Common Coaching Questions that Leaders Should Use More Often

When we coach leaders as part of an enterprise leadership development program, we often also provide mini training sessions to these same leaders on the basic skills of coaching. What always surprises us is how difficult it is for leaders to see the parallels between coaching and leading, and even understand why learning coaching skills is relevant to their growth as leaders.

In Stephanie’s personal experience, the process of getting certified as a coach was one of the most transformative things she did in her leadership journey. She discovered through her coaching practice a set of questions that are so simple and powerful that we use them in all sorts of contexts beyond coaching conversations. Here are a few.

What about that is important to you?

This question is profound in that it helps to uncover hidden motivations, intrinsic values, and a LOT more clarity on where the truth really lies. In business, we see this question transform sales conversations, reshape job descriptions, and empower employees to carve a unique path to promotion. When facilitating meetings with an executive team, this question helps the various functional leaders see below the surface of a proposed strategic direction and align on the best go-forward plan.

It’s important to note the phrasing of this question as opposed to Why is that important? Although it may seem these two questions should yield the same answers, they don’t. Why is that important? asks a person to defend their position, which is intrinsically combative. What about that is important to you? encourages a person to share a core value, which is intrinsically vulnerable and collaborative.

What did you/I learn?

Experience isn’t growth until it is processed and integrated into a story. One of the key skills of a coach is to help clients process their experiences and transform them into stories, and this is a foundational question to do just that. As a leader, this question is crucial for developing high-performing teams. It’s also one of the most important questions a leader can ask herself over and over again. This question grounds a leader in humility, and allows her to build a library of stories about failures and successes as she grows in her career.

What else?

This question is a great question to use in the context of brainstorming. We generally know that the best ideas aren’t the first ideas, so asking What else? just a few more times after the initial glut of ideas are on the table ensures the full scope of possibilities has really been considered.

But this question is useful beyond the brainstorming context. One of Kara’s clients came to her one day with an issue with a challenging team member who complained all the time. Kara challenged her client to give the employee space to vent and simply ask, What else? until they ran out of steam. The following session, the client came back simply giddy! He had tried the strategy and been dumbfounded by two things. First, he’d learned a TON about the dynamics of his team he’d never been privy to before, and the team member had finished the conversation by saying, “Wow. Thanks for the chat. I feel so much better now,” and hadn’t complained since. The client gushed for a while, extolling the virtues of that single question. And of course, what did Kara ask him? What else?

What will you commit to? By when?

It is unbelievably common to discover that expectations around roles and responsibilities aren’t aligned. And even when they are aligned, the breadth and depth of those expectations can still vary. This question makes explicit what can all too often be left unsaid. It also has the side benefit of requiring people to make their commitments public, which has been shown to dramatically increase accountability.

Notice that this question is not a delegation. Leaders who assign tasks to individual team members should not expect that the simple act of delegation is enough to achieve buy-in. Assigning the task and then following up with this question or the variation, Will you do that? is more powerful and effective.

Who do you/I need to be?

Coaches learn about this question in juxtaposition to the question, What do you need to do? The purpose is to disassociate what a person DOES from who a person IS. Two salespeople can present a pitch to a client, but one can be earnest and another can be flippant. Even if they do the same thing, they are being different. Leaders can get caught up in all that needs to be done, but great leaders take the time to set intentions around who they want to be in the process, and help their team members do the same.

There are countless other coaching questions that are relevant to leaders in the workplace. What questions do you like to use, and why?