21 July 2022

Telling Stories To The Boss

This is an exec member exclusive video.

Your job is to tell a great story to your boss—whether she's the CTO, the CEO, or the Board of Directors. Like all great stories, your story about what you or your team are doing should have a beginning, middle, and end; it should have antagonists and drama; it should give the listener a framework and language to fit his or her experiences into. And it should compel changes in thinking and behaviour, whether that's telling customers to wait for the next big release or adding ten contractors to the team.

But far too often, I hear clients "thinking out loud" or giving reams of "context" when the situation calls for a crisp, clean story. Just last week a CTO was explaining the minutiae of her performance tuning in WebAssembly to a board member, when the question on the table simply was, "Do our customers care about making our software faster?" My coaching clients know that I bug them endlessly to define the topic and their question in a sentence, or half of one, not pages and paragraphs.

Let's discuss how and why to create a coherent, compelling narrative about your technology, product strategy, or company trajectory:

How Pixar and the Hero's Journey give you the universal outline for any strategic discussion.
How to "reify" the messy real world, with inconvenient customer demands and unknown market conditions, into the neat boxes of a clear story.
How to give opinionated guidance on topics where your knowledge is limited—or nonexistent.