3 Keys to Coaching Up

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“I love everything we’ve been doing together but I wish somebody was coaching my boss. She could certainly learn some of these skills!” exclaimed Diana.

“What’s going on?” I asked.

“She’s just impossible. She never listens to me when I go to her with a problem, she just tells me what to do and then goes back to checking email.”

“That sounds frustrating. What have you tried?”

“Tried? Are you kidding? I’ve had to come up with major workarounds so I can get things accomplished without dealing with her. It’s hopeless!”

“So it sounds like what you’ve tried are workarounds. Have you actually talked to her? I asked.

“I couldn’t do that! I have no idea how she would response if I gave her this kind of feedback.”

This type of scenario comes up quite often in coaching sessions. My clients have recognized the value of a coaching approach.  They’re eager to experience that kind of interaction with their boss. Instead, the boss gives advice, multi-tasks, and doesn’t listen well.  But they lack the confidence or the skills to communicate to their boss what kind of supervisory relationship they would like.

Ironically, on those occasions where I’ve had a chance to talk to the boss, she usually complains about the same behavior from her supervisor! How do we positively intervene in this chain of unconstructive supervisory relationships?

Well, it starts by acknowledging that the only person you can do something about is yourself. It might feel good to vent about something that you believe is out of your control. Wouldn’t it feel much better to make the effort to improve the supervisory relationship, and reduce the amount of workarounds you have to engage in?

Coaching up is possible. It just requires some extra consideration. Here are three things I’ve found important when approaching this potentially delicate conversation:

Start with a Helpful Mindset

If you undertake the conversation with the mindset that there’s something wrong with that person and your job is to give them feedback so they can change, how do you think it’s going to go? Probably not well. A more helpful mindset is to see yourself as supporting your boss’s ability to bring out the best in you, thereby causing her to shine, too.

If that person hasn’t listened to you in the past, you might be inclined to go in with a “here we go again” mindset. That’s probably going to get you the same result that you’ve had previously! Instead, you might go in with an open, neutral mindset, maybe even with some curiosity about how things will play out. This could increase your chance to…

Have Empathy

When you can put yourself in your boss’s place and see things from her perspective, you might discover some understandable reasons why she behaves as she does. Maybe she’s under great time pressure and doesn’t feel she can invest in helping you think through problems on your own. Or maybe she’s supervised people in the past who did not take initiative, and she’s come to believe she’s got to be directive. Who knows? But if you let your frustration get in the way of empathy, you’re probably not going to find out.

 Focus on Building Trust and Safety

This is where delicacy and finesse comes in. Because it’s your boss, you want to pay attention to the status difference and offset the potential threat of initiating a coaching conversation. Two things that can work well include asking for permission (it lets her be in control) and creating a shared aspiration (“We both benefit from a supervisory relationship that brings out the best in each of us.”)

There’s no guarantee that skillful “coaching up” conversations will produce the results you’re looking for.  But at least it gives you a chance to practice communicating clearly, sensitively and with empathy. Who wouldn’t want that?

What have you learned about coaching up? What has worked and what hasn’t?