6 terrible tech managers—and how to succeed despite them

6 terrible tech managers—and how to succeed despite them

From the Know It All to the Overwhelmer, succeeding beneath a bad manager takes strategy and finesse

No amount of free sodas and beer Fridays are going to wash away the taste of bad leadership. If your dream development gig is turning into a nightmare and your projects are suffering, it might be time to manage up your boss—before your career takes a turn in the ditch.

Management guru and author Peter Drucker said that “only three things happen naturally in organizations: friction, confusion, and underperformance. Everything else requires leadership.”

While there are truly great leaders in IT, not all inspire confidence. Worse, you can’t always choose who will lead your team. But you can always map out new paths in your career. With that in mind, here is a look at some prototypically bad managers you may have already encountered in your engineering departments, with tips on how to deal with each of them. In the meantime, keep your head on a swivel and read on.

The Know It All

Our first bad boss has it all figured out, at all times—despite all evidence to the contrary. The manager we call the Know It All is also maddeningly stubborn.

“[They] always presume that they know more than their programmers,” says Bill Treasurer, CEO of Giant Leap Consulting, and the author of four books, including ”A Leadership Kick in the Ass.” “They’re overconfident, overdominant types who want it done their way, even if their way is wrong. Reasoning with them is not impossible, but definitely hard because they’re mostly unreasonable.”

If you’re under the Know It All, all decisions are made from the top down, and given that you and your dev team can’t reason with him or her, your projects will suffer. Worse, using an agile methodology, which relies on self-managing teams, may actually be in direct conflict with this type of boss. How to get along with this stubborn manager?

“The developer has to be a velvet hammer,” Treasurer says. In other words, you’ll need to stand up for yourself while keeping your message positive. “You have to match their boldness with your own. They gain respect of people who can assert as aggressively as they do.”

The Pushover

In stark contrast to the Know It All, the Pushover can’t make up their mind. No new feature is too insignificant to debate. And no project kicks off without a painful, exhaustive discussion of requirements, with endless revisions.

“The result is that you can’t trust that when they make a decision it won’t get rescinded or undermined later, when the manager hears the opinions of more dominant or persuasive leaders,” Treasurer says.

Managing up when you’re dealing with the Pushover requires more finesse than dealing with the Know It All.

Treasurer says the “velvet hammer” analogy is useful in this situation as well, but with a twist.

“The practical truth is that you may require the sponsorship of other executives who have more backbone,” he says. “So you’ll require more diplomacy when communicating with the [manager] as to why you want to bring other executives into the decision-making or idea-shaping process. In other words, you need to have more velvet.”

The Micromanager

The Micromanager issues commands like an unending waterfall, undermining creativity and team unity. Like other bad bosses, the chaos-causing Micromanager may run up against the principles of the agile movement.

“They ruin the whole team autonomy by their efforts to seek control over every single thing,” says Patric Palm, CEO of Hansoft and Favro. “It gets even worse when they don’t know anything about the domain and what success looks like. This can be because of lack of trust between manager and team, and that can be fixed, but unfortunately it’s often a personality trait of the manager; they simply like control—and the feeling of being in change.”

Palm refers to the management concept of the servant-leader, where the traditional top-down management style is upended. Instead of leading the charge, this leadership style aims to serve first and encourages the team to set aside the self-interests of the individual members. Needless to say, the Micromanager doesn’t follow these principles.

“If they’re not capable of being a servant-leader, you will be in trouble,” Palm says. His advice? It’s time for the developer to step up or move along.

“The best option might be another job,” Palm says. “And if you are ready to risk your job, you might want to openly challenge the manager. If you have your team with you and the manager’s manager is understanding, you might simply win. Do it elegantly, though. Be precise and concrete in your critique and [be] loyal to the company’s vision.”

Greg Law, CEO and co-founder of Undo, a debugging tool for Linux developers, argues that managers, like their employees, need clear responsibilities. When bosses don’t have a good handle on their own role, the entire team suffers.

“Occasionally, when the developers require it, this can mean giving direction,” Law says, “but the best managers will encourage their team to self-manage. The manager’s job is then to make sure that resources are in place and roadblocks are removed so that the developers can do their jobs to the best of their ability.”

The Unexpected Boss

If one of the engineers on your team gets bumped up to management, you may find yourself dealing with growing pains. This newly minted boss lacks experience and training. Surprise—it shows.

Taylor McCaslin, a product manager at WP Engine, advises first patting your former co-worker/new boss on the back.

“Having members of your team being promoted sends a good message that what your team is working on is being successful,” McCaslin says. “While you may not have the full details and context about why your team member is now running the team, usually there is a very good answer, which you may just not be privy to. And that’s OK. Taking a step back, managers don’t need the full expertise of an individual contributor. The skills it takes to run and manage a team are extremely different from skills needed to be a great developer who writes quality code.”

Can this manager get better? Undo’s Law says it’s possible but probably not right away. Natural leaders are uncommon, and some skills and hard-fought wisdom don’t appear on their own.

