
You’ve hired someone into a role and they’re struggling.
If you’ve ever managed people, I suspect you’ve experienced this at least once (and if you’ve managed as long as I have, you’ve likely experienced it multiple times).
It could be a new employee who doesn’t fully grok the responsibilities of the role, or an existing, previously high-performing employee who can’t quite make the transition. Either way, the results are the same—your new hire is on the struggle bus.
Coaching employees to succeed in their roles—and grow in their careers—is one of the most important functions of a leader.
But despite its importance, many leaders avoid coaching employees—especially underperforming ones. We don’t know how to approach the topic. We want to be kind. We want to avoid confrontation. We don’t want to acknowledge our own responsibility in the situation.
Whatever the reason, we do nothing. And our employee continues to struggle.
Which serves no one—it’s not good for the employee or for your organization.
To address the situation, you must first understand why your employee is struggling.
Do they have something going on in their life outside of work that’s impacting them at work—a medical issue, death in the family, new child, move, or a national election, perhaps?
Is the issue more related to the work itself—they don’t have the skills to perform the role, or need to learn to operate at a new level in the organization?
Or is the problem you? Are your expectations reasonable? Is what you want from the role what’s actually needed in it? Did you properly set your employee up for success?
Understanding the context will help determine the solution.
Next, you have to have an honest conversation with the employee.
It’s rare that an employee doesn’t know they’re struggling. But they may not feel that they can acknowledge it or ask for help.
What’s kindest here isn’t avoiding the issue—it’s facing it head-on and creating space for your employee to acknowledge their struggles. And once that happens, you both can take steps to remedy it.

When you do have that conversation, approach it with deep curiosity and an open mind, and …
Listen carefully. Start with an open-ended “How are things going for you?” and then listen … really listen. Your employee might not outright say “I’m struggling” but they may provide clues that you can dive deeper on. “Tell me more" is a favorite follow-on of mine. If you don’t hear any indication of struggle, ask more direct questions like “How are you feeling about the XYZ project?” or even more pointedly “I’m sensing that you’re struggling a little on the XYZ project, but I may not be right. I’d love to hear where you’re at with it and how I can help.”
Reassure them. When an employee divulges that they are, in fact, struggling, reassure them! Let them know that it’s okay to both struggle and to acknowledge it—we all have been there are some point in our lives. Reassure them that they’re safe to share their struggles with you and that you’re there to help.
Clarify issue(s) and expectations. Work with your employee to get to the root of the issue (the “five whys” may help here). It’s easy to get sidetracked with solutions to symptoms—I don’t have enough time so I need an assistant to manage administrative tasks, for example. But why don’t they have enough time? Make sure you fully understand the problem you’re trying to solve for, as well as articulate your expectations for the role and behavior(s) you expect to see.
Identify a path forward. Engage your employee in finding solutions to the issues and expectations you’ve identified. Ask them to share what they can (and plan to) do to address the situation, and what they need to make it happen. It’s okay to help shape or influence this plan to ensure it drives the behaviors and outcomes you’re looking for, but ultimately you want your employee to connect the dots between (and take ownership of) their struggles and the changes they need to make to be successful in their role.
Document the plan. Put everything in writing to avoid miscommunication and misunderstandings. It provides clarity and accountability for both you and your employee, and can be used during regular 1:1s as a checklist or conversation guide. And as much as you hope it doesn’t go here, having everything in writing also provides importance documentation for future performance management actions, if needed.
Through this process, your goal should be to create the best outcome for the employee and the organization. Sometimes we can help an employee build the skills and confidence they need to succeed in a role—and that’s a win.
Other times, there’s a mismatch between employee and role and the right option is to help your employee find a better-aligned role they can thrive in.
And that can be a win, too.