How to Have Amazing 1-on-1s

  • Management

Let’s be honest: most 1-on-1s feel like a weird mix of status update and therapy session. And not in a good way.

Why Most 1-on-1s Kinda Suck

Half the time, the manager is winging it. The other half, the employee is just trying to survive it. And that’s not even counting all the 1-on-1s that get canceled—or never get scheduled at all.

We put people in management roles and give them zero training on how to actually lead a good 1-on-1 conversation. So it’s no wonder new managers feel overwhelmed, seasoned managers feel discouraged, and their teams feel underdeveloped, disconnected, or just… meh.

So what should a good 1-on-1 look like?

It should do more than check a box. It should help your direct reports:

  • Feel seen and supported

  • Get clear on priorities

  • Grow in their role

  • Trust their manager just a little bit more

  • Get timely feedback—even when it’s hard to hear

A 15-Minute Structure That Actually Works

Imagine if there were a simple structure you could follow that covered all five of those, every single time.

There is—and it only takes about 15 minutes. It's built around a simple conversation flow that naturally covers all five areas.

The secret is a lightweight, repeatable structure I’ve used (and refined) across early-stage teams in both startup and scaling environments.

It follows an Ask > Tell > Ask sequence. And here’s what it does:

  • Asks what’s actually working—something most managers skip

  • Taps into employee motivation, not just their task list

  • Gives feedback in two directions (yes, you go too)

  • Makes development an every-session thing, not an annual hope

This one framework touches five core leadership levers in a single sweep:

  1. Positive feedback

  2. Development goals

  3. Constructive coaching

  4. Manager reflection

  5. Relationship maintenance (a.k.a. trust-building)

Sound too good to be true? It’s not.

It takes 15 minutes. No prep. No spreadsheets. Just a manager and a team member, talking like humans.

What to Say, and How to Say It

Start with reflection. Ask your employee to highlight recent progress. This sets a positive tone and surfaces what they view as meaningful work. Example: What’s one win—big or small—from the past few weeks that you’re proud of?

Shift to development. Ask about growth interests. This shows you care about their learning, not just delivery. Example: What’s one area where you’d like more experience or exposure?

Move into feedback mode. First, reinforce a strength—something they should keep doing. Then offer one piece of constructive guidance or a suggestion to build on. Examples: One thing I’ve noticed you do really well is... One shift that might help you go further is...

Then ask for feedback on yourself. This signals humility, openness, and a two-way relationship. Examples: Is there anything I do that’s been helpful or makes your job easier? Is there anything I should be doing differently to make your day-to-day easier?

With a little practice, you can cover all of that in 15 minutes. That leaves the rest of your 1-on-1 to focus on goals and priorities—ensuring your team stays aligned and working on what matters most.

You don’t need fancy software—but do write down the key takeaways after each conversation. It can be a quick email to yourself, a running Google Doc, or a private Slack note. Why? Because when review season rolls around, your job is 10x easier—and your employee’s progress is clearer. Formal reviews should feel like a recap, not a reveal.

(Sidebar: Just be smart about what you write down—HR and legal guidelines vary by company and location.)

Try this in your next 1-on-1. Notice which questions come easily and which ones feel awkward. That’s part of the learning curve.

Stick with it. Your employees might not open up fully right away, but after a few rounds, they’ll start to trust the process—and maybe even look forward to it.

And instead of dreading 1-on-1s, you'll find yourself having the kinds of conversations that actually move people forward.