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Kenneth Berger (exec coach, first PM at Slack)19 May 2024

Why not asking for what you want is holding you back

8Frameworks
13Insights

Episode overview

Executive coach and former Slack product manager Kenneth Berger explains why clearly asking for what you want is essential to integrity, fulfillment, and sustainable work. He presents an iterative process: articulate the desired outcome, ask intentionally and humbly, accept the response, and use rejection as data for the next attempt. Berger illustrates the framework through his account of being fired three times at Slack and argues that vision and joy are more sustainable motivators than fear or discipline.

Key ideas

  • Every complaint implies a dream, so complaints can reveal the better future a person actually wants.
  • The core loop is to articulate what you want, ask intentionally, accept the response, learn from it, and try again.
  • Anything short of an enthusiastic “hell yes” should be heard as a no rather than treated as reliable commitment.
  • Clear asks work best when paired with humility and respect for the other person's right to decline.
  • A no applies to a particular person, time, and form of the request; it is useful data rather than necessarily a permanent rejection.
  • People often underestimate the influence of candidly sharing their informed judgment, even when they lack decisive quantitative data.
  • Berger's Slack experience shows how unspoken expectations, fear, and failure to hear negative feedback can create prolonged suffering.
  • Vision, joy, and meaningful desire can provide more sustainable motivation than fear or short-term discipline.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Influence5 steps

Calibrated Acceptance of No

Don't over-accept a no into a life verdict, or under-accept it into something you can override.

Read →
Communication4 steps

The Articulate-Ask-Accept Loop

Treat wanting as an iterative dev cycle: articulate, ask intentionally, accept the response, try again.

Read →
Self-Mastery5 steps

The Dream Behind the Complaint

You're bad at dreaming and great at complaining. Mine the complaint for the dream it implies.

Read →
Leadership4 steps

The Hell Yes Standard

Anything short of a hell yes is a no. Don't settle for it — negotiate toward it.

Read →
Influence5 steps

The Humble Ask (Influence Without Authority)

State the want clearly, disclaim the authority explicitly, then ask them to reconsider.

Read →
Leadership6 steps

The Relationship Design Conversation

Design how you'll work together before you need to — and assume your founder is terrified.

Read →
Peak Performance5 steps

Vision Over Fear (There's No Tiger in the Room)

Fear and discipline are short-term coping strategies. Sustainable drive comes from vision.

Read →
Mindset5 steps

Working the Resistance by Parts

The part of you that's scared to ask won't go away by being ignored — interview it instead.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 8

  • Kenneth BergerMentionsKenneth coaches startup leaders to help them avoid burnout and live the life that they want. He was the first product manager at Slack.

    “Kenneth coaches startup leaders to help them avoid burnout and live the life that they want.”

    ▶ Watch at ~1:00approx.
  • Kenneth BergerMentionsKenneth coaches startup leaders to help them avoid burnout and live the life that they want. He was the first product manager at Slack.

    “You were famously the first PM at Slack, and then you ended up transitioning into executive coaching”

    ▶ Watch at ~4:30approx.
  • Carol RobinMentionsCarol Robin taught a Stanford class focused on helping people learn how to work with other people.

    “we just had Carol Robin on the podcast who taught this class that she filled at Stanford for a long time”

    ▶ Watch at ~38:00approx.
  • George FloydMentionsmentioned

    “a month after George Floyd was murdered and was facilitated by a black woman”

    ▶ Watch at ~38:30approx.
  • Stewart ButterfieldMentionsStewart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time.

    “Is this going to be my dark secret that I take to the grave? That Stewart Butterfield fired me three times”

    ▶ Watch at ~50:30approx.
  • Matt MocharyMentionsMatt is a full-time executive coach but not just any coach he's worked with folks like nabal the CEOs of openai coinbase Reddit

    “We have a chat I had a chat with Matt Mochary and we spent a bunch of time on dealing with fear”

    ▶ Watch at ~1:03:30approx.
  • Kim ScottCoinedI think radical Candor by Kim Scott is just incredible

    “I love, you know, Kim Scott's writing on that stuff.”

    ▶ Watch at ~1:06:00approx.
  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “I mean, I'm pretty sure you can guess, Lenny.”

    ▶ Watch at ~1:10:30approx.

Resources · 21

  • SidebarMentionscompany · Sidebar

    “Sidebar is a private, highly vetted leadership program where senior leaders are matched with peer groups”

    ▶ Watch at ~2:30approx.
  • WebflowMentionssoftware · Webflow

    “Their visual-first platform allows you to build, launch, and optimize web pages fast.”

