Is a Bad Boss Slowly Killing Your Career?

More types of bosses who can hold you back - Issue #20

Human beings are pretty good at fuzzy logic. We can deal with messy data in an imperfect situation and still make our best guess at how to proceed. We handle ambiguity better than algorithms and AI, for now.

Unsurprisingly, job descriptions — especially for more senior positions — often require that you must be able to thrive in a fast-paced environment and handle ambiguity.

  • Ability to lead change, deal with the ambiguity and the prioritizing need to run a fast-paced environment.

  • Cope well with ambiguity and changes in direction as solutions are developed.

  • Independent, creative self-starter, flexible, comfortable with ambiguity, and thrive in a fast-paced work environment that encourages critical thinking and…

Promotions will also hinge on your ability to manage ambiguity. Entry-level employees usually thrive with specific tasks with well-defined rules and boundaries. But, more senior roles take on increasingly complex tasks that are open to many potential interpretations and solutions.

You do want to be able to make decisions even if you don’t have complete data. Hint: you will never have the luxury of perfect, comprehensive data.

You do want to be able to deal with uncertainty. You do need to be able to take informed risks. You must be able to adapt to a changing environment.

However, you shouldn’t settle for ambiguity in the definition of the roles and responsibilities for your job. Uncertainty will do you no favors in goal setting and establishing success measurements. You also shouldn’t let fuzziness creep into the decision-making process for your promotions and career path.

Make no mistake; ambiguity will slowly kill your career if you let it persist.

The role of your boss

Part of a leader’s job is to reduce ambiguity. It’s one thing to be good at handling ambiguity, but that doesn’t mean they should encourage ambiguity. It doesn’t mean that they should use uncertainty as an excuse for fuzzy goals and amorphous role requirements.

Leaders who do that are often undisciplined, lazy, ignorant, and trying to avoid conflict. No one wins in that situation.

As a career advisor, a number of the people I talk with express frustration with a boss who refuses to be clear about expectations. They describe their boss as being “slippery” and evasive.

When they ask for clear goals, their boss says things like, “You know, do a great job!” or “It’s hard to tell right now. I’ll know it when I see it.

When they ask what they should do to receive a promotion, they hear, “You’re on the right track, but look for opportunities to have a bigger impact!”

As one engineer put it in this story, “…there’s a bigger hurdle for me to move to the next level. It’s not clear how you get from one to the other and whether it’s something you can actually do anything about.”

Anyone who does time-bound project work with teams knows that it’s necessary to have clear goals, well-defined requirements, specific deadlines, and quantitative success metrics. Qualitative measurements do happen, but we all know how open to interpretation those can be.

Years of experiences — both good and bad — teach us to drill down and get very clear and quantitative on what success means:

  • How will we know we have completed what’s required?

  • What does success mean?

  • How will we measure that success?

  • What specific metrics indicate success vs. failure?

  • How will those metrics be measured?

  • Who is responsible for taking that measurement?

  • When will the measurement take place?

  • Who needs to review those measurements and make the call?

  • What decision will be made based on the outcome?

  • Who needs to approve that decision?

These questions may seem detailed and extreme, but fuzziness is not your friend. None of us would tolerate squishy details and fuzzy requirements for our projects. We know that they will come back to bite us later.

So, why would you put up with this for your career growth at a company?

Your boss needs to be transparent with you about his or her expectations for your performance. You need to know what it takes to get promoted, and he or she should provide you with the timeline for when that can happen.

When you have a slippery boss

It drives me crazy when my clients are given fuzzy feedback on their performance by their manager. The boss is also unclear about promotion requirements. They are often even vague with the promotion timeline.

What often happens is:

  • The boss provides a fuzzy explanation of performance requirements (e.g., “Do a great job on your next project”)

  • The manager keeps adjusting the definition of success (e.g., “You did a great job, but you pissed off the engineering manager. Next time, keep engineering happy while you do a great job.”)

  • The manager is always moving the goal line (e.g., “Sorry, I wanted to promote you this cycle, but the company is having a tough quarter and I just couldn’t. Let’s try again next year!”)

  • The manager is constantly changing the requirements for promotions (e.g., “We recalibrated our levels this quarter. I can’t promote you until you successfully lead a much bigger project.”)

How does one read the mixed messages from a boss who loves to communicate with ambiguity? What can you do when you’re stuck in this situation, and it’s starting to feel like Groundhog Day?

Hey, you’ll be promoted next time. I promise!

Diagnose the real problem

There can be several reasons that your boss isn’t clear with you. It can be somewhat unintentional. But, it could also be malicious. You have to figure out what is going on before you can make a plan for how you’ll deal with it.

I know that this may make you feel uncomfortable. Many of us don’t like conflict. It’s not fun to confront someone, especially your boss. But, you can handle it in a very professional and objective manner, which reduces some of the emotion.

You don’t want this to become emotional. You don’t want to become angry. You don’t want to threaten. You don’t want to cry. Your goal is to make this as clear and objective as you would be with any “project.”

You are undertaking a new project that has the end goal of you receiving a promotion. Like any project, you want to establish a timeline, requirements, and success metrics.

You want to know how your manager will handle the decision making. You will gather data. You will meet those requirements, document the achievement of the success metrics, and establish that you accomplished the goal.

But, first, you need to understand why your boss has failed to reduce ambiguity for you. You can test these hypotheses to determine which of them is happening and then take the appropriate action.

  1. Your boss is clueless

  2. Your boss is incompetent

  3. Your boss is busy

  4. Your boss is negligent

  5. Your boss is malicious

The clueless boss

Believe it or not, this is not a terrible situation. In this case, your boss doesn’t know how to map out the career ladder, create a plan for each employee, and track and measure progress.

But, they are willing to listen and learn. They want to do the right thing, but they don’t know how it. They’ve never been mentored and shown how by their management chain.

A lack of training sometimes happens in smaller or less-structured companies. It happens in startups that have been moving fast, hiring quickly, and never took the time to establish robust HR processes.

The solution

A relationship with a boss like this is salvageable, but it requires that you step up and take some ownership. It is additional work, but you’ll be in a strong position to define the levels, roles, responsibilities, and criteria for your promotion.

You’ll need to partner with your manager, other managers, and your HR rep to get this done well and institutionalized. I’ve witnessed this at a surprisingly large company. There was a good outcome, and everyone finally had a clear understanding of the various job levels and what it took to get promoted.

Eliminating ambiguity like this will enable you to take control of your career path.

The incompetent boss

An incompetent boss is a little worse than the clueless one. But, if this is the situation, you probably are already aware that your boss is incompetent. There are other clues in their behavior and performance.

They don’t know how to put together a real career ladder for your organization. They haven’t given a thought to a well-defined promotion path. Worse, they don’t even care to try.

Again, this tends to happen in smaller, unstructured companies. Larger companies with well-established processes and an HR org wouldn’t tolerate it.

Right? I hope I’m right.

The solution

Again, you’re going to have to do some heavy lifting and take ownership. But, this boss is a little different. Make sure that they will support your efforts and endorse the outcome. Otherwise, you will be wasting your time.

As with other things, don’t be surprised if the incompetent boss takes credit for your efforts. But, keep your eye on the prize. A clear promotion path is what you want.

If and when you succeed, you’ll be able to keep moving up and out from under the incompetent boss. Eliminating ambiguity will save your career there. You may even discover later that your boss is out, and you are placed in that management seat if that’s ultimately part of your career path.

The busy boss

This type of boss knows how to create a career plan and promotion path for the team. But, they’ve never got around to it because they’re busy. They also know that it will be a lot of work. Hard work. Ugh.

Like the clueless boss, busy bosses actually will support the career ladder work, but don’t want to do it themselves. But, they will probably be happy to sign off on it.

The solution

I’ve had bosses like this. They weren’t necessarily bad people. They were over-scheduled, or they just loved to hyper-delegate and avoided work when possible.

They wouldn’t go out of their way to create something new (e.g., precise levels and promotions documentation). They probably wouldn’t even consider the necessity of it, unless forced to by their management or HR.

Make their life easy and get it done yourself. Why? Because it will benefit you tremendously. You want a clear promotion path, and you don’t want to wait around forever for your boss to get around to defining it.

Leaving things in an ambiguous state will stall your career.

The negligent boss

These type of bosses are neglecting their responsibility to define your promotion criteria and assess your performance.

They know that they should be defining roles, responsibilities, and levels. They know that they should be establishing promotion guidelines. They know that they should be assessing your performance.

They know how to do all of these things, and you have seen examples of it happening for other employees. But, for some reason, they are neglecting you. They don’t want to promote you.

When a boss neglects you, it is a riskier situation because it’s happening for a reason. Perhaps in their mind, you aren’t even close to a promotion. There is something they see as a serious issue, but they haven’t explained it.

Why does this happen? Sometimes they want to avoid conflict. Or, you aren’t a priority for them. They don’t see you as a high potential employee, yet.

The solution

You can try to change their mind, and that starts with forcing absolute clarity into the expectations for your role and the one above you. You can’t allow fuzziness to persist. You can no longer put up with any vague hand waving when you ask what you need to do to get promoted.

