Are You Missing Critical Moments to Help Your Team Grow?

Picture this: You’re sitting in a meeting, watching one of your team members stumble through a presentation…

And maybe you’re thinking something like:

• “This isn’t going well… I wonder if my boss is second-guessing putting me in charge.”
• “I should coach her soon… maybe after I clear my calendar.”
• “She probably realizes it bombed. She’ll figure it out herself.”
• “I’ll just bring it up at her performance review.”

And then—nothing happens.

Why? Why do so many leaders freeze when it’s time to step up and coach?

It’s simple.

Giving feedback—especially the kind that helps people grow—is uncomfortable.
Most managers either avoid it completely or water it down so much that the message gets lost.

And when they do deliver feedback? It’s often rushed, awkward, or overly harsh—none of which create positive change.

I’ve been leading people for over 20 years, and I’ve seen brilliant, boring, and absolutely disastrous coaching conversations.
The missed ones might be the worst of all.

If you’re not actively coaching your team, you’re passing up huge chances to level up their performance—and your own leadership.

That’s why one of the most requested topics in my Executive Coaching work is mastering effective coaching conversations.
And it’s exactly what we help managers achieve at Coaching Engage+.

Why Coaching Conversations Matter So Much

Companies that encourage open, honest communication crush the competition—by more than 270% over ten years in total shareholder returns, according to research.

The reason?
Engaged employees perform better.
And great coaching conversations are the fuel for that engagement.

So how do you get better at them?

You focus on The Five C’s.

The Five C’s for Powerful Coaching Conversations

1) Clarity: Know What You Need to Say

Before you meet with your employee, take a moment to really think it through.

Get clear on:

• What’s working well? How did your team member’s strengths contribute?
• What needs to change moving forward?
• What exact words will you use to describe what you saw?

Soft skills are especially tricky.
Instead of saying, “You need to show more confidence,” be specific:
“When you spoke, your posture and tone suggested uncertainty. Let’s explore how to change that.”

Specificity makes feedback actionable.

2) Compassion: Remember, It’s a Gift

The goal of feedback isn’t to criticize—it’s to empower.

Yet many leaders dodge hard conversations because they fear conflict or crave being liked.

Lean into compassion.
Be kind to yourself—coaching is hard—and kind to your employee—who’s probably just as nervous.

Empathy and emotional intelligence are your superpowers here.

• Start by framing feedback as a tool to help them succeed.
• Ask what support they need from you to move forward.
• If you’re nervous? Own it.
  A simple, “I’m still working on giving great feedback,” can create trust and openness right away.

3) Curiosity: Talk Less, Listen More

Here’s a game-changing rule:

Talk 10% of the time, listen 90%.

Ask questions that help your employee reflect, rather than lecturing them.

Some great ones:

• “What went well today? Which strengths did you tap into?”
• “What would you improve next time?”
• “Here’s what I noticed—how does that feel to you?”
• “If you mastered this skill, how would it help your career?”

Curiosity shifts the conversation from judgment to discovery—unlocking better solutions together.

4) Confirmation: Make Sure You’re Aligned

Emotions run high in feedback conversations.
That’s why it’s crucial to check understanding—both verbal and non-verbal.

Two simple ways:

• Summarize what they said and ask, “Is that accurate?”
• Observe body language and acknowledge feelings:
  “You look surprised by my feedback—am I reading that right?”

Confirming builds clarity and mutual trust.

5) Commitment: Seal the Deal with Action

Wrap up every coaching conversation with clear commitments:

• What are their biggest takeaways?
• What actions will they take next?
• Who will do what—and by when?
• How will success be measured?
• How will they track progress?

And, if you want to keep getting better at coaching, ask them:
“How was this conversation for you? What can we improve next time?”

The Bottom Line: Coaching Conversations Are Within Reach

Be clear about your message.
Lead with compassion.
Stay curious.
Check for confirmation.
Secure commitment.

You’ll strengthen not only your team’s performance but also your leadership reputation.

Want even more help making coaching part of your leadership DNA?
Visit Coaching Engage+ to learn how we can support you!