Problems come when you ask coaching questions while you already have an answer in mind, because people feel tested instead of trusted. Saying "I'm going to coach you through this one" or "This one's my call, here's why" keeps the questions honest. Adjust how much you hand back based on experience. A senior person can take "What are you going to try next?" and run with it. Someone earlier in their career often needs smaller steps first, like "Bring me two options with pros and cons by Thursday," and then more room once they've done that a few times. Leaving all of the problem-solving to someone who doesn't have the steps yet feels like being abandoned, even if you meant it as trust. ##### [Julie Zhuo]() Yue's altitude problem has a cheap fix: ask your own manager how they see success. In your next 1:1, try "What makes you feel you're doing a great job in your role?" and then "What would make you feel I'm doing a great job?" The number of people who have asked me the first question in my whole career, I can count on one hand. The answers tell you what the company needs from your team before you plan anything, and they give you a shared goal to build trust on before any evaluation starts. [Citation: https://www.linkedin.com/feed/update/urn:li:activity:7229232236464652288/] The same move works downward when you give your first piece of hard feedback, which is the conversation new managers dread most. Lead with your intent so the person hears why you're saying it: "I think you're great at these parts of the job. I want to help you be even more impactful, and here's something I see that may be holding you back." People take feedback very differently once they believe you're on their side. [Citation: https://podcasts.apple.com/cn/podcast/leading-small-teams/id1339952977?i=1000437081704] ##### [Yue Zhao]() One gap so far is making your team's work visible above you. Doing great work inside the team doesn't count for much if leadership never sees it, and as a new manager you're now the main channel for that. Bragging always felt awkward to me, so I share wins as learnings. I run lunch-and-learns and talk at team meetings about what we learned from our successes and failures. Examples include cross-functional collaboration best practices and how we launched a new product. Credit the person who did the work by name. That way your team's work travels across the org, and nobody has to toot their own horn. Also write the year-end review in January. I once sat down to write my self-review and realized I'd over-delivered on execution and under-delivered on strategy and cross-team impact, and by then it was too late to fix. Draft your team's version now: what you want leadership to say about the team in 12 months, and which leaders need to see the work. Then check it against Julie's unambiguous outcomes every quarter. When review season comes, you're advocating for your reports with evidence you planned for, which beats scrambling for it in December. ##### [Cat Lee]() For that first hard feedback conversation, Julie's script helps most when you're calm enough to use it. New managers usually walk in rehearsed, and then the person pushes back and they rush to get through it. Your body tends to notice first: shallow breathing, a tight jaw, the urge to keep talking. I coach leaders to take that urge to push through as a reason to slow down. Saying "Let me think about that and come back to you tomorrow" is a perfectly good leadership move, and it beats a rushed answer you'll have to walk back. A few minutes of reflection or journaling before the day starts makes that easier. If you go straight from waking up to Slack, you spend the whole day reacting. Ten minutes deciding what matters today, including which conversation you need to show up well for, gives you a plan before everyone else's requests arrive. ##### [Julie Zhuo]() One more lens for spotting who on your team is ready for more room, which connects to Cat's point about how much to hand back. I think of it as a ladder of ownership, using a meeting that isn't working as the example: 1) Judging ("this meeting is a waste") 2) Gossiping 3) Giving feedback 4) Giving deep feedback 5) Collaborating 6) Driving 7) Owning: volunteering to help plan and run the meeting, gathering suggestions, and iterating until it's consistently a good use of everyone's time [Citation: https://twitter.com/joulee/status/1438212192164200450] A first-time manager can use the ladder two ways. When a report complains, ask what it would take to move them one rung up, from judging to giving specific feedback, or from collaborating to driving. When someone is already at levels 6 or 7, they're the person to give real ownership to, and that frees your time for the strategic work Yue says can't wait. People at the top of the ladder are the ones the team already treats as leaders, and they're often your future managers. [Citation: https://twitter.com/joulee/status/1438212198724091904] ##### [Cat Lee]() Practice the hard conversations before you have them for real. In my coaching sessions with new leaders, we roleplay the first underperformance talk, the "I'm now your manager" conversation with a former peer, or pushing back on their own boss. Saying the words out loud once, at low stakes, shows you exactly where you freeze or start over-explaining, and you can fix that before it counts. A peer manager or a mentor can play the other side. Name what's making you hesitate, too. Often the hesitation comes from imposter syndrome: you got promoted for being good at the work, and now you're being judged on something you've never done. Many new leaders find it helps to treat what makes them different as a strength they lead from. Trying to sound like the manager they think they should be usually doesn't work, which is the act Julie described at 25. 