    ▶ Watch at ~3:30approx.
  • SlackMentionssoftware · Slack Technologies

    “You were famously the first PM at Slack, and then you ended up transitioning into executive coaching”

    ▶ Watch at ~4:30approx.
  • AdobeUsescompany

    “when I was at Adobe, it's a big company”

    ▶ Watch at ~9:30approx.
  • VantaMentionssoftware · Christina Cacioppo

    “Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risk.”

    ▶ Watch at ~26:00approx.
  • Internal Family SystemsRecommendsother

    “I'm a big fan of internal family systems, which is this sort of psychotherapy technique that really talks about parts”

    ▶ Watch at ~36:30approx.
  • Leaders in TechRecommendscourse · Carole Robin and co-founders

    “I feel like every single person that has gone through, I think it's called Leaders in Tech”

    ▶ Watch at ~38:30approx.
  • Stanford UniversityMentionsplace

    “I took one of Stanford's T-group weekends summer of 2020”

    ▶ Watch at ~38:30approx.
  • Nonviolent CommunicationMentionsbook · Marshall Rosenberg

    “It's somewhat related to nonviolent communication, which is what you touched on”

    ▶ Watch at ~39:00approx.
  • SlackUsessoftware · Slack Technologies

    “I just got in the job as the first PM at Slack”

    ▶ Watch at ~45:30approx.
  • Radical CandorRecommendsbook · Kim Scott

    “Well, I already mentioned Radical Candor. I think that is for sure a modern classic.”

    ▶ Watch at ~1:06:00approx.
  • NetflixMentionscompany · Netflix

    “I really enjoyed Netflix's Break Point cuz it's a documentary on the best tennis players in the world.”

    ▶ Watch at ~1:07:30approx.
  • Break PointRecommendsdocumentary · Netflix

    “I really enjoyed Netflix's Break Point cuz it's a documentary on the best tennis players in the world.”

    ▶ Watch at ~1:07:30approx.
  • LivingRecommendsfilm

    “there's this movie Living from a couple years ago”

    ▶ Watch at ~1:08:30approx.
  • WimbledonMentionsevent

    “I will actually be at Wimbledon this year in London”

    ▶ Watch at ~1:09:00approx.
  • LondonMentionsplace

    “I will actually be at Wimbledon this year in London”

    ▶ Watch at ~1:09:00approx.
  • Tea from TaiwanRecommendswebsite

    “you can check out tea from taiwan.com. That's a good one.”

    ▶ Watch at ~1:10:30approx.
  • kberger.comCoinedwebsite · Kenneth Berger

    “you can check out my website, kberger.com”

    ▶ Watch at ~1:12:30approx.
  • Ask for What You WantCoinednewsletter · Kenneth Berger

    “please follow me there, subscribe to the Ask for What You Want newsletter.”

    ▶ Watch at ~1:12:30approx.
  • LinkedInUseswebsite · LinkedIn

    “you can find me on LinkedIn. I'm Kenneth Berger, b e r g e r.”

    ▶ Watch at ~1:12:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “You can find all past episodes or learn more about the show at lennyspodcast.com.”

    ▶ Watch at ~1:13:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take15:30

It's Not A Yes Unless It's A Hell Yes

Kenneth has a more expansive definition of "no" than most people. Anything short of an enthusiastic, whole-body yes should be heard as a no. Settling for a lukewarm "maybe, I'll try" is what comes back to bite you later when the person doesn't actually deliver. Hearing the world's frequent no's isn't bad news, it's great data for what to try next.

  • Treat anything less than a hell yes as a no
  • A lukewarm yes often means they never really committed
  • Example: a CTO's "maybe May 1st" that predictably misses the milestone
  • Ask "what would it take to get to a hell yes?" instead of forcing agreement

“it's it's not a yes unless it's a hell yes.”

Kenneth Berger · 15:30

“Mostly the world tells us no. It's actually really great data.”

Kenneth Berger · 16:30
#decision-making#commitment#leadership#communication
Hot Take1:01:00

There's No Tiger In The Room: Motivate By Vision, Not Fear

Many high-achieving tech people believe their fear of not being good enough is what makes them great and are scared to let it go. Kenneth's push: fear is for when a tiger is chasing you, and there's no tiger when you're on a Zoom call at your desk. You can motivate by joy, vision, and inspiration instead, and he tells skeptics to just try following a meaningful vision and notice the difference.

