Karen Darrin

How well do you ask questions? From my experience, most leaders don’t think about this skill. After all, you don’t usually find “the ability to ask questions” on any list of managerial competencies. But asking questions effectively is a major underlying part of a leader’s job and is foundational in coaching others.

Effectively probing the thought process of your direct reports, colleagues, bosses, and customers can unearth the basis for their actions. A simple, “Say more” can be enough to reveal their thinking. And when you uncover that, my friends, you can better align with them and come to a deeper understanding of what moves them to action. 

There are three areas where improved “questioning” can strengthen your effectiveness as a leader:

Ask questions about yourself.

We can fall into unproductive habits and the same patterns of behavior. Good leaders, therefore, are always asking themselves and others about what they could do better or differently. This is where having mentorships, a coach or an annual 360-degree feedback process can uncover key blind spots for focused development. 

Get into the habit of asking others what you could have done better or differently. Be open and curious about their perspectives and you may hear a few valuable gems that you can incorporate. Plus, you will be modeling “how to ask for feedback” to others. It’s a win-win.

Ask questions about plans and projects.

The challenge here is to do so in a way that not only advances the work, but also builds relationships and helps the people involved to learn and develop. Probing needs to be in the spirit of accelerating progress, illuminating unconscious assumptions and solving problems.

Many of the best leaders I’ve seen have an uncanny ability to engage in dialog that helps people reach their own conclusions about what can be done to improve a plan or project, which of course leads to much more ownership and learning.

Here, change the pronoun to “we” and ask the same question at the end of your staff meetings, project updates or future plans: “What can we do better or differently here?” Encourage each attendee to toss in their observations. Collect the ideas. You may see themes which the team could consider implementing. 

Asking questions about the organization.

Leaders have an obligation to look for ways that the organization as a whole can function more effectively. To do this, they need to ask questions about practices, processes, and structures: Why do we do things this way? Is there a better approach? Asking these questions in a way that does not trigger defensiveness and that is seen as constructive is an important skill to nurture.

I have a sales executive client who is doing this beautifully. He tried a new method of “delighting his client” and he truly “hit it out of the ballpark,” as those sports analogies go. He didn’t sit back. He went to the CEO and proposed this new method for all existing client engagements in an effort to reverse their market share erosion.

We are still waiting for the final green light, but this sales executive has already modeled leadership — by offering a tested solution for how his company can be better. 


Try using The Three P’s to frame up what you want to know and how to ask your questions. The three P’s are possibilities, probabilities, and priorities. These three are sequentially linked. Learn how to apply different questions to different categories. Certain questions generate possibilities. Other questions sharpen a person’s or team’s ability to assess the probable outcome of potential decisions. The third set of questions help empower team members to prioritize. Give it a try! 

CALL TO ACTION:  Ready to kick-off 2019 by up leveling your leadership skills? Let’s brainstorm strategies to do exactly that. Slot a complimentary 30-min consult here:  Schedule Free Consult.

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