Asking Questions: the Good, the Bad, and the Ugly

Asking questions is how we all learn and grow in our careers. It is how we gain understanding, gather necessary information, and ensure relevance and accuracy towards what we are tasked with doing. Asking questions bridges the gap between intent and ability to generate a valid and accurate response. There are times when asking questions will cause problems at work, though. Sometimes, your questions may not be welcome, and there may be several reasons for that.

The Good

First, I want to be clear that I have always welcomed questions. I love training people, and I'd rather my instruction be clear and understandable. Suppose I have not done an accurate job of decimating information, and someone asks a clarifying question. In that case, it is helpful not only to answer the question but also to document the answer and disseminate it so it is available to everyone on my team.

Sometimes, rather than answer a question outright, it is better to guide someone else to the answer. That way, the logic behind the “why” is embedded along with the answer itself. It can also bring up changes to the answer as you introduce a fresh perspective. I am not always right, and it helps to learn together.

So, to summarize my first point, asking questions is not a bad thing. No one should feel like they cannot clarify a position by asking for more information.

The Bad

When can questioning become a bad thing, though? There are two main situations where I take a pause when someone is asking questions.

The first one is whether they are asking a question about something they should have already mastered in their area of expertise. Suppose someone is already considered an expert in their field, but asks for basic information about what they are working with. In that case, I’m not talking about a situation where you cannot remember how to do something because it’s been a while. We’ve all been there. I am referring to someone who is in a position where they have years of experience but lack a fundamental skill.

For example, a Scrum Master who has been doing Agile for years but doesn’t understand what a sprint is. Another example would be if your organization had hired someone with years of experience in Microsoft network products as a network administrator. Still, they are unfamiliar with the concept of Active Directory. Are these examples “deal breakers” for me? No, but they do make me question how many knowledge gaps I am currently dealing with. It will lower my confidence in the person’s ability until they can prove themselves, and I would adjust training programs to provide them with more focus on their required skills.

Another “bad” situation is when someone continues to ask the same question each time they are faced with the dilemma. I’ll be honest, this one drives me nuts as a manager. This is why I adopted documenting answers and distributing them across the department. That way, I can answer the question and offer the documentation as proof. Eventually, I can guide the person directly to the documentation in the hopes that if they are confused in the future, they know where to look.

Of course, if the documentation is unclear, they are welcome to ask for clarification, and I will update it accordingly. I’m not a monster. It can still be demoralizing when you're asked the same questions, provide the same answer, and then have to repeat the process shortly thereafter.

One of the reasons for this is a lack of confidence. We all suffer from some form of impostor syndrome throughout our careers. If the person asking questions has low confidence in their work or an overabundance of caution, then these are different situations from the manager’s standpoint. Managers should be on the lookout for these situations to help guide the employee to higher confidence in their work.

Note: Although this is how I would handle these situations, my experience at multiple organizations has significantly differed. Typically, if those companies were faced with these sorts of conditions, they would take note of the training needed and, oftentimes, replace the person. I have known many managers who would rather hire someone with the skills rather than train them properly. Of course, they will run the risk of being in the same situation or worse, but that is the risk they face.

The Ugly

This one might be a tad controversial for some, but I’ll push on anyway.

Some coworkers, managers, or even executives do not like fielding questions. Never. Not at all.

There are plenty of people who do not take well to questions, as they find they are in any (or all) of the following categories:

  1. They cannot answer the question

  2. They do not wish to answer the question

  3. They consider the question to be a direct challenge to their authority

If you find you are asking questions and the person does not have the answer, never fear. You can try to find the answer elsewhere, and if you find it, please share it with them. Sometimes this will open a collaborative door with them. If you were willing to help out and add clarity, they might be willing to work with you on answers in the future.

Some individuals may be hesitant to answer questions if they are shy or lack confidence. Some are worried that since they are the primary holder of the knowledge, if they share it, it will diminish their role in the organization. This is especially prevalent in environments where ideas are “borrowed” by others and praise is heaped on the “borrower” instead of the source.

My best advice in this situation is to continue to call out where you get your information. You don’t need to shame the person who didn’t answer the question, but you can indeed praise those who did. If you acknowledge the proper source, others may be more willing to help you in the future.

The final point, where ego is involved, is difficult to navigate for many (myself included). This is especially true for managers and executives, though I have witnessed it at all levels of an organization.

I came from a quality assurance background, so it's in my nature to ask questions, which sometimes annoys those around me. All I am trying to do is gain a better understanding of something, but some people can’t stand that I am prying too deeply into the logic or details of the situation. This has more than once led to those who think I am trying to show I am smarter than they are, or they feel I am trying to make them look bad.

How do you handle that sort of situation? Well, that isn’t always easy. I know I have butchered this situation several times over my career.

One thing I have learned, though, is that everyone should obtain written directions whenever possible. If someone isn’t willing to answer a question, write down your understanding of the situation and communicate it to them (especially if they are your manager). If there is no feedback, then proceed from where your experience lies. That way, if they come back later and say you did something wrong or that you didn’t do it the way they wanted, you can point to your communication as proof that you tried to meet them halfway on an understanding.

If there is no feedback, then you are in a good place. If they do provide some feedback on how you screwed up in their eyes, you can document their feedback as the answer moving forward. Please always keep communicating, though. Ensure that you are not the one where communication breaks down.

Some will argue that this is merely a form of “malicious compliance.” I agree that it can be seen as such, but if you do not have another option, then doing exactly what you are told is your only recourse.

Others will say, “Take it up with Human Resources.” Again, I’ll be controversial here when I say that this has never done anything for me in this situation other than make the person more hostile. Typically, that is when you start being labeled as a troublemaker at your organization. This will likely result in you being passed over for promotions, being moved around within your organization to areas you don’t want, or even endangering your job entirely. Your mileage may vary, but that is my personal experience.

Don’t Lose Hope

Please ask questions. Don’t let any of this “doom and gloom” keep you from learning. When you increase your knowledge, you become more valuable to your organization. This improves chances for career growth and promotion. It also puts you in the position to start answering questions for others, rather than being the one who asks them. Then you can be the one who helps out (and hopefully avoids the “ugly”).

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