The Scariest Question You’ll Ever Ask

One of the best leadership skills you’ll ever develop is the ability to ask wise questions. The best leaders I know are ferocious question askers. They’re always looking to learn, and there’s no one they can’t learn from.

Leaders are readers sure, but the best of them are also questioners.
Questioners of the status quo, questioners of those who are succeeding in their field, and questioners of how much of what most would call impossible really is.

While I don’t know him personally, I imagine that Andy Stanley is a phenomenal questioner. A while back on the “The Art of Inviting Feedback” episode of the best leadership podcaston the planet, he actually introduced a question for leaders to ask their teams that was scarier than any I’d ever heard. In fact as soon as I finished the podcast, even though Andy’s challenge was for the leaders listening to go and ask this question to their teams my first though was, “There’s NO way I could ever do that!”

Simply put I believe the question that Andy introduced is one of the hardest, yet most important questions a leader will ever ask.

What is it? Simply this- Andy encouraged all leaders to ask their team,

If you were me, what would you do differently?

Now maybe you’re a better leader than me, and you read that and think you wouldn’t have any trouble asking that. Good for you! I wish that had been the case for me. Unfortunately it wasn’t.

For me as soon as I heard the question I broke out in a cold sweat. The mere thought of asking the people that I work closest with to comment so directly on my leadership choices was terrifying.

So I avoided it, and I paid the price.

You see what Andy explained so well in the episode is that the question is so important because, no matter what, everyone’s already got an answer.

The people you lead have ideas about how you can lead more effectively. They’ve got insight into things that you don’t. And here’s the kicker, they’re likely already talking about those things with others.

That basic fact of organizational life means every leader has two choices, one that produces short term pain and long term gain, and the other the opposite. Leaders can have the courage to ask the question; to come face to face with some of their most glaring weaknesses so they can have a chance to correct them. Or they can remain silent and enjoy the false peace of a flawed but comfortable culture.

While I wish I had chosen the former, after listening to the podcast I sadly chose the latter. I completely copped out of Andy’s challenge and never got around to asking the question. Until last week.

Last week I had my first opportunity to do an exit interview with one of our staff who’s making a career change and transitioning out of FBC. As I prepared the questions for the interview I remembered Andy’s question and figured I’d ask it. After all, at that point I didn’t have anything to lose.

Any damage that had been done was done, and the risk of the question opening up a relational rift was mitigated. But I could at least learn from the question to hopefully improve in my leadership for the immediate future.

So I asked it, and I was devastated by the response.

I won’t share the response in detail here (that’s another post for another time). But needless to say, what was so damning about the response was what a surprise it was to me. The area of change this individual identified was one that I’d never have thought about changing without having asked, but could have changed oh-so-easily had I just had the courage to ask earlier.

In a moment the foolishness of my avoiding the question all those months became clear as day. All I’d done by avoiding it was to allow an easily fixed problem to fester.

What could have been quickly remediated instead became a stumbling block to my leadership, and cost me the chance to earn further respect from those I led by demonstrating that I care about getting better. I’m grateful that God gave me the courage to finally ask the question, I just wish I’d had it sooner.

What about you? If you’re a leader can you imagine asking this question to those you work with? If you’re on a team, how would you react if your supervisor asked you the question?

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