Career: Plan, Promotion Case, Job Move, Search and Negotiation

career: lead guest team

Diagnose which career decision you are really facing, run the matching play, and leave with a one-page decision brief plus scripts you can send today. Built from 745 insights from 188 Lenny's Podcast guests. Lead team: Phyl Terry, Nikhyl Singhal, Deb Liu.

When to use

• You feel stuck, restless or passed over and cannot tell whether to fix it, move teams or leave.
• You want a promotion case or a calibrated answer to 'why am I not at the next level?'.
• You are choosing between jobs, or deciding whether your company is a dead end (ex-growth, layoffs, no sponsor).
• You are laid off or starting a search and need a system, not a blast of applications.
• You have an offer (or are about to) and need a negotiation script and the right order of asks.
• You wonder whether to go IC, manager, founder or executive, or how AI changes what you should learn.
• You are an aspiring PM (support, sales, eng, design, ops) looking for the entry path.

Step 1 - Diagnose (ask before answering)

If the user attached a resume, self-review, promo doc, offer letter, job description or org chart, read it first and infer. Then ask at most 4:

1. Which decision is on the table? Plan, promotion, stay-or-leave, search, offer, AI-era reinvention, break-in. Routes to the play in Step 2; most people name one and need two (a search needs Play A first).
2. Level, years and track? APM/PM, senior, lead, director+, IC or manager. Early careers optimize for learning and reps; leader transitions hit the 'optics' and 'what got you here' walls (Fareed Mosavat, Ethan Evans, Shreyas Doshi).
3. Company state and your leverage? Growing, ex-growth, laid off; employed with runway or urgent income need. The ability to say no is power, and haste is risk (Jacob Warwick).
4. What do you want in one sentence, with a reason that is yours? If the answer is 'a promotion' or 'VP', ask why until it turns internal (Ken Norton's laddering). If they do not know, start with Play A.

Step 2 - Pick the play

If... (situation)	Use	From	Why
Restless, burned out, or do not know what you want	Play A: energy audit + four quests + features-vs-experiences	Bob Moesta, Nickey Skarstad, Graham Weaver	Turns vague unhappiness into design requirements for the next job
Drifting job to job, or choosing a next step	Play B: career spec + The Skip + 6/12/24-month story	Deb Liu, Nikhyl Singhal	A career is a product; plan the move after the next
'Should I stay or go?'	Play C: environment scorecard + ex-growth test + pushes-need-pulls	Bangaly Kaba, Nikhyl Singhal, Bob Moesta	Separates fixable environment from a real dead end before you move
Passed over, plateaued, or promotion cycle coming	Play D: why-not-promoted diagnosis + Magic Loop + company-problem framing	Nikhyl Singhal, Ethan Evans, Claire Vo, Jackie Bavaro	Finds which of four causes you have, then makes yes the easy answer
Laid off or starting a search	Play E: Job Search Council + two-pager + listening tour + candidate market fit	Phyl Terry	Peer accountability and market research instead of spray and pray
Interviewing, offer in hand or near	Play F: job mission with OKRs + resources-before-salary + live negotiation	Phyl Terry, Jacob Warwick	Negotiate what you need to succeed first; comp second
Worried about AI, or the job is changing	Play G: cross the threshold + ship weekly + stack skills	Nikhyl Singhal, Marc Andreessen, Anish Acharya	Currency now is hands-on building plus judgment
Aspiring PM or switching lanes	Four paths in + do the job before the title	Annie Pearl, Naomi Gleit, Kevin Yien	Internal moves and adjacent roles beat cold applications

Step 3 - Run it

Play A: Find direction (Moesta, Skarstad, Weaver, Ken Norton)

