The ONE Question To Ask When You Don't Know What To Do as a Leader

You’d think that at some point, you’d just know what to do.

That the questions and doubt would go away, and that you’d have a clear answer to the questions and problems that come your way as a leader.

Dream on.

Sure…you get better at calling shots as you mature and grow as a leader. But there are always questions that stump even the best leaders.

Then what do you do?

What if there was a single question that could guide you much closer to the right answer?

I think there is.



I Got A Call The Other Day…

I got a call the other day from a great friend.

He had a tough ethical dilemma. It’s not appropriate for me to go into the details, but it’s the kind of ethical/relational problem that stumps even the brightest leaders.

I could see it from both sides. So could he. And yet the stakes were high.

We talked about what scripture had to say about the issue. But again, you could apply it from several different angles.

There was no clear answer.

After about 30 minutes of conversation, I remembered the question I’ve learned to ask myself when I’m stuck and no one seems to know what to do and scripture isn’t crystal clear.

I gave him the question.


The Question That Can Answer Your Question

The question is this:

Five years from now, what will you wish you had done?

I don’t know why…but for me this is a tremendously clarifying question.

I think you can get a picture of the future you…a picture of you saying things like “I’m so glad I ________” or “I’m so glad I didn’t _________”.

For some reasons, seeing yourself in the future with the result well behind you clarifies things for me.

I wonder if it would for you.


Try It

Think about a situation you’re facing right now in which there is no clear answer.

Then ask yourself the question

Five years from now, what will I wish I had done?

My guess is you might get some clarity:

I will wish I had:

Gone for it


Held back

Spoke the truth

Not said those words

Talked about it face to face

Gone to the event

Stayed home

Started it

Finished it


Held on to my money

At least tried

Died trying (I’ve actually said this to myself…it’s not a bad thing to give yourself completely to a cause you believe in)

Do you see how clarifying this can be?

It’s not that there’s an answer that’s always right. Sometimes you speak. Sometimes you shut up. Sometimes you do it. Sometimes you hold back. Sometimes you try. Sometimes you abandon the idea.

But imagining yourself in the future can lead you to a great answer.

Moreover, this works in





There are things you’re going to regret saying and doing in your marriage, to your kids and in so many other areas 5 years from now, and so many things you will wish you had done.

So just act accordingly.

Seeing yourself 5 years in the future living with the consequences of whatever path you take can be SO clarifying.

In many ways you just need to picture the future you and ask yourself what the future you would tell you to do.

Figure that out.

Then do it.


Ask Around

If you’re a regular reader, you know I’m a big fan of every leader (and person) having an inner circle of wise counsel (if you don’t have one, here’s how to set one up).

You can (and should) go to that inner circle to ask them what to do.

But here’s a twist.

Ask them the question: What do you think I’m going to wish I had done five years from now?

See what they say.

You might also ask them: And if you were facing this, what do you think you would wish you had done five years in the future?

All of this can be tremendously clarifying.

Even if you can’t figure out exactly what to do or are still a bit uncertain, it can break the paralysis that most of us face from time to time and give you a direction that’s worth pursuing.


What About You?

Have you ever asked this question?

Do you have another question you ask when you don’t know what to do?

I’d love to hear from you! Leave a comment!


  1. Jeff on July 25, 2014 at 6:24 am

    I’m not sure how you got my mail rerouted through Canada, but you’ve clearly been reading it. 🙂 Just what I needed right now.

    • Carey Nieuwhof on July 27, 2014 at 8:49 pm

      Ha ha. Jeff…appreciate that. Thanks my friend!

  2. […] What do you do when you don't know what to do as a leader? Asking this ONE simple question can clarify so much and get you unstuck.  […]

  3. Chris Shumate on July 24, 2014 at 8:19 am

    This reminds me of Andy Stanley’s book “The Best Question Ever”. I try to filter many things I do through those three sub-questions:
    1, In light of my current situation, What is the wise thing to do?
    2. In light of my past experiences, What is the wise thing to do?
    3. In light of my future hopes and dreams, What is the wise thing to do?

    If you haven’t read that book, I highly recommend it. It can be in a no time, but takes a lifetime of consistent work to filter questions to come up with the best solution. It’s not always black and white.

    • Carey Nieuwhof on July 27, 2014 at 8:47 pm

      Hey Chris…I have read it and love Andy’s questions. I guess this is a simplified version of it. Never thought of it that way. Thanks!

  4. JJ on July 23, 2014 at 5:18 pm

    Thank you so much for this article.

  5. Andy Eiss on July 23, 2014 at 12:06 pm

    Such an insightful question. I’ve found this truly helpful. Thanks Carey for this post.

    • Carey Nieuwhof on July 27, 2014 at 8:45 pm

      You’re welcome Andy. Thanks for taking the time to comment!

  6. rich birch on July 23, 2014 at 11:28 am

    As always … a great post.

    This was particularly helpful for me today … clarifying.

    • Carey Nieuwhof on July 27, 2014 at 8:45 pm

      Thanks Rich…it’s help me so many times. Thanks for your extremely capable leadership.

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