September 25, 2025 • 7 mins
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.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Anitra St. Hilaire (00:02):
I usually pride myself on being able to
read people, but this time I gotit wrong.
A I wanted to be supportive,so I asked, "Are you thinking
about leaving?
If you are, I absolutely willhelp you figure it out.
" They froze and then they saidquitting was the last thing on
(00:26):
their mind.
That one question, truly meantto help, actually ruined our
relationship, and I have carriedit with me ever since.
(00:49):
Welcome to Off My Chest, wherewe talk about the conversations
that don't leave us alone, theones we misread, mishandled, or
can't seem to forget.
I'm Anitra St Hilaire.
I've spent my career leadingpeople, leading teams and
coaching executives, and ifthere is one thing I've learned,
it's this.
Conversations shape everything: our work, our relationships, (01:01):
undefined
and even how we see ourselves.
But I'm not just here as a coach.
I'm here as someone who stillreplays her own awkward,
messed-up,, , unfinishedconversations in my head over
(01:22):
and over again.
And so I created this space toshare those stories.
Not to fix the past, but toname it, reflect on it, and
maybe let a little bit of thatweight go.
So let me take you back to thatday.
This coworker had been on myradar for a while.
(01:43):
They'd been quieter in meetings, pulling back from
conversations, and I honestlythought I was picking up on a
vibe.
You know that feeling whensomeone just seems elsewhere,
they're not talking as much,you're wondering if they're
really engaged and want to behere, and that's what I thought
(02:04):
I was seeing.
So we had the opportunity tocatch up one day and I thought
to myself okay, here it is.
This is the moment they'reabout to tell me they're
thinking about leaving.
In my mind, I was alreadystepping in the coach mode.
I wanted to make it easy forthem, to show that I was safe
(02:25):
and supportive and I couldhandle tough conversations All
of the things I wanted to be asan HR leader.
And so I skipped the small talkand I just asked hey, are you
thinking about leaving?
Because if you are, I'll helpyou figure out that conversation
and you can just imagine mebeing bright and perky and super
(02:49):
earnest and helpful.
But then came the freeze.
Their face went completelyblank.
They blinked a few times andfinally they said, with their
face slowly reddening.
And finally they said, withtheir face slowly reddening, no,
not at all.
That's the last thing on mymind.
Do people think I want to leave?
(03:10):
Am I in some sort of trouble?
Is the organization trying toget rid of me?
Do you want me to leave?
And I can still see the look ontheir face, this half awkward,
half offended, half shocked,half scared.
And in that instance I realizedI had crossed the line and what
(03:30):
I thought would come across asempathy really came across like
suspicion and what I thought wassupposed to be support landed
like doubt.
And the truth is there was norecovering from that moment.
I tried to undo what I did andsay no, I was just curious and I
(03:55):
wanted to make sure you knew.
If you wanted to have a toughconversation, you could.
And I could feel myself tryingto walk back that question, but
honestly I couldn't.
And our dynamic shifted.
There was this distance Ihadn't felt before and a wall I
hadn't meant to build, but itwas there.
(04:17):
Eventually I ended up leavingthe organization and, as far as
I know, this person is stillworking there, happily.
So I was clearly wrong.
But what stayed with me wasn'tjust the awkwardness of that
conversation.
It was the reminder that myread of a situation is not the
(04:38):
only truth in the room I was sosure I knew the story that I
skipped over curiosity, Iskipped over connection, I
skipped over the fact that Icould be wrong and jumped right
in the conclusions with bothfeet.
Right in the conclusions withboth feet.
(05:01):
And it made me wonder how manyother times I'd done that
without even realizing it.
Because here's the thing inleadership, in friendships, in
family, it is so easy to mistakeassumption for understanding.
Some of us pride ourselves onbeing so good at reading people,
but sometimes we're justwriting our own script and
(05:23):
handing it to them instead ofreally understanding where that
other person is coming from.
That day showed me how quicklytrust can shift, how even good
intentions can change thetemperature of a relationship.
Something my father used toalways say is the road to hell
is paved with good intentions.
(05:43):
And this is definitely one ofthose times.
And, if I am being truthful, itstung not just because I'd
gotten it wrong and I had gottenit wrong and I hated that I got
it wrong, I'd gotten it wrongand I had gotten it wrong and I
hated that I got it wrong, butbecause I knew I probably made
them question my view of themand maybe even their place in
the organization, and that'scertainly the opposite of what I
(06:06):
wanted to do.
So this story just reminds megood intentions don't always
land the way we think they willreminds me good intentions don't
always land the way we thinkthey will.
I thought I was helping, butinstead I made someone feel seen
in the wrong way, completelymisunderstood.
(06:27):
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 likethat a question you wish you
hadn't asked or a silence youwish you'd feel you know how
heavy it can feel.
And what gets me is how quicklythe ground can shift beneath
(06:47):
you.
One sentence and suddenly thetrust feels completely different
.
And I just wonder how manytimes have I done that without
realizing it?
And that's what this space isfor A place to bring those messy
conversations into the lightand see what happens when we
(07:08):
stop carrying them alone.
And this is just the beginning.
Each week I'll share morestories, sometimes mine,
sometimes I'll have someone onto talk about their story, and
we'll name the conversations wecan't shape, because once we
name them, maybe they'll startto loosen their grip a bit.
So if this resonated, followthe show and come back for the
(07:31):
next one.
I'll be here with more storiesto get off my chest and maybe
some you'll recognize as yourown.
