How to deal with bad IT bosses

How to deal with bad IT bosses

Does IT have more than its fair share of challenging bosses? That's debatable, but it's enough of a pattern that the bad IT boss has inspired comic strips and movies. Here are some common challenges – and expert advice on how to improve the working relationship

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Put yourself in the other person's shoes

First, consider where the other person is coming from. “Instead of reflexively reacting without assuming noble intent, I try to mindfully go back to the Six Sources of Influence on Human Behavior, which I learned from Crucial Conversations and Crucial Accountability,” says Dave Egts, chief technologist, North America Public Sector, Red Hat. “The manager may not be a bad person but may be struggling, especially considering how the work environment has changed drastically this year.”

“It’s also quite possible that this manager is indeed difficult or challenging by nature, but all six sources of influence are worth exploring to see if the manager’s natural tendencies are triggered and exacerbated by current circumstances and identifying ways to help them,” Egts says. “To go through all six in this case…

  • Source 1 – Personal Motivation – Maybe the manager has personal problems at home or isn’t well physically or emotionally.
  • Source 2 – Personal Ability – Maybe the manager hasn’t been trained for how to work remotely or manage remote workers.
  • Source 3 – Social Motivation – Do the manager’s peers act the same way and they don’t want to stick out?
  • Source 4 – Social Ability – Do the manager’s peers not recognize that the manager is struggling, and therefore don’t offer to help?
  • Source 5 – Structural Motivation – Is the manager incentivized to not be difficult or challenging?
  • Source 6 – Structural Ability – For example, does the company provide the tools and assistance to facilitate remote work, remote management, and remote leadership?”

Communicate - even the tough stuff

Second, ask yourself if you have been communicating regarding the issues. Communication is a fundamental necessity for improving fraying relationships; don’t wait for the boss to take the first step. It could be the case, for example, that your supervisor is unaware of how their decisions or behavior are impacting you.

“Don’t shy away from an uncomfortable discussion,” Check says. “Talk to your boss and let them know the behaviors they have that are driving you away. This will provide keen insight into whether they are unaware of their behavior and its effect or if they are simply a bad boss.”

Even in the latter scenario, you now have an informed basis for making the eventual decision to leave.

Paul Wallenberg, director of technology recruiting services at LaSalle Network, shares several other communication tips on trying to proactively improve your situation when dealing with a difficult supervisor.

  • Ask trusted colleagues for input: “Solicit the advice of well-tenured peers,” Wallenberg says. “Frame it as soliciting suggestions as opposed to complaining.”
  • Ask (the right) questions: “Ask [the boss] questions, but avoid questions like “Why are we doing it this way?” Wallenberg says. “Instead, ask something like “Are you open to alternative suggestions or approaches?”, “Would you mind giving me your input on this?” , “What can I do to support you or this initiative more successfully?”
  • Address issues with empathy: Taking the first steps can be tough; Wallenberg suggests leading with empathy and even some well-intentioned flattery. That approach might sound something like this, according to Wallenberg: “Your position in the company is challenging, I don’t know how you do it and I don’t want to add to your plate of problems that need solutions. Let’s work together so I can support you most efficiently.”

Consider how the two-way street could be improved

Veteran CIO coach Bob Kantor of Kantor Consulting Group says that one of his core IT leadership coaching topics is “Creating Conditions of Accountability.”

“While most of my clients think about doing this with the folks who report to them, I always invite them to think about how to do the same with their peers across the organization and with their managers above them as well,” Kantor says.

According to Kantor, the framework for this includes:

  • Setting clearing and viable expectations (What and when, not how, along with follow-up)
  • Establishing compelling consequences (Positive and negative, both individual and group)
  • Regular checkpoints (Conversations based on empirical evidence, with a “trust and verify” approach)

Many supervisors have check-ins or checkpoints, but Kantor notes they typically go like this:

Staff Member: “Have you been able to get the management team on board with our recent proposal?”

Boss: “I’m working on it.”

Instead, a more effective checkpoint might go like this:

Staff Member: “What feedback have you had so far from the management team on our recent proposal?”

Boss: “Well, ummm, I haven’t had time to discuss it with any of them yet.”

Staff Member: “Got it, and I know how crazy busy you are right now. What else can I do to help you move this forward since we’ll need to know soon about their guidance if we’re going to hit the target date you’ve given us?”

[ Read also: Digital transformation: A manifesto for moving from good manager to true IT leader by Bob Kantor. ]

When is it time to leave that boss behind?

Sometimes leaving for another opportunity is the right decision. Most career experts don’t recommend it as plan A, but it sometimes is the best path forward, especially when communication and relationship-building efforts don’t improve the situation.

Check from Raytheon Intelligence & Space points out that this decision can be a matter of knowing yourself and what is and isn’t tolerable to you.

“As with life, there are no perfect situations, and there may be some things you can deal with and others that may be your personal kryptonite,” Check says. “Know your kryptonite trigger behaviors, and if they exist, it may be time to move on.”

No matter what your kryptonite is, watch for the warning signs that you’re dealing with too much of it.

“If you find your patience running thin on Sunday night and you’re snapping at your loved ones or can’t sleep well in anticipation of starting the workweek, it is time to leave,” Check says. “Mental and physical well-being are critical for work performance.”

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]


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