One-on-Ones That Work: Coaching Conversations Every Leader Can Run

If you’re a leader, here’s a quick litmus test:

When you finish a one-on-one, does your team member walk away clearer, more confident and more capable — or just… updated?

Across Canadian organizations, many one-on-ones have quietly slipped into “status-check autopilot.” They’re rushed, surface-level. They become a list of tasks, not a space for development. And the impact shows: only 18% of Canadian workers describe themselves as fully engaged (ADP, People at Work Report).

Yet one-on-ones remain one of the most underrated tools available to leaders. When done well, they improve engagement, retention and trust — often in under 30 minutes.

Here’s the mindset shift:

Stop treating one-on-ones like mini project meetings. Start leading them like coaching conversations that include just enough management to keep things on track.

Use this guide to get started.

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Managing vs. coaching: The real difference

Most leaders are naturally strong managers, knowing how to direct work, remove roadblocks and keep priorities aligned. Managing matters.  

But coaching is where development lives... and where engagement grows.

Managing sounds like:

• “What’s the status?”

• “What’s blocked?”

• “Can you get this done today?”

Managing gives clarity and direction. It keeps work moving.

Coaching sounds like:

• “What part of this feels unclear?”

• “Where do you want more ownership?”

• “What's one thing you learned from last week’s challenge?”

Coaching builds capability and confidence. It helps people think, not just execute.

You need both.

But when pressure rises, most leaders default to managing. Coaching is the part that often gets cut — ironically, the part your team needs most.

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What coaching actually looks like (5 real scenarios)

Here are everyday examples leaders face… with both the managing response and the coaching alternative.

Scenario 1: The employee is overwhelmed

Managing: “Let’s cut this list down. Focus on A and B.”
Coaching: “What part of your workload feels most draining? What do you think would make it more manageable?”

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Scenario 2: A mistake keeps repeating

Managing: “Make sure to double-check step three.”
Coaching: “Walk me through your process. Where does it start to feel confusing?”

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Scenario 3: They want to grow

Managing: “We’ll revisit stretch opportunities next quarter.”
Coaching: “Which skill are you most excited to build? What’s a small stretch we can try this month?”

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Scenario 4: There’s tension with a teammate

Managing: “I’ll talk to them.”
Coaching: “What part of that interaction bothered you most, and why? What would you try next time?”

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Scenario 5: The had a win

Managing: “Nice job.”
Coaching: “What are you most proud of in that result? What strengths did you use there?”

Coaching isn’t complicated — it’s curiosity instead of control.

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A practical 30-minute one-on-one flow (you can use tomorrow)

A great one-on-one doesn’t need slides or lengthy agendas. It just needs structure, consistency and a balance of management and coaching. Employees should feel comfortable bringing real questions, challenges and ideas to the conversation.

Here’s a simple rhythm — adapted directly from our internal approach — leaders can use weekly or bi-weekly:

1. Check-In (3–5 minutes)

Start with how they’re feeling, personally and professionally. Try:

• “How are you feeling about work this week?”

• “Anything outside work affecting your bandwidth?”

This sets the tone of the meeting as human, not transactional, and builds trust.

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2. Wins & Highlights (5–7 minutes)

Recognition fuels engagement. About 1 in 4 employees say they don’t feel adequately recognized at work (HCAMag). Take a few minutes to celebrate recent progress and success, big or small. Try:

• “What’s a win from last week you’re proud of?”

• “What went better than expected?”

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3. Priorities & Strategy (10–15 minutes)

Here’s your management moment. Confirm alignment on:

• Top priorities

• Deadlines

• Expectations

• How this week ties to quarterly goals

Script you can customize and use: “Here’s what good looks like for this week. How does this plan feel to you? What do you think might get in the way?”

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4. Challenges & Roadblocks (5–10 minutes)

Now shift into coaching mode. Invite honesty. Dig deeper. Explore root causes, not just symptoms. Try:

• “What part of this feels unclear or frustrating?”

• “What options have you already considered?”

• “What do you think is the best next step and why?”

This strengthens problem-solving skills instead of replacing them.

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5. Longer-Term Goals (5 minutes)

Make growth a habit by connecting weekly work to longer-term goals. Ask:

• “Which upcoming work lines up with your development goals?”

• “Any skills you want to build this quarter?”

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6. Wrap-Up & Next Steps (3–5 minutes)

Close the loop:

• Recap action items

• Confirm who’s doing what

• Identify what support the employee needs

This one-on-one flow keeps the meeting balanced: clarity → connection → direction → development

It’s structured enough to be reliable, flexible enough to adapt.

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Avoid this common pitfall: Solving every problem yourself

It’s tempting to solve challenges for your team members, to be helpful and move things forward quickly. And in fast-paced environments, it can even feel efficient.

But over time, this habit quietly creates dependency and slows team growth. It can create a team dynamic in which the manager becomes the default decision maker, which stifles critical thinking and creativity.

When leaders jump straight to the solution, the employee:

• Stops thinking through solutions

• Becomes hesitant to take initiative

• Waits for direction rather than proposing ideas

The one-on-one becomes a cycle of “Tell me what to do,” instead of “Here’s what I’ve considered.”

This creates bottlenecks, limits autonomy and usually increases the manager’s workload.

Try these coaching-first prompts instead:

• “What options come to mind?”

• “What outcome are you aiming for?”

• “If I weren’t here, how would you approach this?”

• “What’s the root of the issue as you see it?”

You’re still guiding decisions, but now you’re also empowering them to think with you. This approach strengthens problem-solving skills, increases confidence and creates far more autonomous team members. It also helps one-on-ones shift away from troubleshooting and toward development.

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Why strong one-on-ones improve engagement

Employee engagement isn’t built in annual surveys or all-staff newsletters. It’s built in everyday moments, especially with a direct leader. And the relationship between an employee and their leader is the single strongest predictor of how committed and motivated they feel.

Coaching-forward one-on-ones strengthen:

• Trust → because honesty feels safe

• Clarity → because expectations are explicit

• Confidence → because employees learn to problem-solve

• Motivation → because people feel supported, not micromanaged

• Growth → because development is ongoing

When one-on-ones improve, the culture around them improves too.

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One-on-one templates you can customize and use

Weekly Employee-Led Agenda (Paste into your next invite)

Hi [Name],

Ahead of our one-on-one, please come prepared with:

1. A win you’re proud of

2. Your top priorities

3. Any challenges or blockers

4. One thing you’d like coaching on

5. One development goal you want to touch on

Looking forward to our chat.

Best,

[Your Name]

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Three Coaching Questions Every Leader Should Ask Weekly

• “What’s something you learned this week?”

• “Where would you like more ownership?”

• “What support would be most helpful right now?”

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A Simple Close-Out Script

“Before we wrap up, here are our next steps and ownership. Does this feel doable for the week? Anything you need from me to be successful?”

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The bottom line

Strong one-on-ones don’t require more time — only more intention. When leaders blend managing and coaching, team members feel supported, aligned and motivated. That’s where engagement thrives.

If you’d like to explore more leadership resources, interview insights or training opportunities, follow us on LinkedIn for future guides and webinars.