The Two Skills Every Chief of Staff Must Master

⏱️ 2 min read

There are many skills that make a strong Chief of Staff—but two show up again and again as true force multipliers:

Simplify.
Synthesize.

Years ago, I supported a sales leader whose office sat right outside my desk. At least once a day, I’d hear him muttering (sometimes loudly):

“I don’t have time to read all this $h!t. Just tell me what you want.”

Every time, I’d call back: Forward it to me.

He’d send along a fifty-slide deck, two-page email, or epic Slack message. I’d skim it and send him something like this:

Here’s what they want:

  • We need to choose between two locations for Sales Kickoff
  • Option A is expensive but guaranteed to be great (30% more)
  • Option B is cheaper and might be fine… or might not
  • They want you to own the decision
  • Their recommendation: go with Option A

All I did was make the message decision-ready. Slim on details and drama.

Over time, I didn’t just translate—I coached his team to do this themselves:

  • Lead with a TL;DR summary
  • Separate context from decision
  • Make a recommendation, even if it’s imperfect

This is the quiet power of a great Chief of Staff: cutting through noise, surfacing signal, and helping leaders decide faster—and better.

The good news? These two skills—simplify and synthesize—are easier than ever to develop. Strip out confidential details and use tools like ChatGPT or Copilot to summarize long messages. Or lean on simple frameworks:

  • 1-3-1: one recommendation, three reasons, one clear ask
  • Context → Options → Recommendation

If a leader can’t understand your email or Slack in under a minute, the message isn’t ready yet. Simplify and synthesize.

And if the next step isn’t clear? There likely won’t be one.