Your One-on-Ones Are Broken: Here’s How to Fix Them
By Scott Stiver

Let’s be honest. Most one-on-ones aren’t working.

They’re calendar placeholders. They’re pipeline reviews. They’re polite, surface-level conversations that check a box but don’t move the needle.

And it’s not your fault. Most leaders were never taught how to run one-on-ones that actually develop people.

But if you want to build a high-performing team, this is where it starts.

Table Of Contents
  1. What One-on-Ones Have Become
  2. What One-on-Ones Should Be
  3. Shift the Ownership
  4. Why We Call It a One-with-One
  5. Structure the Conversation with Purpose
  6. Don’t Skip the Follow-Up
  7. The Ripple Effect of a Better One-on-One

What One-on-Ones Have Become

Let’s call it out:

  • You spend more time talking than listening.
  • The agenda is vague or nonexistent.
  • The rep shows up passive, waiting for direction.
  • The conversation stays in the weeds: deals, tasks, logistics.

These aren’t development conversations. They’re status updates.

And status updates don’t build better sellers.

What One-on-Ones Should Be

A real one-on-one does three things:

  1. Builds trust and relationship
  2. Surfaces goals, blockers, and patterns
  3. Reinforces and redirects behavior

That’s it.

It’s not about the forecast. It’s not about micromanaging the CRM. It’s about creating space for coaching and growth.

The difference between broken and better one-to-one meetings.

Shift the Ownership

Here’s the mindset change that matters most:

The one-on-one should be owned by your rep, not you.

Yes, you read that right. When you run the meeting, they become dependent. When they run it, they become accountable.

Ask them to show up with:

  • Their personal and team goals
  • Recent wins or challenges
  • Questions, ideas, or asks for support

You still guide. You still coach. But they drive.

Why We Call It a One-with-One

We don’t call it a one-on-one.

That sounds like a performance review. A formality. Something that happens to someone.

We call it a One-with-One because this is a shared conversation. It’s relational, not transactional.

It’s something you do with your team member – not to them.

That shift in language matters. It changes the tone, the expectations, and the outcome.

You don't do a one-with-one to someone. You do it with them.

Structure the Conversation with Purpose

Use the One-with-One model from Excellence in Sales Leadership® as a simple but powerful framework:

  1. Connection: Start with the person. How are they? What’s on their mind?
  2. Progress: What’s going well? Where are they growing?
  3. Roadblocks: What’s getting in the way? Where are they stuck?
  4. Development: What behaviors are working? What needs coaching?
  5. Commitment: What’s one thing they’ll focus on before the next one-on-one?

This turns a meeting into a momentum-builder.

The framework for a one-with-one meeting. connection, progress, roadblocks, development, commitment.

Don’t Skip the Follow-Up

If it’s not documented, it didn’t happen.

Keep a shared doc or note that captures takeaways and commitments from each 1:1. Review it together next time.

This does two things:

  • Builds consistency and trust
  • Shows that you’re listening (and that you expect follow-through)

The Ripple Effect of a Better One-on-One

When done right, one-on-ones are the most efficient way to build trust, coach behavior, and drive performance.

They reduce surprises. They create accountability. They help you lead proactively, not reactively.

And they remind your reps: “You matter. I’m invested in you.”

Ready to start running better one-on-ones? Explore the Excellence in Sales Leadership® program and get the tools, structure, and support to coach with purpose – one conversation at a time.