The best piece of advice I received from a mentor was to ask more questions.

Asking questions seems like a minor skill but can really set you apart in any conversation. Just think of journalists, detectives or lawyers. Asking the right questions at the right time is essential for their success.

If you’d like to become a better question-asker, then this edition is for you. Read on, friends…

Step 1: Asking follow-up questions

My first questions were: how do I start? How do I figure out what questions to ask? And how do I ask questions during a conversation that isn’t completely prepared?

I read books on the topic and watched videos, but what helped me the most was simple: stop talking and start listening.

To keep a conversation flowing, have people share information and open up about their struggles, the best move you can make is to stay quiet more than you usually would.

When they end their sentence, ask follow-up questions rather than taking up time to speak. These include:

  • What happened next?

  • How did that make you feel?

  • What options do you have now?

  • How do you think you could address this?

  • and more…

Practice doing this and you’ll notice it will build your listening skills too, because your follow-up questions need to fit and follow-on from what the other person just said.

Step 2: Adding more depth to your questions

When you’re comfortable with talking less, asking more questions and you find conversations more stimulating, take it to the next level.

In my career coaching I LOVE asking questions. It’s a big part of the value I offer because it directs my clients into directions they haven’t explored before.

When you add more depth to your questions you go from guiding the other person from one step to the next (via follow-up questions) to opening completely new paths for them.

Let’s say you’re talking to a colleague who is struggling with a project. Step 1 would help them figure out what’s going on and what they can do about it. Step 2, deeper questions, means including more of your own experience and helping your colleague think about unconventional ideas. This helps them recognise their limiting beliefs and break through barriers.

Example questions that go deeper:

  • I noticed when you spoke about <project/person>, that you seemed afraid of their reaction. Why do you think they would react negatively?

  • You’ve mentioned you would like to compare option 1 and 2. Have you considered how you could combine the two?

  • You shared your frustration about your colleague not pulling their weight on this piece of analysis. What if you talk to your manager about taking over more of the tasks and taking the responsibility for them?

These types of questions help people leave their comfort zone and discuss options in a safe environment.

My tips for practicing question-asking

It took me a good year to build more questions into my conversations. It requires taking a backseat and giving others the floor.

The great thing about that is that you’ll learn so much and get more opportunities to mentor and guide others. Question-asking moves your leadership skills in the right direction and challenges you in a positive way.

I recommend you start with step 1 and see how it feels. Take notes in meetings, ask questions, prompt further discussion and observe the difference.

You will move to deeper questions automatically. Build your awareness of what you’re doing or not doing and then progress from there.

Let me know how it goes and have a great start to the week 😎.

Eva