Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)

May 19, 2024 1h 13m 11 insights Episode Page ↗
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.
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.