Should You Be Asking More and Better Questions? Five Key Takeaways
Updated: Sep 4
Kathleen’s (not her real name) first performance review as a new team leader in a national not for profit organization didn’t go as she had hoped.
Her manager, whom she considers a mentor and strong supporter began the conversation as he usually did, with a question. A well asked, thought provoking question that opened the dialogue nicely and led to a great exchange where she got to speak way more than she ever had in previous performance conversations with other bosses.
Her biggest takeaway was she needed to strengthen her listening capability with her team and clients and one of the clear paths for getting there ironically enough was to ask more and better questions.
Her initial missteps are extremely common. She shared with me “I put pressure on myself to always know the answer and have been more directive than I really needed to be.” She also told me she asked questions but in hindsight they were probably mostly closed, did little to empower others or stimulate new ideas. Kathleen was attentive enough to recognize that her manager, a great listener and very effective leader modeled the asking of great questions and in fact led through questions.
She began paying a lot of attention to the questions people ask, specifically one of her colleagues who was reputed to have excellent customer service skills. She quickly realized how asking good questions were the tools of many of the people she admired. She also read Just Ask Leadership: Why Great Managers Always Ask the Right Questions by Gary Cohen. Most importantly she became very mindful of when and how she asked questions and the answers they elicited both at work and at home.
Here are a few insights I believe can help us all ask more and better questions:
We are often fearful of asking questions out of concern for being perceived as intrusive or rude or for what the answer may reveal; being in a constant rush is not conducive to asking more and better questions and asking thoughtful and effective questions takes skill, practice and as with all learning, the willingness to be clumsy and awkward in the beginning.
Asking great questions as a leader has enormous organizational impact on problem solving, on creating a collaborative culture and a sense of engagement. From an individual perspective, the questions you ask yourself and others are the key to greater self-awareness from which learning can take place and though it doesn’t guarantee you’ll be a better listener it sets you up for success.
Great questions come from a mindset of curiosity not judgement. Questions are typically most effective when focused on learning the facts, deepening understanding and seeking commonality. They are least effective when asked to prove the other wrong, to debate every point or to criticize. Interrupting the other’s answer, peppering them with closed questions and condescension typically doesn’t work well either.
Great questions are respectful and don’t put people needlessly on the defensive. That said, effective questions sometimes need to be direct and challenging, may make people uncomfortable and may be unwelcomed but when thoughtfully worded shouldn’t be offensive, inappropriate or cause people shut down.
Coaching questions come in threes: 1) Why questions that seek to really understand root causes, (this critical first step is often glossed over rushing to identifying options to a problem that is misunderstood): “Why do you believe this happened?” 2) Identifying options and alternatives: “What has worked for you in the past?” or “What could you try?” 3) Questions that engage others into a commitment or getting things started: “What do you need to get started?” or “What will you do first?”
Kathleen’s next performance review went much better. She scored much higher on the survey that was done with her team most notably in communications and her manager was delighted with her development.
One of her proudest turnarounds came when her team told her how much they now loved their team meetings. As in many workplaces, their team meetings were not the highlight of people’s week until Kathleen asked questions about whether the meetings were effective (scale of 1 to 5) and what they could stop doing, start doing and keep doing to make them worthwhile. Most importantly she asks those same questions quarterly to keep the meetings on track. She also now asks a host of other thoughtfully worded and highly effective questions as part of her ever-evolving leadership practice.
What would happen if you asked more and better questions? How might you start?
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