Early in my career, I managed a team of four. Within months, three of them were gone.

Two I had to fire. One I had to transfer out.

There were reasons of course. Bad hires. Wrong fit. Performance issues.
The truth? I was checking boxes instead of leading.

We had regular check-ins. Project status updates. I gave them technical answers when they got stuck.

I thought I was doing one-on-ones. I wasn’t.

Instead, I was running status updates disguised as leadership. Task lists disguised as coaching. I never asked how they were really doing. Never talked about their career growth. I gave critical feedback constantly and positive feedback scarcely.

I didn’t know when someone was unhappy. I didn’t know when they were headed in the wrong direction until they were so far gone I couldn’t get them back on track. I was operating blind because I didn’t understand the value of truly spending time with my people.

My one-on-ones weren’t effective. And I couldn’t lead. The team fell apart.

Why One-on-Ones Matter

Most leaders think they're doing one-on-ones. They're not.

Real one-on-ones are where leadership actually happens. Where coaching occurs. Where friction surfaces. Where trust builds. Where people grow.

If you're not doing them right, you're not leading. You're just managing.

Research confirms this. Adobe found that regular one-on-ones boost employee retention and lower voluntary exits by almost 33%. Gallup's research shows that managers account for at least 70% of the variance in employee engagement scores. More striking: 50% of Americans have left a job to "get away from their manager" at some point in their career.

The quality of your one-on-ones directly impacts whether your best people stay or leave.

Skip them and you send a message: my time matters more than yours.

Do them well and you send the opposite message: I am invested in your growth and our results.

The Frequency Problem

For your direct reports, one-on-ones should be frequent. Weekly. Biweekly can work with the right people. Monthly isn’t effective.

Research shows employees are three times more engaged when they have weekly conversations with their manager. Gallup found that employees whose managers hold regular meetings with them are almost three times as likely to be engaged as employees whose managers do not hold regular meetings with them.

Even so, I see leaders push back on this constantly. "I have eight direct reports. If I do 30 minutes weekly with everyone, that's four hours."

Yes. That’s your job.

Your impact happens through other people now. That requires time, presence, and consistent touchpoints. Monthly check-ins don't build relationships. They create distance.

People need feedback, direction, encouragement, and help resolving issues. They need it regularly, not when you remember to schedule it.

If you can't find 30 minutes weekly for each direct report, you have too many direct reports.

What One-on-Ones Are Not

Before we get to what works, let's be clear about what doesn't:

Not status updates. If you're going through project lists and asking for progress reports, you're wasting everyone's time. That's what Slack is for.

Not performance reviews. Those happen separately. One-on-ones are ongoing conversations, not formal evaluations.
Not therapy sessions. You're their manager, not their therapist. Be empathetic. Set boundaries.
Not your agenda only. If you dominate the entire meeting talking about your priorities, you've missed the point.

The most common mistake? Leaders treat one-on-ones like calendar clutter.
They show up distracted, half-listening, already late for the next thing.
They cancel and promise to “reschedule.”

That reschedule rarely happens. Silence grows. Problems sink. Then they surface all at once.

I once had a boss who rarely met with me. He'd taken over as CEO after our visionary founder left. He reorganized my entire engineering department, split it into three parts, I led one and he put two of my peers in charge of the other divisions.

Both failed within two months. One quit. The other got fired. I was suddenly acting director of all three departments.

He still wouldn't meet with me.

When I gave him feedback on the reorganization, he didn't care. When things weren't working, he avoided me.

Eventually I told him I was quitting. He said, "Okay, fine. Just don't tell anyone yet."
Then one day he just told me I was done.

That's what happens when leaders avoid one-on-ones. Problems don't surface. Feedback gets ignored. People quit. Usually the best ones leave first.

What Good Looks Like

The one-on-one isn't about you. It's about them.

Start with one question: "What's the best use of our time together today?"

Let them set the agenda. Your job is to listen, ask questions, and help them think through challenges.

Have a running doc or shared notes. Both of you add to it throughout the week. Topics that need discussion. Questions that came up. Issues to address. This keeps the meeting focused and ensures nothing falls through the cracks.

