The art of asking effective questions in various professions

13 Aug 2020

One might think that knowledge work depends on knowing things, but often it’s actually about knowing how to ask the right questions. In many professions this is a core skill you’ll need to learn from the start (eg. journalism, medicine, therapy), but as soon as you move into leadership roles you’ll find that asking questions takes up a lot of your time, no matter which profession you’re in. There are (at least) four hard things about asking questions:

You want to make sure you’re asking the right question.
You can’t ask the exact question you want answered because you won’t get honest answers or you won’t know whom to ask.
You often have limited time to ask questions, so you need to be effective.
Sometimes, the important thing is not what you ask, but how much you ask or when.

Let’s see what effective questions might look like in various roles, situations and professions:

As someone who wants to start a company

Let’s start with a non-profession: A person who wants to start a company but who doesn’t have a business idea yet. I think the most important question to ask yourself is why you want to start a company. You should ask yourself: Do I want to become rich or do I want freedom? If you want to be rich, you’ll need to build something big, which means you’ll probably need external financing of some kind. However, having external investors removes a lot of the freedom. If you want to start a company to be your own boss, this is not the path you should take.

No matter which route you take (big or independent), most successful entrepreneurs I know took a two-step approach:

Try to think like a surfer and ask yourself: Where will the next big wave show up? (where wave = market) Then try to put yourself in a position where you might take advantage of the wave. In my experience most of these waves tend to come from new technology or regulation.
Try to have open conversations with people in that market and ask them: What things often frustrate you?. Stop once you’ve found five people who have the same problem that they desperately want a solution for. If they’re desperate, they will probably be very helpful when you try to solve the problem for them.

As a startup founder

Once you’ve started your company, you’ll want to know if you’re going after a real problem, and if so, if what you’re doing is actually solving it. The founders of Superhuman discovered one question that stood out in order to assess this. They would ask their users:

How would you feel if you could no longer use the product?

and measure the percentage of users who would answer “Very disappointed”. This became their “product-market fit score”, where the magic threshold seems to be 40%. (Source: First Round Review)

Another way of assessing your product-market fit might be to calculate a Net Promotor Score. This is done by asking your users:

How likely is it that you would recommend our product to a friend or colleague? (Scale 0-10 where 10 is Extremely likely)

Research shows that the people answering 9 or 10 are the ones who will actually recommend you product - they are the promotors. The people answering 7 or 8 are passives and 0 to 6 are detractors. Your Net promotor score is calculated as (number of promotors - number of detractors)/(total number of respondents) and can vary between -100 (only detractors) and +100 (only promotors). Generally, an NPS score of more than 50 is considered excellent.

As a startup investor

When investing in startups, most investments actually fail. Therefore, the few investments who are successful will need to compensate for the ones who fail, which is why startup investors will want every investment to have a huge potential. There are three main limits to a startup’s potential: The market, the founding team and their execution. Contrary to what many first-time startup founders think, the idea is not that important since that will change over time. To assess the market, you’ll want the answers to the following questions:

How big is the current market for what the company is doing right now? If it’s not big enough, could the market be made bigger by segmenting, finding new target groups or selling adjacent products or services?
How fast is the market growing? It’s much easier to find a profitable segment for your company if the market is growing.

To assess the team, two questions stand out:

Are the team members intelligent? Starting a successful company means solving problems, and for that you need a combination of brain horsepower and street smarts. A certain “clarity of thought” often helps too.
Can they stand the grind? Running a startup is an emotional roller coaster, and not for the faint of heart. You will want to know if the team has the same level of ambition (extremely important) and if they can show examples of how they’ve handled difficult situations.

To assess the execution, it’s important to understand that many startups go up against big incumbents that they can never outspend. The only way to win when competing with an incumbent is to be faster. Therefore, you will want a clear Yes! to the following question:

Am I impressed by what this small team has accomplished with their limited resources?

As a salesperson

If you’re a salesperson, ultimately you want to know the answer to the questions Who will become my customer? and How much will they buy from me? If you knew the answers to these questions, you could more or less just sort them by contribution margin and start dialing. The problem is that this can be hard to find out, so you will inevitably need to talk to a lot of prospects that will end up not becoming your customers. The key thing for a salesperson is therefore to qualify their leads, i.e. to make sure that they spend as much time as possible with relevant customers.

