Leadership Development: How to Ask Great Questions

“It is better to know some of the questions than all of the answers.” – James Thurber

 

It’s very easy in business to get sucked into being reactive to problems. If you feel you always have to direct and tell, however, you may be missing a critical opportunity to advance the skills of your team.

 

Asking great questions is one of the most powerful talent development tools a leader has. As I discussed in an earlier blog, managers need to brush up on their questioning techniques so they can help their people learn how to analyze situations and build their own leadership skills.

 

Based on readers’ interest, I’d like to delve a little deeper into how to become an effective questioner, using some examples and even – gasp – a homework assignment.

 

Teachable moments occur every day in the impromptu encounters we have with our folks and a few great questions can make all the difference. So, what constitutes leadership-worthy questions? They are distinguished by their ability to:

 

Test assumptions: In the heat of business, it’s very easy to make a decision based on a faulty premise or incomplete understanding. A question around “You seem to be assuming X, however, what if …” prevents a rush to judgment and can lead others to a more accurate view of the situation and all its ramifications.

 

Stimulate innovation: Out-of-the-box thinking is popular in theory but most people settle for the tried and true. It’s good practice to challenge your reports with questions that stimulate alternative ways of thinking about a situation. Great leaders push for greatness in others: “What haven’t you tried yet? If you were not afraid of consequences, what would you try?”

 

Leverage intelligence: A good leader is fully present in the questioning process – not thinking ahead or looking for a pause so she can (finally!) provide the answer. Often the best ideas emerge during a dialogue, when we use our intelligence jointly to explore an issue. Ask questions that also stump you, ones that you are genuinely and deeply curious about. Great questions lead both parties in a new direction and open up avenues that neither anticipated.

 

Foster growth: Questions such as “what do you mean by …” or “help me understand …”can draw out the person’s knowledge, build their analytical capabilities, and show them new ways of examining issues that they can use in other situations going forward.

 

Produce results: Analytical questions are not intended to push someone into a corner. You’re having a dialogue, not conducting an interrogation. That said, skillful questioning is a disciplined, rigorous process that leads all participants to a clear understanding of the issues. By creating a foundation of shared truth, great questions are the catalyst for effective decision-making.

 

I worked with a leader who thought of himself as tough and uncaring, very results-focused. He was a problem-solver with an energetic and directive style. Trouble was, he would walk away from meetings with more decisions to make and problems to resolve – in his words, with “more monkeys on my back.”

 

In our work, we uncovered that he was actually a very empathic leader but the way he expressed this empathy was by engaging in such a way that he fixed other people’s problems. That was how he showed his deep caring.

 

Once he achieved this insight, he was able to use questions as a way to help others solve their own problems and build their capacity for action. The key was to understand that questions used in the right spirit are a way to relate, connect, and lead the business.

 

Here are some examples of effective questions:

 

 

Your homework assignment

I frequently conduct leadership development workshops focused on building questioning skills. One method that participants find effective is to brainstorm specific questions they could ask their direct reports in certain scenarios. You can do this as well by making a list of questions for your direct reports in order to:

 

 

Try out the questions with your reports. What is the impact? What works and what elicits blank stares? Rephrase your questions. Fine-tune the list. Get feedback from colleagues. Over time, you will build a library of go-to questions that can be applied in various situations.

 

Questioning, like any skill, needs to be practiced. If you are unaccustomed to engaging with your people in this way, it may feel awkward at the beginning. Carry on with it nonetheless. Trust the process and you will get to the point where inclusive, development-style questions become second nature to you. And please share your results with us!

 

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