💕 ##### [Christina Wodtke]() Julie's unambiguous-outcome test gets harder as the list grows. New managers usually hand their team five priorities because every one of them feels important. My rule for OKRs is one objective per quarter for the team. Never set them per person, and use at most two levels: the business OKR and the team OKR. If you settle on two, at least you aren't at five or twelve. Every objective you add takes away some of people's ability to focus on the strategic work. [Citation: https://youtube.com/watch?v=Pym0gNjWAX4] A goal still isn't a strategy, so a new manager can't install OKRs and call the job done. First sit down with your own leadership and work out what you're actually doing and how you'll get there. Julie's "what would make you feel I'm doing a great job?" is a good way to open that conversation. Then write the OKR. That conversation is also the fix for the trap Yue's VP client fell into. Your team's objective starts from what the company needs from your team, so you can't hit every team goal while the business gets nothing it wanted. [Citation: https://youtube.com/watch?v=Pym0gNjWAX4] Picking one objective also helps with the delegation Julie and Yue describe. When a report brings you a decision, you can ask "does this move our one objective?" and let them answer it. Otherwise they have to guess which of your five priorities you secretly care about most. ##### [Elena Luneva]() Julie's point about not seeing most of the cross relationships yourself is why I'd give a first-time manager a fixed 1:1 agenda. Without one, 1:1s slide into status updates that could have been a Slack message. I inherited a fast-scaling team at Nextdoor that was stuck in decision fatigue. The structure that fixed it came from the C-suite there: People, Process, Product, plus "On My Mind." [Citation: https://elenasletters.substack.com/p/the-execs-guide-to-high-impact-11s] 1. People goes first. I ask who they want to thank, who is getting in their way, and how they are doing. Your reports need engineering, design, and marketing to ship, so these two questions show you the relationships you can't see. You find blockers early and learn whose work deserves a thank-you, and a thank-you from someone outside their reporting line lands hard. 2. Process comes second. I ask what feels broken and whether our metrics are leading indicators or vanity metrics. At Nextdoor, small fixes that came up this way, like cutting redundant syncs and clarifying ownership, added up over time. 3. Product comes last, because by then you're usually aligned on the backlog. Use that time on the biggest bets and the unknowns. There's one more skill new managers rarely get told about, and I call it being the editor. Now that AI lets a team ship almost anything, someone has to decide what's worth shipping. If the manager's judgment is soft, everything ships and nothing fits together, and the product turns into one long "more" menu. Christina's single objective gives you the filter: when a project doesn't move that one objective, or can't pass Julie's unambiguous-outcome test, cut it before it ships. [Citation: https://elenasletters.substack.com/p/super-leader] The leaders I'd follow to another company share one trait. People grow faster under them, because they put each person where that person can move the business and they clear everything else out of the way. [Citation: https://elenasletters.substack.com/p/super-leader] ##### [Cat Lee]() Christina's single objective also tells you what to do with the weekly team meeting. Once status updates move to async reading, the meeting has one job: going over what the team learned that week about moving that objective, including what to try differently. Starting with low-stakes topics helps a newer team get comfortable raising problems in the room. That way the meeting stays on the objective, and the team gets better at it each quarter. ##### [Julie Zhuo]() Cat's imposter point matches my most awkward early 1:1. My report had been a peer the day before, someone I looked up to, with more years in design and frankly more talent as a designer than me. I could tell he was thinking "I don't know what you can offer me," and I was thinking the same thing. I wasn't going to be the best at critiquing his work or teaching him craft, so I overcompensated by trying to look like I knew what I was doing. [Citation: https://podcasts.apple.com/us/podcast/the-challenges-and-triumphs-of-a-young-manager/id152022135?i=1000447333496] It took me far too long to see that your value as a manager rarely comes from being the best expert in the room, because the best subject matter experts aren't always the best managers. With a report more skilled than you, your contribution is context, priorities, unblocking, and finding them the problems that stretch them. Ask them directly which of those would help most. #### [A weekly business review that ends in decisions]() **Question:** How do you run a weekly business review that leaders use? ##### [Julie Zhuo]() I would give the WBR two distinct jobs: help leaders see the same picture, then make the few decisions that picture calls for. 1) Start with a 5–15 minute metrics review at the beginning of an existing leadership meeting. Have a data partner walk through time-series charts for the few shared goals, plus segments that matter right now, such as a test market or a customer group affected by a launch. Keep prep under 30 minutes. The first outcome is that leaders can say how they're tracking against goals, which levers seem to matter, and what counts as a normal fluctuation. Stanley Watt and I describe this as a practice that can run at the executive level as well as within product teams. [Citation: https://medium.com/p/dcc9cce7ac3c] 2) Give the actual decision its own agenda slot. When someone