In my head, we were all on the same page…
When our oldest was in kindergarten, her school hosted a fall festival.
They sent out a note asking for volunteers—and mentioned that volunteers were welcome to wear costumes.
Well.
This was our first child. Our first school event. We were those parents.
We lined up a babysitter for the younger two, showed up ready to work…
…and dressed in full costume.
I was an angel. Complete with wings and a halo.
My husband was a devil. Pitchfork and all.
And when we walked in?
Not a single other adult was in costume.
Not one.
Turns out “welcome to wear costumes” and “people will actually wear costumes” are two very different things.
And that, my friends, was my first real experience with what I now call an expectation hangover.
File this under, “Phew, I nearly blew it!”
Early in my career, I got a call from a prospective client about designing a leadership retreat for their multi-state team. Big opportunity.
We start talking through what it could look like, and she asks a very reasonable question:
“Can you walk me through the exact flow of the day and what we’ll be doing at what time?”
And I’m over here like,
“Oh, we’ll kind of wing it.”
“We’ll play it by ear.”
“We’ll see what the group needs.”
(You can imagine how that landed.)
What I thought I was communicating: flexibility, responsiveness, reading the room.
What she heard: absolutely no plan whatsoever.
Turns out “we’ll wing it” does not inspire confidence in everyone. Who knew?
Same conversation. Very different interpretations.
Thankfully, I caught it, adjusted, and got much more specific.
And yes—I got the job.
But dang… that one came with a bit of an expectation hangover.
Different situations. Same pattern.
I had a picture in my head of how it was going to go…And reality had other plans.
That gap?
That’s an expectation hangover.
And here’s the thing—most of the frustration we feel isn’t coming from what actually happened.
It’s coming from the story we told ourselves before it happened.
It happens in leadership All. The. Time.
This is where a lot of leadership breakdowns live.
In leadership, most of the communication issues come from assumptions, unspoken or unshared goals, and an unwillingness to feel discomfort.
Not in bad intentions.
Not in lack of effort.
But in the gap between what we meant… and what others actually heard, saw, or experienced.
We assume people know.
We assume we’re aligned.
We assume we’re being clear.
And then we’re surprised when things don’t go the way we expected.
Here’s what I’ve learned—sometimes the hard way:
Clarity can feel uncomfortable in the moment.
It can feel like over-explaining.
Like slowing things down.
Like stating the obvious.
But confusion?
Confusion is expensive.
It costs time.
It costs trust.
It costs momentum.
And more often than not, it leaves everyone with a bit of an expectation hangover.
Ask yourself:
Where might I be making assumptions right now?
What have I said… but not actually made clear?
Where am I expecting alignment… without checking for it?
And what conversation might feel a little uncomfortable now…
that could save a whole lot of confusion later?
You can prevent expectation hangovers.
Because here’s the truth—
most expectation hangovers don’t come out of nowhere.
They come from gaps.
Gaps between what was said and what was heard.
Between what we assumed… and what was actually understood.
And every now and then, those gaps leave you standing in a room…
dressed as an angel… next to a devil…
wondering how you were the only ones who got the memo.
I’m always working on it.
These days, I try to close the gap a little sooner.
Ask one more question.
Clarify one more detail.
Say the thing that feels a little unnecessary.
Because I’ve learned—
expectation hangovers are a whole lot easier to prevent than they are to recover from.
P.S. If you’re reading this and thinking, “Yep… we’ve got a few of those gaps,” you’re not alone. Helping teams get clearer, more aligned, and a whole lot less frustrated is a big part of the work I do with leadership teams and women leaders. Retreats, leadership programs, and keynotes… that’s my jam. If you’d like help with that, let’s talk—grab a complimentary discovery call at jenniferledet.com.
