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GuideThe agent boss, part 46 min read

Culture comes before agents: what AI exposes about how you work

A few months into running agents for my own work, one of them drafted a message that was accurate and polite and would still have hurt a relationship I had spent years building.

Read this for your industry

Optional. Choose your industry and this piece opens with a situation from your world and closes with a first move for you. Your choice carries across the guides and analysis on this site.

Wealth management

You lead the culture of an advice business

The Royal Commission found that failings of culture, governance and remuneration lay at the heart of much of the misconduct it examined, and Commissioner Hayne recommended that every financial services entity regularly assess its culture and fix the problems it finds. Much of that culture had never been written down. It lived in sales targets, in what managers praised and in what nobody questioned.

Agents bring that unwritten culture into the open. If a brief asks an agent to grow ongoing fee clients and says nothing about the client's best interests, the agent will follow the words on the page.

What this means for you

  • Write the values you want into the briefs agents use, including how you speak to clients and when to recommend that nothing changes.
  • Make it safe for paraplanners and advisers to report agent output that feels wrong, even when it is technically compliant.
  • Include agent briefs in your culture and conduct reviews.
Retail

You lead a territory with a culture nobody wrote down

Only 22% of SDA members said their employer's support after an abusive incident was suitable, and 62% said they did not receive a satisfactory response when they reported one. Every store has habits for how incidents are handled and how staff are spoken to, and most of those habits were never written down.

When agents start drafting incident follow-ups, rosters and staff messages, they will reflect whatever is in the brief. If the brief says nothing about how to treat a shaken team member, the agent will say nothing too.

What this means for you

  • Write down how your territory treats staff after an incident, and put it in the brief.
  • Ask store teams to tell you when an agent's message feels cold or wrong, and fix the brief when they do.
  • Show store managers what good follow-up looks like, so the written version matches the real one.
Healthcare

You lead care where dignity lives in daily habits

The aged care Royal Commission concluded that at least one in three people using aged care had experienced substandard care, and called its final report Care, Dignity and Respect. The strengthened Quality Standards now put the older person at the centre of every standard.

Much of what dignity looks like in a home is unwritten: how staff knock, how they speak to a resident living with dementia, what they say to a worried family. An agent drafting a care-plan review or a family update only knows what you have written down.

What this means for you

  • Write the person-centred language you expect into every brief that produces documents about residents or patients.
  • Ask carers and nurses to flag agent drafts that sound clinical where they should sound kind.
  • Make it safe for staff to raise concerns about agent output without being seen as resisting change.
Product engineering and manufacturing

You lead engineering where quality depends on people speaking up

An FAA expert panel reviewing Boeing in 2024 found a disconnect between senior management and other employees on safety culture, and found that some employees feared retaliation for raising concerns. The panel also described procedures that were constantly changing.

Engineering and manufacturing teams carry the same risk on a smaller scale. When people are unsure whether it is safe to stop the line, the agents they brief inherit that uncertainty.

What this means for you

  • Write the stop rules into each agent's brief: when it must halt and ask, and who it asks.
  • Make it normal for anyone to report agent output that looks unsafe, and thank them when they do.
  • Check that what leaders say about quality matches what the briefs and incentives reward.
New energy and trade services

You run crews whose safety habits were never written down

The Clean Energy Regulator found 1.2% of inspected battery installations unsafe, with problems such as loose connections and exposed wiring. Trades businesses have strong safety habits on site, and many of them have been passed from one electrician to the next without ever being written down.

When agents start preparing job packs and reviewing photos, they will only check what the brief tells them to check. The habit of stopping a job when something looks wrong has to be written in.

What this means for you

  • Write your stop-work rules into every agent brief that touches site work.
  • Make it safe for apprentices to question an agent's job pack, the same way they would question a supervisor.
  • Review any job where an agent missed a safety issue, without blame, and change the brief.
The short answerAI agents follow what is written down, so they expose every habit a team relies on but has never stated: how you speak to people you trust, what counts as good enough, when to escalate. Teams need to write that culture down before agents can work inside it. Teams where people feel safe admitting mistakes find and fix those gaps faster.

An accurate message in the wrong voice

The task was simple: tell a long-standing contact that a piece of work would arrive later than planned. The agent’s draft was accurate, polite and well organised.

