Ask for What You Want: Kenneth Berger on Integrity, Hearing No, and Getting Fired from Slack Three Times

Kenneth Berger, the first product manager at Slack who later became a coach to startup leaders, calls asking for what you want his "personal magnum opus," drawn from more than ten years as a founder and operator and seven as a coach. Asked why this one skill matters so much, his one-word answer is integrity. Everyone assumes they already ask for what they want, he says, because we order coffee every morning and nobody thinks of themselves as dishonest.

The trouble is that we fool ourselves about whether we are really pursuing what matters to us. If we ask regularly, listen to the response and expect to hear no sometimes, we can feel we are honoring both our own priorities and the world's answer. If we don't, the cost shows up as stress, frustration and unhappiness, because pursuing what matters is central to fulfillment.

Berger looks for two warning signs in clients. One is stuckness: the same frustrations week after week, which suggests someone is trying the same thing and expecting different results. The other is interpersonal conflict, which can come from holding back or from the opposite mode of entitlement, such as "I'm your boss, you better obey." He admits his own version was being attached to being right, walking into meetings convinced the other person was wrong, which he now sees as fundamentally disrespectful because new data or perspectives can always arrive.

He adds a third signal: high stakes. When he was a founder, unlike his years at Adobe, his vision and reputation felt on the line, and it became hard to be flexible. When stakes feel life-or-death, he says, we focus on the fears we want to avoid rather than the goals we want to reach, and running from fear does not necessarily take you anywhere meaningful.

Lenny Rachitsky admits he often pushes down what he wants because he prefers equanimity and wants others to be happy. Berger says he is far from alone: people pleasing is a classic coping strategy that works in the short term, because you feel safe when others are happy with you, but the long-term cost is not pursuing what is important to you.

His favorite technique is the "dream behind the complaint." People tend to be bad at saying "this is my dream" but very good at complaining about work or a colleague. Every complaint implies a better world where it is resolved, so he lets clients complain and then asks what vision sits behind it. He then checks the size of that dream: if the answer is "I get to speak up a little more in meetings," it is probably not the whole thing.

The check works in the other direction for entitled people. If a dream amounts to "everyone obeys me automatically," it is too embarrassing to own out loud, which signals it is not the right dream. The target is a dream that feels both inspiring and credible, hard enough that you may not get it but worth going for anyway.

Berger sums up the whole process as three steps: articulate what you want, ask for it intentionally and accept the response, then try again. He stresses that the process is straightforward, "not rocket science"; what makes it hard is the resistance, the parts of us that find asking scary and wonder what a no says about us.

Berger defines no more broadly than most people: it is not a yes unless it is a hell yes. He argues it is tempting to settle for "maybe, we'll see," and that this bites later. His example is a CTO who says "I think maybe we can deliver by May 1st," after which May 1st arrives and the milestone is not done.

Instead of treating a lukewarm answer as a failure, he recommends hearing it as a no and as good data about what to try next. A useful follow-up is to say you hear some hesitation about the date and ask what would be a hell-yes date. That way you are not making the other person wrong for saying no; you acknowledge everyone can say no and ask what it would take to get to a real yes.

He notes that some people call this a "whole body yes," because your head can say yes while your gut says no. Berger says his focus on startups matters here: founders know most startups fail, so they have to be willing to go after something meaningful knowing they probably will not get it. In his view that same attitude of wanting something without being attached to getting it applies to anything in life.

Berger says people tend to go wrong on step one in two opposite ways. Some fall into the "it's fine" trap, saying they don't need anything, and he encourages them to tune into subtle emotions like being a little bothered or nervous that signal they want something more. Others state wildly unrealistic goals, like a founder who wants everyone to agree and obey immediately, and for them saying it out loud often reveals that the real want is a team that feels aligned and has each other's backs.

His classic example is feedback. Many of the founders he coaches are genuinely nice and are loved by their teams, so they struggle to deliver hard feedback and, even more, to create consequences when someone isn't meeting expectations. Respecting people, he argues, includes respecting that they make choices and are grown up enough to handle the consequences.

