141. If You Only Meet With Employees When They’re in Trouble, You’re Doing It Wrong

Holly Silva
Mar 24
4 min read

Okay, let’s just jump right in because this one? It matters. Think about this for a second … the last time your boss pulled you aside for a “quick chat” …

Were you like:

“Omg yay, can’t wait!! 😍”

Or were you like:

“What did I do…” 😅

Exactly. Because SAME.

And that’s exactly the kind of environment we realized we never wanted to create inside our business.

Why We Made This Shift (AKA … We Were Lowkey Guilty Too)

We’re gonna be real with you — we were not always perfect at this. A lot of our communication used to happen in:

Group meetings
Team chats
Quick reminders

And then one-on-one convos? Usually meant something went wrong.

🚩 Yeah… we didn’t love that. Because we’ve BOTH worked jobs where:

You only got called in when you were in trouble
Leadership was passive aggressive (you know the vibe 🙃)
You constantly wondered… “Am I doing a good job or not?”

And that creates:

Fear
Anxiety
Disconnection
Employees who feel invisible

Yeah, no. We’re not doing that over here.

What One-on-Ones Actually Do (Hint: It’s Not Just “Evaluations”)

Let’s clear this up real quick: this is NOT just about performance reviews. Yes, we evaluate.Yes, we talk numbers. But the bigger picture? It’s about connection 🤝

Our one-on-ones are for:

Checking in as humans, not just employees
Giving them space to talk (and actually listening 👀)
Catching problems BEFORE they become disasters
Making sure nobody feels like just “another body” on the schedule

Because let’s be honest … people don’t leave jobs over one bad day. They leave when they feel unseen.

Let’s Talk Retention (Because This Is HUGE 🔥)

This is where things get real. If you’re not regularly talking to your employees one-on-one, you are missing SO much.

We’re talking:

Burnout
Frustration
Money concerns
Feeling underworked or overworked

And here’s the thing: most employees are NOT just going to come out and say it. But when you create the space? Oh, they’ll tell you.

We’ve had employees open up about:

Wanting more hours
Feeling overwhelmed
Being unhappy with their paychecks

And because we caught it early — we were able to fix it. That’s the difference between keeping a great employee and losing them out of nowhere,

Okay But Like … What Do Our Meetings Actually Look Like? 👀

We got you. Here’s the behind-the-scenes:

✨ 1. Twice-a-Year Self-Reflection Form

Twice a year, we have our team fill out a form. We ask things like:

What are your goals? (short-term AND long-term)
How are you doing personally?
How do you feel about the company?
What can WE do better?

Yes … we are literally asking our employees to evaluate US too 😅 And honestly? It keeps us in check. It also makes everything feel like a two-way street instead of:

👉 “we talk, you listen”

📊 2. Self-Rating vs. Our Rating (This Part Is SO Interesting)

We have them rate themselves on things like:

Work quality
Attendance
Initiative
Problem solving
Job knowledge

Then we rate them too. BUT — we do ours first so there’s zero bias. And let us tell you … this part gets GOOD 👀 Because sometimes:

They underrate themselves (and we get to hype them up 🥹)
They overrate themselves (and we’re like … okay let’s chat lol)

Either way—it opens the door for real conversations.

📈 3. We Bring RECEIPTS (Facts > Feelings Always)

This is where we might be a little intense … but it works 😌

We track:

Lateness
Absences
Complaints
Compliments
Job timing (ahead/behind)

So instead of:

“I feel like you’ve been off…”

We say:

“Here’s what your numbers show.”

And BOOM 💥 No arguing. No “you’re picking on me.” No weird tension. Because at the end of the day …

👉 It’s not personal. It’s patterns.

🗣️ 4. The Actual Conversation (Keep It Real, Keep It Kind)

Our meetings are NOT scary. They’re normal, expected, usually positive

We:

Start with wins 🎉
Go through their self-reflection
Compare it with our feedback
Talk through any gaps
Set goals moving forward

Even when we’re being honest about improvement, it’s always from a place of:

“We know you can do better — and we’re here to help you get there.”

Radical Candor… But Make It Human 💅

We are BIG on honesty. Like … core value level big. But we’re not here to tear people down. We’re here to:

Be direct
Be respectful
Be supportive

Because avoiding hard conversations? That helps no one. And sugarcoating everything? Also not it.

Let’s Talk Culture (Because This Is Where It Gets JUICY)

This is where most business owners miss the mark 👇

If you:

Call people out in group settings
Speak in vague “some of you …” statements
Avoid direct conversations

You are creating:

🚩 Gossip

🚩 Drama

🚩 Confusion

Your team will literally start playing detective:

“Wait… who are they talking about??”

And now you’ve got a toxic environment brewing. NO THANK YOU ❌

But when you:

Handle things privately
Communicate clearly
Give people space to talk

You create:

✨ Trust

✨ Clarity

✨ Respect

And THAT is how you build a strong culture.

Real Talk: Mistakes We’ve Made 😅

Because we’re not gonna sit here and act perfect. We’ve:

Only held meetings when things were wrong
Skipped one-on-ones for “easy” employees
Been inconsistent

And here’s the truth … even your BEST employees need that time with you. Skipping them? It can quietly make them feel less important. Consistency = everything.

What We Want for Our Team 🤍

At the end of the day, our goal is simple: we want our employees to feel comfortable coming to us. Not scared. Not anxious. Not waiting until something blows up.

We want them to know: