My boss is complete chaos

Dear AVTA,

I sympathise with you, because this really is one of the worst kinds of bosses to have.

If someone is abusive, unethical, or plainly incompetent, at least the problem is addressable. There are rules, processes, and escalation paths for that. In your case there is no obvious complaint to make. Your boss isn’t cruel. He isn’t malicious. He isn’t even bad at his job in the narrow sense that the institution cares about. He has clients, generates revenue, and is broadly liked. From the outside, he looks successful.

And yet, little by little, working for him is degrading your career.

That is what makes this situation so corrosive. The damage is real even if the intent is not malign. Chronic disorganisation, last-minute thinking, and poor communication don’t give grounds for legal redress, but they absolutely impact the workplace. They steal time, energy, and learning. They turn capable junior bankers into professional firefighters who spend their best hours reformatting decks, reordering arguments, and fixing avoidable mistakes instead of understanding clients, markets, and judgment.

It’s also very hard to “regulate” against inattentiveness and inconsideration. Your boss isn’t breaking rules, he’s just operating in a way that externalises chaos on to the people below him.

And because he’s a managing director, this is almost certainly not a new habit. He has been behaving this way for years, probably decades. He has survived, even thrived, doing exactly this. A leopard doesn’t change its spots (but it will eat your face!).

That leads to the uncomfortable truth that you have limited leverage. Internally, very few people will be motivated to intervene on your behalf. As long as revenue comes in and clients are happy, the organisation will likely view the situation as tolerable (unless the whole team stages a protest strike). You may feel like you are drowning, but from the firm’s perspective the boat is floating just fine.

That doesn’t mean you should do nothing. In the first instance, I do think you should try to speak to him. Not in an accusatory way, and not as a grand confrontation, but in good faith. Frame it around efficiency and outcomes rather than stress or fairness.

Be specific; this is key. Explain how earlier notice of meetings or earlier review of materials would materially improve execution. He may respond positively in the short term. He may become a little more careful, a little more considerate, especially if he sees it as helping him rather than criticising him.

I would just caution you not to have particularly high expectations. Even if the conversation goes well, lasting behavioural change is unlikely. Old habits die hard, as they say. Judge him not by what he says in the meeting, but by what actually changes over the following weeks.

Which brings us to the harder, longer-term question. If nothing meaningfully improves, you are essentially stuck unless you can move. That might mean switching teams, switching coverage, or switching banks. None of those are easy, but they are often the only clean exits from this kind of situation.

There are, however, some partial coping mechanisms worth considering if an immediate move isn’t realistic. One is delegation. If your boss is willing to push more execution down the stack, some of the misery can at least be shared and pooled. That doesn’t make the system good, but it can make it a bit more manageable. Another is carving out a niche that is slightly more independent of him. Owning a specific product, client subset, or internal function can reduce how exposed you are to his last-minute impulses and allow you to develop an identity that isn’t entirely tethered to his chaos.

Ultimately, the priorities are to reduce direct dependence on him where possible, and to quietly line up alternatives. Disengagement can be incremental.

Sometimes there isn’t a neat solution. Sometimes the choice really is between increasing your pain threshold and moving on. Neither is morally superior. But pretending that this situation will resolve itself, or that goodwill alone will fix it, is likely to leave you burnt out and bummed out.

Engage with him once, sincerely and professionally. Observe what actually changes. And plan anyway for a contingency.

Sympathetically,

Craig