by Dan Tynan

6 business execs you’ll meet in hell — and how to deal with them

Jul 10, 202313 mins
Business IT AlignmentIT Leadership

Leading IT is challenging enough without bad bosses and misguided business colleagues making a CIO’s work even harder.

Experienced executive manager quarreling with employee on mobile yelling and screaming  about bad report and failure with project, mad boss angry about software bugs in application for work
Credit: GaudiLab / Shutterstock

Everyone, at some point in their career, has endured a bad boss or bad business colleague. Someone further up the chain or a lateral colleague who lacks basic interpersonal skills, demands the impossible, flies off the handle at the slightest provocation, or throws you under the bus the moment a project goes south.

Aside from causing personal angst, executives run amok can also wreak lasting damage to the organizations they work for by driving away talent and squandering business opportunities.

It’s become a truism that people don’t leave bad jobs, they leave bad managers and challenging cultures. According to a recent survey by FlexJobs, a toxic company culture (62%) and poor management (56%) were among the top three reasons given by people who had recently quit. Conversely, companies that hire good managers generate 27% higher revenue per employee.

For technology leaders, difficult executives take a variety of forms. There are the technophobes who don’t want to make any effort to understand technology, they just want it to work. There are executives who ask for the impossible (often because they don’t understand tech). Some are obsessed with the newest, shiniest toy, regardless of whether adopting it makes sense for their business. Some steer clear of anything that smacks of interpersonal conflict, allowing small problems to fester into bigger ones. Many CEOs in particular expect the IT department to provide white-glove support for them and their family.

And some bosses or business colleagues are borderline sociopaths.

How do you deal with these people? We asked experienced CIOs and other tech leaders about the poor leaders they’ve encountered over the years, and how they dealt with them. Not surprisingly, most were reluctant to get too specific, because many of these troublesome executives are still around. In some cases, we’ve had to change names and obscure details to protect the guilty.

The following list is by no means exhaustive. But we’re confident you’ve encountered at least one of these archetypes in your career.

The Impossible Dreamer

Some executives ask for the moon, and expect IT to deliver it. Bringing their expectations down to earth can be a delicate mission.

Roughly a decade ago, Mark Campbell was working as an advisor to the head data scientist of a large communications company. One day the CIO came in, having just stepped off a plane, and declared, “I just read a story about quantum computers; we need to get a bunch of them.”

The man came to Campbell in despair. How the heck was he going to stand up a “bunch” of quantum computers? At the time, a basic 16-qubit quantum computer cost around $30 million, not including the liquid-nitrogen-cooled, seismically isolated, Faraday-caged data center required to house it. The data scientist was on the verge of resigning until Campbell came up with an alternative solution: a company that offered quantum computing as a service.

“So he showed this to his boss and said, ‘We now have access to dozens of quantum computers; what do you want to do with them?’” says Campbell, who is now chief innovation officer for EvotekLabs, a strategic advisory firm. “Because the CIO had no idea what to do with them, and they only had to pay for usage, the project cost the company exactly $0.”

The moral to this story: When bosses ask for the moon, show them what it’s really going to cost to get up there, and see how eager they are.

The Sucker

Fascination with shiny objects, coupled with technical naivete and a fondness for being wined and dined, can be a dangerous combination in a boss or a colleague.

“The most difficult executives are those who believe that shiny new technology objects are a one-size-fits everyone/everywhere/everything solution that will assuage every woe and make them millions at the same time,” says Joanne Friedman, PhD, CEO of Connektedminds, an IT advisory group based in Ontario, Canada.

When she was head of IT at a global outsource manufacturing company, Friedman was asked by an executive to spend as much as $25 million on a tech solution she knew would not fly. The EVP, who was getting a full-court sales press from the vendor, was insistent. After six months of haranguing, Friedman made a deal with him: She would run a proof of concept using the technology. If she was wrong and the solution worked as he believed it would, she would resign. If she was right, the executive would resign.

“I can smell vaporware coming a mile away,” she says. “This vendor had great marketing but crap engineering. We ran the POC and it blew up in their faces — it crashed the sandbox infrastructure, it did all sorts of bizarre stuff because the code had been written like 15 minutes before we started. So I turned to the sales rep and said, ‘That’s what wining and dining the wrong human being will get you.’”

The company ended up going with an alternate product that performed the same tasks much better, for much less. The executive in question did not resign, but he was forced to publicly apologize. He was later fired for other reasons.

“The moral of this story is that vendors sell sizzle, CIOs buy substance,” says Friedman. “Business and IT should be equally trusted partners. But when push comes to shove, to thine own self be true.”

The Technophobe

Some executives have exactly zero aptitude when it comes to the technology that enables them to run their businesses. And you probably shouldn’t expect them to, says Bob Stevens (not his real name), former CISO for a large retail operation. After all, they’re not being paid to think about technology; they’re being paid to sell products.

“The CEO at that retail company was not a technologist,” says Stevens. “He found it totally uninteresting. So when the IT and security teams would present, his attention would quickly wane and he would start answering texts and reading email. He’d say, ‘Unfortunately, technology means nothing to me. I get that it is important to the company and that we have to have it. So I will manage the business value against the cost. Just don’t try to make me understand it.’”

It can be demoralizing, Stevens adds. Worse, because senior leadership doesn’t fully understand the issues in play or the threats to the business, they may not prioritize investments appropriately. And when you try to persuade them that it’s important they pay more attention, they often get defensive, since you are not playing to their strengths.

“You need to realize it’s not an indictment of you or your team, but a vote of confidence,” says Stevens. “The CEO has empowered you to provide options that balance the needs of the company against business risks.”

