4 Great Questions To Help With Your Decision-Making

Not long ago, I was coaching a leader who was faced with a big decision he had to make. The decision had huge implications not only for the organisation – but also, if he was honest, for himself. The stakes were high. The pressure palpable. And he was in a pickle. Stucksville.

So, when he turned up for his coaching session, he wanted to find a way through. To become clearer on what to do next and which route he should take.   

Below are some of the questions we used in his coaching session and that helped him find a way forward. I’ve also used these questions on myself when I’m facing a big decision, and they’ve been super helpful for me too. And now, I’ve decided to share them with you in this week’s post of The Leader’s Digest.

You may not be facing a decision as big as my client but, as a leader, you must make decisions every day. It’s a skill worth working on.

Here are the 4 questions we used:

1. Is there a third option?

In their excellent book Decisive, Chip and Dan Heath warn us to ‘beware the binary’. Narrow framing is a common decision-making trap.  To escape narrow frames, we need to be aware of “whether or not” decisions. Instead, they suggest that when facing a decision between two options, ask:

“Is there a third option? Or “is there any way we can do both?”

And another strategy they refer to as “vanishing options”, urges us to say:

“You cannot choose any of the current options you’re considering. What else could you do?”

Although my client had already explored the options, asking these questions one final time, gave him confidence that the two options left on the table were the right ones given the information he had. It also helped to clarify his thinking around his messaging to key stakeholders as to why the third (obvious) option was a no-go.

2. If this was happening to a good friend of mine, what advice would I give them?

This is one of my favorite coaching questions because so often when we’re in our own head, we can’t see the wood from the trees. But this question gets us outside our head long enough to adopt a more objective perspective. Almost every time I have asked a client this question, they’ve come up with a useful piece of advice for themselves! After the first answer, ask yourself again, “and what else?”

My client’s answer to this was brilliant and so simple, but he hadn’t been able to access this gem until he used this question on himself and answered out loud. It didn’t give him the answer to the decision, but it gave him some useful next steps to help him reach that decision.

3. If I was following my values in this decision, what would they say to me?

I’ve written about it before here and here. Values act as your compass in leadership. My client was very clear about his values (bonus) and when I asked him this question, he immediately found clarity to an important aspect of his decision. It wasn’t the easiest path, but he knew it was one which aligned the most with his values. This brought him comfort. And he reckoned years later, that’s what he would remember when he thought about having made this decision.

4. What decision-making biases might be at play here?

Decision-making is awash with biases. Sunk cost bias, anchoring bias, confirmation bias. All the biases.  We all suffer from them. The trick is knowing which ones might be at play when you’re faced with a decision. This article by Psychology Today has a disconcerting little list of the common ones we fall prey to.

During this client’s coaching session we explored which decision-making biases might be at play for him. Uncomfortable as it was, he uncovered several that he’d been unaware of. He also identified a key stakeholder whose opinion he had not sought yet and whose thoughts would be valuable for him to hear before he made his decision.

My client has found a way forward. He’s made his decision. In his mind it’s still too early to know if it’s the right decision, but he feels some comfort from the fact that in making the decision, he’s been thoughtful and thorough to the best of his ability. Asking these questions helped him get clarity.

So, the next time you are faced with a decision as a leader, ask yourself these coaching questions.

Related: Values Aren’t Just for Companies