Bad Boss BS: “My glass is always half full.”

How do you cope when your boss is relentlessly positive at the expense of reality?

6 min readJan 25, 2022
Four 2d characters stood close to but slightly apart from a 3d bad boss character. The boss character is supposed to resemble a glass which is half-full (or half empty) depending on your perspective.

Some bosses can fall into the trap of their optimism overwhelming their realism. Bosses need to motivate and be the cheerleader for successes. They sometimes play this role by glossing over challenges or failures at the expense of their credibility. A relentlessly positive or optimistic boss who plays down difficulties, disappointments and challenges loses credibility — they seem disconnected from everyday realities and therefore it’s easy to jump to the conclusion that they’re not noticing things or that they don’t care. So, if we have a boss who seems like they’re living in a different version of reality — one full of sunshine and rainbows — what should you do?

Like most issues with an interpersonal dynamic, a good starting point is empathy. We need to devise a strategy where the bad boss understands the importance of reflecting the reality that others are experiencing. Bad bosses can fall into the positivity trap for different reasons.


Some bad bosses see acknowledging failures or difficulties as being personally or professionally undermining. They see any difficulties as their failures, which triggers fear responses. Maybe their boss expects perfection. So, they develop a strategy of protection where they “accentuate the positive”, push back on the negative and ask you to trust in the future — that “even if things aren’t quite 100% right now, they’ll be fixed soon”. They likely have a fixed mindset. They don’t realise that talking about failure is a learning opportunity, and talking publicly about it is a chance to not only learn but also build trust and credibility.

It’s hard to overcome this sort of fixed mindset, especially where fear is also a contributing factor. But as with most bad bossing caused by fear, the first step is to try to help the boss rewrite their relationship to the cause of fear. Try to avoid accusation — it will likely only trigger the fight or flight response which makes communication harder.

Chris Voss talks about ‘tactical empathy’ in negotiations. We can use a similar technique to try to move a boss from a position of unremitting positivity to one of higher trust and transparency. Thinking of the conversation as a negotiation, where the boss is holding the true situation ransom is a useful technique. Build rapport by acknowledging the genuinely good things in the situation. Then ask open questions about the more challenging aspects.

Before you go into this conversation, think about what you need the boss to acknowledge to restore your faith and give you confidence in the future. The conversation is unlikely to change everything — it will still take time for the situation to improve. And it’s unlikely that the boss will immediately shift their tone or perspective. But like in a negotiation, identify what’s the ‘best alternative’ to them shifting to the way you see the world. What’s a realistic acknowledgement or commitment to give you faith that they’ve understood your reality?


Some bad bosses want to motivate people but only have a limited range of techniques that they’ve mastered. Sometimes a limited or inexperienced boss can equate energy and motivation only to positivity. They emphasise and maybe even overplay victories. They might mention challenges. But it’s within the context of improvements that have already been gained or planned, rather than acknowledging the hardship or disappointment of the current moment.

With some types of bad bossing, the easiest solution is to talk directly about the disconnect. Give the boss credit for their efforts to motivate. Avoid accusations as you point out the more negative aspects of your current reality. And then describe how the boss could use acknowledging these to build trust and motivate you. This gives the boss a fresh set of tools they can use to achieve their objective — keep you happy and motivated.


Another reason for relentless positivity might be a fundamental disconnect. Either the boss isn’t aware of the facts or they don’t appreciate the impact these facts have on the rest of the team. They don’t understand why people have a problem, why they don’t trust in the future enough to be satisfied or why they’re not patient enough for things to improve. These are trickier conversations — but like with the other two causes, employing the tools of good communication and negotiation can help.

  1. Focus on the facts — These can include the emotional impact as well as the practical impact of both the disconnect and the actual issues. Try presenting these as questions, rather statements. Questions are more likely to invite open consideration. They’re more likely to enable you both to generate a shared view.
  2. Move to motivation — once you’ve built a shared definition over an area where there is still work to do, move to motivation. Begin to focus on the consequences of not addressing the issue — and tie the acknowledgment of the issue to a sense of urgency. This will help to form a commitment and contract that at the very least, the boss should continue to acknowledge it.
  3. Generate commitment — with agreed facts and motivation in place, it should be easier to generate and sustain commitment and motivation from the boss. We can help by discovering motivators that help to sustain effort. Are they motivated by social pressure or perception? If so try to get a public commitment. Are they more interested in looking good to their boss? Make sure that this person is part of communicating the plans or commitments you’ve agreed.
  4. Feed the fire — bad bosses aren’t bad people. They’re just not quite giving us what we need. In this scenario, the bad boss is too reliant on “positivity” which creates a disconnect with us. Through open dialogue we can generate an acknowledgment of the things that aren’t quite so good. We can use this spark of a shared reality and feed the fire to get commitment and action. ‘Feeding the fire’ is different to ‘keeping up the pressure’. Remember, this boss wants things to feel positive. You can use this desire to get what you need. Generate momentum. If they share quick wins and it looks like they’re declaring victory early, don’t just challenge them, use it as a springboard for further action and commitment.


There’s one final reason for a boss being relentlessly optimistic. It’s just how they’re wired. We all have different preferences, filters and ways of seeing the world. Your boss might genuinely be a glass half full kind of person. It’s not really acceptable to ask them to be glum.

But we can point out the impact that this preference can have on a team — particularly at times of challenge. Relentless positivity can undermine our trust in a leader. It seems they’re not connected with our reality or concerned about the impact on us. We can use a range of the techniques discussed earlier. Meet them where they are. Start with the positives. Talk about the impact that their outlook can have on others. And ask yourself whether you might need something different to the majority in the team. Maybe the boss is doing a good job for the majority, but it doesn’t work for you and a few others. It’s still reasonable to point this out to the boss. But be sensitive to the challenges of communication to broad, diverse groups.

Four 2d characters stood close to but slightly apart from a 3d bad boss character. The boss character is supposed to resemble a glass which is half-full (or half empty) depending on your perspective. The Boss Character is wearing a pair of pants with CP (for captain positive) and now has a cape.

There might be lots of reasons for a bad boss to be Captain Positive all the time. They might genuinely see this as the best way of motivating and leading a team. In this case, pointing out that you need other forms of communication to stay motivated and trust their leadership might work. They might think they’re doing a good job of acknowledging failures or work that is still left to do — but due to some disconnect they’re not doing it in a way that connects with you or the team. Tell them you need a change. They might be motivated by a fear of failure. They might think they need to be perfect, so they try to minimise talk or acknowledgement of failures. Their boss might demand perfection, so they’re uncomfortable and unaccustomed to learning about and talking about failure. When we spend a little time trying to understand the motivations and preferences of the bad boss, we’re always better equipped to understand what we need and develop strategies to ask for it.




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.)