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May 19, 2024 • 1hr 13min
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)
Lenny's Podcast: Product | Growth | Career
In this episode, Lenny interviews Kenneth Berger, an executive coach who works with startup leaders. Kenneth was previously the first product manager at Slack before transitioning to coaching. The conversation focuses on Kenneth's core philosophy of "asking for what you want" - a deceptively simple but powerful concept that he believes is at the root of many career and life challenges.
Kenneth shares insights from his 10+ years as a founder/operator and 7+ years as a coach, explaining why this one skill is so impactful and how to get better at it. He also vulnerably shares his own story of being fired three times from Slack, using it as a case study for what can go wrong when you don't effectively ask for what you want.
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)
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Key Takeaways
- Asking for what you want is a critical skill for career and life success, but many people struggle with it due to fear, lack of confidence, or not knowing what they truly want
- The three key steps to effectively asking for what you want are:
- Articulate what you want clearly
- Ask for it intentionally
- Accept the response (even if it's a "no")
- Complaints often reveal underlying desires - use the "dream behind the complaint" technique to uncover what you really want
- Hearing "no" is a normal part of the process - don't take it personally, learn from it, and try again
- Aim for a "h**l yes" rather than settling for a lukewarm response when asking for what you want
- Fear and discipline are overrated motivators - focus on vision and pursuing what truly inspires you for sustainable motivation
- Staying in integrity with yourself by asking for what you want, even when it's scary, leads to more fulfillment than playing it safe
Introduction
In this episode, Lenny interviews Kenneth Berger, an executive coach who works with startup leaders. Kenneth was previously the first product manager at Slack before transitioning to coaching. The conversation focuses on Kenneth's core philosophy of "asking for what you want" - a deceptively simple but powerful concept that he believes is at the root of many career and life challenges.
Kenneth shares insights from his 10+ years as a founder/operator and 7+ years as a coach, explaining why this one skill is so impactful and how to get better at it. He also vulnerably shares his own story of being fired three times from Slack, using it as a case study for what can go wrong when you don't effectively ask for what you want.
Topics Discussed
The Importance of Asking for What You Want (4:31)
Kenneth explains that asking for what you want is fundamentally about integrity - being true to yourself and what you desire. Many people think they already know how to do this, but often fool themselves.
Key benefits of getting better at asking for what you want:
- Helps you pursue what's truly important to you
- Leads to greater fulfillment and sense of purpose
- Improves relationships and ability to influence others
"If we don't do that well, then we're kind of fooling ourselves that we're actually moving towards what we want. There tends to be all these sort of unexpected secondary and tertiary effects that come out of that right. Of stress and frustration and unhappiness."
Challenges That Arise When People Struggle to Ask for What They Want (6:36)
Kenneth identifies two common signs that someone needs to work on this skill:
- Feeling stuck - trying the same ineffective approaches repeatedly
- Frequent interpersonal conflicts - often stemming from poor communication
He notes that people tend to fall into two problematic modes:
- People pleasing - holding back and not expressing desires
- Entitlement - demanding things without respect for others
A Personal Example of Failing to Ask for What You Want (8:09)
Kenneth shares how his attachment to being "right" as a product manager often led to unproductive conflicts. He would enter meetings convinced of his position rather than being open to other perspectives.
"It's fundamentally disrespectful to go into a meeting already deciding that you're right and the other person is wrong, because you can't know that for sure."
Signs This is a Skill You Need to Work On (9:17)
Additional indicators you may need to improve at asking for what you want:
- Feeling like everything is high stakes
- Focusing more on fears than desires
- Difficulty articulating what you truly want
How to Get Better at Knowing What You Want (10:49)
Kenneth recommends the "dream behind the complaint" technique:
- Identify something you frequently complain about
- Envision a world where that complaint is resolved
- Explore what that implies about your deeper desires
He emphasizes checking if the dream feels both inspiring and credible. If it's embarrassing to say out loud, it may not be the right dream.
"Let's imagine you get that. That's the world of the future that you get. How does that feel? Is that big enough, or is it kind of meh?"
Why Hearing "No" is a Normal Part of the Process (15:28)
Kenneth advocates for an expanded definition of "no" - anything short of an enthusiastic "h**l yes" should be considered a no. This helps avoid settling for lukewarm commitments that often lead to disappointment.
He emphasizes that hearing "no" frequently is normal and provides valuable data to refine your approach. The key is to keep iterating rather than giving up.
Getting a "Yes" vs. a "H**l Yes" (17:29)
Kenneth explains the importance of aiming for a "whole body yes" or "h**l yes" rather than settling for reluctant agreement. Signs of a true "h**l yes":
- Enthusiastic verbal agreement
- Aligned body language and tone
- Follow-through on commitments
"You can really feel in your body when you've got a h**l yes. Right. When all of you is fully in and ready to do this."
