Overcoming the Toughest Common Coaching Challenges

by Amy Gallo

Great managers strive to do right by their employees — treat them well, motivate them to succeed, and provide the support and coaching each person needs. This is often easier said than done, especially when it comes to coaching. That’s because coaching takes time, skill, and careful planning. And there are certain types of people who may be particularly challenging for managers to coach. Think about the Eeyore on your team who is pessimistic at every turn, or the person who refuses your advice with a smile on his face. It’s not fair to you or to the employee to give up, so what do you do?

I spoke with Susan David, a founder of the Harvard/McLean Institute of Coaching and author of the HBR article “Emotional Agility” to get her insight on some of the more vexing coaching situations managers face and what to do about them.

As with most interpersonal difficulties at work, the first step is to take a look at yourself. David says that the problem often starts in the manager’s head. “When a leader is coaching someone who they’ve identified as ‘challenging’ it means that manager has an attachment to an idea about that person,” she explains. You might think, This person is such a pessimist, or This is going to be difficult. “There’s a fair amount of research that shows that kind of orientation is not going to be helpful,” she says. Being “stuck” to those ideas leaves little “space for change, hope, or optimism.”

To overcome this mindset, there are several things you can do.

  1. Assume change is possible. If you go into any coaching situation presuming that people are who they are, you’re setting yourself and your coachee up for failure. “You’re on a fool’s errand because you can’t help someone change if you don’t think they’re capable of it,” says David. Ask yourself whether you’re going into the context with a preconception that is fundamentally undermining what you are trying to do. If so, try the next few steps.
  2. Take an alternative view. If you find yourself thinking negative thoughts about the person you need to coach (e.g., He’s so negative. She’s such a downer. I don’t really trust him.), it’s difficult to show compassion or curiosity. “One of the critical tools of an effective coach,” says David, “is to take a different perspective.” Instead of thinking, “This person is…” try “One view of the person is that he can be quite negative. What are other options?” Think about the other people he works with. Is there someone who doesn’t seem to share your view and genuinely enjoys working with him? Try to put yourself in that colleague’s shoes. Look for disconfirming evidence or instances when your direct report does the opposite of what you expect — taking a positive or neutral stance, for example.
  3. Manage your emotions. When you sit down with your coachee, you bring all of your emotions and stresses with you. “Coaching is not done in a vacuum,” says David. You might be feeling afraid, frustrated, or anxious. Perhaps you’re worrying that if you don’t help this person change, you won’t be seen as an effective leader. All of these uncomfortable emotions are normal—don’t try to ignore or repress them. “If you go into a coaching session unaware of your emotions, they might be amplified. Or you get emotional leakage, where your real feelings show despite your attempts to stifle them.” explains David. It’s far better to spend time recognizing how you feel before you go into the session.

Not only will this make you feel better, it will also help the coaching process. In fact, says David, the type of mood you bring to and create in the session has a big impact on what you’re able to accomplish. “Positive moods lead to more big-picture, ‘it’ll be ok’ thinking whereas negative moods lead to more analytical, critical thinking,” she says. Think through what you’re trying to get done in the coaching meeting and try to match your mood accordingly. For example, if you want to engage the coachee in thinking strategically about how to push his project to the next level, you’re better off going in with a positive mood. And if you project a negative and frustrated attitude, you’re unlikely to be able to reach your goal.

This is not to say that you should go into every coaching session with a happy-go-lucky approach. Sometimes a positive tone isn’t appropriate. Perhaps you want to help your coachee analyze a situation that went poorly. The key is to think about what you’re trying to achieve. Then, when your objective is clear, match the mood to the task.

I also asked David about what to do in a few specific, tough scenarios. Of course, every situation is different and what you do will depend on the content of your coaching, your relationship with the coachee, and the culture of your organization, but these suggestions may help you get started:

Scenario #1: Your coachee is pessimistic and defensive.

Your direct report messed up an important part of a project and she refuses to admit it. Instead, she insists that she followed directions or that her approach would’ve worked if other people had done their jobs. This can be frustrating, but the good news is you don’t need to bang your head against the wall. “Sometimes leaders get hooked on trying to get the other person to see the facts,” says David. If you’re desperately trying to get her to acknowledge her mistake, you may never succeed. “People are designed to self-protect and if someone is defending themselves, it may be near impossible to persuade them of ‘the facts,’” she says.

 

 

Give up the need for the coachee to see things exactly your way. “Some managers approach coaching as a means to get someone to do what they want them to do,” she says. Instead, think about what the defensiveness is indicating. “Chances are they feel threatened,” posits David. “And as a coach, it’s your job to help the person feel psychologically safe.” One way to do this is to create a shared perspective. Focus on what you do agree on. Get her to describe her version of events and indicate where you see eye-to-eye. “It doesn’t matter that the person has a different perspective as long as you can move into problem solving together,” she says. “Coaching works best when you walk in the other person’s shoes and come to a shared version of what needs to happen.”

Scenario #2: Your coachee lacks confidence.

You have a talented employee who just doesn’t believe he has what it takes. Because of this insecurity, he undermines himself in front of others and doesn’t do all that he’s capable of. David acknowledges that it can be really tough to build confidence in these types of people. But it’s not impossible. She explains: “If you say to someone, ‘Gee, you don’t have the self-confidence to see that you’re good at your job and you’re undermining your ability to get yourself promoted,’ it isn’t helpful.” And paying compliments doesn’t help either because more often than not, the person will discount any compliment you give her, thinking, She’s just saying that to make me feel better.

One solution is to have her own a compliment. Instead of giving broad praise like, “You’re really good at your job,” focus on something specific she has done well. Then help her to analyze it, unpacking her skills and strengths. Ask: What does that compliment mean to you? Why do you think I’m choosing to give it to you? “Research has shown that this kind of intervention has long-term effects on low self-esteem,” explains David. You can also help a direct report own a compliment given by someone else. For example, you might say, “I heard John tell you that you did a good job with the quarterly report. Why do you think he said that? What about the report do you think he was particularly impressed with?” This will guard against any discounting that the person might do.

You can then take it a step further by helping your direct report to apply those skills in other places. “My boss said that you’re really good at problem solving. How can we take that strength of yours and expand it to other areas? How can you better problem-solve with your peers?” David explains: “You’re looking for ways to embed the positive thinking.”

Scenario #3: You don’t trust your coachee.

One of your team members has been dramatically inconsistent. Sometimes he knocks a project out of the park. Other times he barely makes his deadlines. You’re not sure if you can trust him but you want to coach him to be more reliable.

The good news is that the coaching process is meant to build trust. “Monitoring and checking in is built in from the beginning so it doesn’t look like you’re checking up on them when they’re doing something wrong,” says David. Don’t get too hung up on how trustworthy the person is. Trust the process. You may want to set explicit expectations, saying something like, “OK, let’s map out what this might look like. What are the three steps you’re going to take and by when?” Then you can follow up appropriately.

But if you think the person is dishonest or repeatedly fails to meet the objectives you’ve mutually agreed upon, then remember that there are limits to coaching. You may need to seek help from HR, hire an outside coach, or let the person go.

“Coaching is meant to be about positive change,” says David. Of course, you will run into tricky circumstances, but remember that worrying or focusing on those challenges won’t move you, or your direct report, forward. Make room for the change you want to see.

Source: HBR

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