Tech Manager—Eight Questions You Should Be Asking Your Boss

In the previous article we reviewed six questions we did not want our boss to ask us. If the boss comes to your office and asks them, you need to be ready with an answer. Better yet, work hard so your boss won’t be asking these questions at all.

This time we look at a longer list of questions you should be asking your boss.

I take away a lot from the questions people ask me. They are usually tipping their hand to what is on their minds, if they are not just asking for data or on a fact-finding mission. If it is an open-ended question, there is usually some perspective or stance behind it. When you talk to your boss, he or she may be thinking, like I do… “Why are you asking?” And your boss may actually say that.

I usually ask that same thing to wide-open questions, unless I think the person just wants information. Then about halfway through my dissertation I realize that they are blurry eyed and overwhelmed, so I stop and ask, “What were you wanting?” So make sure you have some backstory behind your questions.

Sometimes there is something you want to get across and the best way to approach it is to pose a question to introduce the topic. I find that if I want to start a conversation, a question is a good place to begin. And yes, you have to listen to the answer and take any advice given. Don’t ask a question you are not ready to hear them answer.

What to Ask your Boss

Ask your boss: What’s next?

What you are telling them: I know what we should do, let me tell you.

As a manager of people and technology, you should know what will be coming next. If you are a planner, you have a good idea of what the firm needs. But you may not have the entire picture. You see only what is shared with you. You see only what people want you to see.

What about those items that upper management has not shared yet? They might be roadblocks. Ask this question, then listen to the response to see if it meshes with what you have in mind. Don’t just spill out your magic roadmap to the future. Let management tell you where they think you are headed. If is blends with your ideas, then bring them up. If it does not lean toward your defined target, maybe you need to rethink things before launching into your master plan for productivity and progress.

Ask your boss: Why are we doing that?

What you are telling them: I have a better way.

Like many of these questions, what the boss is thinking might be positive or negative. They may take what you say as a challenge to their authority or an encouragement to think. You may not know how it will be taken. This question is one that could go both ways. The question may be related to their pet project or some outdated process or procedure that they created back in the day. Go lightly into these waters. You need to listen to the response and validate what they provide. It may be that something was done specifically for some reason and you should not propose changes. Other items may lower the boss’s brow in contemplation of a change because they do not know why something continues as it has since the dawn of time. They may be ready to change, or they may dig in their heels. Be ready.

Ask your boss: Can I help you with anything?

What you are telling them: I am ready for a new challenge.

Most bosses will take this as an offer to help. Others might take it as a questioning of their competency. If your relationship has been built over the years, your boss will take this in the spirit in which it is intended. You really are willing to help. They seem stretched and you are offering to take something off their shoulders. Be prepared to take on whatever they give you. It may not be the best task, but it helps them out. Embrace it.

Ask your boss: How did you get where you are?

What you are telling them: I want to advance with the firm.

This is asking them for career advice. You want to know what steps they took. Who they connected with. What training they received. How they made the jump in job titles in the past. So often we turn away from the best career coach we may have—our boss. They have the talent and skill to navigate the firm’s ladder. They have advanced inside and outside the company. They know a lot about career planning. Make sure they understand that you want to grow with the firm, not jump ship.

Ask your boss: How would you suggest I approach this?

What you are telling them: I value your knowledge, wisdom, and advice

Your boss has been down the road farther than you (most of the time)—worked on tech longer, or with people more, or on diverse projects. They have the skills needed to do their job and they can help you do yours. They may have another point of view that you have not thought of. Take what they tell you and put it into practice (if it is on target). When the boss gives advice, you need to put it in play.

Ask your boss: What is most important to you?

What you are telling them: I want to know what you need me to get done.

This is a really open-ended question… are you asking about life in general, tech tasks, project lists, initiatives, character traits, or what? I kind of like these types of questions and usually tell the person I am asking that they can take it any way they want. If their reply is way off base from where I may have wanted to take it, I thank them for the info and then I divert back to my focus, “…and how about software upgrades? What is most important to you with those?” A little back and forth and clarification, then you have your marching orders. The boss may say, “Don’t do too much too fast, get upgrades done after hours, include training, and if a project is almost done, hold on the upgrade until after the submittal.”

Ask your boss: How am I doing?

What you are telling them: I am hoping for some encouragement.

You are hoping for some positive feedback. A hearty pat on the back. But you might get some negatives, too. Hopefully, your boss will offer some positives. They like that you are checking in and that you are willing to make some course corrections as you move forward.

Ask your boss: What should I be doing differently?

What you are telling them: I am also open for critique.

You are open to changing how you do things, right? This one is inviting adjustments. It gives your bosses an opening to discuss areas of improvement. If they are coaches, they will seek to shape and mold your approaches and stances. They will optimistically give you feedback that makes you a better employee. They want you to succeed.  But if they are harsh critics, then go cautiously with this question. They will expect instant, exact, and lasting changes.

With these, and more that you can think of, you will be opening a conversation with the boss that, with any luck and a good boss, will end in improved relationships and expanded opportunities at work. Be bold and ask.

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