Another example is disagree and commit. Founders often say they respect a differing opinion and thank the person, but won't take the extra step of saying "this is the call and I need you to follow through," even though rolling with that is part of the role. Rachitsky notes how scary it is to admit you want to do something that might upset people.

For a general check, Berger returns to integrity and asks whether you have fully expressed yourself. If you keep thinking for three or four days that you really want to say something to someone, you are probably out of integrity. Holding things in, such as telling yourself it is inappropriate to say you're bored in a meeting, creates more suffering than saying it, and others might even be grateful.

For step two, Berger says the key word is intentionally. People pleasers hope others will read their minds, while control freaks order people around; neither would claim it works, they just haven't embraced another way. The work is recognizing the rut and the narratives behind it, such as "it's too risky" or "they'll say no anyway," which come at a real cost. He asks whether you want people at your funeral to say you played it safe and nobody was ever mad at you.

When Rachitsky asks how to ask without upsetting anyone, Berger says that question itself is part of the resistance. In theory asking is easy: try something, see how people react, then iterate. But if you refuse to ever upset anyone, you never get to iterate, and there is no way to guarantee how others will feel. He suggests bringing compassion to yourself, since we all want to be sure our ask will be effective and nobody will be mad, but that is not on offer.

For people without formal power, such as a product manager, he recommends balancing clarity with humility. You can say you really disagree with a product decision and would prefer another, that you know it isn't your call and you're one opinion among many, but it matters that they know, and ask whether they are willing to reconsider. Berger and Rachitsky both think this is much less scary than staying silent.

Berger says people underestimate their influence. PMs are trained to lean on data like A/B tests, but relationships matter, and your opinion alone is often enough because colleagues care about you. He argues that gut opinions from subject matter experts are as important as anything from the SQL database, and that withholding them because you lack data deprives the room of that information.

Rachitsky points out that the opposite of asking is complaining later, like "I knew this deadline was terrible." Berger sees complaints as great inspiration but a poor way to communicate. He goes a step beyond radical candor: don't just share feedback, say what you want to see happen. Following the frustration down to a desire and then thinking about how to communicate it effectively requires embracing the whiny part of yourself that you might be ashamed of.

He draws on internal family systems, the psychotherapy approach built around the "parts" of ourselves that disagree. He likes that we already say "part of me thinks this." Working through resistance means validating all parts, including the one that is scared to ask. If a part fears your whole reputation is staked on this and you'll be found out as an imposter, he suggests acknowledging that it makes sense to be scared while also reminding yourself you are an experienced professional.

Rachitsky brings up Carole Robin's feedback template of describing a behavior, saying what you feel, and explaining why you're telling them. Berger teaches the same idea and notes that nonviolent communication and dialectical behavioral therapy's "DEAR MAN" share it. What they have in common is staying factual: you can know your thoughts, your feelings and what a video camera would have recorded, and "I feel like you're an asshole" is a story, not a feeling.

Berger calls step three, accept the response, the trickiest. People are biased toward hearing yes, so they must learn to hear a no even when it arrives as a facial expression, without over-accepting or under-accepting it. Over-accepting is concluding that no means never and the dream is dead, when it is really a no from this person, now, in the way you asked. Under-accepting is the control-freak move of dismissing the answer because they're your direct report or don't know what they're talking about.

He says respecting a no can make you more influential, because asking is about influence and that requires good relationships. His example: if someone says they can't deliver on time, tell them you'll give the project to someone else. They may then realize that was the consequence and find a way to finish, and you haven't coerced them. Rachitsky connects this to Mihika Kapoor's idea that no is really "not yet," and Berger agrees a no may reflect how you asked.

Berger says acceptance is "primarily an emotional regulation issue." Once the emotions settle, the world usually says no, and the useful question becomes what you learned and what to try next. He estimates 99 percent of the challenge is the feelings that come up on hearing no, and that getting good at asking means accepting you will hear no all the time and that this is normal.

