If you're feeling stuck, today's episode is for you. After a decade in the tech industry (including being the first PM at @SlackHQ), Kenneth Berger (@kberger) transitioned into coaching on a mission to help startup leaders change the world by learning to ask for what they want, live with integrity, avoid burnout, and build genuine relationships even with the people they find most challenging. In our conversation, we dig into: 🔸 Why asking for what you want is so powerful 🔸 Three steps to effectively ask for what you want 🔸 The “dream behind the complaint” technique for uncovering what you want 🔸 Why hearing “no” is a normal part of the process 🔸 Kenneth’s experience of being fired three times from Slack 🔸 Why discipline is overrated 🔸 Much more Listen now 👇 - YouTube: youtu.be/KSCjl_VIdak - Spotify: open.spotify.com/episode/0N0… - Apple: podcasts.apple.com/us/podcas… Some key takeaways: 1. Signs you may not be asking for what you want include feeling stuck, having frequent interpersonal conflicts, or a pervasive sense that the stakes are extremely high. 2. There are three key steps to asking for what you want: a. Step 1: Articulate what you want: Get clear on your desires, dreams, and goals. If you struggle with this, look at your complaints—they point to an implied better future you envision. b. Step 2: Ask for what you want intentionally: Don’t expect others to read your mind. Ask clearly and directly while being open to their response. Come from a place of humility rather than entitlement. c. Step 3: Accept the response: Reframe a no as valuable information rather than failure. It’s not a final destination but an invitation to get curious, iterate, and try again. 3. Learn to respect a no. This means not under-accepting or over-accepting it. Under-accepting a no is when you treat it as invalid and refuse to learn what you can from the experience. Over-accepting a no is when you treat it as too valid, to the point where you assume you’ll only ever hear no’s again in the future and therefore should stop asking for things you want. When you hear a no, learn from the experience and push forward with the understanding that you won’t always get what you want, and that’s OK. 4. Practice the “dream behind the complaint” technique: When you catch yourself complaining, use it as an opportunity to uncover what you truly desire. Every complaint implies a vision of a better scenario. After identifying the dream behind the complaint, assess its inspiring nature. Is it compelling enough to motivate you? If not, dig deeper to uncover a dream that truly excites and motivates you. 5. Even if you’re not a founder or in a position of traditional power, you still have influence. Whether you’re a product manager, individual contributor, or part of a team, your opinions and perspectives matter more than you might realize. Don’t underestimate the impact of voicing your concerns or suggestions. Even if you’re not the decision maker, sharing your perspective can lead to meaningful discussions and potentially influence the outcome. Be willing to express disagreement respectfully and offer alternatives or solutions.

Always trust yourself to make the right decision. You will.

If you're feeling stuck, today's episode is for you. After a decade in the tech industry (including being the first PM at @SlackHQ), Kenneth Berger (@kberger) transitioned into coaching on a mission to help startup leaders change the world by learning to ask for what they want, live with integrity, avoid burnout, and build genuine relationships even with the people they find most challenging. In our conversation, we dig into: 🔸 Why asking for what you want is so powerful 🔸 Three steps to effectively ask for what you want 🔸 The “dream behind the complaint” technique for uncovering what you want 🔸 Why hearing “no” is a normal part of the process 🔸 Kenneth’s experience of being fired three times from Slack 🔸 Why discipline is overrated 🔸 Much more Listen now 👇 - YouTube: youtu.be/KSCjl_VIdak - Spotify: open.spotify.com/episode/0N0… - Apple: podcasts.apple.com/us/podcas… Some key takeaways: 1. Signs you may not be asking for what you want include feeling stuck, having frequent interpersonal conflicts, or a pervasive sense that the stakes are extremely high. 2. There are three key steps to asking for what you want: a. Step 1: Articulate what you want: Get clear on your desires, dreams, and goals. If you struggle with this, look at your complaints—they point to an implied better future you envision. b. Step 2: Ask for what you want intentionally: Don’t expect others to read your mind. Ask clearly and directly while being open to their response. Come from a place of humility rather than entitlement. c. Step 3: Accept the response: Reframe a no as valuable information rather than failure. It’s not a final destination but an invitation to get curious, iterate, and try again. 3. Learn to respect a no. This means not under-accepting or over-accepting it. Under-accepting a no is when you treat it as invalid and refuse to learn what you can from the experience. Over-accepting a no is when you treat it as too valid, to the point where you assume you’ll only ever hear no’s again in the future and therefore should stop asking for things you want. When you hear a no, learn from the experience and push forward with the understanding that you won’t always get what you want, and that’s OK. 4. Practice the “dream behind the complaint” technique: When you catch yourself complaining, use it as an opportunity to uncover what you truly desire. Every complaint implies a vision of a better scenario. After identifying the dream behind the complaint, assess its inspiring nature. Is it compelling enough to motivate you? If not, dig deeper to uncover a dream that truly excites and motivates you. 5. Even if you’re not a founder or in a position of traditional power, you still have influence. Whether you’re a product manager, individual contributor, or part of a team, your opinions and perspectives matter more than you might realize. Don’t underestimate the impact of voicing your concerns or suggestions. Even if you’re not the decision maker, sharing your perspective can lead to meaningful discussions and potentially influence the outcome. Be willing to express disagreement respectfully and offer alternatives or solutions.