Tech & Engineering Blog

Power Questions for Managers

Managing people and projects encompasses a lot of different moving parts. An approach I like focusing on is the one focusing on three essential tasks each manager has:

  1. Asking questions
  2. Making decisions (or making sure decisions are made)
  3. Clearing the path of obstacles

While there are books written about each of these, I’ve noticed a lack of materials and examples on asking good questions. So, that’s what I want to expand on here.

“Just Ask” leadership style is especially important in cognitively heavy environments (such as tech). Remember that even if you were the best engineer or analyst in your team, a few weeks into your new managerial position (not to mention years), you know less about the subject than your subordinates.

The reason is simple: you spend more time managing and less time doing hands-on work. At the same time, your employees focus on the tasks, learn new practices, and gain proficiency.

As a manager, it’s important to understand that you aren’t the most competent person in the room and that your advice might not be as good as you think. This helps to move the state of mind from knowing to not knowing.

Being modest and not jumping to conclusions, combined with conscious and competent questioning, forces you to be in the moment, listen to answers, and drive better decision-making.

When considering what to ask, knowing the common biases is especially important:

  1. Negative bias — leaning too much on negative past experiences. “Last time we did this, we failed; we can’t try the same approach again.”
  2. Frequency bias — thinking something that happens often will keep happening. “We had this problem 3 times already…”.
  3. Recent Bias — Focusing too much on a recent event. Giving disproportional weight to a recent event compared to the situation.
  4. Attachment bias — This is common. It’s overwhelming. Think about how many times your engineers fell in love with their code and didn’t want to refactor or throw it away.
  5. Escalation bias — When you start down the path, you look for evidence to support your direction and, at your peril, choose to ignore warning signs.

I also like to talk about Pluralistic Ignorance, an extensively researched topic, primarily academic. In our context — each person in the room thinks they are the only ones who didn’t understand (or know) something, so they don’t ask. While in reality, most of the participants are in the same position. This leads to no one asking and everyone not understanding.

So my recommendation is — always ask. Worst case, you really are the only one who didn’t understand, and after asking you are not anymore.

Let’s focus on two methods of asking, open vs. closed questions. Both are very useful.

Closed Questions

Usually start with Where, When, Who

“Where is Waldo? When should we recheck progress? Who is the project manager?”

These types of questions elicit facts, and are very useful when that is what you are after. Also useful when you don’t need background information, detail, opinion, or theory.

Open Questions

Start with Why, What, How

“What is your opinion about…? What happened? What will you do now?”

Open questions lead to a discussion, allowing you to get a more well-rounded answer and discover new ideas.

They are helpful in project follow-up, giving and receiving feedback, assessing milestones, and debriefs.

Note that using these questions doesn’t mean the employee should answer in prolonged or unclear answers. Pay special attention if someone answers open questions as if they are closed. They are either uncertain or evading. It’s a warning sign you should push further on.

My Rolodex of questions

  • What do you think?
    If they only brought a matter to my attention, I want to know their thoughts. If it’s a decision to be made, let’s hear ’em out first.
  • How would you do it?
    Often I hear suggestions better than what I had in mind, so better to listen before making the next move.
  • Is there another option?
    If none was presented, maybe they fell into one of those bias traps.
  • What do you need from me?
    In this case, it helps to give some guidance — do you need a decision? Are you just letting me know of a situation?
  • Can we stop doing that?
    It’s incredible how often the frequency or attachment biases can be seen using this question.
  • What are the risks?
  • What will cause it to fail?
    A classic from the project management books.
  • Anything you are worried about?
    I use it for specific things, such as high-risk projects or “type 1” decisions.


It’s just another tool

As with anything, overdoing it can lead to opposite results! Knowing which questions to ask and how is an essential tool in your managerial arsenal. Use it wisely and consciously. Practice and seek feedback.

Further Reading