Hone your questions

The twenty-first newsletter is about empowering people

Has someone ever said to you: ‘wow, that’s a good question’? Only to fall silent, with their eyes drifting up, suddenly lost in thought as if they were miles away.

If so, good job. You really did ask them a good question I suppose.

Do you remember the question? Why did they think it was good? What even is a good question? Apparently not one with a straightforward answer.

In the last newsletter I talked about how we have Socrates to thank for spearheading a conversation-based way of using questions for the purpose of better understanding our thoughts.

While the Socratic method is usually associated with debate, discussion, and grilling people, asking strong questions is just as essential when supporting someone’s thinking process. Coaches do this all the time, and you can too.

When you ask questions on someone else’s behalf, you help them think out loud and get to the core of their issue. Creating a powerful experience for the person on the other end.

Powerful questions

The Socratic method revolves around high quality questions. I would imagine Socrates himself being very good at formulating probing questions for his conversation partners. Selecting the right question at the right time, with the most impact.

A coach takes on the same challenge in service of their client. Finding the most impactful question, removing the fluff, and aiming straight for the heart of the situation.

In coaching, ‘good questions’ (i.e. the most helpful for the client) are called “powerful questions”. 

Powerful questions are designed to get people to think about their own life and help them create a greater awareness of themselves. They require deep reflection, sorting through information, and invite them to explore new possibilities.

For a question to do all this, phrasing matters.

Articulating a clear, evoking, and constructive question takes practice and there’s definitely an art to it. Luckily there’s also a recipe to get started and create ourselves some powerful questions.

The mechanics

We can sharpen up our questions with a few rules of thumb. A powerful question has three elements: it’s short (and singular), open-ended and difficult to answer.

Let’s break those down:

• Short and singular

A short question is often more impactful than a long one because it takes less effort for someone to take it in and understand. With a short question someone can start thinking immediately, instead of spending their energy on deciphering what you mean.

The same goes for asking multiple questions at once. Although it's tempting to ramble on and refine your question while you’re posing it, challenging yourself to stop talking when the first question has left your lips is key. Brief and concise always beats long and detailed. 

• Open-ended

Open-ended questions can’t be answered with a simple yes or no, they ask for a longer response and elicit a thoughtful response.

Open-ended questions have a lot of things going for them. They invite reflection and elaboration, and affirm autonomy (you can go wherever you want with it). They also demonstrate genuine interest, and have an inherent nonjudgmental tone.

If you don’t know where to start, the words ‘what’ and ‘how’ have a tendency to lead to open questions. To make practicing easy on yourself, start your questions with these two and see what roles out of your mouth (instead of, for example, ‘have you…’, ‘will you…’, or ‘is that…’, which will lead to closed ones).

• Difficult to answer

This means that they don’t have a clear, obvious, or straightforward answer. Maybe they don’t even have an answer at all. These are questions you have to really think about. It requires imagination and going to places you might not have been to before.

‘When’s your birthday?’ is a short, singular and technically open-ended question. Of course, it’s not difficult to answer and doesn’t require you to think very deeply. Hopefully.

‘What do you value?’ on the other hand, or ‘what would success look like?’ Now those turn on your brain. They’re not easy to answer but still short, singular, and open-ended.

Let’s look at some examples that use all three elements:

• What personal strengths can you leverage to overcome this challenge?

• How have you successfully dealt with a similar situation in the past?

• What would you do if you knew you could not fail?

• How can you turn this obstacle into an opportunity for growth and learning?

• What small step can you take right now that would bring you closer to your goal?

Two side notes to the mechanics

• The formulaic trap

When you’re just starting out paying attention to your questions, it can be difficult to sound natural and spontaneous. People might pick up on that and you might sound a little, well, mechanic. Trust that this will get better with practice and experience.

It’s tempting to make a list of these and learn them by heart. Don’t do that though. Powerful questions aren’t scripted. They arise from real conversation. Your genuine curiosity is the navigation here. The rest is practice.

• Silence

When you’ve asked your powerful question, don’t forget to listen to the answer. These questions are powerful. This means that people won’t have their answers ready and, if all goes well, will think deeply about your question. Let them think.

Don’t jump in because you feel awkward. Don’t ‘rescue them’. You’re not leaving them hanging, you’re allowing them to find an answer on their own.

Also, because these questions are so powerful, they need a lot of ‘padding’ (read: silence). Otherwise it might start to sound and feel like an interrogation: ‘What is important to you?’, ‘what’s next?’, ‘how will you start?’, you get the point. These questions need to breathe.

When their eyes move up and they squint a little; bingo. You’ve asked a question they really need to think about deeply. This is the aim. Now sit back and listen to the answer.

Empowering questions

These questions are so powerful because they aim to help someone recognize their own strengths, capabilities, and potential. Because of how they’re designed, they have the ability to inspire confidence, promote self-awareness, and foster a sense of agency.

Ultimately, by asking powerful questions, you empower someone to delve deeper into their own thoughts, beliefs, and emotions, enabling them to gain valuable insights.

All from a few carefully crafted words.

What will you ask them next?