10 Coaching Questions To Ask Yourself to Solve Your Leadership Challenges

10 Coaching Questions To Ask Yourself to Solve Your Leadership Challenges

I spend a lot of time discussing leadership challenges with leaders at all levels. The reason for all of these discussions? Leading people is difficult. It requires a commitment much greater than doing “just a job”. It requires positivity, resilience, and a lot of self-awareness and introspection.

Oftentimes, leadership challenges start out sounding something like:

“I don’t know how to coach my employee on this – they just aren’t getting it!”


“My team member needs to improve her attitude – it’s affecting the rest of the team.”


“My team member isn’t dealing well with the recent changes and I don’t know how to motivate them.”

When we start to dissect these various situations, what we often find is that the problem isn’t the initial one the leader has raised. It often goes deeper than the surface issue, and may not even be the employee’s “fault”.

An employee “not getting it” may be due to the leader never having actually shared the new expectation with them in the first place – most likely because it may have required a “difficult” conversation. That employee with the attitude problem? She may be someone who no longer feels valued, so her leader needs to work to find out why. A team member seemingly not dealing well with change may be a reflection of  a leader who themselves is feeling unsure and unmotivated in the new world, and isn’t being honest with themselves or their team about what these changes mean.

When you’re knee deep in the situation, though, it’s difficult to see your way through to the root of the problem. Here are a few coaching questions to ask yourself before you throw in the towel with that employee…

1. Has this employee ever done this particular part of the job successfully in the past?

It is important to realize that as things change in a job (new software, new team, new manager, new rules of the industry, new responsibilities), there is a learning curve for your employees, even if they are experienced in the overall role. This question stems from Hersey-Blanchard Situational Leadership Model, and helps you to diagnose whether the problem with the employee is competence or motivation. If you have never actually seen them do this task successfully, to your expectations, then it may actually be that they need more direction and training, so start there.

2. How long has this been a problem?

Has this employee always been this way or have they changed? What else has changed for them – is there a possible link? It might be a new aspect of the job or a new process. If so, see question 1. Maybe it’s a new manager, new teammate or disruption of status quo. If this is the case, then it’s time for an open discussion with the employee to find out exactly what’s affecting them. The most important thing here is to never assume. If there is one thing I’ve learned after coaching and leading hundreds of people, it is that you can never predict why a person is behaving in a certain way. We all have different experiences, motivations, skills, emotions and more, and they all affect how things affect us. Talk openly with your employee!

3. How clear is your expectation?

Now, this is difficult for you to answer on your own. What I often hear is “I’ve told them how to do it many times”, or something to that effect. But consider this – just because you’ve told someone something does not mean they have heard it the way you intended. Ask questions to find out what the employee’s expectation is. Discuss it to ensure you’ve both been heard and understood. A little time spent discussing a clear expectation at the outset could save a lot of time later.

4. In the bigger scheme of things, how important is this?

Sometimes, if we can step back and look at the whole picture, we realize that this one problem with this one employee isn’t really that important after all. It has become important because we’re spending so much time dealing with it. Other times, when we look at the whole picture, we realize that it  is critical because it’s causing bigger problems for others and for you (see next question!). If this is the case, it is important to make sure the employee realizes how important this is, and ultimately, how important their job, done well, is.

5. What is this problem costing you?

How is this challenge affecting you? Your team? Your organization? Your customers? What is the cost of letting it continue? What would be the value of fixing it? The higher the cost, the more important it is that you deal with this effectively, right away. If it is costing a lot, it’s time to go deeper about why this is a problem – see the next question.

6. What role have you played in creating this challenge?

Yes, leader, you have a role to play here as well! It starts with setting clear expectations (remember question 3 above?) and when problems arise, leaders often change their own behaviour, which causes further challenges. This might manifest as avoidance of the person, delegating to people differently, or generally treating this person differently. It may be done subconsciously, because you quite simply find them difficult or don’t like them. It’s time to get real with yourself about how you are dealing with them.

7. If you were to end this employee’s employment, what wouldn’t you feel 100% great about?

As a leader, it is your job to make your team successful – which in turn makes you  more successful. If you were to terminate the person’s employment, what things would you wish you had done to help them improve? I most often hear leaders say they wish they had been more upfront and direct about the problems the employee’s behaviour was causing. Having difficult conversations takes courage, and requires you to truly expect the best from the person, but finding that courage and entering the conversation with positive intent can make a huge impact on the person and the outcome. It will also help you to feel better about the situation if you do end up making this sort of tough decision.

8. If another leader that you were mentoring came to you with this challenge, what advice would you give them?

People are really great at solving other people’s problems. What if this wasn’t your problem? What questions would you ask? What advice would you offer? When you remove yourself and your emotions from the situation, it is often more easy to see it clearly and to come up with viable options.

9. What outcome do you want? How will you know that you achieved it?

Why are you dealing with this at all? What is your goal? It’s important to be truthful about that. Is the outcome that you want to remove this person from your team? If so, will you be able to move past this if they do improve? Or is that something that will always be a challenge? Is the outcome to improve team morale? If so, how will you know that you’ve done that? Be clear about what you want out of the situation so that you can enter into it with that intention, and so that you can celebrate when progress is made.

10. What kind of leader do you want to be? Are you being true to that with this person?

This is the most important question, and will help you with all of the others. It is amazing how few leaders have often taken the time to consider what their philosophy of leadership really is. I hear all sorts of cliches like: “lead by example”, or “servant leadership”, or “someone people want to follow”, but what does all of that really mean for you? What do you want people to say about you after you leave? What legacy do you want to leave? Are your daily actions aligned with this? This last question is one we work with leaders and have them consider at least weekly as they become more authentic, trusted leaders.

If you don’t have the support of a formal coach or a Leadership Development program, asking yourself these 10 questions will help you to work through possible ways to deal with the leadership challenges you face.

If you want to learn more about our Leadership Development program (it’s probably different from what you’ve been a part of before) check it out here.

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