Top 10 Toolbox Questions for Leaders Who Coach Their Teams

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Complete this sentence: If you want better answers, you have to…

If you’re like 100% of the leaders I train and coach, you probably said …you have to ask better questions.

I’ll tell you what I tell them: you’re close!

Throughout the last 18+ years training professional coaches, and now training leaders to integrate coaching into their everyday work conversations, I realized this statement should be modified to:

If you want better answers, you have to CRAFT better questions.

We all know how to ask questions. We’ve been asking questions since we started talking. But too often the questions that pop into our heads and come out of our mouths are not all that great, and might actually be counterproductive or maybe even destructive. More often than not, these random, poorly thought out questions waste a lot of everyone’s time, money, energy, and sanity.

As a leader, it’s important for you to hone your ability to intentionally and strategically craft powerful questions that both build positive relationships with your team members and focus on tangible results. This is the heart of facilitating efficient and productive Coaching Conversations* at work.

(*The dual intent of a Coaching Conversation is to (1) create a positive, collaborative connection, and (2) efficiently move the conversation through a concise and focused exploration that leads to a specific plan of action and accountability.)

The good news is that putting words together in a specific and deliberate way to get the desired outcome is a learnable skill that can be practiced and mastered over time. A great place to begin honing this craft is to add some basic coaching-style questions to your leadership toolbox that you can pull out as needed and tailor to different situations you encounter with team members.

Here are ten of my favorite “toolbox” coaching questions, along with what makes them so powerful. Not all of them will be appropriate in all situations, and you will likely adjust the wording a bit to fit your own communication style or team’s culture, but this is a solid place for you to begin.

(To customize the question, fill in the “ … ” with the specifics of the particular situation.)

1. If you could design the perfect outcome for …, what would that look like?

This is a “begin with the end in mind” (Stephen Covey) question and gives your team member permission to let their creativity come out and explore, without getting hung up on the HOW yet. It also tells them you value them: their opinion, perspective, and expertise. The results may look different in the end, but it gives you both a place to start the exploration and move towards a resolution.

2. How will you know when you’re successful with …?

I love this toolbox question because it asks your team member to project forward to the point of success and start creating evaluative parameters up front so they can track their progress. This is a lot better than staying stuck in re-hashing the past, which is a gaping black hole where nothing will ever get created, other than frustration.

3. What else is possible when you make … happen?

This question helps your team member connect the dots between a particular solution and the bigger picture, rather than looking at a situation or challenge in a vacuum — because everything is connected at work. It also helps them anticipate the possible ripple effects of solving a particular challenge.

4. What can you do with the time/resources/budget you do have?

This is my favorite toolbox question to ask a client who gets stuck in “I don’t have time to…” and feels stuck in an either/or dilemma: they have to either do all of it or they can’t do any of it. When a team member is feeling restricted by time, resources, or budget, this will help them reframe their focus out of the mental dead end and into possibility thinking.

5. What will it take to …?

This is one of my all-time favorite toolbox coaching questions. It both assumes success and kicks their problem-solving brain into high gear. Even if a team member’s initial answer is “I don’t know,” trust that their brain is getting engaged. Some options for completing this are:

What will it take to …

… move this forward?
… turn this around?
… make this right?
… leverage this so it becomes a benefit?
… do what you need/want to do?
… make this a reality?

6. What has to be in place in order to …?

This is another strong strategy-focused and creativity-engaging question. You’re asking a team member to anticipate the foundational needs to ensure success, and to begin putting all the pieces together in their mind. This will make it easier for them to organize those pieces into a viable plan.

7. What can you do about this situation right now?

This question brings your team member’s focus back to the here-and-now. It’s important to balance creating and tracking the vision of success with what has to happen today in order to reach that vision; it’s gets them thinking about the next doable step to take in the longer term plan.

8. On a scale from 0-10, how committed are you to …?

I like quantifying commitment for a few reasons. Although I’m sure you want to assume that your team members are fully committed to their work, the team, the project, the company, and the customers, asking them outright in certain situations can set the stage for accountability. If they say “10”, it’s been stated out loud, which makes it more compelling to live up to.

This question can also open the path for growth. If you’ve built a trusting relationship where they know they can be honest with you, and it’s less than a 10, this opens the door to more coaching, mentoring, or training to figure out how to move them towards a 10.

9. How will this action help you move forward toward …?

This question creates continuity from one action or plan to the next, helping them connect the dots from where they are to where they want to go: their final goal or deliverable. And once an action step or plan has been identified, this question will also help your team member identify the relevance of their action — WHY doing it matters. This relevance is critical to sustaining employee engagement, motivation, and enthusiasm.

10. How does this action/plan help the team/company achieve its mission?

Another important facet of relevance and employee engagement is helping your team members easily connect the dots between their daily work and your organization’s larger vision and mission. Nothing will sink the productivity ship faster than team members disengaging because they feel their efforts have no connection to the big picture.

BONUS Toolbox Question: When will you do this?

All the Coaching Conversations in the world won’t move your team member forward without identifying when something will be done – then doing it. Attaching a day and time to the action resulting from a Coaching Conversation with give both you and your team member clear accountability. And notice this question isn’t When can you do this? It’s When will you do this? This small tweak makes a big difference.

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There are a lot more questions (over 40 more in the Coaching Skills Quick Start self-study training guide and desk reference!) to add to your leadership toolbox, and hopefully these have given you more ways to engage your team members in meaningful and results-oriented Coaching Conversations at work.

What other powerful questions have you asked your team members? Please share them in the comments below. I’d love to learn from you, too, because that’s how we create a more collaborative world!

It's time to coach your team with confidence!

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Laurie Cameron, ACC

Laurie Cameron, ACC

Mentor Coach for Mission-Driven Leaders who are committed to building a sustainable Coaching Culture that supports a fully engaged, resilient workforce.