Chris Kobylecki"We should get someone to do a session for us!"
I hear this all the time from leadership teams. And I get it - when things aren't working, training feels like the answer.
But here's what I've learned after years of working with organizations: Your team doesn't need more training.
They need to know when to mentor, when to coach, when to train, and when to facilitate.
The Four Approaches Leaders Confuse
Most leaders, even experienced CEOs, blur the lines between these four approaches. It's completely normal. But this confusion is often why clarity doesn't land, why initiatives stall, and why teams keep asking the same questions.
I use a simple framework with leadership teams: Content vs. Process | Individual vs. Group.
Here's how it breaks down:
Mentoring
You share your experience one-on-one to help someone navigate a specific challenge. This is about transferring wisdom through storytelling and guidance.
When to use it: An individual faces a situation you've handled before, and your experience can help them avoid pitfalls.
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Training
You deliver structured content to transfer knowledge a group doesn't have. This is about building skills or understanding that's currently missing.
When to use it: Your team lacks specific knowledge or skills they need to do their work effectively.
Coaching
You ask questions that help an individual discover their own answer. This is about unlocking someone's existing capability through inquiry.
When to use it: The person has the capacity to solve their own problem—they just need help thinking it through.
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Facilitation
You design a process so the group reaches their own conclusion. This is about creating the structure for collective discovery and decision-making.
When to use it: The team needs to align on something, and the answer must come from them—not you.
The Costly Mistakes
The most common mistake?
Using training when you need facilitation.
You stand at the front of the room sharing your perspective, when what the team actually needs is a structured conversation to work through their own thinking.
Or using mentoring when you need coaching.
You tell someone what you would do, when the more powerful move is asking questions that help them discover what they should do.
The pattern underneath all of these? Sharing your answer when the team needs to find theirs.
How to Choose the Right Approach
Team clarity doesn't come from more content. It comes from choosing the right approach for the moment.
Before your next meeting, offsite, or session, ask yourself:
- Does the team lack knowledge, or do they need to process what they already know?
- Is this about one person's development, or collective alignment?
- Am I the expert here, or is the wisdom already in the room?
The answer to these questions will tell you exactly what your team needs.
Chris Kobylecki
Cofounder of Leave a Mark
Chris builds magical experiences that help people to excel.
He focuses on strategy and team development. Applying his decade long experience of Venture Capital & Private Equity Firms