“I think the often-asked question of whether leaders are born or made is like asking whether tennis players are born or made,” Law says. “Whether it’s tennis or leadership, everyone has a natural limit to their abilities, but everyone will benefit from training and coaching.”

Part of the problem, says Hansoft and Favro’s Palm, is when a new manager gets stuck in a role, acting based on what they think a manager should do. There’s no malice, simply a lack of real-world experience.

“Provide feedback to the manager one on one and help her or him become better,” Palm says. “Build trust. If it works out, you will have built a strong bond. If it doesn’t, maybe you should be the manager instead.”

The Fearful Manager

Like other inefficient managers, the Fearful Manager operates from a place of worry and stress. That fear can translate into condescending behavior, a short fuse, or an attitude that comes off as unnecessarily brusque.

“Try to understand where that badness comes from,” Undo’s Law says. “Often, especially with new managers, it’s a lack of confidence. There’s a real skill in managing up.”

In other words, despite the natural instinct to pull back, when you’re dealing with a person who leads engineers in this chaotic way, it’s better to reach out.

“If your boss seems panicked about the state of your project, the best thing you can do is communicate,” WP Engine’s McCaslin says. “I don’t mean every single detail of the project; communicate major milestones of the project. How is the team trending toward meeting those milestones? Empower your manager to have the answers to the questions their management is asking them. Communication is how you build confidence, remove fear, and create alignment.”

It’s not necessary for your boss to be a rock-star programmer or know the details of your project as well as you do. And clearly communicating what you’re doing can help reduce the fear that can lead to bad decision making and micromanaging.

A good manager, McCaslin says, will “give you and your team the space to solve a problem. They are there to facilitate success, block distractions, provide needed resources, and communicate back to other teams, stakeholders, and upper management.”

If you’re wondering how things are going to get better, you may, in fact, be the person that manager needs to help you and the rest of the developers on your team.

“I have seen it work quite effectively where a senior developer becomes a kind of lieutenant for the manager,” Law says, “and helps that manager to focus on what they should be focusing on.”

The Overwhelmer

Management experts say code, like food, can be made fast, cheap, or good—pick two. The Overwhelmer wants all three ... yesterday. This boss can’t decide what’s most important, gives little notice for urgent requests, and rarely wants to budget for what it actually takes to create software that does its job.

Learning to live with the Overwhelmer means finding a way to give real feedback that will keep your projects on track. You have to set boundaries with this boss, and it won’t always be welcome.

“Don’t say, ‘You’re too demanding,’” Hansoft and Favro’s Palm explains. “Say, ‘When you do this, it makes me and my team feel this, I would like you to instead….’ Works every time.”

Some agile practices, like daily scrums or slimming down goals to meet deadlines, are designed to keep the workload reasonable. With a nod to this approach, Palm recommends forcing the manager to prioritize.

“First, have a product backlog and make that the negotiation ground with your manager,” says Palm. “Ask: ‘I know you want all this done in one week, but what is the most and second-most important item for you?’ Then this person can feel in control and make priorities. And you can commit the top-priority items to your workflow board at a scope you can handle in one- or two-week iterations. Then you get on top of your work and establish a rhythm, getting you out of a feeling of constant stress.”

Giant Leap’s Treasurer says developers need to be able to give honest feedback if they want to succeed—especially if the boss is stressing out the team.

“The trick is to tie the feedback to what the boss is trying to achieve,” he says. “For example, every time your boss tasks you with a new item he or she tells you is urgent, point out that because everything seems to be urgent, it’s challenging to understand which priorities are most important, and how ultimately helping them achieve their goals will require a higher degree of focus on a smaller number of ‘urgent’ items.”

Get ahead of the game

Of course, the best course is to steer clear of bad bosses to begin with. Although this is often out of your hands, there may be warnings worth looking for before committing to a job—suggestions that this might not be best next step for you. You can check Glassdoor, for example—and shared connections—and be alert to signs during an interview that things aren’t likely to go well.

“Ask your interviewer what’s important to them,” Undo’s Law says. “Remember that at an interview, you are interviewing them as much as they are interviewing you. If you’re good, the supply-and-demand dynamic is firmly in your favor. If the interviewer says nice words—like ‘the team is empowered to make decisions’—ask for a recent specific example of when this was done. If they can give you one, then ask for a second example. This should give a good feel as to whether there is substance behind the interviewer’s words.”

If it’s too late and you’re dealing with a boss you can’t stand, try to empathize and do some research.

“Learn a bit about psychology and be able to recognize when your manager is behaving emotionally and when they’re being rational, and engage only when they’re rational,” Law says.

You want to be loyal to your team and your organization, but if you’re not in the habit of making sure your needs are met, you need to know what you want, and frame it in a specific way that you can communicate.

“Count these as the four most important words in the English language,” says Treasurer. “'What do you want?' You need to be able to answer that question with a high degree of specificity if you intend to have a fulfilling career and life.”

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