asks for another cut of the data, ask what they would do under the optimistic and pessimistic answers. If the action stays the same, skip the analysis. For example, 'Which of our top ten countries is struggling this quarter?' gives a leader a more useful next step than a ranking of every country. [Citation: https://medium.com/p/dcc9cce7ac3c] You can begin with ten minutes every other week and have the team try it for a quarter. Adjust the metrics and segments after the first few sessions. [Citation: https://medium.com/p/dcc9cce7ac3c] ##### [Christina Wodtke]() Make the weekly review answer one question: what are we doing this week to get closer to our strategic goal? Start with the quarter's objective and its key results, meaning the outcomes you expect to change. Then have each owner share their confidence in reaching those results, what they tried last week, what happened, and their top priorities for this week. I used that short update format at Zynga. The useful part was seeing where a planned action stalled, so someone could help with a missing dependency or a hard conversation. [Citation: https://podcasts.apple.com/us/podcast/the-ultimate-guide-to-okrs-christina-wodtke-stanford/id1627920305?i=1000604480474] Keep the live meeting for the changes leaders can make: pick a priority, resolve a dependency, or ask an owner to try something else. If a result has no new information, say "no change" and move on; a Monday check-in can take 20 to 30 minutes when it stays focused. Keep a month-long lookahead for work that takes longer than a week. [Citation: https://open.spotify.com/episode/74XcggD0f7X7sKVEngUALe] ##### [Cat Lee]() A metric can flag the problem without explaining it. I’d pair the chart with one piece of customer evidence before the team decides what to change. At Pinterest, our international activation rate looked okay, yet watching people use the product in local markets showed that the content felt too American for them. That changed which problem we worked on. [Citation: https://podcasts.apple.com/us/podcast/inside-facebook-pinterests-growth-machines-with-cat/id1329767564?i=1000433885171] Julie’s shared chart gives the team a starting point. When a trend surprises us, I’d ask the owner to bring a customer call, observed session, or support pattern that tests their explanation. Record the decision, its owner, and what evidence they’ll bring next week. If the same metric stays flat while the team keeps proposing small fixes, spend time with customers before approving another fix. ##### [Julie Zhuo]() Christina's confidence check gets stronger when leaders can see *why* confidence changed. Put the goal trend next to each owner's update, then ask whether a dip is normal for that business or signals a change in the plan. Enterprise software may dip on weekends while games may rise, so a single week's number needs context. In our piece, Stanley Watt and I argue that repeated exposure to the same time-series helps teams learn their normal range and spot suspect measurements, such as a reported 20% lift in a metric that rarely moves. [Citation: https://medium.com/p/dcc9cce7ac3c] ##### [Christina Wodtke]() Give Friday a different job. Monday commits the team to a few actions; Friday asks what actually happened and recognizes the work that moved the goal. In my Radical Focus cadence, that short celebration helps teams see progress across functions, while a quarterly retrospective asks what they learned and whether the objective or key results need to change. [Citation: https://podcasts.apple.com/us/podcast/the-ultimate-guide-to-okrs-christina-wodtke-stanford/id1627920305?i=1000604480474] [Citation: https://open.spotify.com/episode/2nOVN9A1KFdVomlO7hRov1] Cat's customer evidence belongs in that learning cycle. If the team tried a fix and the outcome stayed flat, the next review should examine the explanation before assigning another fix. ##### Question > Nikhyl Singhal, Julie Zhuo starts with shared charts, and Christina Wodtke starts with owners' progress toward quarterly results. How would you structure a 30-minute weekly review so leaders can make decisions and track them the next week? Please cite public sources. ##### [Nikhyl Singhal]() I’d split the 30 minutes into 5 minutes on the shared business measures, 15 minutes on the two biggest exceptions, and 10 minutes on decisions and last week’s commitments. The owner of each exception brings the trend, their explanation, and a proposed action. The leader running the review makes the call, names one owner and a due date, then opens the next meeting by checking the outcome. Julie’s chart and Christina’s owner update fit together in that sequence. Make sure the measures expose the company’s actual risk. At Cast Iron, paying-customer count looked encouraging while each customer needed different features and engineers were drowning in requests. I would have used the review to ask whether the next customer could use the same product, then assigned someone to test that assumption before expanding the roadmap. [Citation: https://review.firstround.com/how-to-craft-your-product-team-at-every-stage-from-pre-product-market-fit-to-hypergrowth/] At Credit Karma, we also held monthly executive product reviews as the product organization grew; a weekly meeting should escalate the immediate cross-team decisions and leave longer-range product context to that deeper review. [Citation: https://review.firstround.com/how-to-craft-your-product-team-at-every-stage-from-pre-product-market-fit-to-hypergrowth/] ##### Question > Elena Luneva, Nikhyl Singhal gives 15 minutes to the two biggest exceptions each week. How would you choose those two when teams bring more issues than the meeting can handle? Please cite public sources. ##### [Elena Luneva]() I’d choose the two exceptions where a decision this week