1. Energy audit (2 weeks). After every meeting or project, mark it red (drained), yellow (baseline) or green (energized). Nickey Skarstad recolored her whole calendar this way. List the 2-3 moments in the last 12 months where you left with 2-4x the energy you entered with, and the biggest drains.
2. Dig to cause, not label. For each green and red, ask: why, and what was a specific good day versus bad day? Stop at the causal mechanism that transfers to other jobs, not 'I like the beach' (Moesta's three layers of language).
3. Name your quest (Moesta, from 1,000+ switch interviews): Get out, Take the next step, Regain control, Realign to what you are good at. Count pushes honestly; people leave when about 3-4 pushes stack up and a pull gives direction. If quest is 'get out' (burnout), a time-boxed low-demand 'jobcation' is legitimate.
4. Translate features into experiences. Title and money are static features; money usually stands for respect, bills or falling behind. Write the experiences you want (autonomy, a team that has your back, craft time).
5. Three-factor filter for any option: does it compound my learning, overlap my strengths, and will I have fun (Mayur Kamat)? Add Graham Weaver's check: when comparing A and B, notice which one has your energy; you may be talking yourself out of it.
6. Done when: you can write 'I do my best work when ___, I get drained by ___, and my next job must give me ___' in three lines.

Play B: Career spec + The Skip (Deb Liu, Nikhyl Singhal)

1. Write the spec. End state in 5 years (not a title: what you build, with whom, what you can do), milestones, skills to acquire, and success metrics. Check every future decision against it (Deb Liu).
2. Find the skip. Define the job after the next one. Choose the next role for what it teaches toward that skip, not for the immediate title; stay in an ambiguous situation if it builds a needed skill (Singhal). Lateral escapes from a bad boss rarely help.
3. Explore, then exploit (Ada Chen Rekhi): early, treat each role as a hypothesis (try startup, growth, marketing) and stack complementary experiences; once something is rich, tell your manager what you want to learn and optimize for that over title.
4. Write the skip-job story in the first person for 6, 12 and 24 months: problem solved, skill built, headwind faced, how I overcame it. Use 'I', not 'we'. If the story is weak, change your work (Singhal).
5. Run the learning loop (Fareed Mosavat): execute on a real problem, generalize the lesson as a hypothesis, communicate it, then earn more scope and execute again. Revisit the spec yearly; Jason Shah warns that most moves rest on about 10 hours of signal, so hold plans loosely.
6. Done when: the spec is one page, the skip job has a name, and your current role has a written 'what this teaches me' line.

Play C: Stay or leave (Bangaly Kaba, Nikhyl Singhal, Bob Moesta, Paige Costello)

1. Score six environment variables 0-2 in quarter steps: manager, resources, team, scope, compensation, culture (Kaba). For each low score ask: can it change, and will it?
2. Fix before you flee. Tell your manager dispassionately which variables hurt your output and ask for a plan; the manager is the variable that moves the others. If they will not or cannot, a new manager is the lever.
3. Run the ex-growth test. Still searching for product-market fit but valued in the hundreds of millions or more? You are at an ex-growth company; consider leaving (Singhal). Exceptions: the biggest role you can get, real bounded loyalty. Fear of finding another job is not a reason to stay.
4. Check the learning curve (Costello): is the steepness of my curve doing me a favor, is the environment healthy (staffing, advocates), is the problem interesting? Ada Chen Rekhi's frog test: is the temperature rising or falling on what I learn?
5. Check the push-pull count. Pushes alone make you a complainer (Moesta). Name the pull you are moving toward, and the 'lateral move' trap: leaving only for a bad boss or slow shipping is short-term (Singhal).
6. Verdict: Stay-and-fix (with a dated ask), Move internally (new manager or team), or Leave (with the pull named). Build the pros-and-cons spreadsheet, then 'put on the coat of the job': imagine the commute, the lunch, the problems of the day, and trust the gut reaction (Ami Vora, Tom Conrad).

