The Evaluator Trap: Why Smart Leaders Struggle to Coach
Fourteen years ago, I was looking for work.
My contract as head of school in Atlanta had not been renewed, and I was standing at a crossroads. One road led to another school leadership position. Those were few and far between, especially ones with enough responsibility to support my family. The other road led to going out on my own.
Option B meant coaching and training. Around that time, I learned about an organization that coached leaders in independent schools. I reached out, and the director was excited to include me in their training program in Manhattan.
That was no small thing. It meant travel, arrangements, and days away from my wife and young children. It meant money and time I didn't have much of. But I went, and I gave it everything.
I completed all four days. By every sign I could see, I excelled. With years of running a school behind me, I was more qualified than anyone else in the cohort by a mile.
And then I wasn't accepted as one of their coaches.
"Too quick to judge, too quick to solve"
The director had brought me in, but the director wasn't the one who made the final call. The person who was really in charge had a concern. After years as a head of school, she believed I had developed an evaluator's mindset, not a coach's mindset. I would be too quick to judge. Too quick to solve. Not patient enough to coach.
Not because she knew me. Just because that was “the way it is” for school heads.
So, despite my completing the training, and despite my qualifications, she declined to accept me as a coach in their program.
I wasn't happy, to put it mildly. I needed the opportunity and the income. I had invested real time and money. And I simply didn't agree with her read on me. Fourteen years of successful coaching since then have given me plenty of evidence that she was wrong.
But I've come to appreciate something about that moment. She was wrong about me. She was right about the risk.
The evaluator trap
Most leaders got where they are by being good at answers. They spotted problems faster than others, made sound calls, and fixed things. That's what got them promoted.
The trouble is that the skill that earns you the title can quietly undermine you once you have it.
When someone brings a problem to an evaluator, the evaluator does what comes naturally. Assess. Judge. Fix. It feels efficient and even generous. The issue gets resolved in five minutes, and everyone moves on.
But look at what was actually learned. The leader learned nothing new. The team member learned one thing: next time, bring it to the boss.
Repeat that a few hundred times and you get a familiar picture. A leader who is buried. A team that waits. Decisions that stall whenever the leader is out of the office. The leader has become the bottleneck, and correcting is how they got there.
What coaching actually is
Coaching is not the absence of standards, and it's not endless questions to avoid ever saying what you think. It's a shift in who does the thinking.
Correcting asks, "What's wrong, and how do I fix it?"
Coaching asks, "What do you see, and what will you do about it?"
The first produces a fixed task. The second produces a more capable person, and capable people are the only way to build a team that runs without you.
In practice, coaching looks like this:
Ask before you answer. "What do you think is going on here?" Your first instinct to solve is the one to pause.
Get curious before you get critical. "What have you tried so far?" You'll often find they're closer than you assumed.
Widen the options. "What else could you do?" The first idea is rarely the best one, for them or for you.
Hand back ownership. "What will you do first, and when?" The person who names the next step owns it.
Offer your view last, if at all. When you do share it, it lands as input rather than a verdict.
When correcting is the right call
There are moments when you should simply correct. Safety issues, ethical lines, a client about to be harmed, a deadline in an hour. Coaching is not a reason to watch someone walk off a cliff.
The problem isn't that leaders ever correct. It's that correcting becomes the default, used in moments that called for coaching.
For school leaders, this is doubly hard
If you lead a school, you live this tension daily. You are required to evaluate teachers. You write the observations and sign the reviews. That's legitimate and necessary.
But evaluation tells a teacher where they stand. Coaching helps them grow. A post-observation conversation that opens with "Here's what you need to fix" will get compliance. One that opens with "What did you notice about how students responded?" will get reflection, and reflection is what changes practice.
The best principals I've coached learn to wear both hats and to know which one they're wearing at any given moment.
What I took from being turned down
I still believe she misjudged me. But I'm grateful she named the trap so clearly, because I've watched many capable leaders fall into it. I've had to guard against it myself.
The instinct to judge and solve doesn't disappear when you decide to coach. You manage it, one conversation at a time.
So here's a question for your next conversation with someone on your team: who will do most of the thinking?
If it's you, you're correcting. If it's them, you're coaching. Only one of those builds a team that can run without you.
Has your team learned to bring every problem to you? That's a fixable pattern. Book a free 30-minute Bottleneck Call and we'll identify where decisions are getting stuck and what to change first. calendly.com/nhoff/bottleneck
Naphtali Hoff, PsyD, is the founder of Impactful Coaching & Consulting, helping executives, school leaders, and nonprofit professionals lead with more clarity and less overwhelm. He can be reached at nh@impactfulcoaching.com or 212.470.6139.