  • The belief that fear of failure is what drives greatness is widespread and false
  • Fear is functional against real danger, not office Zoom calls
  • Alternatives: motivate by joy, vision, and inspiration
  • The practice is reminding yourself there's no tiger in the room

“fear is for when there's a tiger chasing you and there's no tiger chasing me. I'm sitting in my office in a desk chair on…”

Kenneth Berger · 1:03:00
#fear#motivation#mindset#burnout
Hot Take1:04:00

Contrarian Corner: Discipline Doesn't Last

Kenneth's contrarian belief is that he's not a big believer in discipline. Like people-pleasing, discipline is a short-term coping strategy: it gets you to the gym for a week, not a year. The people who show up for a year do it because they genuinely want to. So instead of playing drill sergeant, he looks for true long-term, sustainable motivation rooted in vision and wanting.

  • Discipline works but only short-term, like people-pleasing
  • It gets you to the gym for a week, not a year
  • Long-term consistency comes from genuine desire, not force
  • He refuses the "drill sergeant" coaching role as unsustainable

“discipline will get you in the gym for a week, but it's not going to get you in the gym for a year, right?”

Kenneth Berger · 1:04:30
#discipline#motivation#habits#contrarian

Explainer· 3

Explainer05:00

Why Asking For What You Want Is Really About Integrity

Kenneth Berger argues the whole skill of asking for what you want comes down to one word: integrity. Everyone assumes they already ask for what they want and already have integrity, but most people quietly fool themselves about whether they're actually pursuing what matters. When you ask regularly, listen to the response, and respect the no's, you can honestly say you're honoring what's important to you.

  • The single root of the skill is integrity, not tactics
  • Almost no one thinks they lie to themselves, yet most do about what they truly want
  • You can't guarantee getting what you want, but asking regularly keeps you honest
  • Not asking produces secondary effects: stress, frustration, unhappiness

“if I had to answer in one word, it would be integrity.”

Kenneth Berger · 05:00
#integrity#self-awareness#coaching#motivation
Explainer22:00

Why Nice Founders Struggle To Create Consequences

The founders who are kind and beloved by their teams often can't bring themselves to deliver hard feedback or create real consequences when someone underperforms. Kenneth reframes it: people always get to say no, but no's have consequences. Respecting someone as a grown-up means letting them own the outcomes of their choices, including disagree-and-commit expectations.

  • Nice founders fear that consequences aren't "nice"
  • Everyone can say no, but no's carry consequences
  • Respect means treating people as adults who can handle outcomes
  • "Disagree and commit" is a fair expectation to state out loud

“the thing about other people's no's is that sure, they can always say no. Everybody gets to say no whenever they want, but there are…”

Kenneth Berger · 22:00
#feedback#leadership#management#consequences
Explainer36:30

Embrace The Scared Part Instead Of Shaming It

Kenneth draws on Internal Family Systems to work through the resistance that blocks asking. We're comfortable with the "virtuous" parts of ourselves and ashamed of the whiny or scared parts, so we ignore the very part that's terrified to ask, and stay stuck. Turning toward that fearful part with curiosity, rather than shame, is what actually softens the fear.

  • IFS: we're made of parts that don't always agree
  • We favor the "good" part and disown the scared or whiny one
  • Ignoring the scared part keeps you stuck
  • Validating the fear (e.g. impostor fears) is how it softens

“by embracing that instead of ignoring that and being ashamed of that, that is often how we soften those fears”

Kenneth Berger · 37:30
#psychology#resistance#fear#self-work

Story· 1

Story45:30

Fired Three Times From Slack As The First PM

Kenneth tells the story that shaped his coaching: he was fired three times in his single year as Slack's first PM. He came in overconfident and never clarified expectations, got fired, apologized his way back, then spent a year in people-pleaser mode too scared to ever say what he wanted, and was pushed out of product before finally being let go for good. The lesson: he never articulated what he wanted, never asked, and never heard the no's, so the outcome was no surprise.

  • First firing came from naive overconfidence and unset expectations
  • He apologized back into the job, then spent a year too scared to ask for anything
  • When he finally wrote a proposal and asked, he got his product role back
  • The core failure: no articulation, no asking, no hearing the no's

“I was fired from Slack three different times which I feel like has to be some kind of startup record.”

Kenneth Berger · 45:30

“Turns out when you actually ask for what you want out loud, you're much more likely to get it.”

Kenneth Berger · 50:00
#slack#first-pm#career-story#self-reflection

Q&A· 1

Q&A06:30

Three Signs You Need To Get Better At Asking

Lenny asks how you know this is a skill you personally need to work on. Kenneth names three tells: feeling stuck in the same place week after week, recurring interpersonal conflict, and a sense that everything is high-stakes. When stakes feel like life-or-death, people fixate on the fear of what they don't want instead of what they actually want.

