confused minds say no

Why Do Bad Bosses Always Win?

Doesn’t it seem like the bad guys frequently get the promotions and advancements at work? Have you ever wondered why or how that happens?

First let’s clear out one issue. Just because I don’t like my boss, that doesn’t mean he.she is bad. It takes a wide range of experience and observation to declare a boss bad. But some of them make the decision so easy.

OK, so yes, there are often bad bosses at work. They keep getting promoted. But why?

Authority Rules

As much as we hate to admit it, we still operate most business in a hierarchical structure. Somebody has to have ht final say in what gets done. So we build org charts to describe who has what power.

The power of the position is never a replacement for good leadership. Too often the person who gets to sit in a particular box on the org chart is not worthy of the power that comes with the position.

Authority is often given a “free ride”. We feel stuck or even powerless to confront bad management. We wait for the process to take them down, but seldom does that happen.

Bullying and Intimidation

If you have a boss that is just the adult version of the neighborhood bully, you have a big problem.

Yet just like that mean kid on the playground, boss bullies carefully pick targets for bullying, knowing full well that the targets are unlikely to retaliate, and bystanders will not intervene because they fear becoming the next target.


Poor Organizational Process

Companies with a large number of bad bosses have very poor systems in place to manage people. If the rating process for managers does not accurately and effectively get stakeholder feedback, then bad behaviors can survive.

If there is no accountability for employee satisfaction and turnover, then poor managers get to keep doing the bad things they do.

Bad Bosses Don’t Have to Violate Employee Rights

Someone can be a bad boss by just failing to create an environment for people to grow. Their actions do not have to be obvious attacks on character, gender, or ethnicity.

I’ve known a few really bad bosses who were not racist nor sexist. They were just bad. They made poor decisions, didn’t hear people, and generally failed at inspiring anyone.

I once had a boss who never rated his people any higher than he was rated. He didn’t get rated very well. Let’s call it a C+. Working for him meant you’d get a C+ if you were lucky.

I and two of my peers were in the same boat. It took us the first year of rating to figure him out. All three of us were producing record high returns, metrics and deliverables, yet we could never get past a C+. We did what most people do, we tried harder the next year and delivered yet again, but got the same poor ranking.

That impacted raises and bonuses. It was a terrible two years in my career until he got moved elsewhere. He was just bad. Actually, a nice guy, but a terrible boss.

Speaking Truth to Power

We all know how hard it can be to try to speak up, especially when it is ‘up the organization.’ There is a concept called “Speaking Truth to Power.” There are studies around the subject. See “Emperor Has No Clothes.

In September 2015 the leadership team at Volkswagen was shamed by an issue regarding emissions that was known about by some employees, but not spoken up about (or listened to) effectively.

The previous month an animated Jeff Bezos, CEO of Amazon, announced that he did ‘not recognize’ the ‘bruising culture’ and the consequent accusations voiced against his organization by employees and reported in a New York Times article.

In the July 2016 report by the UK Financial Reporting Council, ‘Corporate Culture and the Role of Boards’, the following observations and recommendations were made that directly address the issue of speaking truth to power:

“Good governance means a focus on how [openness and accountability at every level] takes place throughout the company… A healthy ‘speak up’ culture breaks down the barriers that can often exist between the workforce and the board… A key ingredient of a healthy culture is a willingness on the part of senior management to listen to their employees… Employees usually want their organization to succeed, and have good ideas about how to make this happen… A culture of engagement and ‘permission’ is required for employees to feel able to voice their ideas and concerns.”

Leadership development programs focus on developing specific skills to address conversational situations experienced as problematic, for instance training for ‘difficult conversations’. They train leaders to be ‘impactful’ in what they say, valiantly attempting to introduce coaching skills to executives who have paradoxically been promoted based on their individual capacity to ‘know answers’.

Whistle Blowing

Meanwhile the issue of challenging authority is increasingly addressed through whistle blowing procedures, part of continuing attempts to control certain conversations through formal processes.

Yet it would be far more productive if companies didn’t have to wait on whistle blowers, but relied instead on their employees to speak openly and candidly.

The Entrepreneur’s Plight

In small business, the egocentric owner can be a stumbling block for truth at work. After all, it is their idea and their company, so how can anyone confront the owner?

Usually this is nothing more than inflated ego getting in the way of good management and leadership.

What Can You Do?

When you want to confront a bad boss or speak truth to power, several key questions come up.

  • What happens in the moment of choice of whether to speak up or stay silent?
  • How does an appreciation of the complexities of this moment inform effective leadership?
  • How might individuals make more informed choices regarding speaking up?

Here are some key principles to think about if you are the one needing to speak up.

Conviction – How strongly you believe in the value of your opinion. Pick your battles.

Risk Awareness – Do you have a realistic grasp of the consequences of speaking up. In a healthy environment, these risks are low, always.

Political Awareness – Do you understand the political games being played inside your company? Can you navigate that swamp?

Social Awareness – Understanding of how to work within the social climate around you so that people will listen.

Judgement – Some call is discernment. Knowing what to say, who to say it to, and when.

We Live in a BLURT World

The rise of social media has created a BLURT World. What is that? You just blurt something out whenever you feel like it without regard to any of the key principles above.

When you blurt, there is no consideration for your real conviction on the topic. Likely no assessment of the risks included with the comment.

Definitely, there is no social awareness (Ironic isn’t it that lack of social awareness happens on ‘social’ media.)

The habits we create for our behaviors on social media will spill over into the workplace. It’s unavoidable.


Sure, we all have bad bosses. To help solve the problem, employees at all levels need to be able to be heard.

However, there is a catch. To enable a positive and productive conversation or to be heard at all, there are principles that need to be followed.

The next time you hear someone shouting about injustice or fair treatment, see if any of these principles are being followed.

By the way, in my coaching, every time my client has trouble in the workplace with the bad boss, I never forget to remind them, they can leave. It’s true in domestic violence, it’s true at work.

If you firmly believe the system is severely flawed, you just may need to leave.

Author’s Note: Special thanks to Ron Riggio for reminding me of this need to address bad bosses. Also, thanks to the good folks at Hult Research, specifically Megan Reitz and John Higgins for their amazing study on the ability to speak truth to power. Lastly, my good friend George Head at LHH for keeping me inspired to help others with this important topic.

Introducing the WHY.os. Learn YOUR why, how, and what that drives your passion and motivation.


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