Boss Level Challenge: The Man Who Knew It All (Or So He Thought)

If you work in Learning & Development, then you’ve surely encountered the ultimate Boss Level Challenge: the Manager who knows everything. He’s the one who hears the word “training” and checks his watch with the same enthusiasm as waiting for water to boil.

For him, training is a waste of time because—according to himself—he already has all the knowledge he could ever need. In reality, though, his brain is stuck in “Windows95 mode” and needs a good update. So how do you deal with him?

1 “The Know-It-All Syndrome”

The “I-know-everything Manager” suffers from a rare but very common condition that neuroscience calls overconfidence (also known as the Dunning–Kruger effect). The less he knows, the more convinced he is that he knows everything. And the more convinced he is, the less open he becomes to learning. It’s a vicious cycle…

But fortunately, we know the antidote: a strong dose of reality check!

2 Use the “Matrix Effect”

Remember the moment Neo realized he was living in a fake reality? That’s exactly what you need to do with the all-knowing manager: show him that his world is more limited than he thinks.

How? With targeted questions:

1. “If we travel back to your glorious early days as a manager… is there anything you wish you had learned earlier that would’ve saved you a few headaches?”
2. “When was the last time you learned something new in management and thought: ‘Wow, this actually works—why didn’t anyone tell me this sooner?’”
3. “If you were the ‘new blood’ in the company today, what would you want to learn from a more experienced manager like yourself?”
4. “If you know everything, why aren’t you CEO yet?”

(OK, maybe don’t say the last one out loud…)

3 The Trojan Horse of Training

If you say “we’re doing training,” the answer will be “I don’t need it.” But if you invite him to a “strategic leadership lab for the future of management”, he might show up out of curiosity.

The trick here is to serve him training without him realizing it. Instead of theory, use real-life case studies, interactive challenges, or even a good story about other “know-it-alls” who failed because they stopped learning.

4 The Success Plot Twist

The greatest leaders in the world all share one thing: they never stop learning. From Steve Jobs to Jeff Bezos, all of them had (or have) an ongoing thirst for new knowledge.

If you want to convince the know-it-all manager, hit where it hurts:

1. “The best leaders are the ones who invest in their continuous growth. You want to be one of them, right?”
2. “If you stop learning, how will you evolve as a professional?”
3. “Since you know everything, why not teach others?” (By putting him in a trainer role, he’s forced to confront his own gaps.)

5 The Final Twist

If nothing works, play the AI card.

1. “If we don’t keep evolving, in 5 years we won’t be managers… we’ll be replaced by an AI system that actually knows everything!”

Boom. Suddenly, training sounds far more appealing, doesn’t it?

Mission Accomplished

Convincing a “know-it-all” manager to accept training is like asking Tony Stark to work as a team player—difficult, but not impossible. With the right strategy, a bit of humor, and a few smart questions, you can help him realize that knowing a lot doesn’t mean knowing everything.

And then, maybe—just maybe—he’ll finally click on that e-learning module that’s been waiting for him all this time…