A Worried Manager,

I understand the pressure you're feeling as a manager when an employee’s personal struggles start affecting their work. Balancing empathy with accountability is tough, especially when mental health is involved.

Let’s first talk about the generational aspects here. You refer to your employee as a “kid,” which, as a Boomer, could mean anyone under 35! If they are just starting out in their career (say, between 21-25), they may be overwhelmed, worried about losing their job, and unsure how to open up to you about what’s going on. And this could apply to anyone, regardless of age.

The fact that they’ve previously shared mental health struggles with you shows some level of trust, but it also suggests they might be holding onto the hope that things will magically get better on their own. It’s a coping mechanism that can be present at any age.

Here’s where generational differences might play a role:

• Your employee may be young and inexperienced, struggling to communicate their challenges with you.

• You, as a Boomer, may feel uncomfortable navigating a conversation about mental health, especially given the stigma that existed when you were growing up. But I would encourage you to see this discomfort not as a generational gap, but simply a lack of experience. This is an opportunity for you to expand your perspective and feel more confident in these types of discussions.

The good news is that mental health is increasingly being viewed like physical health. The stigma is fading, and it’s now common for people to openly discuss mental health issues. You might be surprised how many people you know have dealt with similar struggles, whether personally or through loved ones.

Now, let’s focus on the management side of things.

I recommend approaching this with the mindset of defining reality—as Max De Pree said, “The first responsibility of a leader is to define reality.” Your employee’s work isn’t meeting expectations, and it’s impacting the team. Ignoring it won’t help anyone. A simple approach would be to say, “I’ve noticed you haven’t been yourself lately,” and ask, “What’s going on?” or “How can I help?” This creates a space for open dialogue.

You don’t need to be a therapist, but you do need to be willing to talk about the human side of leadership. It’s okay to admit that you’re not experienced with mental health challenges, but that you’re open to learning. You can tell them that your goal is to support them and help them return to the level of performance you know they’re capable of. And you can do this without needing them to share anything more than they’re comfortable with.

Next, check your company’s employee handbook for policies on health-related leave or benefits. Many companies have provisions for flexible leave, therapy, or counseling services—information that can be incredibly helpful. Your HR team can also clarify what resources are available. If your company offers Employee Assistance Programs (EAP), you can share those options with your employee, and if not, point them to external resources like the National Alliance on Mental Illness (NAMI).

When you talk with your employee, focus on providing solutions and helping them develop a plan to manage their workload and personal challenges. The key is to do this in a way that doesn’t force them to share more than they feel comfortable with but helps them get back on track.

As for whether you should be the one talking about mental health—no, you're not expected to be a mental health expert. However, it is your responsibility to help them navigate how to balance their personal issues with their work. That might mean discussing how they can take care of themselves and still meet work expectations, and finding ways to support their long-term success.

If the conversation pushes your employee too far, it could signal that they’re not currently fit for work, and you may need to involve HR to explore next steps. However, if they’ve been avoiding the conversation and wish they could get back on track, they may be grateful for the chance to be honest and find a supportive way forward.

In the future, if an employee shares similar challenges, you can ask how it impacts them, what their preferred approach to dealing with it is, and set clear expectations for how to handle it going forward. This helps create a workplace where everyone can bring their full selves to work, even when they face personal difficulties.

I know you’re compassionate and thoughtful. This is not a huge leap for you, and you can definitely prove that Boomers are not out of touch with these conversations.

Best,
YS

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