What to Say When Someone on Your Team Isn’t Okay

Someone on your team tells you they are struggling, and within about ten seconds you’ve offered them a story of something similar from your own experience, and how you got through it. You meant it as a form of connection and to offer hope. There is a good chance it felt to them like dismissal.

That gap between wanting to help and knowing how to help is something I talked about on an episode of Suits and Sneakers: Leadership Unfiltered with Lindsay Calder Recknell. Lindsay is a psychological health and safety advisor and mental health skills trainer who works with leaders and organizations across Canada.

Lindsay pointed out that most of us have been through plenty of leadership and management training over the course of our careers. They cover strategy, tools, and models for leading organizational teams. But almost none of them prepare you for how to actually talk to someone who is struggling. As Lindsay put it, "we've never been taught like literally the words, the language, what to say."

I've been thinking about that a lot lately throughout conversations with my clients. I think a lot of leaders carry a nagging sense of inadequacy around these ‘softer’ moments, as if not knowing what to say means something is wrong with them. Lindsay offers a helpful reframe: instead of thinking it’s a character flaw, call it a ‘skill gap’. And like any skill gap, it can be learned.

One of the things she talked about is how often leaders accidentally minimize what someone is going through, because they try to relate it to a similar experience of their own. The intention is good - usually to suggest the person is not alone. The impact though, often isn't.

What most people need first is to feel heard, not compared.

There is a difference between sharing a story and offering empathy, and most of us were taught to treat them as the same thing… The moment I start telling you about my version, I have moved back into my own frame. I am sorting through what I remember, how I felt, and how it ended, while you are still sitting inside your own situation.

Brené Brown draws on the work of nursing scholar Theresa Wiseman, who studied professions where empathy matters and named four attributes of it. Two of them are perspective taking and staying out of judgment. Neither of those is telling a story. Both ask you to stay in the other person’s frame long enough to understand how they are experiencing this, rather than how you once experienced something that looked similar.

Brown adds something that makes this harder rather than easier. To connect with you, she says, she has to connect with something in herself that knows that feeling. So, that means your own experience is not irrelevant, but use it to tap into what that person is feeling.

What to do instead:

You do not know what they have already tried, or how it sits in their body, or which earlier experience is colouring this one.

What she offers instead takes about the same amount of breath. Say that it sounds hard. Then, ask what would help. Do they want you to hold the space while they talk it through? Do they want help finding resources? Do they want you to try to solve it? Let them pick. And if they do not know yet, which happens often when someone is overwhelmed, that is a fine answer too. Ask questions that help them think rather than questions that steer them somewhere.

The last time someone on your team brought you something difficult, what did you say first? And what do you think they heard?

I'd love to hear if this resonates with you. Drop a comment and share what you've found helpful, or where you still feel stuck.

Lindsay’s full conversation on Suits & Sneakers: Leadership Unfiltered goes further than this, including what she calls the duty to inquire and how she uses the science of hope when a project hits a wall. It is worth your time.

You can listen here: Episode Link. Thank you to Lindsay Calder Recknell for such a generous and grounded conversation.

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