Ask More Questions

I was perusing r/projectmanagement on Reddit and I found a post from a new IT PM who asked, “How do you gauge severity of testing issues that you don't fully understand?”

I didn’t weigh in on the conversation because I agree with a lot of the advice already provided: Lean on the technical experts on your project. Ask them for the detail you need to track your project—and do your job—well.

My earlier post “7 Strategies for Managing Tricky Technical Work” covers many approaches you could take in a situation like this, but in this post I really want to highlight the value of asking questions. We know it’s a tool we need to use regularly as project managers, but especially if you’re new to project management, you might face barriers to asking the questions you really need to ask.

Sometimes you need to be strategic about when and how you ask your questions, but in general, I believe we are more successful as project managers when err on the side of asking more questions, not less.

Let’s talk about some of the common barriers we face to asking the questions we need to ask. We can handle those situations shrewdly while still getting the answers we need.

Barrier #1: They seem busy.

Does the person you need answers from seem to be juggling 100 balls at once, and you’re worried if you interrupt them with one more question, all the balls might hit the floor?

It’s great to be kind and thoughtful about interrupting someone who is busy. At the same time, you need to do your job and to do that, you need information. Here are some good options:

• Consider alternative people. Can you think of anyone else who might know the answer?
• Enlist help with the timing of the ask. Is there somebody who works closely with this person, such as an administrative assistant or a functional team member, who will have a sense of the least disruptive time to ask the person questions, or could even ask on your behalf?
• Use the person’s preferred medium. Do you seem to get faster or clearer answers from this person by email? Instant message? Phone? Scheduled meeting? Popping by their office? Lean on the communication medium they prefer, and if you don’t know what that is, ask somebody who works more closely with them.
• Time a follow-up with their workload in mind. Have you already asked and not gotten an answer? For the work cadence at my company, I typically wait until the second day without a response before asking a question again or sending a reminder. However, if I know a person or team is in a busy season—or if it’s a senior leader who is always busy–I might extend that to 3 days, a week, or multiple weeks. Pick a timeframe that balances the person’s schedule with the importance of the answer.
• If you need answers on multiple topics, prioritize. For a busy person, I rarely send them questions about more than one topic at a time. I’ll ask about the most important topic first, and after I get the answer, then I’ll send questions on the next topic. At some point, too many questions become noise and a person will tune them all out because they can’t process them all. Getting one answer is better than getting zero.
• Interrupt anyway, and explain why. If your question really is that important, you should interrupt, whatever that takes. It’s part of your job to keep stakeholder attention on priorities, and if you have a priority, you should tell the stakeholder. You don’t need to make excuses like “Sorry, do you have a minute? It’ll be really quick, I’m sorry…” But it’s good communication to lead with the value of your request, such as, “Could I have a minute of your time? High Priority Project X is stuck, and I need some information from you to get it moving again.”

Barrier #2: It’s always been done this way.

Is your project team using a method or a system that doesn’t make sense to you, or seems to be holding the project back, simply because they seem comfortable with the system? Are you seeing a need to "question" the current system for your project to succeed?

If you aren’t just a new project manager but you’re also new to your company, you actually have an asset here: a grace period to ask “stupid” questions! A question that would sound awkward coming from an employee of a few years or more will come across as innocent and forgivable in your first year, especially your first 6 months. Use this timing to your advantage. You may have an easier time creating change in situations like this than tenured employees would.

But let’s say you’re not new. That doesn’t mean you’re stuck—you just might need to be more strategic with your questions and approach. Here’s what you can try:

• Find out the history first. The idea of ‘not moving a fence until you find out why it’s there,’ attributed to G.K. Chesterton, has been very relevant at my company and in my career. Basically, without the history of why something is done a certain way, you could cause a new problem in the process of solving the one you’re working on. You can learn the history by checking company documents and databases, by asking questions of other employees who won’t be affected by the change, or by asking careful questions of those directly involved, such as, “Hey, do you happen to recall when we started doing X?” You may realize you don’t want to make the change you had in mind, or you may gain some really helpful information to help you approach the change effectively.
• Be direct, but lead with the value. Ultimately, while you want to be aware of and kind with people’s feelings, it’s usually healthy to treat people like adults and be honest with them, regardless of how they’ll react. In the long run, transparent communication builds trust. But when you’re asking questions about a possible change that people might have a reaction to, be sure to explain the value of the change—to them, to the company, to the project, whatever value there is—up front. It will reduce people’s defenses somewhat when they understand why and see the bigger picture. This is also part of transparent communication.
• Be empathetic toward people’s feelings. You can move forward with a change while still caring how people feel. It will mean a lot to give somebody a listening ear about how doing something differently feels uncomfortable or hard. People are more okay with a change they don’t like if they feel their point of view was at least taken into account.
• If you implement the change, overcommunicate. Sometimes the barrier to a change isn’t emotional or direct resistance, but inertia in the more familiar direction. People may need a lot of kind reminders, or repeated training, before they form habits around a new method. Give them what they need to fully make the transition.

Barrier #3: You’re nervous or don’t know what to ask.

Then sometimes, the barrier is you. Either you’re afraid of somebody’s reaction, or you don’t know what you don’t know, and you aren’t sure how to get there.

Nerves are sometimes part of the job as a project manager, especially when dealing with conflict or potential conflict. If facing anxiety is new to you, know that you’re safe. Even though you feel uncomfortable, you will be okay. Consider giving yourself a reward after you’ve faced a hard situation, or asking your friends and family for encouragement beforehand or afterward. It’s an obstacle you can overcome. It will even help you relate to team members later when they face anxieties in their roles, because we all have to face them.

It's okay. You can do it. Ask the question.

And if you don’t know what to ask, try going to the person most likely to have insights, and explain your situation and where you’re stuck. Ask, “What am I missing here? Can you see any solutions? Can you see a way forward?” Give them the opportunity to help you with the questions as well as the answers…or to point you to a different person who’d be a good fit to do so in your situation. Let your team come around you and help you, and you’ll stumble your way to the answers you need!

When you have questions, don’t let barriers hold you back from getting answers. Take the situation into account, but don’t let it stop you. Questions are one of a project manager’s most well-worn tools for climbing their way toward project goals. Pick up this tool more and more every day, and you’ll find more and more project goals within your grasp.