Play D: Promotion case (Singhal, Evans, Bavaro, Vo, Manik Gupta)

1. Diagnose which of four causes (Singhal): no advocate; the next role does not exist; impatience (leadership levels take longer than annual promotions); or a real development area you will not hear. Asking your manager alone often will not reveal it.
2. Prerequisite: be seen as solid in your current job, and 'good' is defined by your manager's view (Evans). Ask how you are doing and close any named gap first. Tamar Yehoshua: you will not get the next job unless you knock out the current one.
3. Say the goal, framed in the future (Jackie Bavaro): I would like at some point to grow into [role]. What should I work on now so I am ready when it opens? Then ask the manager's peers and people who have promoted others the same. Keep career talk a tiny share of 1:1s (Claire Vo).
4. Run the Magic Loop (Evans): do the job well; ask how you can help; do what they need, even unglamorous; then ask for work that serves them and moves you toward your goal; repeat. Early: ask how to help. Mid: suggest what needs doing. Senior: act and keep the leader informed, but only after trust is built. It works because managers help those who help them.
5. Make yes easy. Frame the promotion as the company's problem (span of control, unmet need), and when an org gap opens draw the org chart with your name in it, plus a JD and rollout (Claire Vo).
6. Evidence in three parts (Gupta): the what (end-to-end impact, rallying others behind a hypothesis), the how (creates clarity and energy), and followership (smart people choose to work with you). Add the seat test: a director has 6-8 reports, so check whether the role exists (Evans).
7. Make impact legible. Impact = work x your ability to show it, including teaching the org how your area works (Mosavat). Deb Liu: market your work like a product marketer; reframe the self-review as educating your manager.
8. Done when: you hold a one-page case (what, how, followership), a named sponsor, and a dated conversation with the decision maker.

Play E: Job search system (Phyl Terry, Never Search Alone)

1. Form a Job Search Council: 6-8 peers, a volunteer moderator, a first trust-building meeting. Fast seekers (out of work) meet twice a week; slow seekers (employed) every two weeks. Terry's councils average a three-month search.
2. Write the Mnookin two-pager: what you want and do not want in the next role. A draft is fine; read others' lists to spot what you forgot.
3. Run the listening tour (three conversation types): reverse exit interviews with past colleagues (what was I good at, what am I a fit for, do I project it accurately); broader network using the golden question If you were in my shoes, how would you approach this?; and recruiters, asking what you are a fit for, not for a job. You are doing market research and creating invested 'listening posts'.
4. Write the candidate market fit sentence: 3-4 attributes (company stage, industry, level and function, culture) in one sentence, e.g. director of product at a Series B healthcare startup in San Francisco. Spear, not net; your council signs off, then you broadcast it. Expect your fit to be set by supply and demand (a director may fit senior-manager roles in a glut); consider a two-step path to a stretch target.
5. Keep it alive: send a monthly update to everyone you spoke with, even with no news; debrief right after every interview with a peer; keep recruiter relationships warm before you need them. Stalled searches stopped networking, left their council and never updated their fit.
6. Done when: you have the one-sentence fit signed off by your council, conversations booked in all three listening-tour types (Moesta suggests 10-15 informational interviews before you apply anywhere), and a council meeting rhythm.

Play F: Interview to offer (Terry, Warwick, Nan Yu)

1. Write a private job mission with OKRs while interviewing: the outcomes you would be accountable for. After a couple of rounds, present it live (call, Zoom, coffee, never email) and ask what is and is not part of the role.
2. Find the hiring manager's burning problem (Nan Yu): ask their OKRs this quarter and how you could help. Ask for an intro to an engineering manager on the same problem.
3. Before the offer: do not name a number early; say you do not discuss compensation until you understand scope, then what did you have in mind? (Warwick). If the loop reveals a bigger role than the posted level, ask to restructure comp and level.
4. At the offer: resources first, then money (Terry). Agree OKRs with the hiring manager, name what you need to hit them (budget, headcount, tech-debt allowance, training or mentorship for juniors), ask whether they will commit, only then discuss comp. A company that reacts badly is a red flag.
5. Ask for more, softly: thank them, take a few days, then What is the chance there could be a little more? (Warwick). He sees about 20% improvement from simple pushback, around 40% with coaching. Terry reports most direct asks succeed. Never split the difference by reflex.
6. Negotiate live with the hiring manager, not by email through a recruiter. If stalled: If you were in my shoes, what would you explore? Check Adam Fishman's people-mission-financials criteria and back-channel references before signing.
7. Done when: you have the written agreed OKRs, a resources list, and a counter you can say in under three sentences.

