Three Questions a Leader Must Master

Eitan Rothman
3 min readMar 23, 2021

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The original title for this story was “Lessons from Coaching that impact the way I live my life.” My friends I pitched it to made all sorts of jokes about a Dr. Strangelove tie-in, but at its core I wanted to impart some of the lessons I learned from coaching rowers to those in a professional environment.

Slim Pickens in Dr. Strangelove or How I learned to Stop Worrying and Love the Bomb — a fierce leader even in the most dire of circumstances as Major ‘King’ Kong

These lessons included some cliche advice like “everyone has a story” and “everything is a learning opportunity” but at its core I didn’t find these messages to be a whole lot different from those that I had touted in my previous articles.

What did stand out to me is the power that a question can carry. For that I’ve broken down the three types of questions it’s important for any leader to master.

Type 1: The question you ask to get an answer

This question is used when you want to learn something. Whether it’s asking your team who just got back from lunch the temperature outside or asking someone if they can meet a deadline, this question is simply about gaining knowledge you didn’t have previously.

Oftentimes as a leader this is a great opportunity to humanize yourself. Asking questions like this admit that you have shortcomings, so the ability to do so with grace and professionalism is paramount. As a coach I found it important to recognize when I needed more information to make a decision. In asking whether a rower is stressed or whether the team is excited for a race helps you gain insight into group dynamics that will allow you to connect on a deeper level as you show genuine interest.

Type 2: The question you ask to get your point across

This question is what we call rhetorical. The question to get a point across almost never requires a response because the question itself wasn’t meant to be a question but rather a statement.

Often times this question starts with a why. For example, “Why did your score drop at the end?” means: You looked tired, either you’re out of shape or need rest.

This question is rarely received well, especially if its done in a confrontational manner as above. The key takeaway here is: sometimes this is necessary, but it has to be done deftly.

Type 3: The question that can influence someone’s opinion

This last question is far trickier. You can’t consciously lead the witness otherwise it becomes a rhetorical question, but there are ways to ask questions to change people’s minds. This becomes useful with those who don’t want to listen. You can’t give them advice, but you can ask questions.

As we learn from pollsters asking leading questions to get results. This isn’t just an art, but more of a science.

I have always found this question to work best when it elicits some sort of mental mapping exercise. To an athlete it looks more like “Which muscle group did you feel like you took the catch with?” instead of “I think you should do x instead of y.”

What’s interesting here is I know the answer to this question, but I ask it in such a way that the receiver has to go through a thought process that makes them arrive at the same point as me.

Eventually, they learn because they’ve traced your steps without even realizing it.

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Eitan Rothman
Eitan Rothman

Written by Eitan Rothman

Product @ Macy's and Part Time Rowing Coach

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