1 Question Every Leader Should Ask

1 Question Every Leader Should Ask

Creating high-performance teams


Hi there ????. Ready to lead? "Acts of Leadership" helps people, (irrespective of title or tenure), expand their leadership range one experiment at a time. Each issue shares a [pro/e]vocative definition of leadership, an idea and an experiment.


Creating something better than you can imagine

I was in tech for 25 years and I’ve been supporting people with leadership in one way or another for 30.

My hardest work in that time has been developing my own leadership—expanding my own leadership range and impact.

I’ve done things I never thought I could.

I felt fear and acted anyway.

It’s true that I’ve missed more than I’ve been on target. And I hit targets I never dreamed possible.

The key to accessing my potential on these transformational occasions came from someone else. And in each case that key was just one short question.

Now I use this question with the leaders I coach. And I’ll share it with you.


Sometimes you need someone else to see what is possible for you.

A Definition…

"Leadership is... helping others create outcomes that are better than they can imagine for themselves."

An Idea…

Challenge someone to something big

Two simple words— (an invitation)

“Will you… [name the challenge]”

Think of a time when someone asked or suggested something you thought was unachievable AND felt equal excitement and fear about.

Something that if left to your own devices you would not dare to consider as possible?

How to believe impossible things?

Here are some of my impossible things— the stuff that excited me and felt out of reach, that someone challenged me with…

?? “Will you take lead on facilitating our leadership development program?”

?? “Will you move to New York City and lead the team there?”

?? “I think we should have you aim for a sub 3.30 marathon. – Sound good to you?”

?? “Will you fly to Mexico and co-lead the expedition?”

?? “I think you’ve got this. Wanna give it a go?” (standing at the bottom of a climb I’d always wanted to climb and been too scared to try)

How to be the first follower*

Here’s how it works…

  1. Ask “Will you…”
  2. Add the bold/audacious/big goal that you (truly) see as a possibility for them.
  3. Offer ‘yes’, ‘no’, or a counter-offer as the possible responses.
  4. Stay quiet and sit with them in whatever comes next.

The measure of a challenge

If they say yes without hesitation you’ve pitched the challenge too low. What you thought was a challenge they see as easy. Actually you just kind of insulted them! Lift your sights and see what is possible for them.

If their mouth opens and shuts repeatedly, without words; if they look to the sides for the door; then you’ve pitched it right. Your challenge lifts them up.

You’ve shown them a reflection of themselves they’ve not dared see before.

The offer of a bold challenge is a serious compliment

The biggest act of leadership is to see the greatness in others they cannot see for themselves; to hold your people larger than they hold themselves.


An Experiment…

?? - A Challenge: Will you offer 20 challenges to people this week? (yes, no, counter-offer)


An invitation to explore…

?? TED: Derek Sivers “How to start a movement ” (The power of the first-follower)


Leadership needn't be lonely!

Lead when ready!


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