Are you getting the right information at work? The kind of information you need to really do your job well?

Then you’re probably not asking the right questions.

There can be reluctance in some quarters on posing queries — lawyers for example famously never ask a question they don’t know the answer to — largely driven by concern that admitting you don’t understand or fully know something is a sign of weakness.

But this doesn’t hold water.

Sure, asking “stupid” questions (note: simple does not mean stupid) that have no thought behind them can make you look bad, the act of asking pointed questions is one of the main ways of exchanging information and increasing understanding.

“The ability to ask the right question is more than half the battle of finding the answer” – IBM founder Thomas J. Watson

Influential leadership writer John Maxwell has laid out nine values of asking questions.

  1. Without questions you don’t get answers
  2. Questions connect people
  3. Questions unlock doors of information
  4. They create humility
  5. Questions let you direct a conversation
  6. Questions make ideas better
  7. They give us different perspectives
  8. They challenged established ways of thinking
  9. Questions let us stand apart and build influence

Think of asking questions as a tool. A tool that gets you information you otherwise wouldn’t have access to.

So let’s sharpen it up with the no-go zones of asking questions and then the yes-go zones.

Types of questions you should NEVER ask

Before you can consistently ask really good questions, you’ll need to know what goes into asking a bad question — the kind of words that will close off potential answers before you ever hear them.

Let’s take a theoretical work situation to illustrate how NOT to ask questions. A project has fallen behind, and the team lead is trying to figure out how to get it out of the ditch and back on track. The lead thinks throwing another person on it may do the trick, but doesn’t want to rule out any other options.


This is a question that has two questions inside it.

Example: What do you think is the best method of speeding up this project, and should we put Jim on it?

Double-barreled questions are problematic because they’re non-specific — they give your target two choices to pick from when it comes to answering.

This muddies the waters, to say the least. It prevents you from getting the answer (information) you really want. And it can also result in suboptimal answers, as the respondent may try to cram two answers into a space for one response. Or they will simply answer the question they feel most comfortable with, which means that you won’t get the information you’re seeking at all.


Closed questions are those that can be answered with a simple binary: yes/no, right/wrong, agree/disagree, black/white, hot/cold, etc.

Example: Should Jim be brought in on this project to speed it up?

This type of question is a problem because it closes off answers. Closed questions can actually be answered with a simple non-verbal head nod — and if you’re asking someone a question that is so shallow it can be answered with a body gesture, then is it really worth your time (or theirs) to ask?

Better: What do you think about bringing Jim on to speed this project up? OR How can we make this project move faster?

Sometimes, you really just do need a simple yes/no answer. If so, great, go for a closed question. In other instances, think again.


A query that includes a strongly suggested answer or direction of response is a leading question. The answer, in other words, is presupposed.

Example: How great would it be if we got Jim involved in the project?

Note that for the above question, any answer would be about Jim being a good addition to the project. It makes Jim the topic of the question — getting away from the real subject, which is making the project itself work better.

Better: How can Jim help us improve this project?

Even Better: How can we improve this project?

Doing it right: Structuring questions for best answers

Asking questions the right way (the way that gets you the best possible answers) means, for most instances, pausing for a moment to consider just what you’re asking — what information do you expect to get? — and then taking a step back to remove any assumptions from that proto-question.

“We need to ask the right question to reveal the answer” — Dr. Jonas Salk, Polo vaccine creator

This is the time that you screen your budding question for the above no-go words and phrases: can it be answered with yes/no, does it presuppose an answer, etc.

Abstract it when necessary

A good rule of thumb here is to take your question and move it up one rung of abstraction — going from the specific to the general.

Example: Should Jim be brought in on this project to speed it up?

Better: How can Jim help us with this project?

Even Better: Who can we bring on to help with this project?

And, depending on the situation you can make it even more abstract:

What can Jim do to help our team?

Or: How can we speed things up?

Again, different situations warrant different levels of assumptions or specifics. Just don’t worry about the question sounding too broad or open.

Keep it simple: Use as few words as possible

Talk less, listen more. How? Make your questions as short and to-the-point as possible.

Or, to put this in a more digestible form, a good rule of thumb is that if you’ve starting asking your question, and then pause, stop right there. This is because a good number of bad questions take the form of question, then opinion.

As in “What do you think about adding more staff for this? (brief but noticeable pause)… Let’s bring on Jim?”

The first half of that question is great: simple and open. The last part, though, flushes this down the toilet by turning it into a yes/no question.

Once you get used to asking questions the short and simple way, this becomes less of a (pause) issue.

Don’t cut: Interject after they’re done answering

Some of us are good at getting the meat of an answer quickly. For others, they need to warm up a bit before providing a substantive answer. Problem is, we all react this way depending on the situation.

So give people space to complete their answer by not jumping in with your reaction or thoughts. If you’re especially antsy and bad at jumping in (we all do it) then make sure you pause for long enough to breathe in and out before giving voice to your thought.

Otherwise, you might be interrupting the response before it’s even really gotten going.

Ask simple follow-ups

You know someone has given an incomplete answer, what do you do? Ask simple follow-up questions.

Again, short is sweet. There’s the classic “What do you mean by that” or “tell me more.” To break ambiguity, ask for examples or for them to explain a hypothetical where their answer would apply.

This gets people thinking very specifically about their answers, tying them down to specific real-world situations. The result will be more concrete information, that is much less abstract.