Why do we suck at asking question at work?

  • Post by Maxime Cote
  • Jul 30, 2021

The ability to ask beautiful questions, often in very unbeautiful moments, is one of the great disciplines of a human life. And a beautiful question starts to shape your identity as much by asking it, as it does by having it answered.

Ever stopped yourself for a moment and thought about the importance of asking a good question? Good questions are surprisingly underutilized, yet they are one of the crucial parts of knowledge work. Moreover, asking good questions is a skill that needs to be trained and maintained since it often goes against our defaults. That is especially true when working remotely since so much communication will be in written form in a chat application. So if asking a good question is so crucial, why are most of us not doing it? Before going into why many of our questions are wrong, let’s first look at why we’re doing it in the first place. Also worth noting, most of the questions asked so far are not good questions (!)

Why don’t we ask good questions?

A lot of devs don’t like to ask for help in front of their peers. Speaking up to admit you’re blocked is really hard for some people.

One of the reasons for this is that asking a question requires us to show vulnerability. It requires telling someone else there’s something we don’t know, and we need help, which can be challenging. In some companies/teams, when there’s no or little psychological safety, that display can be even more complicated since it could endanger your position. In that scenario, fear will take over and result in a “protective” question. Often those questions will be oblique or very narrow to prevent the person answering from realizing the issue. Doing that will “shield” you from being seen as “bad,” but at the same time, it prevents most of the usefulness of a good question.

Another reason for not wanting to ask good questions is that they are often difficult to asks. Because a good question as requirements and attributes (more on that below) and requires meeting them. For the same reasons asking that type of question will require more time because of its added complexity. Defaulting to “how do we do x?” is a lot easier to write than taking the time to write something good. It can be challenging to lay down a problem in some scenarios to get an answer from someone because we’re not used to doing it.

The final reason why we might not take the time to ask good questions is simply that we often default to the lowest friction option. When we don’t take time to reflect on why things work the way they do, we often don’t realize there are other ways. Since no one likes friction in their life (especially in communication), we will instinctively default to the option with the lowest friction possible. The problem with that is like we’ve seen above, good questions have friction to them. Even though the benefits can be a lot bigger, you need to get over the friction points. Defaulting to “poor” questions instead means no one gets the advantage, and it also creates more problems over time as the culture of quick “1-minute” questions grows.

What is a good question?

Now that we’ve seen why we don’t, what exactly is a good question in the work environment? First, a good question needs to be clear and explicit. It needs to communicate the requirements and urgency that relate to it clearly. For example, are you stuck on this problem for the past three days, and the deadline is incoming, or is it a minor fix that needs to be done next week? That information needs to be with the question. Most communication applications have some flag or marker that explicitly shows the importance of a message; consider using it when needed. Clarity is also critical since otherwise, you might not get the correct answer, or it may take a lot more time to get it. On the clarity front, a lot of it comes from giving the proper context and information to the question, which is also the next thing that makes a question good.

A great question needs to be self-contained. It should have all the information required to be answered by the person you ask. What’s the context of the question, what’s the issue, what you tried, what do you think might be the problem. All of that information will make answering easier and make it more likely that you will get the correct answer. Typically when we work on something for a time, we immerse ourselves in the context, and things seem “evident” for us. But when asking a question, you need to remember the other person is in a different context, and nothing is “evident” for them. Taking the time to make a “dump” of the context also makes it easier to save that question for later so others can compare and see if the answer might work for them.

The final thing that makes questions great is the balance between narrowness and openness. It can be tempting to ask very narrow questions so it would be “easier to answer,” but too narrow a question creates another issue. Often very narrow question requires a ton of context, or you might get a misleading answer because the person answering couldn’t see the big picture and spot other possible issues. On the other hand, a too open or vague question will require context digging from both parties to be answerable. That sort of balance will often be evident when you start to write the question and gather all the necessary parts. Are you writing the other person “a novel” so that they know everything to reach the point where they can answer? It’s probably too narrow. Are you unsure what context to even put because it’s too “evident”? Then it’s perhaps too open.

Why should we ask good questions?

The what? and where? and when? questions may reveal facts. But the why? question uncovers motives. And that is how self-reflection begins to emerge.

Now that we’ve seen why good questions can be difficult let’s look at what we get out of them in return. One of the biggest reasons for doing it is knowledge sharing. One of the best ways to gain expertise and grow knowledge in a domain is by asking good questions to people who know more than you. Simply by getting those answers, you gain some of the same expertise in that domain you questioned them about. That’s why good questions are some of the best ways to break down expertise silos and reduce the knowledge gap in teams. The more an expert can answer good questions in a way that you can share, the more that knowledge will spread. Of course, the question needs to be correctly asked and saved for later for the exchange to work as its full potential, but it can still be very potent even without the complete workflow.

Another thing enabled by good questions is discovery around that subject/process/modules. Often taking the time to formulate a good question will reveal a lot of new information or lack of knowledge. For example, some questions will come up like: Was the task not straightforward? Did the documentation lack some parts? Was that process unclear? While some of those could be “weaponized” with the wrong team dynamic or mindset, the problem is still there. You could also look at a higher level and discover a pattern of questions being asked often around a concept or a piece of the product. That could signify that people need better training on that part, or more documentation needs to be added.

In the same vein, good questions are a great way to reflect and grow. That comes from the fact that, just like in another form of writing, you need to put down your thoughts and force them in a logical order to ask a good question. That forcing function can lead to realizations and sometimes a new path to try or even a solution. As you get better at writing down good questions, you will also get better at synthesizing your thoughts logically, which is a powerful skill to develop.

The skill

In the end, asking good questions is a skill, and like any other skill, it requires practice and some discipline, especially at the start. However, the nice thing is that it can be honed very quickly and become a common thing because of its reflection and discovery element. On top of that, it’s very much worth the trouble because of the knowledge-sharing aspect, since you will get better at most things by asking good questions.