Off My Chest - Conversations We Can't Stop Replaying

Foot-in-Mouth Leadership: When "Are You Quitting?" Goes Terribly Wrong

• Anitra St. Hilaire

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I thought I was being supportive when I asked a quieter-than-usual coworker, “Are you quitting?” Instead, my attempt at empathy landed as suspicion, and it changed our relationship overnight.

In this first episode of Off My Chest, I share how one well-intentioned question went terribly wrong, what it taught me about leadership and assumptions, and why conversations we misread can linger long after they’re over.

If you’ve ever replayed a moment you wish you could take back, this one might feel familiar.

Off My Chest is created and hosted by Anitra St. Hilaire. If you'd like to hear more from me, sign up for my newsletter, Mirror Truth.

Anitra St. Hilaire:

I usually pride myself on being able to read people, but this time I got it wrong. A I wanted to be supportive, so I asked, "Are you thinking about leaving? If you are, I absolutely will help you figure it out." They froze and then they said quitting was the last thing on their mind. That one question, truly meant to help, actually ruined our relationship, and I have carried it with me ever since.

Anitra St. Hilaire:

Welcome to Off My Chest, where we talk about the conversations that don't leave us alone, the ones we misread, mishandled, or can't seem to forget. I'm Anitra St Hilaire. I've spent my career leading people, leading teams and coaching executives, and if there is one thing I've learned, it's this. Conversations shape everything: our work, our relationships, and even how we see ourselves.

Anitra St. Hilaire:

But I'm not just here as a coach. I'm here as someone who still replays her own awkward, messed-up,, , unfinished conversations in my head over and over again. And so I created this space to share those stories. Not to fix the past, but to name it, reflect on it, and maybe let a little bit of that weight go. So let me take you back to that day.

Anitra St. Hilaire:

This coworker had been on my radar for a while. They'd been quieter in meetings, pulling back from conversations, and I honestly thought I was picking up on a vibe. You know that feeling when someone just seems elsewhere, they're not talking as much, you're wondering if they're really engaged and want to be here, and that's what I thought I was seeing. So we had the opportunity to catch up one day and I thought to myself okay, here it is. This is the moment they're about to tell me they're thinking about leaving. In my mind, I was already stepping in the coach mode. I wanted to make it easy for them, to show that I was safe and supportive and I could handle tough conversations All of the things I wanted to be as an HR leader. And so I skipped the small talk and I just asked hey, are you thinking about leaving? Because if you are, I'll help you figure out that conversation and you can just imagine me being bright and perky and super earnest and helpful.

Anitra St. Hilaire:

But then came the freeze. Their face went completely blank. They blinked a few times and finally they said, with their face slowly reddening. And finally they said, with their face slowly reddening, no, not at all. That's the last thing on my mind. Do people think I want to leave? Am I in some sort of trouble? Is the organization trying to get rid of me? Do you want me to leave? And I can still see the look on their face, this half awkward, half offended, half shocked, half scared.

Anitra St. Hilaire:

And in that instance I realized I had crossed the line and what I thought would come across as empathy really came across like suspicion and what I thought was supposed to be support landed like doubt. And the truth is there was no recovering from that moment. I tried to undo what I did and say no, I was just curious and I wanted to make sure you knew. If you wanted to have a tough conversation, you could. And I could feel myself trying to walk back that question, but honestly I couldn't. And our dynamic shifted. There was this distance I hadn't felt before and a wall I hadn't meant to build, but it was there. Eventually I ended up leaving the organization and, as far as I know, this person is still working there, happily. So I was clearly wrong.

Anitra St. Hilaire:

But what stayed with me wasn't just the awkwardness of that conversation. It was the reminder that my read of a situation is not the only truth in the room I was so sure I knew the story that I skipped over curiosity, I skipped over connection, I skipped over the fact that I could be wrong and jumped right in the conclusions with both feet. Right in the conclusions with both feet. And it made me wonder how many other times I'd done that without even realizing it. Because here's the thing in leadership, in friendships, in family, it is so easy to mistake assumption for understanding. Some of us pride ourselves on being so good at reading people, but sometimes we're just writing our own script and handing it to them instead of really understanding where that other person is coming from.

Anitra St. Hilaire:

That day showed me how quickly trust can shift, how even good intentions can change the temperature of a relationship. Something my father used to always say is the road to hell is paved with good intentions. And this is definitely one of those times. And, if I am being truthful, it stung not just because I'd gotten it wrong and I had gotten it wrong and I hated that I got it wrong, I'd gotten it wrong and I had gotten it wrong and I hated that I got it wrong, but because I knew I probably made them question my view of them and maybe even their place in the organization, and that's certainly the opposite of what I wanted to do. So this story just reminds me good intentions don't always land the way we think they will reminds me good intentions don't always land the way we think they will.

Anitra St. Hilaire:

I thought I was helping, but instead I made someone feel seen in the wrong way, completely misunderstood. And that's what sticks with me. It's not just the words we said, it's what those words left behind. And if you've had a moment like that a question you wish you hadn't asked or a silence you wish you'd feel you know how heavy it can feel. And what gets me is how quickly the ground can shift beneath you.

Anitra St. Hilaire:

One sentence and suddenly the trust feels completely different. And I just wonder how many times have I done that without realizing it? And that's what this space is for A place to bring those messy conversations into the light and see what happens when we stop carrying them alone. And this is just the beginning. Each week I'll share more stories, sometimes mine, sometimes I'll have someone on to talk about their story, and we'll name the conversations we can't shape, because once we name them, maybe they'll start to loosen their grip a bit. So if this resonated, follow the show and come back for the next one. I'll be here with more stories to get off my chest and maybe some you'll recognize as your own. Thanks for listening.