Get the performance expectations documented. Your boss promoted others, so what were the justifications for those promotions? You may need to work with your manager and HR to force the issue professionally.

You want a clear and documented understanding of how to give your best to the company. You’re asking for role clarity, performance guidelines, level expectations with examples (e.g., what kind of project work do you expect for a senior designer here?), and quantitative success metrics.

How will you know that you’ve met and exceeded those expectations? You can’t tolerate any more ambiguity about this. Life is short, and the best years of your career are even shorter.

Find a way to move up or make a plan to get out. Don’t sit and wait for years for your boss to recognize you and care about your career. You care the most about you, so pursue your ambition and make it happen.

The malicious boss

Dealing with a spiteful boss is the worst type of situation. You have a suspicion that your boss doesn’t like you. They are unsupportive of your career growth. They don’t seem to care about your or your future.

This boss is capable of defining the career ladder for your organization, and probably already has. They may have promoted others, or they may be one of those bosses who are stingy with promotions. However, they’ve left enough legal wiggle room in the guidelines for performance reviews and promotions to ensure that they have a lot of discretion in who they promote.

You may have already made your case and provided plenty of examples of great work. You may even have the support of others. But, your boss gives ambiguous explanations for why you aren’t ready yet.

You get the idea. Malicious bosses are extracting value from you, but they don’t want to reward you.

Why does this happen? It’s hard to say. Sometimes it’s just a personality conflict. They should be professional enough that it doesn’t matter, but they feel like you rub them the wrong way.

Perhaps there is something in your background that bothers them, although they’ve never admitted it to your face. I remember one leader who didn’t respect anyone who didn’t have a degree from a shortlist of universities that she deemed worthy. If you came from a different school or had learned on the job (i.e., self-taught), there was an invisible ceiling restricting your career growth.

Maybe you’re not enough like them or their circle of friends. Perhaps they are secretly racist or sexist. There can be so many reasons that they are maintaining the ambiguity that enables them to explain why they can’t promote you.

Ultimately, they may feel threatened by you. Your boss fears that promoting you will give you more power in the organization and they can’t have that. They worry about their job.

The solution

These types of bosses are career killers. You can engage in political warfare to try to force the issue. You can threaten with lawsuits, which rarely ends well.

But, as I said before, life is too short. There is a world of opportunity, and many more bosses who will treat you well. Get out.

If you work in a larger company, you may be able to move into a different organization (if your boss doesn’t blackball you). Otherwise, seek greener pastures outside of the company.

Moving on isn’t a bad thing. I recommend that people stay within a company when things are going well, and it’s great for their career. A good boss. A stable career path. A regular rhythm of raises and promotions.

But, when it stalls or worse, moving on can give you much faster career growth. It maximizes your earning potential more than struggling to get tiny raises within a company that’s making you miserable.

Eliminate ambiguity to fuel your ambition

It’s hard to win the game when you’re blindfolded, and someone keeps moving the goal. Success is hard enough to achieve under the best of circumstances. Don’t let yourself be hobbled by a slippery boss who won’t support you with a clear and well-defined career path.

I know that it is never easy to force clarity, but it is necessary. It’s a challenging discussion, but you can handle it professionally and objectively.

If you succeed, you’ll be able to chart a clear career path for yourself within the company. Even if you don’t, you’ll know what to look for in your next opportunity.

You’ll be able to ask the right questions, detect any red flags, and find a company and boss who will help you thrive and tap into your full potential. Most importantly, you will have taken full ownership of your career going forward.


What I’ve Been Reading

  • Speaking of bad bosses here’s How to Spot a Bad Boss During an Interview. Plus, you shouldn’t be afraid to reach out to people who used to work for that person. You’d be surprised by the number of people who are willing to share their experiences, both good and bad.

  • In Great Leaders Make Decisions, Then Take Action, Trever Cartwright talks about something he calls leadership “Rubicon decisions.” He notes that “I have found that one of the most common challenges many leaders face is not necessarily making the Rubicon decisions that need to be made in their organizations, but rather having the courage to set those Rubicons into motion—to actually walk into the river fully understanding the consequences, yet move forward with focus and resolve.”

  • I read some interesting research that shows you can be perceived as too qualified for a job. When a candidate is overqualified for a position, the hiring manager doubts that he or she will stick around. They know that you will have other prospects and suspect that you will leave as soon as something better comes along. This is one reason that I tell people to have stretch goals when job seeking. Why take a lower-paying position that is beneath you anyway?