How to ask questions at work: A guide you didn’t ask for, but now need more than ever

Many of us in the profession have suddenly found ourselves in a new world: everyone working remotely, indefinitely. I wrote this article before the coronavirus pandemic arrived in the United States, but now, in this confusing time, the ability to ask questions at work becomes all the more important.

“The answers are all out there,” Oscar Wilde once famously said, “we just need to ask the right questions.” As true as this aphorism is, it’s equally true that some people have more trouble asking questions than they do finding answers. The fear of asking for help or information is a common one, and its consequences are always negative. At best, a failure to ask for a hand at work will result in lowered efficiency. At worst, it can hamstring internal relations and lower client satisfaction. To avoid these undesirable outcomes, all you have to do is ask. So why do so many people struggle to do so?

An anxiety about looking weak or coming off as awkward keeps people from asking for what they need.

“There is a tendency to act as if [asking for help is] a deficiency,” Garret Keizer, author of “Help: The Original Human Dilemma,” told The New York Times. “That is exacerbated if a business environment is highly competitive within as well as without. There is an understandable fear that if you let your guard down, you’ll get hurt, or that this information you don’t know how to do will be used against you.” Banishing that fear is difficult, but the rewards are more than worth it. If you struggle to ask for help at work, you need a framework for getting over the hump.

I recently spoke to Melissa Galasso of Galasso Learning Solutions about the difference that developing the ability to ask for help made on her life. She went from being a person so scared to ask for help that she didn’t even tell her friends she was taking her driving test when she was in high school to now championing the values of assistance and collaboration because of the benefits she has gained in her life.

“What I have found is that when you help others and others help you, it becomes this agreement,” she told me. “It's grown.”

There are plenty of excellent resources out there detailing professional situations when you can and should seek assistance, but this guide offers something a little different. What follows is a set of ironclad insights about asking for help that will lead you to ask better questions, ask them with more confidence, and get the answers you’re looking for.

You can ask anyone for help

In many workplaces, the chain of command is rigid. If you need to ask for paid time off, you go to a certain person. If you need supplies, you go to another. There is no such structure when it comes to asking for guidance, clarity or collaboration. The person you should ask for help is the best person to provide it. It’s just that simple. You should also be willing to ask for help or advice from team members underneath you. In fact, relying on your team and leveraging their expertise is one of the qualities of a great leader.

Ask early, ask often

Just because you’ve missed an official window to ask questions, it doesn’t mean that window is closed forever. When you are in the middle of a project and hit a roadblock, it can be tempting to power through rather than stopping and getting your bearings. While asking questions before the beginning of an assignment is optimal, you will usually come across problems you didn’t anticipate during the course of a project. When these challenges arise, there’s absolutely no shame in soliciting a hand or mind in overcoming them.

There are different types of advice

You should alter your approach, depending on the nature of your question or request. If you have a clerical or administrative question, you’ll likely need an exact answer. There’s no ambiguity in these matters, so the answers are black and white. That’s different from asking for perspective or input on a project. In these instances, you needn’t take someone else’s word as gospel. In either case, however, you should listen to the person providing the response and give them your respect.

Frame your question to get the answer you want

People often reframe or soften their line of questioning in the interest of being polite. For example, have you asked your significant other if they “want” to pick up the groceries? I’m guessing what you really wanted to know is whether they would do it. That may sound like a small thing, but in a professional context it can prove disastrous. Try to figure out exactly what you’re asking before you ask it. To do this, it can be helpful to write out a few versions of your question deciding on the best one.

Don’t look for the response you want to hear

Confirmation bias is the tendency to prioritize that which validates our preexisting beliefs over that which calls them into question. If you’re a Cubs fan, for example, you probably tend not to surround yourself with pro-White Sox opinions. In the workplace and in life, it’s important to seek out a variety of opinions and give them equal weight. After all, it’s not worth asking a question if you’re unwilling to hear the answer.

If you’re unsure, ask again

Not every answer is going to be crystal clear. If you receive one that is ambiguous or leaves you scratching your head, don’t be afraid to follow up. Maybe the person you’re speaking with didn’t understand you or perhaps you need to rephrase your request. Don’t worry about being a pest, because it’s much more bothersome to have to return to ask follow-ups rather than getting all you need in one shot. Whatever the reason for a miscommunication, don’t walk away pretending you have an answer when you don’t. If you really feel you can’t do anything else to better frame your request or inquiry, you’re better off looking for an alternative source.

Growing a culture of open communication starts by asking questions and seeking assistance. So let me ask you: What are you waiting for? See how this can not only benefit your career, but your life.