Great leaders take risks. There are no sure things, in life or leadership!

That’s why I coach CEOs, founders, and startup executives to pursue their boldest ambitions by embracing risk instead of avoiding it. Instead of waiting to be sure, we experiment and prove empirically which style of leadership works best for them.

I’ve spent 20+ years in the tech world pursuing my own bold ambitions: as a founder backed by top investors, an operator at companies like Slack and Adobe, and now a coach and trusted confidant to startup leaders.

In my experience, there are four key risks that great leaders take again and again:

Great leaders risk pursuing their boldest ambitions.
They risk asking for help.
They risk admitting when they fail.
They risk changing how they lead.

  1. Great leaders risk pursuing their boldest ambitions.
    They don’t compromise or wait around for a sure thing. 
  2. Great leaders risk asking for help.
    They don’t coerce others or do it all themselves. 
  3. Great leaders risk admitting when they fail.
    They don’t blame others or deny their failures. 
  4. Great leaders risk changing how they lead.
    They don’t just stick with what’s familiar or give up entirely.

By taking these risks every day, my clients quickly learn what works and what doesn’t to achieve their ambitions. Sure, taking risks every day can feel stressful at first. But it’s also an opportunity to learn to manage their stress and build their capacity for risk-taking over time.

Can you name your boldest ambitions? Have you asked for help achieving them? Have you admitted where you’ve failed thus far? Will you change your approach and try again?

If you’re not satisfied with your answers, you’ve got an opportunity to master embracing risk—and I’d love to help. To me it’s a tragedy how often we give up on our ambitions by accident, and it’s my mission to change that.

Are you a CEO, founder, or startup executive interested in working with me 1:1? Let’s talk.