Step 1: Articulate What You Want (19:20)
Kenneth outlines common pitfalls in articulating desires:
- Saying "it's fine" when it's not
- Expressing unrealistic or entitled demands
He recommends:
- Tuning into subtle emotions and preferences
- Saying desires out loud to reality-check them
- Digging deeper to uncover core emotional/social goals
Doing an Integrity Check (24:07)
Kenneth suggests doing an "integrity check" by asking:
- Have I fully expressed myself?
- Am I tuning into my true feelings?
- Is there something I keep thinking about saying but haven't?
"Articulating what you want is really about mindfulness because it's about checking for all these things like, yeah, what is the part of me that's not fully expressed?"
Step 2: Ask for What You Want Intentionally (26:56)
Kenneth emphasizes the importance of asking intentionally rather than falling into habitual patterns. This involves:
- Recognizing your default asking style (e.g. people-pleasing, demanding)
- Challenging narratives that make you resist asking differently
- Being willing to feel uncomfortable
"Part of asking for what you want effectively is really just recognizing the rut that you get stuck in and sort of working through all those narratives that make us resist asking in a different way."
Understanding Your Influence (30:45)
Kenneth notes that many people, especially individual contributors, underestimate their influence. He recommends:
- Recognizing the value of your opinion and relationships
- Expressing views humbly but clearly
- Not relying solely on data - your perspective matters
"Your relationships matter and that just your opinion because you believe something or because you want something, often that's enough."
Using Complaints as Inspiration (34:48)
Kenneth reiterates how complaints can reveal underlying desires:
- Identify a frequent complaint
- Envision resolving that complaint
- Explore what that reveals about your deeper wants
- Frame it as a positive desire/request
Internal Family Systems (36:24)
Kenneth briefly touches on Internal Family Systems therapy, which views the psyche as made up of distinct parts. He recommends embracing and validating all parts of yourself, even those you're less comfortable with.
Giving Feedback (38:00)
Kenneth references the "Radical Candor" framework and suggests a structure for giving feedback:
- Describe the specific behavior
- Express how it made you feel (using a feeling word)
- Explain why you're sharing this
- Make a clear request for change
Step 3: Accept the Response (41:24)
Kenneth explains that accepting the response is often the trickiest step. Key points:
- Anything short of an enthusiastic "yes" should be considered a "no"
- Don't over-accept (giving up entirely) or under-accept (ignoring the no)
- View "no" as valuable data for refining your approach
- Respect others' right to say no - it builds better relationships
"The challenge of accepting the response is often that of hearing the no, but not over accepting or under accepting it."
Kenneth's Experience of Being Fired Three Times from Slack (45:22)
Kenneth vulnerably shares his story of being fired three times from Slack in his first year there. He breaks down the mistakes he made in each phase:
- Initial overconfidence - not articulating his desires or seeking clarity on expectations
- People-pleasing mode - afraid to ask for what he wanted after first firing
- Blaming others - unable to hear and accept the "no" he was receiving
He reflects on how this painful experience taught him the importance of integrity and effective asking.
"I spent that year being fully out of integrity with myself, never saying what I really wanted, how I really felt, because it didn't feel safe. I was too scared. I kept it all inside."
Advice on Being the First PM at a Company or Startup (57:30)
Kenneth's tips for succeeding as a first PM:
- Focus on building a strong relationship with the CEO/founders
- Recognize founders are often operating from a place of fear
- Have clear conversations about expectations and working styles
- Design the relationship intentionally rather than making assumptions
Contrarian Corner: Anti-Discipline (1:04:58)
Kenneth shares his contrarian view that discipline is overrated. He believes:
- Discipline is a short-term coping strategy, not sustainable long-term
- True motivation comes from pursuing a compelling vision
- Focus on finding sustainable sources of motivation rather than forcing yourself
"The people who are in the gym for a year are doing it because they want to. Right. There's actually something that's motivating for them in that that's not just, oh, I hate this, but I'm going to go anyway."
Conclusion
Kenneth Berger's approach to "asking for what you want" offers a powerful framework for improving communication, relationships, and overall life satisfaction. By articulating desires clearly, asking intentionally, and gracefully accepting responses, individuals can move towards greater integrity and fulfillment. While it may feel uncomfortable at first, embracing this practice can lead to profound personal and professional growth.
The conversation highlights how many high-achievers rely on fear and harsh self-discipline, but there are more sustainable ways to motivate ourselves. By connecting to genuine desires and inspiring visions, we can pursue our goals from a place of enthusiasm rather than anxiety.
Ultimately, the skill of asking for what you want is about having the courage to express yourself authentically, even when it's scary. It's a practice of aligning your outer actions with your inner truth, leading to more meaningful relationships and a greater sense of purpose.
