How to Tell Your Boss You're Worried About Them (Without Losing Your Job or Their Trust)

This is the hardest part, and it's the reason most executive assistants never say anything.

You've seen the pattern. You're fairly sure what it is. And you're stuck, because your entire role is built on discretion, on not making things about you, on never presuming to know what's going on inside the person you support. Raising a mental health concern with the person who signs your reviews feels like a violation of every unwritten rule of the job.

It's not. But it does need to be done carefully. This article is about how.

It might not be. If your executive has a spouse, a close friend, a chief of staff, or a board member who's already aware and engaged, your role may be to support that person's efforts rather than to open a separate front.

But often there is no such person. Or the people who should be seeing it are too far away, too busy, or too deferential. If you've looked around and realized that you might be the only one who sees the whole picture, then yes, it's your place. Not because you're obligated, but because silence has a cost, and you're watching it accrue.

Before you say anything, be clear with yourself about three things.

What you've observed. Specific, behavioral, factual. "You've canceled eleven external meetings this month." "You've asked me to re-send the same document four times." "You've been in the office before six every day for three weeks." Not "you seem depressed." You're not qualified to diagnose, and leading with a diagnosis invites denial.

What you're asking for. Not that they confide in you. Not that they explain. Only that they consider talking to someone qualified, and that they know you've noticed and you're not judging.

What you'll do if it goes badly. They may be defensive, embarrassed, or cold. That's the illness talking, and it's also a person protecting their dignity. Decide in advance that you won't take it personally, won't retreat entirely, and won't bring it up again in a way that feels like pressure.

Not in a meeting. Not by email. Not when they're already in a bad state. A quiet moment, in private, at the end of a day that wasn't a disaster. If you have a standing one-on-one, that's ideal. If you don't, ask for ten minutes.

Keep it short. Something like:

"I want to say something, and I want to say it once. I've noticed some things over the past couple of months that worry me. You've been cancelling meetings you'd never have cancelled before. You seem exhausted. You don't seem like yourself. I'm not asking you to tell me anything. I just want you to know that I've noticed, that I'm not judging, and that if you ever wanted help finding someone to talk to, I'd handle it quietly and completely. That's all."

Then stop. Let the silence sit. Don't fill it with reassurance or explanation.

• Don't name a diagnosis. "I think you're depressed" invites an argument about the label.
• Don't reference the trauma directly unless they do."Ever since the divorce" makes it about the event; they need it to be about now.
• Don't suggest a vacation. They've heard it, and it implies the problem is fatigue.
• Don't compare them to anyone. "My uncle went through this" shifts the focus.
• Don't promise anything you can't deliver. Discretion, yes. A fix, no.
• Don't bring up the business impact in this conversation. They know. Making it explicit feels like a performance review.

They shut it down. "I'm fine. Thanks for your concern." You say, "Understood. The offer stands," and you let it go. You've planted something. People often come back weeks later.

They get angry. Rare, but possible. Stay calm, apologize for the timing if it helps, and don't argue. Don't retreat from the role; go back to work as normal. The anger usually passes into embarrassment, and then into something more open.

They break. More common than you'd think. Some people have been waiting for someone to say it. If this happens, your job is to listen, not to solve. When they've said what they need to say, that's when you offer the next step.

They ask what you'd suggest. This is the outcome you're preparing for, and it's why the third article in this series exists. Have an answer ready.

When they ask "what would I even do," you need something concrete and low-friction. Not "you should see someone." A specific option, with a phone number, that you've already looked into and can describe in two sentences.

For someone who has been through trauma and is now caught in a depressive spiral, especially someone who may already have tried medication or therapy and is still stuck, one of the most relevant options is SAINT, an FDA-cleared, accelerated form of transcranial magnetic stimulation developed at Stanford. It's a five-day treatment, not a six-week one, and in clinical trials it produced remission in 79 percent of people whose depression hadn't responded to medication, with an average time to remission of 2.6 days. It's delivered at Verified SAINT Providers, including Neuro Wellness TMS Centers of America, which offers private outpatient care with weekend availability.

You can call them yourself, in advance, to understand the process well enough to explain it. You can't schedule treatment on someone's behalf, and you shouldn't. But you can hand your executive a name, a number, and a one-line summary, and say, "I looked into this. If you want, I'll set up the first call and put it on the calendar as whatever you want it called."

That's the whole job. See it, say it once, have the answer ready.

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If your executive says anything that suggests they're thinking about ending their life, treat it as an emergency. Encourage them to call or text 988 (Suicide & Crisis Lifeline), or call it yourself for guidance on how to help. This article is for educational purposes and is not a substitute for individual medical advice.