Play G: Stay current in the AI transition (Singhal, Andreessen, Acharya, Cat Wu)

1. Cross the threshold: decide that staying current outranks other priorities for the next two years (Singhal). Builders are wanted; PMs whose value was relaying information up the chain are most exposed.
2. Ship one small thing a week with an AI builder or agent (Anish Acharya); keep a silly 'chassis' project you iterate on with each new model. A full week solving a real problem end to end puts you in the top 1% of tool users by his estimate (Anton Osika).
3. Retry what failed with each model release (Ian Silber, Dan Shipper, Amol Avasare); do not marry your process, marry the outcomes you uniquely deliver (Andrew Ambrosino).
4. Stack skills (Andreessen): stay deep in your craft, add design/build/PM with AI as tutor; a job is a bundle of tasks, so list yours and swap the automatable ones for higher-level scope. Hand off the repetitive parts and use the freed time on work nobody had bandwidth for (Cat Wu).
5. Own what you ship (Zevi Arnovitz): 'AI built that' is never an excuse. Judgment and taste are the scarce layer.
6. Done when: you can show 3-5 shipped artifacts and a one-line answer to 'what do you build with agents?'

Where the experts disagree

• Plan it vs follow people. Camp A: write a spec and work backward (Deb Liu, Nikhyl Singhal, Lauren Ipsen). Camp B: skip the five-year plan, take little bets and follow the best people (Tamar Yehoshua, Sanchan Saxena, Raaz Herzberg). Use A when the destination is concrete (CPO, founder, board seat); B when you cannot yet say what you want or are under 5 years in. Default: plan the skip loosely, run bets, review yearly.
• Optimize for promotion vs optimize for impact. Camp A: impact only, do not want it too badly (Shweta Shrivastava, John Mark Nickels, Chris Hutchins, Ian McAllister). Camp B: visibility and brand are part of the job (Deb Liu, Jeffrey Pfeffer, Laura Schaffer, Sriram Krishnan, Aarthi Ramamurthy). Impact without legibility stalls; visibility without substance fails. Default: impact first, then make it legible; at 50+ person orgs, budget for optics work (Doshi).
• Generalist vs spike. Camp A: refuse to specialize, fill the bingo card (Casey Winters, Shaun Clowes, Lauren Ipsen, Marc Andreessen). Camp B: double down on strengths, live on the edge of the triangle, get deep first (Jules Walter, Mayur Kamat, Hari Srinivasan, Tom Conrad, Noam Segal). A for an executive path; B in the first 5 years and when you are burning out trying to be everything. Default: one spike plus 1-2 adjacent stacks.
• Learn to code in the AI era. Camp A: yes, depth lets you steer and debug (Amjad Masad, Marc Andreessen, Scott Wu, Bret Taylor). Camp B: optimize for judgment and taste; titles collapse into builder (Boris Cherny, Lazar Jovanovic). A if you want technical or infrastructure leverage; B is enough for most PMs. Default: build weekly, learn enough to read and debug what the agent produces.

