Archive - Lessons

Leavers vs. Stayers

Over the years, I’ve come to see that many of us fall loosely into two career archetypes: the leavers and the stayers.

Jun 26

May 2025

Make It Easy to Draw the Elephant

Great communication is simple if you think about it as “connect the dots”. It isn’t about talking more—it’s about creating clarity and alignment. Your…

May 13

April 2025

10x the Problem

When you're stuck—when you're agonizing over a decision, or when it feels like there’s no obvious answer—I have a simple tool I use with founders and…

Apr 30

February 2025

There’s No Such Thing as a Generalist

Generalists vs. specialists — which is better and why? You’ve probably come across at least one think-piece or thread on this topic. It’s everywhere…

Feb 28

December 2024

Molly's TED talk: Jumping Off Career Cliffs

Applications are now open for the next cohort of Glue Club! Glue Club is a leadership development community that helps you be better and feel better at…

Dec 3, 2024

November 2024

Some Lessons for Rapid Scale

The best and worst part of scaling companies is that everything changes all the time. Your job is to get good at change.

Nov 7, 2024

September 2024

Founder Mode: A Liar’s Perspective

If you work in tech, there is no doubt you have stumbled into a conversation in the last week about Paul Graham’s article, Founder Mode.

Sep 10, 2024

August 2024

Work Grief is something we don’t talk about enough. And it is everywhere.

Aug 15, 2024

July 2024

Deciding when it's time to fire someone

One of the hardest things to do as a manager is decide to fire someone. Particularly if you're a new manager, you tend to spend a lot of time blaming…

Jul 16, 2024

Molly's June Tidbits: Optimizing Anthills

I started a thread this month inside our Glue Club slack about work regrets. As always, the Glue Club crew really showed up with self-awareness…

Jul 10, 2024

June 2024

Captains is an ownership model that we implemented at Lambda School that is much simpler than models like RAPID or RACI. It is an elegant and simple…

Jun 19, 2024

Molly's May Tidbits: Saying no

I’m trying a new format to share, once a month, some things I’m reading and listening to, people I admire and you should know about, and things that…

Jun 11, 2024

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