10 Coaching Questions Every Leader Needs to Ask

by Brad Bridges

The best coaches also receive coaching. They also regularly coach themselves. Let me explain.

If you are like me, your are enticed by routines because they allow you to feel comfortable. They help you manage the constant change in your world. Routines diminish the pressure to change and remind you that you are on the right track.

But routines can deceive you quickly. How many times have you allowed yourself to continue doing the same thing over and over even though you continue to get sub-par results?

A simple example is exercise. Another might be eating. But what about your work? What about your parenting? What about your marriage?

I’d like to challenge you to take a quick step back to evaluate at least one area of your life (ie coach yourself). The coaching questions below give you and your team a quick and effective way to step back, clarify, assess, and articulate a new plan forward.

You could look at any time period. However, I’ve provided a quick list of coaching questions for the next quarter. This process is called periodization. It challenges you to break the year down into 3 month segments and deliver results quarterly rather than just annually. (For more on periodization, take a look at Brian Moran’s book “The 12 Week Year“).

Give it a shot. Ask these coaching questions of yourself. Go through them with your team. No matter what you do, pursue clarity around what you are trying to achieve, how you’ll get there, and how you’ll know and measure that you did in fact deliver the intended result or arrive at the intended destination.

10 Coaching Questions Every Leader Needs to Ask

coaching questions

1) What are we trying to accomplish over the next 90 days? (Measure it)

This foundational question will likely be something you’ll need to return to regularly.

Be clear. Put it in writing. Make sure those around you have given input and are bought into what you are trying to accomplish.

2) What has gone well recently?

For you as a leader to properly assess yourself, your team, or your organization, I think you should celebrate the wins (both big and small).

What has been successful lately? What worked? Who do you need to applaud and learn from? But don’t stop there.

3) What hasn’t delivered your desired results?

This question is asking the opposite of #2. Here you are identifying what didn’t go very well.

Don’t be afraid to name these actions or projects. Failure isn’t a big deal unless you fail to learn from it. Identify where you or your team fell short and ask why. Determine if it was a process issue, a misaligned goal, or a lack of resources.

4) What could you do differently?

Figure out what you could do differently. Again, put this in writing. Start with a list of ideas before you narrow it down and prioritize.

Evaluation without shifting action is esoteric and exhausting. Make sure evaluation drives changes and creates innovative plans to achieve a different result next time.

5) Who could you ask for help?

I can’t tell you how many times I’ve failed to do this. Don’t be like me.

Think outside the box about who could help you or your team. If you still aren’t sure, ask a colleague or trusted friend who you should ask for help. They’ll likely have some ideas that you can benefit from.

Asking for help creates a leadership development opportunity for you to delegate and for another person to lead. Don’t steal opportunities from others by hoarding all the responsibilities.

6) What tools are out there to improve your process(es)?

Tools can reduce your time spent and improve your work. Many leaders state that they are too busy for social media. While that may be the case, it usually is more of a process, tools, or strategy issue than a time issue.

Simple tools like BufferApp (scheduling social media posts), Dropbox (cloud storage and document sharing), and Nozbe (project management for individuals or teams) can shave off large amounts of time. Many leaders refuse to lead differently by using these because they’ve gotten comfortable with what HAS “worked” in the past.

I’ve written blog posts on each of the tools mentioned above. Why? These tools work and they make a difference on my team and many others. You don’t necessarily need to use these as they are only examples of the abundance of tools available for you or your team to use.

7) What are at least 2-3 things you should stop doing?

This question hurts. Frankly, it always seems easier to identify something you can add to your plate. But we all do things that don’t produce our intended result.

In the words of Bob Newhart, “Just stop it.” Take a risk and decide NOT to do 2-3 things you have been doing. This will also help you to guard yourself from over committing.

The simple rule: if you add something, something else must be taken away by stopping it, delegating it, or automating it.

8) How could you better train and develop others?

Oftentimes your results in whatever project fail to impress because you’ve failed to train others.

Never assume that you have no more training to do OR that you don’t need anymore yourself.

9) When will you evaluate and how?

Determine the frequency and the way in which you will evaluate. What gets evaluated is what gets done.

When you know a project or task will be evaluated, it creates positive pressure to get it done on time and well.

Make sure to clarify how you will evaluate as well. Otherwise you will meander through a vague evaluation that gets little done and people will think you wasted their time.

10) If everything goes well, how will your life be different?

This question creates excitement. Give yourself and your team a chance to picture how life will change if you succeed.

People respond to vision and clarifying how life will be different will put flesh on your vision for the future. Vision dearth leads to inaction and depletes passion. Communicate your excitement about a new future and paint a vivid picture that lights a fire under yourself and others.

If the coaching questions in this post have been helpful for you, I would like to know how. Feel free to also share how it could be improved or what questions you would add to the list.

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About gabulmer

Christian apologist, husband, father, runner, blogger, leader with LIFE Leadership.
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