How to notice and change dysfunctional culture in your organization

Executive overview

Most organizations add new cultural initiatives without first acknowledging the dysfunction already in place — and that sequence fails. Culture is shaped by impact, not intention; what people do and say matters more than what they mean.

Jonathan Raymond argues that the CEO or team lead must open the door first — by naming what they don't know, not by launching programs. Psychological safety is the precondition, and its absence is itself the signal that action is needed.

If you're not hearing uncomfortable feedback, it's not because things are fine — it's because it isn't safe to tell you.

Existing agreements that shape culture

• Every organization runs on unexamined agreements: "bring solutions not problems," "good intentions excuse bad impact," "sales people get a pass."
• These agreements were in place before you arrived and go unquestioned precisely because everyone is inside them.
• The shift required: move from evaluating intentions to measuring impacts.
• Intent does not equal impact — this gap is where most cultural damage accumulates.

The high-performer blind spot

• Organizations routinely allow top performers to behave in ways that would be unacceptable from anyone else.
• Leaders over-privilege the revenue or output side of the ledger and ignore the cost side: damage to peers, colleagues, and culture.
• Better math means asking: if we account for all the costs this person generates, are we still ahead?
• "No brilliant jerks" is easy to say; the mechanism for enforcing it is explicitly naming the costs and making them part of the conversation.

Acknowledging before fixing

• The instinct to move immediately to solutions skips the human moment that actually creates trust.
• People want acknowledgement first: "I see that this impacted you negatively, and that's on me."
• Combining acknowledgement and solution in the same breath undermines both — the acknowledgement needs room to land.
• Leave the fix for tomorrow's conversation; slowing down here speeds up the overall resolution.
• This applies equally to interpersonal situations and organizational culture shifts.

Personal and professional growth as one inquiry

• Separating "work leadership development" from "personal growth" creates two incomplete paths.
• The challenges people face as managers — relating to risk, communication, time — are the same challenges they face at home.
• Leaders who frame growth as one unified inquiry get more engagement from employees, especially those with short expected tenure.
• With average tech worker tenure at ~1.6 years, the 10-year vision is less compelling than "how will I grow while I'm here?"

Opening the door: what it actually looks like

• The CEO or team lead must go first — not by asking "what feedback do you have for me?" but by naming what they suspect about themselves.
• Asking others for feedback still puts the burden on them; real vulnerability is doing your own proactive digging first.
• The shift: "I've never heard you say this directly, but I think there's something I do that is way worse than I realize — I wanted to name it."
• That moment is the signal that you mean it, not just that you're saying the right words.
• If you are not receiving uncomfortable feedback, that is not a sign of health — it is evidence that it isn't psychologically safe to give it to you.
• The same logic applies at team level: a manager not hearing pushback should treat its absence as a red flag, not a green one.

The disgruntled employee as spokesperson

• The person who keeps pushing back in meetings or redirecting conversations is often a messenger, not a problem.
• The other seven people in the room may share that view but lack the safety or confidence to raise it.
• Mature response: separate the message from the delivery, address the delivery directly, and treat the message as data.
• "I noticed this pattern over the last few meetings — I want to understand what's behind it" opens the conversation without dismissing the signal.

The Marcus story: proactive cultural listening

• A CEO with an open-plan office and an open-door policy was completely unaware of hostile dynamics directed at women by a senior leader.
• His visibility actually reduced safety: there was no private space to raise something sensitive, and the senior leader's continued presence implied the CEO was fine with his behavior.
• The CEO had not gone looking — he waited for problems to surface rather than starting from an assumption that they existed.
• Proactive stance: "We have a leadership team that's mostly men. I can only assume that's problematic in some ways. I want to know how."
• Treat culture like customer data: if customers aren't raving, you go looking for why — apply the same urgency to internal signals.
• A useful recalibration: if you think you micromanage "a little," assume from your team's perspective you micromanage constantly.

Two steps to cultural change

• Step one: The senior leader opens the door — explicitly acknowledges what they don't know and invites uncomfortable truth.
• Step two: Build the structural conditions for psychological safety before expecting people to use it.
• Adding positive cultural programs before addressing existing dysfunction papers over the problem; the dysfunction reasserts itself.
• Acknowledgement of what went wrong must precede any forward-looking initiative.

Technology versus human investment

• Leaders under-invest in high-touch leadership development and over-invest in people-tech that cannot solve interpersonal and cultural problems.
• Technology can play a supporting role, but cultural dynamics are human problems requiring human solutions.
• The momentum toward technological fixes is strong; resisting it requires deliberate choice.