Bad Boss BS: “…the seeds of my own destruction.”

Strength/Weakness pairs show how strengths can become weaknesses, and how this realisation can suggest solutions to bad bossing behaviours

6 min readApr 6, 2022
Four 2d characters stand close to but slightly apart from a 3d bad boss character.

In the last post I described the dangers of falling into ‘unconscious incompetence’ when a former strength becomes a weakness and remains in an unidentified blindspot due to inattention blindness. Bad Bosses are prone to this. They’re usually busy people. And they’ve usually experienced successes and developed proficiency in multiple areas. This combination of time poverty, past success and often broad yet complex responsibilities makes being a boss challenging. When we’re challenged we’re likely to focus our attention more tightly where we think it will help us most. We get a sort of tunnel vision. That means we miss things. And we’re likely to rely on things that worked in the past to achieve success in the present. That sometimes makes us inflexible, inefficient and ultimately ineffective.

Bad bosses are hard to work with — they’re like a gadget without an instruction manual. We can try a sort of brute-force attack to try to get them working properly. But it’s hard to do this in a scientific way and control variables to identify what works. But, like good scientists we can still carry out experiments once we’ve formed a clear hypothesis. ‘Strength/Weakness pairs’ are one way of forming a hypothesis about a bad boss. It’s a reflective technique to help us consider why a boss might have become bad, and it helps us to think about ways of helping a bad boss become better.

‘Strength/Weakness pairs’

The central idea behind a Strength/Weakness pair is that it’s easy for a strength to become a weakness. Most bad bossing is the result of the boss doing a thing too much, or doing a thing right but in the wrong context. If we can identify the Strength/Weakness pairing(s) for our bad boss we can try to find ways to ‘moderate’ the behaviour, pulling it out of the realm of unconscious incompetence and unlocking the core strengths beneath the incompetence. Here are some ‘Strength/Weakness pairs’.


Pragmatism is great — it gets things done. But it also makes a boss more unreliable. They’re more willing to compromise to make progress, which means they change direction to get things done. An ‘ultra-pragmatic’ boss can make compromises that are sometimes difficult for us to accept. The boss can undermine previous directions. And it can seem like they don’t believe in anything or have any strongly held opinions. That can shake our confidence in their leadership and erode trust as they seem to contradict themselves as they try to navigate the realities they’re faced with.

Solutions: Try to get the bad boss to be clear on fundamentals, red lines and commitments they’re unwilling to compromise on. Reinforce issues you find hard to compromise on, explain why and try to get them to commit out loud. If you’re worried about certain areas, try to exploit the weakness, making your preferred outcome appear to be the most pragmatic. You can do this through carefully stating your case and breaking down recommendations into smaller, incremental steps and achievements.

Confident/Belligerent-Arrogant (violent)

Bosses need confidence. They need the inner belief to lead — and whether they do it through inspiration, instruction, direction or a range of leadership behaviours, they still need reserves of confidence to take the lead. But like lots of strengths, unchecked confidence can result in negative behaviours. The confidence of a boss can fill a space, leaving little room for us to contribute. And confidence can expand into arrogance, leading to blind spots and dominating behaviours which not only compromise our ability to deliver but distance the boss from our shared reality. Confidence can also be a contributing factor to bullying or belligerent behaviours. A low confidence boss might actually mask their confidence issues by resorting to ‘violent’ dominating communication and behaviours. More on this below…

Solutions: As with all Strength/Weakness pairs we can think about the fundamental forces which underpin the behaviour and see how we might use them. Confidence is usually linked to ego. You might be able to do some ‘ego stroking’ to make the boss more aware of the impact their confidence-linked behaviour has on others. And by balancing praise, feedback and requests for support we might be able to break the blindness of arrogance and invite a boss to consider the impact of their confidence on ours.

Doubt/Under-confident caution

The secret behind Strength/Weakness pairs is that any perceived strength can become a contributing factor to bad bossing when it’s taken to extremes or done without thinking. Doubt is useful in lots of situations. It increases our attention and encourages us to adopt an experimental mindset — which usually means we learn more. But carrying doubt into every situation makes a boss reluctant to make decisions and take action.

Solutions: Just as the strength contains the potential of the weakness, we can also use elements of the weakness to return to the strength. We can encourage a boss to adopt that experimental mindset — form a hypothesis and establish the measures of success for a decision. By framing a decision as a measured experiment or innovation we reduce the risk while still making progress.


I find it hard to think of kindness as a form of weakness in any context. But there are times when a boss becomes challenging because they duck the difficult conversation. This can be for reasons other than kindness — doubt, aversion to conflict and laziness can all see bosses compromise accountability in a team. But bad bosses can just be trying to be kind, and find it difficult to enforce standards when it might put individuals under additional pressure.

Solutions: Strength/Weakness pairs prove that sometimes a boss is laser focused in one area and is missing signals in other areas. A boss that is compromising performance in one area is likely unaware of the impact on the rest of the team. Pointing out that “kindness” in one area might be having a larger, disproportionate impact in a wider context can sometimes knock the boss out of their current behaviours and help them find another strategy to support everyone.


I’m pretty sure “baggaged” isn’t a word. But I’m not going to let the fact that no-one has used it in the past hold me back. Bad bosses sometimes let the past define them. They carry forward experiences and fall into the trap of their pattern-matching abilities limiting their options. Experience is great. Through experience we develop a repertoire of skills, techniques and processes. We learn from our successes and failures and this brings efficiency and the building blocks for innovative practice. But it can also weigh us down, haunt us, limit our options, reinforce prejudice and lead to bad bossing.

Solutions: Try to get to know the boss. What are the defining experiences that shape their outlook and approach. What do they value? What motivates them? What scares them? Negative experiences can have the biggest impact in bad bossing. But they’re usually harder to uncover and talk about. So pay attention. Stress the unique and new factors at play in the current situation and try to move the boss from an automatic response driven by experience to explore situations from multiple perspectives.

The power of reflecting, not reacting

The bad boss character looks at a reflected self.

Strengths become weaknesses when a boss uses their abilities reactively. It’s hard to do anything well when we do it “unthinkingly.” And this is a danger that bosses who are spread across lots of things and have lots of responsibilities are exposed to all the time. They over-rely on things that worked in the past. Their brains conserve energy by focusing their attention and they miss things.

If we’ve mastered the art of giving feedback, we can often break the unconscious incompetence of their reactive automatic responses and encourage a more effective and reflective practice. And sometimes we can leverage the power dynamic at play between us and our boss to sort of ‘reverse coach’ them out of complacency by asking them to support us as we practice a skill or behaviour. The conscious attention this requires might break a bad bossing cycle and make our life easier and more rewarding by making them more effective.




I'm a Creative director at the BBC. I like words, design, data and magic. These are all my own views (apart from retweets. I borrowed those to look clever.)