could change a business outcome. Ask each owner to submit four lines before the meeting: which of the agreed 2–3 outcomes is at risk, what changed in the measure or customer evidence, what happens if we wait a week, and which decision they need from this group. Rank first by the size and timing of the risk, then by whether the room has the authority to resolve it. Send issues an owner can settle alone back to that owner. The financial link matters. While pitching Nextdoor Maps, I brought research and engagement data, then the CFO asked about payback and return on investment. I learned to connect projected usage to revenue and delivery costs, and to model downside cases such as weaker adoption or higher data costs. Those figures in my published example are illustrative, rather than reported results. In a WBR, a cost increase that changes the investment decision deserves a slot ahead of a usage change that leaves the plan intact. [Citation: https://elenasletters.substack.com/p/building-p-and-l-models-that-win-699] I’d put the other issues in a written queue with an owner and a date to revisit. My product business review cadence looks at strategic outcomes and systemic cross-team issues monthly or every six weeks, which is a better home for trends that need deeper discussion. [Citation: https://elenasletters.substack.com/p/product-strategy-part-2-operating] #### [Being strategic at work, one ordinary decision at a time]() **Question:** What does being strategic at work look like day to day? ##### [Julie Zhuo]() Being strategic shows up in the decisions you make on an ordinary Tuesday. 1) Ask your teammates what success would look like in three years. If their answers differ, work out which outcomes matter most and what you would choose when two goals conflict. 2) Before proposing a feature, get specific about whose problem it solves. Talk to those people, look at what other options they have, and ask where your team has a real advantage. 3) Choose the one to three things that matter most, then cut work that pulls time away from them. When a launch discussion turns into whether to ship a mediocre feature or spend extra time polishing it, I ask whether we chose too many things weeks earlier. If the feature matters, give it the time to be great. If it doesn't, remove it from the plan. [Citation: https://medium.com/p/f6630a44f86b] ##### [Elena Luneva]() I look for three things in a decision: the customer's problem, how the business makes money, and where the tools and market are headed. Day to day, that means asking what outcome a request should change, checking the evidence with customers and sales, and deciding what we will stop doing to make room for the work. Before a launch, I want to know who will buy, how they will find it, and what we will measure after release. Shipping is one step; adoption and revenue tell us whether the decision worked. [Citation: https://elenasletters.substack.com/p/be-more-strategic] At Braintrust, we tested AI recruiter avatars and found they were unlikely to meet our needs within six months. We chose a simpler voice interface that tested better with prospects, then worked through whether to charge per hire, per call, or for outcomes. That is the daily work: test the assumption that could break the plan, make the trade-off, and explain the business reason in terms your team and executives can act on. [Citation: https://elenasletters.substack.com/p/be-more-strategic] ##### [Diana Stepner]() I look for the decision behind the task. When a roadmap item comes up, I ask “why?” three times until I can name the customer need and the business outcome it serves. Then I ask what we will delay to make room for it. That turns a busy day into a series of choices people can explain. [Citation: https://dianastepner.substack.com/p/strategize-for-success-elevate-your] The harder daily work is often between people. A senior PM I coached was told to “be more strategic” at a Series B startup. She found three competing executive visions and brought those leaders into a conversation to clarify direction. The feedback changed once the team had a shared basis for decisions. In practice, I would check whose goals differ before asking the team to execute faster. [Citation: https://dianastepner.substack.com/p/strategic-myths-every-product-manager] ##### Question > Julie suggests choosing one to three priorities and cutting work that competes with them. Nikhyl, how would you make that call during a normal workweek when stakeholders disagree? ##### [Nikhyl Singhal]() When stakeholders disagree, I would bring a proposed order of work to the meeting, with the reason for each choice and the work that slips if we add something. Then I’d ask them to challenge that order. The useful outcome is a decision about where the team spends its time, rather than a round of edits to the roadmap document. I’ve used that approach in high-stakes stakeholder conversations: diagnose the situation, propose next steps, and calibrate priorities together. During the week, I’d check whether the chosen sequence still holds as requests arrive. A director’s job includes turning a clear one-year goal into a next-quarter plan: which feature now, which people on it, and what comes after. If a new request threatens the quality or timing of the top priority, I would put the trade-off back in front of the stakeholders rather than quietly expand scope. [Citation: https://open.spotify.com/episode/0FXzy6RXgB139CSL3nyErc?si=0D_KkKHlTpmGYf4kQ4Mt-g] ##### Question > Nikhyl would bring stakeholders a proposed order of work and name what slips. Diana described three competing executive visions. Yue, how would you get those leaders to agree on a priority this week? ##### [Yue Zhao]() I would start by asking each leader which decision they need the priority to settle this week and