How to Ask Great Questions

There are two parts to a great question:

1. The Content – What it’s about.

2. The Delivery – Why it’s being asked and what that means.

I’ve noticed between the two most people are pretty good content wise if they structure the problem effectively. However, most people have substantial room for improvement on the delivery side of things.

Why Delivery is Important

Let’s say you’re feeling sick and decide to take a trip to the doctor’s office to figure out what’s going on. You end up meeting with a Dr. Smith, and the conversation goes as follows:

Note* – I am not a doctor, do not use this article to diagnose your own symptoms.

Dr. Smith: What are your symptoms?

You: Uh, well I feel nauseous and I have a bad headache.

Dr. Smith: Do you have a cold?

You: No

Dr. Smith: Do you have a rash anywhere on your body?

You: No.

Dr. Smith: Are you an alcoholic?

You: No.

Dr. Smith: You have a brain tumor. We need to get you to the operating room immediately.

How would you feel? You’d probably want a second opinion, right? And yet, the vast majority of people ask questions in their cases in the above manner, without any context / rationale at all.

So let’s say you get a second opinion from a Dr. Jones.

Dr. Jones: What are your symptoms?

You: Uh, well I feel nauseous and I have a bad headache.

Dr. Jones: Ah I see. Well those are pretty common symptoms. It could either be a viral infection, which is the most likely scenario, or a bacterial infection. Let’s pursue the virus angle first. Have you had a cold recently?

You: No

Dr. Jones: OK fair enough, so it’s probably not a virus. Let’s pursue the bacterial infection angle. Have you had a rash recently anywhere on your body?

You: No.

Dr. Jones: Hmm OK, so we’ve exhausted the most likely two scenarios. Usually the other circumstances in which those symptoms present is some sort of liver disease or brain cancer, though these are statistically unlikely. Do you consume much alcohol?

You: No.

Dr. Jones: I see, well it’s possible that you might be suffering from some a rarer bacterial / viral infection or perhaps some sort of brain cancer (though this is less likely). I’d like to order a few tests to be sure.

What would you think now? You’d probably have a little bit more faith in Dr. Jones’ judgment, right? Let’s examine why, and how this can help you during cases.

Characteristics of Great Questions

So the question is why do you trust Jones’ judgment more than Smith’s? In other words, what is it about the way Jones asks questions that makes him more credible than Smith? I think there are three things:

1. Jones’ questions have context. It’s obvious that he’s asking them for a reason, and that he cares about / respects you enough to clue you in as to why he’s asking.

2. Jones’ questions are tentative. He’s actively refining his hypothesis of what’s actually going on based on data.

Also, he effectively creates contrasts between hypotheses and conclusions by asking questions in this manner. You know what it sounds like when he’s unsure and when he’s sure. In other words, when he delivers his conclusion about what he thinks the problem is, it’s much stronger because you know what it sounds like when he’s not sure.

With Smith, you can’t tell when he’s sure because he doesn’t clue you in on what he’s thinking. You can’t tell if what he’s telling you is a conclusion or not because you don’t know what it sounds like when he’s not sure about something. That’s a problem, because without understanding his field it’s hard for you to tell if he’s correct or not.

3. Jones explains what your answers mean. Part of asking a great question is also explaining why the answer is important. How does it affect your hypothesis of what’s going on and why? What further evidence do you need? Where do you go from here?

How To Ask Great Questions in Cases

There are three parts to asking great questions in a case:

1. Explain the context behind the question / what hypothesis you’re trying to test (i.e. why you’re asking the question and what it could potentially mean)

2. Ask the questions in a tentative way in the beginning, and as evidence starts to accumulate you can be more confident.

3. Explain what the client’s answer means in the context of your hypothesis. Were you right? Were you wrong? What further evidence do you need to make you materially more confident that your hypothesis is correct?


Most people ask pretty good questions, but are lacking on the delivery side because they don’t communicate their intentions. There are three parts to asking great questions:

1. Explain the Context.

2. Actively Refine your hypothesis, but be tentative until then.

3. Explain what the client’s answer means and how it changes things.

Hope it helps!


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