10 Ways to Know it’s Safe to Not Play it Safe

Mr. Young Leader gave his first update on an overseas project to the organization. It was OK. He’ll do better next time.

In our follow up conversation, he said, “I probably should have waited.”

I said, “I’m glad you didn’t.”

fire hydrant

There are two types of leaders, those who hold back and perfect before they go, and those who press forward and learn as they go. Mr. Young Leader leans toward holding back. I lean toward pressing forward.

Every organization feels tension between hold-back and press-forward leaders.

Hold-back leaders protect gains and preserve stability. Press-forward leaders take new ground and create instability.


Press-forward leadership fails quickly. Hold-back leadership fails slowly.


Press-forward AND hold-back leadership is essential to organizational success.

Press forward when:

  1. The people you serve know and trust you.
  2. Growth and risk-taking is valued in the organization.
  3. Your trackrecord trends upward. When your trackrecord trends downward, it’s usually better to hold back and perfect a win.
  4. The timeline is short and the initiative is worth the effort.
  5. You’ll do the project again. Learning-as-you-go is most valuable when you’ll use what you learn in the same context, again and again.
  6. Experience is transferable to other projects.
  7. The leadership team supports you as you learn-as-you-go.
  8. Falling short won’t be catastrophic. Ask yourself, “What’s the worst that could happen?” If the worst isn’t that bad, what are you waiting for?
  9. Learning excites you more than failure defeats you.
  10. It’s more risky to do nothing than to try and fail.

When is it better to hold back?

When is it better to press forward, even though you don’t feel ready?

Learn how to navigate tensions between hold-back and press-forward leaders in, “Focus,” by Heidi Grant Halvorson Ph.D., and E. Tory Higgins Ph.D.