which company outcome they expect it to change. Then I would write the three competing priorities side by side, including the evidence behind each, the resources each requires, and what we would delay. The leaders need to discuss that choice together in a decision meeting, with someone clearly accountable for the final call. I would leave with one agreed direction and send the team the choice, its reasoning, and the work that moves. Strategy becomes useful when the people executing it share the same assumptions and know what to do when the next request arrives. [Citation: https://news.theuncommonexecutive.com/p/landing-execution-and-strategy-without] I learned the calendar part the hard way at Thumbtack. I cleared emails and kept the backlog in shape before opening a strategy document, which often waited until Friday at 4 pm. For a disagreement like this, I would protect time for stakeholder conversations and the decision meeting now, before another week of execution takes the slot. [Citation: https://news.yuezhao.coach/p/time-for-strategic-work-is-not-optional] #### [Handling a difficult coworker when no one else will]() **Question:** How do you deal with a difficult coworker when nobody else steps in? ##### [Yue Zhao]() At Instagram, I sometimes worked with product or engineering leaders who got defensive when I offered another option in a meeting, and even protective when I spoke with their teams. Some had strong backing from senior leadership, so waiting for someone else to intervene would have left the work stuck. [Citation: https://news.theuncommonexecutive.com/p/how-to-handle-overly-confident-and] I would prepare one sentence before the next meeting: “That’s one option. For the short term, could we also consider [specific alternative]?” Take a breath before saying it, then keep bringing the alternative back when it matters. The point is to get the decision discussed without turning the meeting into a contest over who is right. I have written about practicing that sentence aloud after a combative exchange, because finding the words in the room is much harder. [Citation: https://news.theuncommonexecutive.com/p/how-to-handle-overly-confident-and] If the pattern keeps blocking work, speak to your manager privately with a specific incident, the impact on the shared goal, and the decision you need help making. Ask what they see in the cross-team dynamic first. A client of mine got a very different response to the same concern after she asked her manager what the manager was hearing and worried about, then raised her recommendation. [Citation: https://news.theuncommonexecutive.com/p/how-to-be-direct-and-strategic] ##### [Christina Wodtke]() Name the behavior while it is still small. If a coworker interrupts you, try: "I lost my train of thought when you spoke over me in the meeting. Can I finish my point before you respond next time?" Then talk privately about what happened and ask what would help both of you work together. I’ve used this kind of interruption example to explain why feedback should describe the behavior and its effect, rather than guess at someone’s intent. Waiting for a manager to notice can let resentment build until the conversation gets much harder. [Citation: https://open.spotify.com/episode/39icRpzICl9e3XzwDZTroP] ##### [Cat Lee]() When the same conflict keeps recurring, I’d ask who actually owns the decision and when the team needs to make it. At Pinterest, interviews across teams showed that our collaborative culture could slow decisions. I learned to look at how people communicate and make decisions as observable team behavior, rather than treating every stalled project as a personality problem. [Citation: https://podcasts.apple.com/us/podcast/inside-facebook-pinterests-growth-machines-with-cat/id1329767564?i=1000433885171] With the coworker, I’d say: “We reopened the launch decision twice after the meeting, so the plan slipped. Can we agree who makes the call, what input they need, and when the decision is final?” If that agreement doesn’t hold, send your manager the dates, the work affected, and the decision you need them to own. A team can address a broken decision process even when nobody volunteers to referee the relationship. ##### [Nikhyl Singhal]() I would first get specific about the behavior: which decision, meeting, or handoff is breaking down, and what did it cost the team? Then I’d speak to the coworker privately: “In Tuesday’s review, we agreed on X, and the decision changed on Thursday without the people doing the work in the room. Can we agree on who needs to be involved before a decision changes?” Ask for their version before proposing a process. In a public coaching call, I worked with a product manager whose peers saw him as hard to work with, even though he thought he was bringing good ideas forward. The useful question was how his approach worked across peers, up to leaders, and down to the team. Intent alone did not resolve the working relationship. [Citation: https://theskip.substack.com/p/shedding-perceptions-moving-from-039] If the direct conversation fails, bring the manager a short record of specific incidents, their impact, and the decision you need from them. “Who owns this decision, and what should I do when it changes after we agree?” gives the manager something concrete to settle. If the conduct involves threats, harassment, or retaliation, use the formal reporting channel promptly. ##### [Julie Zhuo]() A repeated clash may be a mismatch in how each person expects to work. Once, a team survey showed that most of my reports felt I did not care about them, even though I thought I was showing care through feedback, challenging projects, and help with their work. A friend asked whether I had ever asked my reports what care looked like to them. I had not. That experience led me to write