This is not an uncommon scenario, notes Deb Gildersleeve, CIO at First, a global brand experience agency.

“There are definitely leaders who still believe that everything about the tech is the CIO’s responsibility, with no ownership in the department using the tech,” she says. “You end up spending a lot of time educating them about why they need to take more ownership, over and over in different ways.”

Sometimes executives need to experience the consequences of not paying enough attention to the right things, or see the impact of that on a competitor. And sometimes you have to bypass the decision makers and enlist the support of people who actually work with the technology, says Gildersleeve.

“That’s probably been the most effective way for me,” she adds. “There are usually people in the organization who get it and want ownership of these things. They want their lives to be made easier, so they’re willing to put in the effort. It’s my job to back them up when their manager asks, ‘Why are you working on that?’”

The Excessively Entitled

In addition to managing a company’s IT infrastructure and driving innovation initiatives, many tech leaders are also asked to tend to their boss’s personal IT needs — and sometimes, those of their family.

Many CEOs expect concierge-level tech support, and most of the time they get it, says Len Tateyama, director of IT for Alvaka Networks, a managed services IT provider.

“For many executives, there’s no real boundary between work life and personal life,” he says. “They’re working 24-7. So it’s reasonable to expect you to support the machines they use for work at home. The difference is when they start asking you for help with family stuff.”

The key, adds Tateyama, is establishing boundaries between support calls that serve a business purpose, and those that are purely personal. At three different companies in his career, he has set up systems where requests beyond the scope of the job were handled outside his IT budget.

“I would ask my teams, ‘Who wants to make a little money on the side?’ and then connect my highest performers with the CEO’s personal assistant to work out the payment details,” he says. “We were able to still provide that white-glove treatment, while also putting limits around it. You never just say no to the boss. But you can say, ‘Yes, and here it is what it will cost you,’ and then maybe they will decide to take a different route.”

(Tateyama adds that occasionally executives further down the chain asked for similar treatment. They didn’t get it.)

But going the extra mile and establishing a closer connection to the C-suite can be good for one’s career, notes Dion Hinchcliffe, VP and principal analyst at Constellation Research.

“Junior IT people can become trusted associates of C-suite leaders, and both sides learn and benefit,” he notes. “Thirty-five years ago, my super IT bedside manner landed me the job of supporting the whole C-suite of a Fortune 1000 company. I fixed problems on their business and personal devices, and even babysat their kids when they brought them to the office. I learned the business from their POV, and it fast-tracked my career in IT.”

The Conflict Avoider

When business leaders never want to hear bad news, small problems become big ones, and big problems can derail or even destroy an organization.

“Honestly, the most difficult executives to deal with are the conflict-avoidant ones,” says Jonathan Feldman, CIO for Wake County, N.C. “I can solve a problem if we can have a constructive conflict, but I can do nothing if we don’t even know about it.”

One common difficulty is executives who see no difference between constructive conflict and destructive conflict, or who take well-meaning criticism personally, Feldman adds.

“When people don’t conflict, they end up doing workarounds that are incredibly frustrating, like wasting money on projects that then have to be redone, or forcing people to work late nights and weekends because no one was brave enough to say, ‘This plan is crap,’” he adds. “It gets in the way of making things better.”

Constructive conflicts are always about problems, not personalities, Feldman says. Everyone should get the chance to tell their story about what happened without worrying about getting their heads chopped off.

“Anyone who kills the bearer of bad news quickly joins the ranks of the uniformed,” he adds. “Bad stuff gets buried much deeper, because as a leader you’ve taught people through your behavior that making a unique mistake is not OK. In this scenario, executives whose only source of input is their direct reports are likely to hear roses and sunshine at all times, and it prevents them from taking corrective action when needed.”

The Screamer

Then there are the executives desperately in need of anger management training. Campbell once worked at a well-known global company for an executive, we’ll call him Darryl, notorious for blowing up and screaming at people.

“Calling him ‘abrasive’ would be like calling a great white shark ‘a nibbler,’” says Campbell. “We’re talking spittle forming at the corners of his mouth and veins throbbing in his forehead, just because you used ‘they’ too many times in a sentence.”

When he joined the program, Campbell was the newest member on a team of 24. Then one of the data centers crashed, and Darryl started chopping off heads. Before the year was out, Campbell was the senior staffer. Everyone else had been fired, transferred, or quit.

“The reason I survived wasn’t my business acumen,” adds Campbell. “I’d only been there a few weeks when the data center crashed, and nobody knew who the hell I was. If they had, I’m sure I’d have been fired, too.”

Because he had managed to survive, the company asked Campbell to put together a training program (called Darryl University) that everyone on the team had to go through before they were allowed to talk to Darryl — words that triggered him, topics to avoid, how to phrase bad news, and so on.

“So many hours wasted, so many talented people, so many antacids,” adds Campbell.

There are always two sides to every relationship, adds Feldman. If you don’t like your boss, odds are your boss doesn’t like you. And if you can’t manage to repair your relationship (or if your boss is a sociopath) your only viable option may be the door.

“You’ve got to take care of yourself first,” he says. “That means there are times you’re going to have to go.”

Fortunately, Screamers (like Dreamers, Suckers, and Conflict Avoiders) tend to be the exception, not the rule, says Campbell.

“There’s a ton of bad executives out there. But the ethical, brilliant, hardworking, and moral ones are far and away the most successful.”

by Dan Tynan

Dan Tynan is an award-winning journalist whose work has appeared in Adweek, Fast Company, The Guardian, Wired, and too many other publications to mention.

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