Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)
Kenneth Berger, former first PM at Slack and now an executive coach, shares his "magnum opus" on the critical skill of asking for what you want. He covers how to identify desires, overcome resistance, ask effectively, and accept responses, emphasizing integrity and sustainable motivation over fear.
Deep Dive Analysis
14 Topic Outline
Introduction to Kenneth Berger and 'Ask for What You Want'
The Importance of Integrity in Asking for Desires
Challenges and Signs of Struggling to Ask
Techniques for Discovering and Articulating What You Want
The Concept of 'Hell Yes' and Accepting 'No'
Step 1: Articulating Your Desires Clearly
Step 2: Asking for What You Want Intentionally
Leveraging Influence and Relationships in Asking
Using Complaints as Inspiration for Desires
Step 3: Accepting the Response and Learning from 'No'
Kenneth's Story: Fired Three Times from Slack
Lessons from Being the First Product Manager
Contrarian View: Why Discipline is Overrated
Lightning Round Highlights
5 Key Concepts
Integrity
Integrity, in the context of asking for what you want, means genuinely pursuing the things that are important to you, honoring the world's response (including 'no's), and moving forward towards your desires. It's about not fooling yourself about what you truly want or your actions towards it.
Dream Behind the Complaint
This technique suggests that every complaint implies a dream or a better world where the complaint is resolved. By analyzing what you complain about, you can uncover underlying desires and articulate a vision for a more satisfying future.
Hell Yes
A 'hell yes' signifies enthusiastic consent, a 'whole body yes' where all parts of a person are fully committed and in agreement. Anything less than a 'hell yes' should be interpreted as a 'no' to ensure genuine buy-in and avoid future disappointments.
Over/Under Accepting 'No'
Over accepting 'no' means treating a single rejection as a permanent end to a dream, leading to giving up too easily. Under accepting 'no' involves disregarding the 'no' or disrespecting the other person's right to decline, which damages relationships and hinders learning.
Internal Family Systems (IFS)
A psychotherapy technique that views the mind as composed of various 'parts' with different perspectives and motivations. Embracing and validating all these parts, including those that are scared or resistant, is crucial for understanding oneself and effectively asking for what one wants.
7 Questions Answered
Signs include feeling stuck in your career or life, experiencing recurring interpersonal conflict, or feeling that situations are consistently high-stakes, which often shifts focus to fear rather than desired goals.
A key technique is to identify your complaints, as every complaint implies a dream or a better resolved world. Also, perform an integrity check by noticing how fully you express yourself and tuning into subtle emotions or unsaid thoughts.
Hear anything short of an enthusiastic 'hell yes' as a 'no'. Recognize that 'no' is normal and provides valuable data for what to try next. Avoid over-accepting (giving up entirely) or under-accepting (disregarding the 'no') the response.
Ask clearly but with great humility, acknowledging that it might not be your call but expressing what is important to you. Recognize that your relationships and personal opinion often carry more influence than you might think, even without hard data.
Complaints are valuable inspiration because they reveal what frustrates you and, by extension, what kind of better future you envision. Embracing this 'whiny part' of yourself can lead to compelling and useful desires.
Recognize that fear is often an emotional response to perceived threats that aren't truly existential. Instead of letting fear drive you, focus on an inspiring vision and what you want to achieve, which provides a more sustainable motivation.
Discipline is seen as a short-term coping strategy that is unsustainable over many years. True long-term motivation comes from joy, vision, and pursuing what you genuinely want, rather than relying on external pressure or fear.
11 Actionable Insights
1. Master Asking & Accepting
To effectively pursue your goals and live with integrity, articulate exactly what you want, ask for it intentionally, and then genuinely accept the response, using any “no” as data to learn and try again. This iterative process helps you move forward towards your desires.
2. Complain to Discover Dreams
When unsure what you want, pay attention to your complaints, as every complaint implies a dream of a better world where that issue is resolved. Use this to envision a future that feels inspiring and credible, rather than just “fine.”
3. Practice Intentional Asking
Recognize your default asking style (e.g., people-pleasing by not asking, or control-freak by ordering) and consciously choose a different, more effective approach. This involves expressing who you are and what you stand for, rather than staying stuck in old patterns.
4. Embrace “Hell Yes” as the Only “Yes”
When asking for something, consider anything less than an enthusiastic “hell yes” (or “whole body yes”) as a “no,” to avoid settling for lukewarm commitment. If you receive a “no,” ask, “What would it take to get to a hell yes?” to find a mutually agreeable path forward.
5. Confront Asking Resistance
Address the internal narratives (e.g., “too risky,” “not worth it,” “they’ll say no anyway”) that prevent you from asking for what you want. Embrace and validate all parts of yourself, including the scared parts, to soften fears and move past being stuck.
6. Ask with Humility and Clarity
When expressing a desire or disagreement, especially as an individual contributor, state your opinion clearly while also demonstrating humility (e.g., “I know it’s not my call, but it’s important to me that you know this”). This approach makes your ask less threatening and more influential.
7. Value Opinion Over Data
Don’t let the absence of hard data prevent you from expressing your opinion or gut feeling, especially in product roles. Your relationships and personal belief can be powerful leverage, as people you work with often care about your perspective.
8. Structured Feedback Protocol
When delivering feedback, use a factual and feeling-based template: “When you do [behavior], I feel [feeling], and I’m telling you this because [what you want them to change].” This helps ensure the feedback is received and understood without judgment.
9. Vision-Driven Motivation
Shift your primary motivation from fear (e.g., fear of not being good enough) to joy, vision, and inspiration. Operating from a place of desire for what you want to achieve is more sustainable and fulfilling than constantly running from fears.
10. Proactively Design Founder Relationships
If you’re a first PM or reporting to a founder, proactively engage in “relationship design conversations” to clarify expectations and collaboratively define effective ways of working together. Assume founders are often terrified, which can help you understand their behavior.
11. Rethink Discipline’s Role
Recognize that discipline, while effective in the short term, is often unsustainable for long-term motivation. Instead of relying on a “drill sergeant” approach, cultivate motivation based on an inspiring vision and genuine desire for what you want.
7 Key Quotes
If I had to answer in one word, it would be integrity.
Kenneth Berger
Every complaint implies a dream.
Kenneth Berger
It's not a yes unless it's a hell yes.
Kenneth Berger
What would it take for us to get to a hell yes?
Kenneth Berger
Your relationships matter and that just your opinion because you believe something or because you want something, often that's enough.
Kenneth Berger
My fear of not being good enough is what drives me to be great.
Kenneth Berger
Discipline will get you in the gym for a week, but it's not going to get you in the gym for a year.
Kenneth Berger
2 Protocols
Three-Step Process for Asking for What You Want
Kenneth Berger- Articulate what you want.
- Ask for what you want intentionally.
- Accept the response (and try again, as it's an iterative process).
Framework for Giving Feedback (Carol Robin)
Carol Robin (as described by Lenny)- When you do [a specific behavior].
- I feel [a specific feeling].
- I'm telling you this because [what you want them to change/the impact].