Tech Manager—Six Questions You Don’t Want to Hear from Your Boss

As a Tech Manager, you still report to someone else. The person you report to may be a Manager, Director, VP, or even the CEO. They have desires and expectations. They have due dates and projects. Like you, they do not want any headaches, more troubles, or disasters—especially from the people who report to them. Even if you are not a Tech Manager, you don’t want to hear your boss asking these six questions.

Boss asks: Did you know about this?

Boss is thinking: You are out of touch with what is happening.

As a manager of people and technology, you should know what is happening with everything you oversee—staff, software, projects, everything. You need to be aware of the status and progress of everything that is going on. If you are caught off guard and unaware, it seems like you are out of touch. This is not good. Sometimes there will be things that your staff or project team members do not report on. They do not tell you everything. They may not have time (they are fighting the fire) or they may not have the desire (they are behind and they know it).

For things under your purview, you need to be keeping track of all you oversee at some level and be asking key questions, which include: What progress have we made? What is our target finish date? Is the project on track? Are we having troubles? Do you have everything you need to complete the work?

For things not under your management such as projects and tech use by other departments, you need to be aware of changes that might impact you. Let’s take accounting as an example. They pay the bills, but they do not order the software. Are you reviewing the invoices that come in for technology? You may have seen the quote, worked with the vendor for installs, and more, but are you seeing the final invoice? You need to verify that your firm is paying for what you get and getting what you paid for. Monthly billings that are recurring also need to be monitored. If you subscribe to software, have accounting send you copies of the billing so that you can verify the subscription counts.

Boss asks: Did you even talk to them?

Boss is thinking: You are not communicating on this and other things.

Communication is key to staying in touch and up-to-date. When things happen, the first thing you should be doing is talking to others. Phone conversations are preferred, digital tools are acceptable. Your manager expects you to stay in touch and make connections. Keep the conversations flowing and tap into as many teams as you can. I have covered this many times in past articles.

Boss asks: Why aren’t we doing that?

Boss is thinking: We are falling behind and you are not keeping us up-to-date.

Adopting new software and processes is a daunting task. Falling behind is always a concern. When your boss or your boss’s boss hears about what other firms are doing, they get concerned. Your goal should be that other firms are trying to keep up with yours.

When the boss asks this question and you start squirming in your seat because you are now in the spotlight, keep it in perspective. No firm can be ahead in every category, but you can strive for that. You should ask some questions. When I hear of others making progress, I tend to ask direct questions: “Are they doing that on every project, every office, every client?” “What percentage of their projects are using XYZ every day?” Most of the time firms are putting their best foot forward and their cutting-edge efforts, but that is far from the day-to-day grind of real project work. You could ask your manager if others mentioned the advanced tech that you are doing. Did your manager tell them about your new software or project delivery method? This does two things: reminds your manager that you are ahead of the curve in many areas and it reminds your manager to brag about it.

But don’t avoid the point. They want to stay ahead of the competition. Make sure you remind your manager of the areas where your firm leads the pack.

Boss asks: What were you thinking?

Boss is thinking: You are not thinking or planning.

If the boss thinks that you are not thinking, it is a red flag. They expect thoughtful planning. They expect you to ponder the outcome of your plans and have backup plans. This question usually comes after something has gone wrong with unexpected consequences. Your planning was not good enough to cover this contingency.

If the unexpected outcome was unavoidable, just say so. If your plans did not take into account this eventuality, just say so. Be straightforward, apologize, and take control of the clean-up efforts. Take ownership.

Boss asks: Are you done yet?

Boss is thinking: You are not moving fast enough.

Technology moves fast and so must tech managers. Some think that we are not moving fast enough. They may not understand all the issues surrounding software purchasing, configuration, licensing, deployment, and customization. We need to do our homework and due diligence prior to rollouts. But these are our problems and not theirs. Bosses may have no clue concerning what it takes to make things happen, unless we tell them what needs to be done.

Explain the complicated issues that impact technology and project completion. You have plans and you are executing, but things take time. Make sure your manager knows what your timelines are and then accelerate them if you can. Let your manager know your other priorities that others are waiting for, also. Can you improve on your research speeds? Can you reduce configuration time? See what can be done to deliver sooner.

Boss asks: Why does this keep happening?

Boss is thinking: Fix this, and make sure it does not break again.

Repeat problems are really annoying. They bother me and I am sure they bother you. They bother your boss, too. When you have recurring issues that fall into the same bucket of troubles, you need to do some deeper thinking and proactively move toward repairs or replacement. You can explain that things are impacted by cost cutting, old hardware, etc., but do not stop there. You were hired to make things work, so knuckle down and see what can be done. Put in alerts and safeguards so you find out first if something breaks. Take the time to make it right. We all have hundreds of things on our To Do list, but recurring issues should jump to the top of the list.

Rehearse Your Answers

When the boss comes to your office and asks any of these six questions, you need to be ready with an answer. Think over these questions and how you would respond. Are you planning your upgrades and deployments? Are you communicating well? Are you making advances that put your firm in the lead? Think hard on what to say to your boss. Be respectful and accountable. Then work hard so your boss won’t be asking these questions at all.

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