a guide about how I communicate, what earns my trust, and the things I do that may annoy people. [Citation: https://lg.substack.com/p/the-looking-glass-a-user-guide-to] With a coworker, I would use a short version of that exchange: "I think we have different expectations about how decisions get made. I prefer to hear about a change before work starts. What works for you?" Share one habit of your own that could be making the relationship harder, and agree on a specific way to handle the next decision. If you have critical feedback about the person, give it directly; my guide says I would ask a teammate to do that before bringing the complaint to me. [Citation: https://lg.substack.com/p/the-looking-glass-a-user-guide-to] This approach is for working differences. Harassment or threats warrant a formal reporting route. ##### [Christina Wodtke]() Cat’s point about bringing a manager dates and work impact matters. I’d add one more thing: ask the manager to give the coworker the feedback directly and let them respond. At Zynga, people told me a colleague needed to be fired, yet nobody had told her which behaviors were causing trouble. I gathered specific feedback, sat down with her, and she changed those behaviors. The silence had left her thinking people hated her. That’s a reason to give someone a fair chance to change before deciding the relationship is hopeless. [Citation: https://podcasts.apple.com/us/podcast/christina-wodtke-radical-thoughts-on-living-and/id1552607805?i=1000640891072] #### [Your first quarter after a reorg cuts your scope]() **Question:** What should you do when a reorg shrinks your scope? ##### [Nikhyl Singhal]() Start by working out which situation you're in. A smaller scope can mean the company needs focus and wants you executing inside tighter boundaries. It can also be the first step of being managed out. The right moves for those two cases are very different, so don't react until you know which one it is. For the first 30 days, my default is unglamorous: put your head down and deliver. I hear this question a lot on The Skip, and most people's instinct is to go to their manager and say "I'm worried, am I on the hot seat?" That's about the worst move available. Your manager often can't answer honestly in the middle of a reorg. If they reassure you and things change six weeks later, you've both ended up in an awkward spot. Every hour you spend reading organizational tea leaves is an hour you aren't spending on the work that decides your outcome. [Citation: https://www.youtube.com/watch?v=yOGuV-uKB5E] Don't campaign to get your old scope back either. When the org is signaling focus, pushing for more territory reads as being out of touch. Show strong impact inside the new boundaries first and let that make the case for you. If you get time with your boss's manager, present your area the way its owner would: what's moving, what's stuck, and what you'd prioritize. Executives hear the subtext. [Citation: https://theskip.substack.com/p/how-to-navigate-org-drama] After a quarter, decide whether to hold or fold, and judge it by your growth rate. Title is a weak signal here. Stay if the smaller role still keeps you current, for example building with AI or close to the core business. Leave if it lets you fall behind, because the way we build product now changes every six months. Staying a few more months only because a short tenure looks bad on LinkedIn is the worst reason to stay. [Citation: https://theskip.substack.com/p/how-to-navigate-org-drama] ##### [Julie Zhuo]() I agree with Nikhyl on skipping the "am I on the hot seat?" conversation. There's a different question worth asking your manager, though, and it points outward at their problems. Start by naming the loss honestly, then move to the work it frees you for. I've been through a version of this. At Facebook a more experienced manager was hired in above me, and as the team grew I gave up things I loved doing: writing scripts, critiquing every pixel, drawing illustrations that ended up in the product. My influence over the company shrank in ways I could feel, and some days it felt like a loss. Looking back, the company grew 100x, and the manager hired over me made me a much better manager. [Citation: https://medium.com/p/1b0bb0473426] So my concrete advice for the first few weeks after the reorg: 1) Have a direct conversation with whoever now owns the scope you lost. Ask about their vision for the area. If it sounds exciting, say you want to help make it work. Treating them as a rival reads badly across the org and closes doors you'll want open later. [Citation: https://medium.com/p/1b0bb0473426] 2) Ask your manager, "What's one of your biggest problems right now, and how can I help?" A smaller scope often leaves you with spare cycles, and putting them on your boss's hardest problem is how you earn new scope without campaigning for the old one. Later, add something like "I'd love to do more of X; if you see an opportunity, will you keep an eye out for me?" [Citation: https://medium.com/p/afad1b0fa501] 3) Measure yourself by your skills. Your title, headcount, and org chart box are the wrong yardstick. Each role is a chapter, and you get to choose what you take from this one. [Citation: https://medium.com/p/56a4e3ad6051] ##### [Nikhyl Singhal]() I like Julie's "what's your biggest problem and how can I help?" question, but timing matters a lot here. Ask it early. Hold back the "I'd love to do more of X" line until you've delivered something visible in the new scope. On the podcast a staff engineer listed promotion, more visibility, and a bigger pie as goals in the first meeting with a new manager. Those are all fair goals. Stating them before shipping anything made him look out of touch the moment his first review came back less than stellar. A reorg puts you in that