Thanks for listening.
I usually pride myself on being able to
read people, but this time I gotit wrong.
A I wanted to be supportive,so I asked, "Are you thinking
about leaving?
If you are, I absolutely willhelp you figure it out.
" They froze and then they saidquitting was the last thing on
(00:26):
their mind.
That one question, truly meantto help, actually ruined our
relationship, and I have carriedit with me ever since.
(00:49):
Welcome to Off My Chest, wherewe talk about the conversations
that don't leave us alone, theones we misread, mishandled, or
can't seem to forget.
I'm Anitra St Hilaire.
I've spent my career leadingpeople, leading teams and
coaching executives, and ifthere is one thing I've learned,
it's this.
Conversations shape everything: our work, our relationships, (01:01):
undefined
and even how we see ourselves.
But I'm not just here as a coach.
I'm here as someone who stillreplays her own awkward,
messed-up,, , unfinishedconversations in my head over
(01:22):
and over again.
And so I created this space toshare those stories.
Not to fix the past, but toname it, reflect on it, and
maybe let a little bit of thatweight go.
So let me take you back to thatday.
This coworker had been on myradar for a while.
(01:43):
They'd been quieter in meetings, pulling back from
conversations, and I honestlythought I was picking up on a
vibe.
You know that feeling whensomeone just seems elsewhere,
they're not talking as much,you're wondering if they're
really engaged and want to behere, and that's what I thought
(02:04):
I was seeing.
So we had the opportunity tocatch up one day and I thought
to myself okay, here it is.
This is the moment they'reabout to tell me they're
thinking about leaving.
In my mind, I was alreadystepping in the coach mode.
I wanted to make it easy forthem, to show that I was safe
(02:25):
and supportive and I couldhandle tough conversations All
of the things I wanted to be asan HR leader.
And so I skipped the small talkand I just asked hey, are you
thinking about leaving?
Because if you are, I'll helpyou figure out that conversation
and you can just imagine mebeing bright and perky and super
(02:49):
earnest and helpful.
But then came the freeze.
Their face went completelyblank.
They blinked a few times andfinally they said, with their
face slowly reddening.
And finally they said, withtheir face slowly reddening, no,
not at all.
That's the last thing on mymind.
Do people think I want to leave?
(03:10):
Am I in some sort of trouble?
Is the organization trying toget rid of me?
Do you want me to leave?
And I can still see the look ontheir face, this half awkward,
half offended, half shocked,half scared.
And in that instance I realizedI had crossed the line and what
(03:30):
I thought would come across asempathy really came across like
suspicion and what I thought wassupposed to be support landed
like doubt.
And the truth is there was norecovering from that moment.
I tried to undo what I did andsay no, I was just curious and I
(03:55):
wanted to make sure you knew.
If you wanted to have a toughconversation, you could.
And I could feel myself tryingto walk back that question, but
honestly I couldn't.
And our dynamic shifted.
There was this distance Ihadn't felt before and a wall I
hadn't meant to build, but itwas there.
(04:17):
Eventually I ended up leavingthe organization and, as far as
I know, this person is stillworking there, happily.
So I was clearly wrong.
But what stayed with me wasn'tjust the awkwardness of that
conversation.
It was the reminder that myread of a situation is not the
(04:38):
only truth in the room I was sosure I knew the story that I
skipped over curiosity, Iskipped over connection, I
skipped over the fact that Icould be wrong and jumped right
in the conclusions with bothfeet.
Right in the conclusions withboth feet.
(05:01):
And it made me wonder how manyother times I'd done that
without even realizing it.
Because here's the thing inleadership, in friendships, in
family, it is so easy to mistakeassumption for understanding.
Some of us pride ourselves onbeing so good at reading people,
but sometimes we're justwriting our own script and
(05:23):
handing it to them instead ofreally understanding where that
other person is coming from.
That day showed me how quicklytrust can shift, how even good
intentions can change thetemperature of a relationship.
Something my father used toalways say is the road to hell
is paved with good intentions.
(05:43):
And this is definitely one ofthose times.
And, if I am being truthful, itstung not just because I'd
gotten it wrong and I had gottenit wrong and I hated that I got
it wrong, I'd gotten it wrongand I had gotten it wrong and I
hated that I got it wrong, butbecause I knew I probably made
them question my view of themand maybe even their place in
the organization, and that'scertainly the opposite of what I
(06:06):
wanted to do.
So this story just reminds megood intentions don't always
land the way we think they willreminds me good intentions don't
always land the way we thinkthey will.
I thought I was helping, butinstead I made someone feel seen
in the wrong way, completelymisunderstood.
(06:27):
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 likethat a question you wish you
hadn't asked or a silence youwish you'd feel you know how
heavy it can feel.
And what gets me is how quicklythe ground can shift beneath
(06:47):
you.
One sentence and suddenly thetrust feels completely different
.
And I just wonder how manytimes have I done that without
realizing it?
And that's what this space isfor A place to bring those messy
conversations into the lightand see what happens when we
(07:08):
stop carrying them alone.
And this is just the beginning.
Each week I'll share morestories, sometimes mine,
sometimes I'll have someone onto talk about their story, and
we'll name the conversations wecan't shape, because once we
name them, maybe they'll startto loosen their grip a bit.
So if this resonated, followthe show and come back for the
(07:31):
next one.
I'll be here with more storiesto get off my chest and maybe
some you'll recognize as yourown.
Thanks for listening.
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