Most Supervisors Avoid This Moment

And It’s Costing Them Their Team.

Reading time 2-3 minutes

The Moment Everyone Dreads

There is a moment every supervisor eventually faces.

You see a mistake.
You notice a pattern.
You feel the tension rising.

And instead of addressing it clearly, you hesitate.

You soften the message.
You delay the conversation.
You hope the issue fixes itself.

BUT, it rarely does.

In my upcoming book Lead. Manage. WIN!, I argue that challenge is not a personality trait—it’s a skill. One that must be used deliberately, situationally, and with discipline.

Most people don’t avoid challenge because they’re weak.
They avoid it because they don’t know how to do it without damaging trust, morale, or momentum.

That’s where the CHALLENGE framework comes in.

How to CHALLENGE

A practical system for difficult conversations (Leadership & Management)

My CHALLENGE framework is designed to help supervisors navigate hard conversations with clarity, confidence, and purpose. This way they can do it without defaulting to aggression or avoidance.

C — CONTEXT

Set the stage clearly and specifically.

Context answers the question: Why does this conversation matter right now?

• Management Context:
  “I need to talk with you about the calculation error in today’s client presentation. This directly impacts our credibility with the client.”

• Leadership Context:
  “I want to discuss the pattern of calculation errors I’ve noticed over the past month. I want to help you develop bulletproof analytical excellence.”

H — HEART

State your positive intent.

Heart clarifies whether this is about immediate correction (management) or long-term development (leadership).

• Management Heart:
  “I’m bringing this up because we need to maintain our standards and protect client trust.”

• Leadership Heart:
  “I’m having this conversation because I believe in your potential and want to see you grow.”

A — ACTION

Describe the specific behavior—factually and cleanly.

No exaggeration. No character judgments. Just observable reality.

• Management Action:
  “On slide twelve, the growth rate is listed as 15%, but the correct figure is 8%.”

• Leadership Action:
  “I’ve noticed calculation errors on March 5, March 18, and again today—each tied to verification gaps.”

L — LISTEN

Create space for their perspective.

Challenge without listening becomes control.
Listening turns tension into collaboration.

• Management Listening:
  “Can you walk me through how you approached this calculation?”

• Leadership Listening:
  “Help me understand what’s making validation challenging in your process.”

L — LEARN

Explore root causes together.

This is where leadership and management begin to diverge.

• Management Learn:
  “Where did the process break down? What resources do you need right now?”

• Leadership Learn:
  “What patterns do you notice? What would help you catch this earlier next time?”

E — ENGAGE

Co-create solutions.

Even corrective conversations benefit from engagement.

• Management Engage:
  “Here’s the methodology we need to use. What questions do you have about applying it?”

• Leadership Engage:
  “What kind of validation system would actually work for you long-term?”

N — NEXT STEPS

Clarify expectations.

Ambiguity after challenge recreates the problem.

• Management Next Steps:
  “Please correct the calculation and send the revised slides by 3 p.m. today.”

• Leadership Next Steps:
  “Build a validation checklist and let’s review it together on Friday.”

G — GROWTH

Connect the moment to development.

Challenge without growth feels punitive.
Growth reframes the moment.

• Management Growth:
  “Attention to detail builds trust and credibility.”

• Leadership Growth:
  “Mastering validation positions you for higher-impact work.”

E — EMPLOY

Follow up.

Challenge is not a drive-by event.
Leadership requires reinforcement.

Why This Matters

Most supervisors either over-manage or under-challenge.

The CHALLENGE framework gives you a third option:

• Clear without being cruel

• Direct without being dismissive

• Supportive without being soft

If you want people who can think, grow, and perform under pressure, this is how you talk to them.

👉 This framework is explored in depth in my upcoming book Lead. Manage. WIN!