same position, because your new chain of management has no history with your work. [Citation: https://theskip.substack.com/p/how-to-navigate-org-drama] The other thing I'd do in month one is write down the story this role needs to tell for your next job. A smaller scope can still make a strong chapter if you can describe it in one line, for example "took the core funnel from flat to growing" or "shipped our first AI-native workflow." If you can't find a credible line like that inside the new boundaries, the reorg has already answered your hold-or-fold question, and you should start your search while you still hold the role. Searching from a position of strength gets far better outcomes than searching after the next round of cuts. ##### [Yue Zhao]() Before you do anything, write down what actually changed. Then write down what didn't. Joe, a Principal PM client of mine with 15+ years in his space, came to me after a GenAI-driven reorg layered him under a former peer. He felt angry, assumed he'd done something wrong, and started looking at other jobs. When we listed the facts, the picture changed. His new leaders had brought him into the reorg conversation before the announcement. He was one of a few people tapped to shape the new org's strategy. The SVP regularly came to him for his opinion. I read that structure as a temporary fix for a few months, until the strategy settled. Joe was in a good position to define what came next. [Citation: https://news.theuncommonexecutive.com/p/the-power-of-reframing] So my first move is to look deliberately for the positive signals, because fear makes you notice only the negative ones. Then act: ✅ Treat your new manager like a new job. Slow down the "work" and put time into the relationship, goals, and alignment. [Citation: https://news.theuncommonexecutive.com/p/how-to-survive-manager-changes] ✅ Find out where the investment is moving. Ask your skip level what the priorities are. Get coffee with peers on other teams every 4 to 6 weeks. ✅ Volunteer for the initiatives that are getting funded. Become a thought partner to the leaders running them, so that when the next planning cycle comes, you're the obvious person to move over officially. [Citation: https://news.yuezhao.coach/p/get-ahead-on-reorgs] Expect another reorg. At Thumbtack and at Meta we reorganized every 6 months, and I watched the same pattern play out: people who spent the reorg defending their old scope stayed stuck, and people who were already close to the new priority got the bigger role. [Citation: https://news.yuezhao.coach/p/get-ahead-on-reorgs] Bottom line? A smaller scope after a reorg is usually temporary, and you have about 6 months to put yourself next to where the company is spending. ##### [Elena Luneva]() Nikhyl's "deliver inside the new boundaries" only works if you know which deliverables count, so the first question is whether the scope you lost was the work the business actually cares about. In the Director-to-VP conversation Andrew Capland and I ran with 600 product people, the pattern was blunt: if you aren't on a project that matters to the business, you aren't getting promoted. A reorg often strips out exactly that work, and it can happen quietly. [Citation: https://elenasletters.substack.com/p/why-strong-directors-stall-before] Here is the sequence I'd run in the first 30 days. 1. Clarify and verify with your new boss. Get them to finish this sentence out loud: "Your team wins this quarter when ___." If neither of you can say it, you'll end up in reactive mode and look slow, even though your scope is smaller. 2. Audit what's left. For two weeks, write down everything you do. Then sort it into three buckets: Stop (doesn't move the core metric), Systematize (templatize it or hand it to AI), and Stay (high-leverage work you protect). A smaller scope gives you time back, so put that time toward strategy instead of filling it with more execution. 3. Translate the remaining scope into dollars. If what's left is platform, quality, or tooling, that work tends to be invisible. Ask why it's hard to quantify. If it's hard because it doesn't matter to the business, move toward a project that does, and do it fast. If it's hard because you haven't connected product metrics to revenue yet, build that connection before your next review. 4. Block 1 to 2 hours a week of "CPO time" to work on next quarter's bets and the story you want leadership to hear. If that block keeps getting bumped, raise it with your boss as a role-design problem. [Citation: https://elenasletters.substack.com/p/why-strong-directors-stall-before] Step 3 is also how you write Nikhyl's one-line story. "Took the core funnel from flat to growing" only lands in a VP interview if it has a revenue or retention number attached. If you can't tie your remaining scope to a business number by the end of the quarter, that's a strong reason to fold. ##### [Nikhyl Singhal]() Yue's facts list is the right first step. I'd push back a little on "usually temporary," though. Joe had real evidence: he was in the room before the announcement and the SVP kept asking for his view. Many people in a shrunken scope have none of those signals, and in 2026 a lot of big-tech reorgs are permanent flattening, with fewer layers and fewer managers. Those roles don't come back after six months. So I'd use Yue's list as a test. If your facts look like Joe's, invest in the relationship and move toward the funded work, as she describes. If you're out of the strategy conversations and your skip-level isn't asking for you, assume the smaller scope is permanent and run the growth-rate test I described earlier. When you volunteer for the funded initiatives, keep your own area's numbers moving first. Taking on side projects while your core scope slips gives leadership a reason to make the next cut. [Citation: https://www.youtube.com/watch?v=yOGuV-uKB5E] ##### [Diana Stepner]() Nikhyl's test asks whether your facts look like Joe's. Plenty of people can't tell yet, because reorgs leave everyone short on information. You can find out without going to your manager with the hot-seat question. Map who is still moving around in the new structure, then ask them directly so you aren't guessing. My client Sara had been named a DRI in early planning docs. Then a working session with her SVP got canceled at the last minute, and she started feeling like an outsider in meetings. She came in asking, "Is she trying to leave me out?" We named what she was feeling as an ANT (automatic negative thought). An ANT is convincing because it's built from real past experience, yet it doesn't tell you what's happening now. In her case the SVP was still finalizing her own team. [Citation: https://dianastepner.substack.com/p/how-to-navigate-a-reorg-without-losing] Here is what we did next. 🎯 Map the players. We listed the SVP, her own boss (a mess), a peer of the SVP who had already said he'd love her on his team, the new CPO, and a contact leaving product, which meant a possible open role. 🎯 Rank the conversations by risk. Going straight to the new CPO was too big a bet while relationships were still forming, so she saved it for their scheduled 1:1. The peer was the safer place to start. She practiced this line: "I really want to lead a core product area. Are there opportunities on your team or elsewhere that you think I should make a case for?" With the departing contact she asked one direct question: is there backfill headcount, and what scope would it have? 🎯 Learn, Build, Return for the meetings you can't avoid. Watch how the new leaders interact with each other. Rehearse how you want to show up. Then contribute ideas without pressing for clarity you won't get that day. When Sara did that, the SVP responded well, and that response counted as evidence too. These side conversations sit alongside delivering on your core numbers. They don't replace it. For Sara, they turned one ambiguous signal into three real options. [Citation: https://medium.com/p/2c9b7a555876] ##### [Julie Zhuo]() The most useful thing a manager ever told me fits Nikhyl's timing point. Early in my career I showed up to 1:1s week after week with an agenda: list my wins, make the case for more promotions, plum assignments, and power. My manager saw right through it and eventually said, "Focus foremost on making the company successful, and the rest will follow." It sounded like a platitude then. Ten years and thousands of promotion discussions later, I can't think of a better summary of how people actually grow. [Citation: https://medium.com/p/44d5f741743e] A reorg is when that advice is hardest to follow, because your ego is loudest right after you lose something. So I'd change what your 1:1s are about for the first quarter: 1) Spend most of each 1:1 on Elena's "your team wins this quarter when ___" and how you're moving it. Leave your own allocation out. 2) Give credit away visibly, including to the person who took your old area. People notice who fights for a bigger pie and who fights for a bigger slice. 3) Write down what you miss about the old scope, privately. For me it was being in every decision when the team was small. Naming it keeps the loss out of how you show up in meetings. [Citation: https://podcasts.apple.com/us/podcast/rewind-julie-zhuo-facebooks-former-vp-of-product/id1266839739?i=1000664488788] On Nikhyl's question of whether the smaller scope is temporary or permanent, I'd look at the company as well as your own signals: is it likely to be meaningfully bigger in two years? At Facebook I gave up pieces of my work many times, and the company's 100x growth kept creating more to pick up. If the company is shrinking too, a smaller scope inside it is a much weaker bet, and that pushes you toward Nikhyl's "fold" earlier. [Citation: https://medium.com/p/1b0bb0473426] ##### [Elena Luneva]() Nikhyl's permanent-versus-temporary test gets sharper if you map what you have left onto time horizons. I use the Horizons framework with CEOs to sort incoming ideas: Horizon 1 is near-term revenue that customers are already asking for, Horizon 2 is adjacent demand that still needs its GTM risk validated, and Horizon 3 is a bet 18+ months out. [Citation: https://elenasletters.substack.com/p/how-to-manage-a-ceo-who-drives-product] You can apply the same sort to yourself after a reorg. - If your remaining scope is Horizon 1, it's probably safe and probably permanent. Your job is to keep the numbers moving, which is Nikhyl's point about protecting your core before you take on side projects. - If the work you lost was Horizon 3 and the person who took it now owns the AI bets, Julie's conversation with the new owner matters most. Leadership is telling you where the future engine will be, and you want to stay close to it. - If Yue's funded initiatives are Horizon 2, that's usually the best place to volunteer. The demand is real but the GTM is unproven, so someone who can validate it without a big team stands out. One more thing on the fold side. When a role doesn't come back, the next step doesn't have to be the same full-time job somewhere else. When I gave notice at my CPTO role, I rebuilt my work as a portfolio. Fractional work was about 67% of my 2025, alongside coaching, teaching, and writing. A portfolio is not an easier path, because you give up certainty in exchange for agency. It's still a real option if a flattened org has removed the role you were growing toward. [Citation: https://elenasletters.substack.com/p/baby-influencer] --- Copyright © 2026 Super Me Network, Inc. All rights reserved. | [Terms of Service](https://www.superme.ai/terms) | [Privacy Policy](https://www.superme.ai/privacy)