Make It Easy to Draw the Elephant
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. (If you want to learn more about how Lessons and the community work, you can read more here.)
Ever played a game of telephone inside a startup? It starts with someone whispering, "We need to focus on user growth," and by the time it reaches the last person, it's somehow turned into, "We're pivoting to enterprise AI."
If you're leading a growing company, you’ve probably felt this pain: people are working hard but are misaligned, projects that should have been simple turn into messes, and teams waste time fixing misunderstandings instead of building momentum. It all comes down to communication—or, more specifically, bad communication.
The Elephant Problem: Why Communication Falls Apart
Remember these “connect the dots” puzzles from when we were kids? You were given a picture like the one below and told to connect the dots. Once you did, it revealed an animal or a person or something fun.
One way to think about running a company is to imagine that you are giving different teams at your company a picture like this one. By doing things like communicating a vision, setting goals, and reiterating priorities, you’re asking them to own and fill in separate parts of a dot-grid picture. You’re giving Marketing 1-20, Sales is assigned to 21-35, Engineering gets 36-45, and so on.
Your job is to give them the outline; their job is to connect the dots.
But as anyone who played this game will remember, there are very different versions of these dot drawings — some are easy and some are more challenging.