It also spoke to someone I have worked with for years as if they were a stranger: formal, careful and distant. Between people who trust each other, that tone reads as a sign that something has gone wrong.

The agent had followed its brief. I had never written down what made that relationship different, because I had never needed to. It lived in my head.

It was the third time in three months something like that had happened. After the first, I thought I had briefed badly. By the third I could see a pattern. The agents were showing me gaps that already existed in how I worked.

Handing over the keys

It is a bit like going away and leaving a house-sitter in charge. In your own home everything works because you know which drawer sticks, which switch runs the porch light and that the back door needs a shove. Hand over the keys and each of those quirks becomes a small problem for someone else, because none of it was ever written down.

Every team runs on that kind of knowledge: how direct to be with whom, what “done” means, when a decision needs a second opinion, which shortcuts are fine. People pick it up over months by watching, getting things wrong and being corrected by a colleague. An agent has only the brief, so it finds every gap in its first week.

The safety to say so

These gaps get fixed only when someone says they have found one, and that takes some courage.

Amy Edmondson’s study of work teams found that psychological safety, a shared belief that the team is safe for interpersonal risk, supports learning behaviour such as asking for help, discussing errors and seeking feedback. AI adoption needs exactly that. Someone has to be comfortable saying, “The agent got this wrong, and I think it’s because we never agreed how we handle this.”

Where admitting a mistake feels risky, people fix the agent’s output by hand and move on. That is a sensible choice for them in the moment, and it leaves the gap in place for the next person.

Leaders make a measurable difference here. In BCG’s AI at Work 2025, the share of frontline employees who feel positive about generative AI rose from 15% to 55% with strong leadership support. Only about a quarter said they received that support.

Writing culture down

Start with near misses. When an agent’s output is correct but feels off, ask which unwritten rule it broke, and write that rule down.

Write about relationships as well as rules. I keep short notes on how I work with different groups of people: the tone, what they care about and what to avoid. My agents read the relevant note before drafting anything.

Set “good enough” for each task. A first draft for my eyes and a message to a senior stakeholder need different standards, so the brief should say which one applies.

Make reporting gaps normal. Ask in a team meeting, “Where did an agent get our culture wrong this week?” Thank the people who answer.

What this means for leaders

Before you scale agents, spend an hour with your team writing down how you actually work: the real rules, the ones a house-sitter would need. Most of them will be things you assumed everyone knew. A few you will want to change once you see them on paper.

This closes the agent boss series. Everything in it comes back to one skill: being clear with others about how your team works. Agents make that skill easier to see, and they reward the teams that practise it.

Your first move: wealth management

Read the brief for your most-used advice agent as if you were a client. Add one sentence that says what the practice puts first, and ask two advisers whether it matches how they work.

Your first move: retail

Read the last five incident follow-ups from your stores. Write one paragraph on how you want staff treated after an incident, and make it part of the brief for every agent that touches incidents.

Your first move: healthcare

Ask a senior carer to read five agent-drafted family updates. Note every phrase that would upset a family, and rewrite the brief together.

Your first move: product engineering and manufacturing

Pick one agent that touches a safety or quality decision. Read its brief with the people who use it, and add the stop rule they would expect a new engineer to follow.

Your first move: new energy and trade services

Ask your most experienced electrician what they check on every site that is missing from the checklist. Write those habits into the job pack and into the review agent's brief.

Questions readers ask

Can culture really be written down?

Some of it can, and that part is what agents need. Start with the habits that keep tripping people up: tone with different relationships, what good enough looks like, and when to stop and ask.

Does this apply to people as well as agents?

Yes. Every unwritten rule an agent breaks is one a new starter breaks too. Writing it down helps both.

Who should write it?

The people who hold the judgement, with leaders setting the norms. The team adds to it as new gaps come up.

Sources

  1. Psychological Safety and Learning Behavior in Work Teams, Administrative Science Quarterly (Edmondson), 1999
  2. AI at Work 2025: Momentum Builds, but Gaps Remain, BCG, June 2025

The views here are my own, not those of my employer or its clients.

About the author

Dan McMahon

Dan McMahon spent fourteen years running retail operations and digital businesses, from the store floor to general manager at Dick Smith and BIG W, and the decade since building consulting and product engineering practices across Asia-Pacific. He is a Managing Director at Avanade. Three Cubes is his independent publication, and the views in it are his own.

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