Does the customer need to solve the problem that our product can solve? Please note the focus on problem here, and google Jobs to be done for more theory.
Is the person you are talking to allowed to spend money on solving the problem? If not, you might want to talk to one of their colleagues.
Does the customer have a budget allocated? If not, at least make sure they allocate money next year if they’re interested in your product.

As a buyer

If you work in procurement (ie. buying things for your organization), you might think that you should be asking questions about deliveries, contracts, price levels etc. However, the most effective question is often:

What do we actually need in order to do our job?

You might find that not everyone in your company who asks for a new computer, phone or car actually needs one in order to do their job. Similarly, you might be able to cut down on software that’s not being used, or downgrade SaaS licenses to plans with less features.

As a recruiter

Hiring people is of course all about asking questions. What you really want to find out is Is this candidate worth trying to hire? (Will they be able to do the job? Do they have potential beyond the current job scope? Does the candidate have better options than working for us?) How can you assess all of this during a short interview? You can’t cover all aspects, of course. However, it will be really hard to predict the candidate’s future job performance if you spend the entire interview digging into one single question or case study. Instead, you’ll want to ask as many different questions as possible during the interview. The reasoning behind this is that one big case study might overlap poorly with your skillset by accident, but if you fail on ten unrelated questions after each other you’re more likely to fail in a real work settings. An example: If you’re hiring developers you might want to try to spend the interview discussing several pre-made code examples instead of having the candidate write code (which takes much longer). A great blog post on this topic here.

As a software developer

The most important thing about asking questions as a software developer isn’t really which questions to ask, but having the courage to ask them sooner rather than later. One of the most rewarding things about developing software is solving problems, but the desire to solve them yourself can easily lead to a lot of wasted time. However, as long as you have actually tried to solve a problem, you’ll learn as much by asking someone for help as you would by solving it yourself. Sometimes it even helps explaining the problem to someone.

As a UX researcher

If you are interviewing users of a product in order to learn about potential improvements, the key is to ask open-ended questions. You’ll want to avoid asking Show me how you’d use the product to do X, because the user might not even be aware that you could use the product to do X! Instead, you’ll want to ask things such as What do you use the product for? and Can you show me how? Also, you might want to dig deeper into all thing you discover by asking Why? several times. Google The five whys for more info on this method.

As a doctor

I am not a doctor, so I won’t dive to deep into medical practice, but as I’ve understood it there is a big difference between being a primary care physician (where you meet one patient at a time and you’re not in a rush) and an emergency-care physician (where the patient might actually die within five minutes). As a primary-care physician, you’ll want to start high-level and ask open-ended questions, in order to find out things that you might want to dig deeper into. You’ll also want to make sure that the patient understood everything, and check whether they are actually using the medicine you prescribed last time. As an emergency-care physician, you want an immediate triage: What is the emergency? What is the patient’s temperature, blood pressure, pulse rate and respiratory rate? These pieces of information will give you enough to prioritize the most urgent patients.

Generally, I think this in an interesting distinction. In many professions you’ll be faced with urgent and non-urgent situations, and knowing how they differ and which questions are applicable to which situation can be very useful. It might make sense to build up a “panic checklist” of questions for emergencies, whereas you can afford to ask much more open-ended questions when you’re not in a rush.

As a trial lawyer

In trials, the jury tries to figure out beyond all reasonable doubt whether someone has committed a crime or not. As a defense lawyer, your job is therefore to create as much doubt as you can. This can be done by asking many different questions and convince the jury that they need to have a clear answer to all of them before they can pass their verdict. This might be questions such as Are we sure the witness can be trusted? (He was drunk, it was dark outside), Can we be sure that the victim died because of the drug, or because they had an existing medical condition? etc.

On the other hand, if you want to convince the jury that the person is guilty, you should try to simplify the case into one single question that feels easy to answer. For instance, in the current case about the death of George Floyd, such a question might be Do you think a person can put their knee and weight on a man’s neck for 8 minutes and 46 seconds and not know they’re killing him?

Summary

In many fields there are effective questions that will give you a proxy answer to the question you really want answered. It is not always about which questions to ask though. Sometimes it’s more important that you ask sooner rather than later, and sometimes you want to ask many questions rather than a few.

Writing this essay really spurred my interest in effective questions. If you have any suggestions on how to improve it or want to connect in general, follow me on Twitter!