We spend a lot of time discussing leadership challenges with leaders at all levels in our workshops, peer learning discussions and coaching. The consensus amongst leaders is that leading people is difficult – or more than that, leading people WELL, is difficult. Being an effective leader requires a commitment much greater than doing “just a job”. It requires optimism, resilience, and a lot of self-awareness and introspection. In fact, I’d argue that self-reflection is one of the most important responsibilities of a leader.

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!”

Or…

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

Or…

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

However when you start to dissect these various scenarios, we find that the challenge is a little different. Oftentimes, the leader has misinterpreted an employee’s actions or has not communicated effectively or clearly. An employee “not getting it” may be due to the leader not being clear about a new expectation with them in the first place – either because it was assumed the employee would connect the dots or because it may have required a “difficult” conversation. And that employee with the attitude problem? She may be someone who no longer feels valued, so as a leader, it’s important to find out why. A team member 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. If you’re not participating in coaching whether externally or with peers, you can coach yourself through your challenges. 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 employee, 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? What has changed?

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, consider the advice from question #1. Maybe it’s a new manager, new teammate or disruption of the 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’s one thing I’ve learned after coaching and leading hundreds of people, it’s 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 play a part in how things affect us. Talk to 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 understanding of your expectation is – “What do you think a good job will look like in the end?” or “what steps will you take to get there?” or “Why don’t you walk me through what you think the expectation is?” Discuss it to ensure you’ve both been heard and understood. A little time spent here 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 may realize that this one problem, with this one employee, isn’t really that important after all. It has become important because we’ve spent so much time dealing with it! When we look at the whole picture, we realize that what is critical is that it’s causing bigger problems for others – and ourselves (see next question!). The other part of this, is to make sure the employee realizes how important it is, and ultimately, how important their job 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 and right away. If it is costing a lot, it’s time to go deeper about why this is a problem. The next question will help with this too.

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

Yes, leader, you too have a role to play here! It starts with setting clear expectations (remember #3). When problems arise, leaders often change their own behaviour, which causes further challenges. This might manifest as avoidance of the person, delegating to others differently, or generally treating this person differently. It’s also possible you’ve been recognizing behaviour (consciously or sub-consciously) that’s leading to this current behaviour. It may be that you quite simply find the employee 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. Most of us have some level of fear when it comes to difficult conversations. Being honest about critical behaviour takes courage and compassion, and requires you to truly expect the best from the person. Finding that courage to enter into the conversation with positive intent can make a huge impact on the person and therefore the outcome! It will also help you to feel better – like you’ve done all you could – 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. When they are our own problems, we’re emotionally attached and it’s difficult to see through that to the rational parts. 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 easier 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?

It is important to know why you’re dealing with this at all. What is your goal – and be truthful about it! 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 it something that will always be a challenge? Maybe the end goal is to improve team’s morale? If so, how will you know that you’ve done that? What metrics would you apply? 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 it will help you with all of the others. It is amazing how few leaders have 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 regarding alignment is one we work on with leaders and ask them to consider it at least weekly as they become more authentic and trusted leaders.

If you want support in developing leadership within your organization, check out our Blue Rebel Leadership programs! We’d love to hear from you. 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.