  • Stuckness: trying the same thing and getting the same result week after week
  • Interpersonal conflict from either holding back or coming in with entitlement
  • A pervasive high-stakes feeling that hijacks decision-making
  • High stakes shift focus from goals to fears

“when the stakes feel high, we're kind of focused more on the fear of what we don't want to happen than on actually achieving what…”

Kenneth Berger · 10:00
#self-diagnosis#conflict#career#fear

Tool· 2

Tool11:30

The Dream Behind The Complaint

Most people are bad at articulating a big dream but excellent at complaining. Kenneth's favorite technique flips that: every complaint implies a better world where the complaint is resolved. You surface the complaint, extract the implied dream, then check whether that dream is actually big and inspiring enough to motivate you past your fears.

  • People find dreaming scary but complaining easy and even fun
  • Every complaint points to an implied better world
  • Check the surfaced dream: is it inspiring enough, or too small?
  • For entitled people the same check catches unrealistic dreams

“every complaint implies a dream, right? It implies a better world where that complaint is resolved.”

Kenneth Berger · 12:00
#technique#self-awareness#goals#coaching
Tool40:00

Stay Factual: Thoughts, Feelings, And What The Camera Saw

Kenneth and Lenny compare feedback templates: Carol Robin's "when you do X, I feel Y, I'm telling you this because Z," nonviolent communication, and DBT's DEAR MAN. What they share is staying factual. The only things you can truly know are your own thoughts, your own feelings, and what a video camera would have recorded, so anchoring an ask to those makes it far clearer than the stories we layer on top.

  • Carol Robin's template: behavior, a real feeling word, and why you're saying it
  • NVC and DBT's DEAR MAN converge on the same factual core
  • You can only truly know your thoughts, feelings, and observations
  • "I feel like you're an idiot" is a story, not a feeling

“we can know our thoughts, we can know our feelings cuz no one else can know that better than us. And maybe we can trust…”

Kenneth Berger · 40:30
#feedback#communication#frameworks#clarity

Takeaway· 3

Takeaway31:00

You Have More Influence Than You Think (Even Without Data)

PMs and ICs are trained to justify everything with data and feel they can't speak up without evidence. Kenneth counters that relationships and your plain opinion are often enough. Asking clearly but with genuine humility works whether or not you hold power, and it feels more vulnerable than hiding behind an A/B test but carries real weight because people actually care about you.

  • Data is valuable but not the only legitimate input
  • Your relationships and stated preference carry real influence
  • Ask clearly and with humility: acknowledge it's not your call
  • Gut opinions from subject-matter experts are as important as the SQL database

“I know it's not my call and I'm just one opinion and a lot of people are going to see things differently and that's fine.…”

Kenneth Berger · 31:30

“your relationships matter and that just your opinion because you believe something uh or because you want something, often that's enough, right?”

Kenneth Berger · 33:00
#influence#product-management#humility#communication
Takeaway41:30

Don't Over-Accept (Or Under-Accept) A No

Accepting the response sounds simple but is the trickiest step. People who fear asking over-accept: they treat one no as forever and let the dream die. Controlling types under-accept: they skip past the no entirely. A no is just from this person, right now, in the way you asked, and says nothing about the next person, time, or approach.

  • Over-accepting: hearing one no as "no forever"
  • Under-accepting: ignoring the no because you outrank them
  • A no is bounded to this person, moment, and phrasing
  • It leaves the door open to a different person, time, or ask

“The no is just from this person right now in the way that you asked, right? Which doesn't necessarily mean anything about the next time…”

Kenneth Berger · 42:30
#rejection#resilience#emotional-regulation#communication
Takeaway58:00

First-PM Advice: Assume Your Founder Is Terrified

For anyone reporting to a founder, Kenneth offers a reframe: if your founder's behavior is confusing, assume they're terrified all the time and see if that makes it make sense. Founders carry everything on their shoulders and often feel constant high stakes. Meeting them where they actually are, rather than wishing they were different, is the path to a healthy working relationship, and without one you won't get anything done.

  • Confusing founder behavior often reads clearly through the lens of fear
  • Founders feel everything is on their shoulders
  • Work with the founder's real state, don't wish it away
  • No healthy relationship means no meaningful progress

“imagine that they're terrified all the time. Right? And see if that makes their behavior more clear.”

Kenneth Berger · 58:30
#founders#first-pm#relationships#empathy