3 Coaching Questions for Leaders to Ask When a Team Member Feels Discouraged
By: Leanne Lagasse
Tags: Leadership, Work, Listening, Leadership Development, Management

“I’m just not good at this.”

I’ve heard this phrase countless times as I’ve trained and mentored others over the years. I’ve heard it from team members who were genuinely in over their heads and I’ve heard it from employees who were exceptional in their roles. Discouragement does not discriminate.

I used to think that my discouraged team members just needed all the affirmation and all the motivational speeches. When they were vulnerable enough to share insecurities, fears, and perceived or real failures with me, I was quick to jump in and give advice. I was well-intentioned and well-reasoned.

But the thing was — they usually left feeling no different than when they arrived. All my encouragement and advice was a small band-aid for a big wound.

And that’s how a lot of leaders approach these difficult conversations. We genuinely care about our team members and want to build them back up before the discouragement takes root. This instinct is good. But many of us miss the mark when choosing a method for instilling confidence.

We immediately assume we understand the source of the discouragement, assume what the team member needs to hear, and start giving advice based on those assumptions. This is a method that rarely works.

The good news is there is a much better strategy that empowers our team members when they feel inadequate and discouraged about their job performance.

The secret?

Asking great questions and listening.

You might be underwhelmed with that reveal. But, truth is that most leaders don’t do these things well. In fact, according to Gallup’s 2017 State of the American Workplace Report, only 13% of U.S. workers strongly agree that their organization’s leadership communicates effectively. That includes listening.

If you learn to ask the right questions and listen to your employees, they’ll often diagnose and treat themselves. Instead of you telling them how to solve the problem, you’ve empowered them to discover the answer themselves, thus bolstering their confidence.

Stop giving advice, ask these 3 questions, and listen.

1. “What is the specific task or goal that feels unmanageable or unreachable?”

It’s important to start here. In my experience, when a team member is discouraged or anxious about a task, he/she often tries to explain first in more abstract or vague statements.

“I just feel like I’m failing.”

“I don’t know if I’m cut out for this kind of project.”

“I don’t understand why this isn’t working.”

Phrases like these often reflect strong emotional reactions. If as a leader, you jump in and say, “No, you aren’t!” or “Why would you feel that way?” you might think you are encouraging him, but it’s likely you are communicating that his feelings aren’t valid. Even if you disagree with his assessment, you still want to show him you hear him and understand he’s struggling.

When you ask your team member to clarify and use concrete words or identify specific tasks that feel unmanageable, you’ll help him dig underneath the strong emotional reaction and identify the trigger or source.

Sometimes when I ask this question, my team members are able to identify specific goals that cause them anxiety. Sometimes they aren’t able to identify specifics but realize they are struggling more with setting their own unrealistic expectations. Sometimes they’re dealing with something outside of work that’s causing them a lot of stress in their role. I’ve learned that my assumptions about the root causes are rarely accurate.

Another great follow-up question to ask at this point is, “What’s the real challenge here for you?”

This one is recommended by Michael Bungay Stanier, author of “The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever,” who says that this question “defuses the rush to action, which has many people in organizations busily and cleverly solving the wrong problems.”

By asking your team member to get specific and dig underneath the discouragement, both of you will end up having more clarity around his thoughts and motivations. This will better position you to provide feedback and insight as you move forward in the conversation.