Lenny Distilled

Why not asking for what you want is holding you back

May 19, 2024

Featuring: Kenneth Berger (Executive coach, first PM at Slack)

7 quotes · 6 insights

Watch Full Episode

Hell yes or rework the request

It's not a yes unless it's a hell yes. You really want enthusiastic consent. Not just, 'Maybe, kinda. I'll try. We'll see. But yeah, absolutely, let's do this.'
Kenneth BergerExecutive coach, first PM at Slack 16:26
What would be a hell yes day for you where you could say, absolutely, we can deliver on that? That way we're not making them wrong for saying no. We're saying, 'Of course you get to say no. Everybody gets to say no whenever they want. But let's get to a hell yes. What would it take for us to get there?'
Kenneth BergerExecutive coach, first PM at Slack 00:17:03

Vulnerability and authenticity build stronger influence than authority

If you go the other direction and you're humble and you say, 'I know I can't make you do anything, it's not my call to make. But man, this is really what I want. I'm just going to put it out there and ask.' That I think it feels really vulnerable and uncomfortable to not lean on data as a sort of way of saying, 'No, no, I'm right, so you should believe what I believe.'
Kenneth BergerExecutive coach, first PM at Slack 00:33:13

Quitting late is worse than quitting early

The core idea is ask for what you want. Turns out when you actually ask for what you want out loud, you're much more likely to get it.
Kenneth BergerExecutive coach, first PM at Slack 00:00:23

Ask for what you want - the worst is status quo

If you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind. And if you're sort of more in the control freak camp, maybe you're used to ordering people around and saying, 'Go do this now.'
Kenneth BergerExecutive coach, first PM at Slack 00:00:34

Crisis is inevitable - prepare your mindset

Imagine if you're confused about how your founder is behaving. Imagine that they're terrified all the time, and see if that makes their behavior more clear.
Kenneth BergerExecutive coach, first PM at Slack 00:58:05

Detachment from outcomes improves performance

My fear of not being good enough is what drives me to be great. And I just want to come out here and say there's other ways to motivate. You can motivate based on joy, based on vision, based on your inspiration in this vision of what you want.
Kenneth BergerExecutive coach, first PM at Slack 01:01:34

The Missing Stamp

Every episode of Lenny's Podcast, distilled into the insights that matter and the quotes that make them stick.

LENNY WAS HERE__STAMP_DATE__

Lenny, if you're reading this, the stamp's ready when you are. 🧡🔥