Don't Reflex an Answer: Use Questions to Find the Real Problem

The standard process for solving problems: ask Questions to define and solve the Problem.

Question-driven problem solving spends more time using questions to define the real nature of the problem, and less time looking for the answer. The core isn't reflexively producing an answer — it's spending time understanding the situation first, so the conversation doesn't get pulled in the wrong direction.

A lot of people think problem solving means finding a Solution.

But how?

Some rely on experience
Some search the internet
Some pull everyone into a meeting
Some consult an expert

The textbook answer is: Ask a question.

Why does problem solving start with asking?

If I had 1 hour to save the world, I'd spend 55 minutes defining the problem and 5 minutes finding the solution.

PS: A lot of people attribute this to Einstein. He didn't say it. Source unknown. XD

How do we define a problem?

We define it by asking questions.

I was talking to a client recently and they asked: Can you build us an email marketing system on the website?

Email marketing systems are usually very complex software services. Almost no one self-hosts one on their own site.

The cost is too high, and even if the client had the budget, we don't have the know-how.

So instead of answering, I asked:

What email marketing system are you using right now? Why do you want to self-host one?

The client said: We're not using one yet, but we figured we might need one for marketing later.

I asked further: What functional requirements does your marketing team have for an email marketing system?

The client said: We haven't actually started running marketing campaigns, so we're not sure what features we'd need.

See the problem?

The client didn't actually know what an email marketing system was.

So I spent some time explaining, and recommended a few SaaS platforms for their marketing team to look at.

If I had jumped straight to answering the original question, I would've said:

We can do it, but it'll cost a lot — don't recommend it
Can't do it, too complicated, find another vendor

I would never have learned what the client's real problem was.

The client doesn't always know what their own problem is.

Asking questions is how we both figure out what the problem actually is.

From this case, you can see asking instead of answering does three things:

Clarifies whether the client's stated need is a "real need" or an "imagined need"
Avoids taking on work that's outside your capability and creates downstream disputes
Shifts the conversation from "can you build it" to "why do you want it" — and finds a better fit

Why do questions need direction? Reflexive questions pull the discussion sideways

When solving problems, we have to be patient about understanding the Scenario.

Don't reflexively start asking or chasing the answer.

I once had a junior on my team. When a client asked: Can you build OO?

He immediately fired back: Do you mean OO with the XX feature?

It sounds like he's confirming the question, but this kind of question pulls the discussion sideways.

If the client doesn't actually know what they want, they might say: Yeah, I want something "like that".

He gets his confirmation, comes back to me and the engineers and says: Client wants OO with XX feature.

The engineer frowns and asks: But that's not in our scope?

And I'd ask: Did the client say why they need that feature?

A wrong direction creates huge communication cost, and friction between people on the team.

Asking "Why" is the foundation of questioning.

If we're "too eager" to find the answer, we're more likely to find the wrong one.

If we misunderstand the situation, our questions will be wrong.

And every follow-up question we ask will keep being wrong.

The point here is: patience.

Patiently understanding the situation — the point isn't the understanding, it's the Patience.

PS: Don't rush to find an answer.

How do open and closed questions differ? When do you use which?

The direction of a question determines its form. Open questions are for exploring. Closed questions are for converging — pick the wrong type and the question does nothing.

There are two ways to ask:

Closed questions: yes/no questions, used to confirm and filter
Open questions: used to explore new possibilities

Closed questions: filter layer by layer with yes/no

If the same questions come up often, we can turn the asking into an Standard Operation Procedure.

Once it's a process, we can use yes/no questions to filter what the client is asking.

Running an agency, you sometimes get a flood of pitches and partnership inquiries during peak season.

You can filter potential partners fast with yes/no questions:

Are they offering a pitch fee?
Do they have a clear, defined need?
Do they have a clear budget range?
Do they have a positive reputation in the industry?
Does what they want to build fit our company's direction?

You can ask a lot of questions to filter — the goal is effective decision-making.

The same setup works for "interviews."

Personally, I use yes/no questions for managing work. Three questions sum up the status of any task:

Is task A done?
Will task A be done on time?
Does task A need me to step in?

Three yes/no questions usually tell me where I stand on something. Most of the time I only get to question two.

If I have to ask question three, it means things are probably really bad.

When to use open questions: when you're facing something you've never seen before

Open questions are for problems "you've never encountered before."

They're typically used in career development, new product ideation, and creative brainstorming.

I have a friend who's a freelancer.

One day he asked me out for coffee, and out of nowhere brought up whether he should go back to a regular job.

I asked: Why are you thinking about it?

He thought for a while, then said he'd been watching his friends grow in their careers and felt like he wasn't really progressing.

Maybe he should leave his comfort zone and try working a regular job again.

I asked: Do you think going back to a job would teach you something you can't learn now?

He thought about it, laughed, and said: Probably not. I already learn whatever I want to learn.

Freelancing doesn't have a clear promotion ladder like working at a company, so it's easy to fall into self-doubt sometimes.

Through open questions, we realize a lot of our worries aren't actually concrete — they're just feelings.

If you try to put the feeling into words, you'll often find the problem isn't really that big.

When I'm designing a product, I always ask myself: Why am I designing it this way?

After I answer myself, I ask again: Will this actually achieve what I want?

After sitting with it, I ask once more: Is there another way to get the same result that I haven't thought of yet?

Asking and asking again pulls things into view that we've never considered.

Asking questions is using questions to look at the problem fresh.

When we look at a problem from a different angle, we see different answers.

Solving problems starts with asking.

FAQ

Q: If a client asks me a question and I ask one back, do I look unprofessional? A: No — as long as you're asking "why" and asking about the situation. The point is to understand the need.

Q: When should I use closed questions, and when open? A: Use closed (yes/no) when you need to filter, confirm, or decide quickly. Use open (why / how) when you need to explore directions, clarify thinking, or generate new ideas.

Q: Don't open questions cause the conversation to spiral out? A: They can — that's why open questions are usually followed by a round of closed questions to converge. Diverge first, converge after. That's the basic flow of questioning.