3 Coaching Questions for Leaders to Ask When a Team Member Feels Discouraged

Guest Post by LeAnne Lagasse

“Archetypal managers tell people what to do; coaches ask questions that help their people move forward.” -Vipula Gandhi, Gallup

“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 answr themselves, thus bolstering their confidence.

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.

When a task or goal feels impossible, it’s often because it requires us to operate in areas of lesser talent. For example, when I’m asked to think creatively or brainstorm new and innovative ideas, I typically feel discouraged and defeated before I’ve even started. That’s because these patterns of thinking, feeling, and behaving don’t come as naturally to me.

It isn’t enough to just tell myself, “Be creative! Think of new and exciting ideas!” Pulling myself up by my bootstraps, so to speak, doesn’t work. Instead, I’ve got to make connections between my natural talents and the desired outcome. When I’m asked to be creative, I’ve got to use what I’ve got! That means instead of wasting time trying to make myself think creatively, I’m going to identify and reach out to the most creative and innovative person I know who would have the most insight and connection to that specific project and ask him/her for help. My ability to understand the unique qualities of unique people means I am going to intuitively know the right person for this task. And when I’ve done this in the past, it’s almost always worked. Ideas that would take me hours (if ever!) to generate are readily accessible to a person more talented in this area.

You can help guide your team member through this exercise in aiming his/her strengths by asking how his natural patterns of thinking, feeling, and behavior might connect to the task or goal. It’s important that you let your employee answer this question before you jump in to make a suggestion. It’s possible you have eyes to see things he doesn’t and your suggestion will provide an “aha moment.” But many times, managers are too quick to assume and lead employees down a path that isn’t as fruitful.

Top performers in a given role deliver the same outcomes using different behaviors. As a developer and supervisor of many educators over the years, I can tell you that exceptional teachers come in all sorts of packages. They all use different talents to build rapport with students, manage their time and administrative responsibilities, inspire creativity and innovation, mediate conflict, and so on and so forth.

Great leaders don’t expect their employees to approach every task exactly as they would. Rather, they are specific about the outcome they expect, but give employees the freedom to decide the most effective way to approach the task.

At this point in the conversation, it can be helpful to turn the corner and discuss some logistics and action steps. Have your team member focus on what does come naturally to him so that he can think creatively and strategically about how that talent could be leveraged to accomplish the challenging task or goal.

Again, do not rush to suggestions. Instead, let your team member brainstorm ways to tackle the task or goal in light of his strengths. Help him refine his ideas.

Ask follow up questions such as, “Who can you partner with on this project?” or “How can I support you best as you work towards this goal?”

Stay curious. By asking good questions, listening, and providing feedback about what you’re hearing him say, you’ll empower him to take control and make plans in light of his strengths.

*A Quick Note! If after discussing these questions together, both of you are still struggling to see any clear connection between his talents and the task, goal, or even his current role, it might be time to reevaluate. Is he discouraged because you’re asking him to operate from a place of weakness on a regular basis? If this is the case, it’s no wonder he feels inadequate! Do what you can to position him to use his strengths on a daily basis.

Today’s employee, especially The Millennial Employee, isn’t satisfied with simply reporting up to a manager. She desires a supervisor who invests in her, coaches her, and focuses on her continued learning and development.

Next time you find yourself with a discouraged employee, resist the temptation to immediately jump in and solve the problem or offer advice.

Instead, be a coach.

Ask the right questions.


And then watch her grow in confidence and self-awareness.

LeAnne Lagasse


LeAnne Lagasse, SHRM-SCP, is the Co-founder of ROI Talent Development, a Texas-based training and consulting firm that specializes in helping organizations reduce turnover and improve employee engagement by equipping their frontline managers to grow as communicators and drive peak performance. LeAnne is a former Professor and Administrator at Texas Tech University and currently serves as Adjunct Faculty at Missouri State University where she teaches business communication courses to their MBA students.  LeAnne invites you to join her Facebook ROI Group.


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