by Bob Lewis

10 steps to becoming a horrible IT boss

May 29, 2020
IT Leadership

Good-bye, IT peers; hello, power to abuse at your whim

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Credit: phaustov / legato film / Getty Images

It’s legendary: A CIO promotes his best developer or IT pro into a management role, losing an excellent tech worker and gaining a bad manager.

The art of management isn’t so much about assembling a dream team, helping others be successful, or solving technical problems. It’s about aligning everything you do in service of the business — the business of yourself.

If you’re new to IT management, here’s an infallible guide to breaking bad — all the way to the top.

Step 1: Enjoy your newfound authority

Life is too short to do anything else.

In your previous roles you had to beg for money, even for such rounding-error expenses as buying your team the occasional pizza. No more! As a manager you have an actual budget. You can buy your team the occasional pizza without having to ask anyone’s permission.

But that isn’t where you get to enjoy your authority. You get to enjoy it when a project manager who reports to you wants to buy pizza for her team. That’s when you make your authority clear: You require a solid cost justification for expenses like that.

Step 2: Coach

About that pizza cost justification: Don’t simply insist on it. That would be autocratic. This is a coaching opportunity — a teachable moment.

Call the project manager into your office. Close the door. Or, if she works remotely, schedule a video call. Don’t just call. Scheduling it adds gravitas; video lets your expression do some of the heavy conversational lifting.

Quietly and patiently explain why justifying discretionary expenditures matters, even for something as seemingly innocuous as a pizza lunch for a hard-working team. Why is it so important? Here are some possibilities to choose from:

Attitude: Buy too many teams too many pizzas and you’ll foster a sense of entitlement. After a few repetitions the pizzas will no longer be considered a reward or expression of gratitude, and it’ll be expected, simply because everyone is doing their jobs.

Opportunity cost: Even seemingly small expenses add up. The sum of all pizzas can eventually become high enough to exceed the cost of a productivity software license. Does your project manager really want to be the reason some poor employee won’t be able to word process?

Shareholder value: This is the big coaching opportunity. See, in your industry the stock price is expressed as a multiple of corporate earnings; maybe the industry average is a 12:1 price/earnings ratio. That means every expense has to be multiplied by 12 to calculate its impact on the price of a share of stock.

As employees, we all have not only a fiduciary responsibility, but a moral imperative to maximize shareholder value. Is the pizza really as important as our ethical integrity?

Don’t limit yourself to this list. Innovate — come up with your own based on the coaching opportunity. After all, one of the reasons you were promoted was your willingness to take initiative.

Step 3: Hold everyone accountable

Everyone knows a critical element of an effective organization is that everyone knows what they’re accountable for. If it’s important, someone’s name is on it.

Of course, this means that if something important goes wrong, the person whose name is on it failed.

 You certainly don’t want an organization of failures. You need people who succeed. If someone in your organization fails, take them behind the metaphorical woodshed and do what needs to be done.

In the long run you’ll be doing them a favor, teaching them the consequences of failing.

Step 4: Regularly re-read the article that says IT managers should be business people, not technical people

There’s really only one article. It’s been popping up in IT trade publications over and over again over the past 25 years or so, with slightly different text and a different listed author. But the differences are trivial. You have to read only one of them — actually, the headline alone — to absorb the message.

Because it’s important: Just as chief financial officers and their management teams should be business people, not financial people; just as chief marketing officers and their management teams should be business people, not marketing people; just as chief operating officers should be a business person, not an expert in how to run day-to-day operations, so you should be a business person, not a technology person.

Once you cross this great divide you’ll no longer have to be troubled with setting a technical direction for your teams, because you’ll be a business person, not a technical person.

Of course, that isn’t entirely fair. You will set technical direction, based on events held for IT managers in luxurious settings and with golf-filled agendas, in which your hosts will give you the level of technical detail — and Full Buzzword Compliance — appropriate for IT managers-who-are-business-people.

Nor will you ever have to again endure a detailed discussion of what things should actually cost and how much time they’ll actually take given what goes right and wrong with real-world technology, not to mention what to do about it when it does. These complexities are, after all, concepts that technical people, not business people, have to understand.

Step 5: Make new friends

Memorize this phrase and use it frequently in conversations with your former peers: “I’m not here to make friends.” Drop it in whenever “that’s why they call it work” doesn’t quite fit the situation.

But life gets lonely when you have no friends. So make new ones.

Choose carefully, though. Apply the same level of due diligence you’d use in selecting a mission-critical technology.

No, scratch that. You’re a business person, not a technologist, so apply the level of due diligence you’d insist on the technologists reporting to you would use. In any event, you want your new friends to be well-connected, politically safe, not overly talented, yet also willing to introduce you.

Introduce you to whom? To people who won’t care if you’re their friend, but are delighted to experience your talents at knowing who to kiss, when, and where.