Berger tells the story of spring 2014, when he became Slack's first PM, shortly after splitting with his co-founder. He came in overconfident, assuming he knew how to do the job, and never clarified what success looked like or what the culture expected. The core team had been through layoffs and wanted someone humble who would earn their trust, which he wasn't hearing. Six weeks in, after a backpacking trip, he found an email saying he was fired, then profusely apologized and had his job back Monday morning.

In the second era, fear was present every day and he went into full people-pleaser mode. For a year of one-on-ones with the CEO, he says, he never said out loud that he wanted a good partnership and to build a great product. After his honeymoon, he was told product management would be eliminated and he'd move to user research. This time he could articulate what he wanted, wrote a proposal for the management team, and within a week had his old job back, which taught him that asking out loud makes you far more likely to get it.

The third firing was final, because by then the company had HR. Berger says he couldn't tolerate the repeated nos from Stewart Butterfield and the management team, because accepting them meant feeling he might not be good enough, so he blamed his boss instead. He spent a year out of integrity, kept everything inside, and says recovery took six months or more, during which he and his wife had a baby.

Looking back, he says the reality was simple: he hadn't articulated what he wanted, hadn't asked, and hadn't listened to the nos that answered his non-ask. "I wasn't the victim. Stewart wasn't the villain. It was just ineffective asking." That experience, combined with seeing how many people suffer similarly, is how he became a coach, and he stresses that a year of pain and fear is why this advice isn't fluffy to him.

Rachitsky notes the three phases had different causes: overconfidence at first, fear later. Berger adds that even the first phase was an articulation failure. Had he said he wanted to do a good job and build good relationships, he would have thought about intentional relationship-building and success metrics in what was a processless early-stage startup.

Asked what he would do differently, Berger says he would have asked for what he wanted: to do the best work of his life, to have a deep partnership with the CEO and the team, and to produce work people loved. He can't say whether he would have lasted; he might have been fired sooner. Asking makes the outcome more likely, but you do it to stay in integrity and avoid suffering, not for a guarantee.

He says the mistake is treating the outcome as a severe existential threat and going into fight or flight, when the honest response is "I'm disappointed, I wish it had worked out." He could have found another job at another startup. Rachitsky calls this a profound point: the practice is about feeling that you did what you needed to do and won't regret it later.

On the classically hard role of first PM, Berger says it comes down to the relationship with the CEO or founders. His clue for people confused by a founder's behavior is to imagine the founder is terrified all the time and see whether that makes the behavior clearer. Being a founder is scary because everything rests on your shoulders, and working with the real state of the people you work for beats pretending or wishing it were different.

To judge fit, he says it is hard to generalize, but it is about understanding expectations and asking "what do you really want?" Founders write job descriptions, then meet a real human with strengths and weaknesses. He suggests clarity about expectations and collaboratively working out how to work together.

He recommends that founders hold a "relationship design conversation" with each of their first ten to twenty employees when they join. Rather than assuming you will do things the way you always have, it asks how best to work together given who is here and what the company needs, and it should not be a performance-management exercise.

Berger says founders often resist letting go of fear, because they believe it is what made them hardworking and smart. The first time he heard this it broke his heart, and he has since heard it dozens of times. His message is that there are other ways to motivate, such as joy, vision and inspiration, and he asks skeptics to try following a meaningful vision and see what it is like not to live in fear all the time.

Asked whether the fear is that you'll stop proving yourself, he says managing fear is a lifelong practice and he isn't done. The shift he sees in clients is from "my fear is keeping me safe" to "fear is for when a tiger is chasing you," and sitting in a desk chair on a Zoom call there is no tiger. The practice is reminding yourself of that and focusing on what you want to achieve rather than on avoiding fears.

His contrarian view is that he doesn't believe in discipline. Some clients come wanting a drill sergeant, but he says discipline, like people pleasing, is a short-term coping strategy: it gets you to the gym for a week, while people who stay a year do so because they want to. He refuses to be the drill sergeant and instead looks for sustainable motivation grounded in vision and pursuing what you want.