Deliverable

# Career Decision Brief - <name>, <date>
**Decision:** <plan / promotion / stay-or-leave / search / offer / AI reinvention>
**Context:** level, tenure, company state, runway, leverage
**What I want (3 lines):** do best work when ___; drained by ___; next role must give ___
**Spec & skip:** 5-year end state ___ | skip job ___ | 6/12/24-month story (first person, with numbers)

## The play
<Play name, who it is from, 5-8 numbered steps, with owners and dates>

## Evidence
- Environment scorecard (6 x 0-2) or promo case (what / how / followership) or candidate market fit sentence
- Open risks and how each is tested

## Scripts (paste-ready)
- Manager conversation / listening-tour ask / offer counter / sponsor ask

## Verdict
Stay-and-fix | Move internally | Leave | Negotiate | Stretch role (reason, date to revisit)

## Next 3 actions (this week)
1. ___ (owner: me, by: ___)
2. ___
3. ___

Grade existing work

Score a career plan, promo doc, search plan or self-review 1/3/5 per criterion.

Criterion	1	3	5
Destination	A title or 'grow'	Role named, no why	Internally defined end state plus the skip job (Singhal, Norton)
Evidence of impact	Task lists, 'helped'	Outcomes without numbers	Numbers, 'I' language, others can cite it (LeMay, Ipsen)
Market test	Assumed	A few chats	Listening tour or leveling check with named fit statement (Terry)
Narrowness	Net: any PM role	Stage or industry only	One-sentence fit, 3-4 attributes (Terry)
Sponsor and network	Mentor only, or none	Mentors, no advocate	A named sponsor plus weak-tie pipeline (Mosavat, Pfeffer)
Manager alignment	Waiting to be noticed	Goal stated once	Future-framed ask, Magic Loop running (Bavaro, Evans)
Learning rate	Same work for 2 years	Some stretch	Recent 'oh shit' stretch moments, one skill at a time (Lane Shackleton, Vikrama Dhiman)
AI currency	No hands-on use	Uses chat tools	Ships weekly, owns outputs, can show artifacts (Singhal, Acharya)
Output: score per criterion, total /40, and the top 3 fixes each naming the play and guest behind it.

Red flags

• Asking how to get promoted before asking what the promotion is in service of (Singhal).
• Spray and pray after a layoff, skipping the deliberate 'what do I want' pause (Terry).
• Leaving for a bad boss or slow shipping alone, when the same problems exist next door (Singhal).
• Waiting for the manager to manage your career (Evans).
• Visibility without substance, or presentation polish over product outcomes (Pfeffer, Nickels).
• Logo collecting, or being loyal to a fault while the company tanks (Lauren Ipsen).
• Treating 'more money' as the reason; over half of those who said so did not get more (Moesta).
• Negotiating by email through a recruiter, or naming a number early (Warwick, Terry).
• Blaming engineering for missed deadlines in interviews (Ipsen); faking passion for a product (Deb Liu).
• Staying an information mover, or defending the old way of working that made you successful (Singhal's 'shadow superpower').

Receipts

"when you're looking for a job, you need a spear and not a net. With a net, everything slips through." — Phyl Terry, Lenny's Podcast (00:31:02)

"the best career advice is always not thinking about the next move, but the move after." — Nikhyl Singhal, Lenny's Podcast (01:08:26)

"Lateral moves are by definition not forward moves." — Nikhyl Singhal, Lenny's Podcast (00:07:33)

"what your manager should do and $4 will get you a cup of coffee at Starbucks." — Ethan Evans, Lenny's Podcast (00:11:12)

"Now, 87% of the time, Lenny, when you ask for more money, you get it." — Phyl Terry, Lenny's Podcast (00:59:50)

"You make a light bulb, but you're selling light." — Deb Liu, Lenny's Podcast (00:35:28)

Go deeper

• references/frameworks.md - every framework in this skill, how to run it
• references/quotes.md - verified quotes with timestamps
• Related skills:
  • hard-conversations - when the promotion ask or feedback talk needs a script
  • influence - when the blocker is a missing sponsor or stakeholder
  • exec-comms - to sharpen the self-review, promo doc or skip-job story
  • decide - when stay-or-leave needs a pre-mortem and reversibility check