That’s all metaphorical, of course, and if not, please don’t tell me.

Step 6: Be decisive

Tired of analysis paralysis? Excited by book titles like Fail Fast and Blink! that extoll the virtues of action over the tiresome detail of extensive research and careful thinking?

The next time an important decision floats into view, just make it, and having made it, don’t allow those reporting to you to second-guess the direction you’ve set.

Why not? Re-read Steps 1 and 4.

But “just make it” is a bit of an oversimplification. You want to talk it over (briefly) with your new circle of friends, maybe involve one or two of them in the endeavor.

That’s important because when you fail fast and learn that failing fast is something the company’s executives say when they support a losing idea — it doesn’t extend to those who toil in the trenches a few layers down — when you fail, whether quickly or at a more leisurely pace, you’ll want to have a scapegoat primed and ready for deployment.

Step 7: Subordinates

They used to be your peers. They used to be your friends. You used to eat pizza with them (see above), drink the occasional beer with them, and gripe about lousy management with them.

Now they report to you. They’re your subordinates, as in “sub,” which means “under,” and “ordinate,” which means “the vertical value in a pair of coordinates.”

When someone is your subordinate, they are by definition beneath you.

You don’t have to be pompous and overtly arrogant about it, but you need to make it clear to everyone in that position what your relative positions are.

But be nice about it. It’s OK to call your subordinates terms like “rank and file,” “the troops,” “the great unwashed,” or “cannon fodder,” but only to your new circle of friends.

For the men and women who report to you, “subordinate” sums up your expectations quite nicely without being offensive. Well, not too offensive.

Step 8a: For on-site subordinates, remember that management is a lot like parenting

Children need parents: people who keep an eye on them, make sure they don’t head in the wrong direction, don’t make the wrong friends, don’t succumb to peer pressure, or otherwise commit any of the mistakes their parents did and learned from.

Subordinates are like that too. If you keep a close eye on them to ensure they make no mistakes, they’ll commit fewer mistakes, which means you won’t have to explain to your manager how one of your subordinates goofed up.

Meanwhile, they’ll become dependent on you to make decisions that have any risk at all attached to them — more childlike, as it were, and therefore less likely to want to pursue their own ideas and directions.

Extra credit: Many of your subordinates are, when they leave the workplace, parents themselves, doing their best to raise their own children. Since, as a manager, you’re now an expert in child rearing, make sure to give these folks the benefit of your wisdom on the subject. They might not thank you for it, but then, do children ever thank their parents?

Step 8b: For remote subordinates, take ‘If you can’t measure you can’t manage’ seriously

They’re remote. How do you know they’re working on company business and not busily spending their time on Facebook and Instagram, or socializing with their buddies on Zoom?

Answer: Make your relationship with them transactional, based solely on the tasks you assign them and whether they successfully guess what you meant when you assigned them and complete them in the time you allotted.

Or, if they’re production workers, whether their outputs keep pace with your inputs.

Relish the time you save by not having to get to know them as human beings, not to mention the additional time you save by not having to deal with team dynamics anymore.

In the old days you had to. With everyone face to face and interacting socially as well as professionally, you couldn’t pretend you didn’t know about conflicts and interpersonal distrust.

With remote employees, in contrast, all that matters is making sure each one has enough tasks and assignments stacked up that you can measure their productivity. Even better, you can structure their work so they never have to interact with each other except when they hand off work in progress to whomever is responsible for what has to happen next.

Team dynamics? With remote employees, who needs teams?

Step 9: Value your subordinates’ contributions

Value them so much that they never move to other opportunities.

Because you know Marcia will get the job done when it comes to making sure the general ledger closes properly every month. After all, she’s made sure of it every month for the past 10 years. If she moves into a different role, you’ll risk the wrath of the CFO if Marcia’s replacement has a rocky month or two getting the hang of things.

You can help ensure Marcia stays where she is by dropping the quiet word here and there that while she’s very good at what she does, she isn’t that versatile — she’s a specialist who’s found her niche.

Self-fulfilling prophesy can indeed be your friend.

Step 10: Lead from in front

Leaders are people other people follow, so make sure to lead from in front.

If, for example, your team does something amazing that would be of interest to the executive leadership team, be sure they create the PowerPoint version and thoroughly brief you on the contents so that you’re fully prepared to present the accomplishment.

After all, you’re the one who built a team capable of accomplishing whatever it is, and you’re the one who would have been held accountable if the team hadn’t done the job.

It only makes sense that the ELT should associate you with the success.

In conclusion

Here’s the best part. Manage your troops like this and you can be confident at least a few of the ones who are most overpaid will decide to pursue other opportunities.

Which means you’ll finish the year under budget.

Promotion to the next level, here you come!