Did You Learn to Manage On the Fly?

Why most of us became accidental managers, and how supervision meetings can finally break the cycle.

No one who managed me ever taught me how to manage. Not intentionally, anyway. I was promoted because I was competent. Reliable. Good at getting things done.

And then suddenly… I had people.

No one said: Here’s how to coach someone. Here’s how to give hard feedback. Here’s how to run a supervision meeting that actually develops someone.

Mostly, I learned by making mistakes. Trying something. Cleaning it up. Doing it a little better the next time.

Does that sound familiar? I hear that all the time from people I coach. 

• "I just figured it out as I went." 

• "I copied what my old boss did." 

• "I wish someone had shown me how to actually do this." 

It turns out this isn’t just anecdotal. It’s systemic.

The Chartered Management Institute found that 82% of people stepping into management roles have had no formal leadership training.
And they found that when people take on new responsibilities without support, 44% say they learn primarily through trial and error, while only 27% receive structured training.

Most managers aren’t developed. They’re improvised. We promote strong individual contributors and hope leadership magically appears.

It doesn’t.

Instead, people default to whatever they experienced. Good habits. Bad habits. Blind spots. And that’s how the cycle continues.

The Accidental Manager Problem

When management isn’t taught, it becomes reactive. Supervision turns into: status updates, fire drills, and task lists. “Anything you need from me?”

Work gets discussed. But capability doesn’t grow. People leave knowing what to do, but not becoming better leaders. And then, when they get promoted? They repeat the same thing.

What Supervision is For

Supervision isn’t oversight. It's coaching. 

The goal is not just to get the work done. It’s to help that person become the kind of leader who can get the work done well, consistently, and through others. Tasks are the context. Development is the point.

A good supervision meeting uses the work as raw material for learning.

Instead of:

• “Did you finish this?”

Try:

• “What did you learn when handling this?”

• “What would you do differently next time?”

• “Where did you use your strengths?”

• “What conversation are you avoiding?”

• “What support or stretch would help you grow this week?”

The work becomes a classroom. And you’re not just managing performance. You’re building a leader.

A Simple Shift That Changes Everything

High-impact supervision meetings tend to include:

• Wins and learning
  What worked? What did you figure out?

• The work
  Priorities, obstacles, decisions

• The person
  Strengths, patterns, skills to develop

• Commitments
  Who’s doing what by when

• Opportunity for Feedback
  For you as the manager, and for your direct report

Same 30 minutes. Completely different outcome.

One approach manages tasks. The other builds managers.

Why This Matters
If you never got coached, it’s easy to assume that’s just how it works. But every week you’re running supervision meetings, you’re making a choice.

You’re either reinforcing: “Figure it out on your own, like I did.” Or modeling: “Leadership is a skill. Let’s practice it together.”

Most of us became managers by accident.

But the people who work for us don’t have to. Supervision is where the cycle either repeats…

…or finally breaks.

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