I started my career keeping paper files on each employee. Eventually I migrated to a notebook. Then to cloud documents. Now I put the agenda in the meeting invite so both people can edit it and come prepared.

A basic framework:

Check in personally, build rapport (5 mins)
Their agenda items first (8 minutes)
Your agenda items next (8 minutes)
Career development and growth (5 minutes)
Action items and next steps (final few minutes)

That's 30 minutes. Block 30 minutes. (Don't default to an hour because that's what your calendar suggests.)

Questions that Actually Matter

Stop asking "How are things going?"

It’s the easiest question in the world. Also the least useful. It signals interest without effort and puts the weight on them to decide what matters. Often they’ll simply answer, “Fine” or “Good.” Then what?

Real leadership means showing curiosity about the hard stuff: the decisions, the tensions, the growth.

Ask specific questions that create real conversations:

About their work:

"What's blocking you right now?"
"What decision are you stuck on?"
"If you could change one thing about how we're approaching this, what would it be?"
"What am I not seeing that you're seeing?"

About the team:

"Who on the team is crushing it right now?"
"Where are you seeing friction?"
"What are people not telling me?"

About their growth:

"What do you want to get better at?"
"What part of your job energizes you most?"
"What are you doing now that someone else should be doing?"
"Where do you want to be in a year?"

About you:

"What should I stop doing?"
"What should I start doing?"
"How can I help you be more effective?"

Notice what these questions have in common: they require real answers. They can't be answered with one word.

Silence is okay. Thinking takes time. Don't fill every pause with your voice.

When you’re done? Write it down. Decisions and next steps live beyond memory.

You Can’t Make Withdrawals Without Deposits

Think of your relationship with each employee as a bank account.

When you need to deal with difficult situations, with conflict, with coaching, you need to make withdrawals. You can't make withdrawals unless you've made deposits.

So what are deposits?

Positive feedback. Listening. Asking about their career. Their life outside of work. When they say their dog is getting surgery, write it down so you remember to follow up. “How’d Roxy’s surgery go?” That “What you remembered?” goes a long way.

One-on-ones are where you make deposits.

Early in my career, I barely gave positive feedback. If everything was fine, I said nothing. I only gave critical feedback.

You can't build trust that way. You can't lead that way.

Career Development Can’t Be an Afterthought

"We'll talk about your development when we have time" means you'll never talk about it.

Build it into every one-on-one. Even if it's just five minutes. Even if it's just one question about what they're learning or what they want to work on next.

People don't leave jobs. They leave managers who don't invest in their growth.

According to Gallup, 32% of employees cite lack of career advancement or promotional opportunities as their reason for leaving—the single biggest driver of voluntary turnover. At least 75% of the reasons for costly voluntary turnover come down to things managers can influence.

Career development doesn't always mean promotions and title changes. It means:

Giving them stretch assignments

Connecting them with people who can teach them
Creating space for them to build new skills
Showing them the path forward, even if it's not immediate

If you're not talking about their growth regularly, someone else will. Then they'll leave. And when they do, it won’t be because of the company. It’ll be because they outgrew you.

The Real ROI of One-on-Ones

The ROI of one-on-ones isn’t on a dashboard. It’s in your people. You see it in:

Problems surfacing before they become crises
People feeling heard and valued
Trust building over time
Retention of your best people
Team members growing into bigger roles
Faster decision-making because communication is strong

The numbers back this up. When employees are highly engaged, turnover drops by 51%, employee well-being improves by 68%, and productivity increases by 23%.

Skip your one-on-ones and watch what happens. People stop bringing you problems. They stop asking for help. They stop telling you what's really going on.

By the time you realize something's wrong, it's too late.

Bottom Line: Show Up Consistently

One-on-ones aren't optional. They're not nice-to-haves. They're the most important meetings on your calendar. The leaders who master one-on-ones don’t just have happier teams. They have better results.

Block the time. Protect the time. Show up prepared.

Run them like they matter. Because they do.