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GuideThe agent boss, part 26 min read

The delegation trap: why capable people and agents keep doing the work

Over four days my coordinating agent did three jobs it was supposed to hand to someone else. I recognised the habit straight away, because most managers have had it at some point.

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 advisers who still do their own paraplanning

Between 700 and 1,000 advisers retire each year, while only 569 new entrants joined the profession in 2025, and support staff are just as hard to find. When support is thin, experienced advisers fill the gap themselves. They draft the Statement of Advice at night because it feels quicker than briefing someone, and the number of clients they can look after stays the same.

Agents change that arithmetic once the adviser hands the work on. An adviser who keeps redrafting the agent's output by hand carries the same workload as before, with a new tool to manage on top.

What this means for you

  • Agree which parts of advice preparation agents own, and write that down for every adviser in the practice.
  • When a draft misses the mark, send it back with the reason, so the brief improves for every adviser who uses it.
  • Protect the time advisers get back for client meetings, and measure it.
Retail

You lead store managers who are stuck on the register

In the SDA's Under Pressure report, 77% of retail workers surveyed were at high risk of harm from psychosocial hazards, with understaffing, workload and a lack of support from managers among the causes. In the SDA's 2025 member survey, 60% wanted more follow-up from their managers.

When a store is short, the manager covers the gap personally, and the coaching, follow-up and planning wait for another day. Agents can take a share of the administrative load once store managers hand it on, and that happens much faster when you, as area manager, make it the expected way of working.

What this means for you

  • Name the administrative tasks that agents own in every store, such as roster drafts, order suggestions and incident write-ups.
  • Ask store managers on each visit what they handed on that week, and what came back wrong.
  • Use the time saved for the follow-up conversations that staff say they are missing.
Healthcare

You lead clinicians who are buried in administration

In the RACGP's Health of the Nation 2025 report, 77% of GPs were dissatisfied with the amount of administration in their work, up from 70% a year earlier, and 69% reported burnout. In aged care, homes are working to a sector average of 215 care minutes per resident per day, and every minute a nurse spends on paperwork is a minute away from residents.

Clinicians are used to carrying everything themselves, because a missed detail can hurt someone. That habit makes delegation hard, even when an agent could prepare the referral letter or the care-plan review for them to check and sign.

What this means for you

  • Agree which administrative tasks agents prepare and clinicians approve, and make that the default at every site.
  • Give clinicians a quick way to send a draft back with a reason, so the brief keeps improving.
  • Measure the time returned to care, and share the result with the team.
Product engineering and manufacturing

You lead senior engineers or buyers who redo the agent's work

DORA's research found that AI speeds up the first draft of code, while the time saved is often spent again on auditing and verification. Senior engineers feel this most. When an agent's output needs fixing, rewriting it can feel quicker than explaining what went wrong.

Each rewrite done alone keeps the lesson in one person's head. The same thing happens in sourcing, where a buyer who redoes the agent's supplier comparison by hand will see the same mistake again next week.

What this means for you

  • Expect senior people to send agent output back with a reason, and count that as real engineering or sourcing work.
  • Keep specialist work with specialist agents, and keep the coordinating agent focused on coordination.
  • Review how much time senior people spend rewriting agent output, and treat a high number as a briefing problem to fix.
New energy and trade services

You own an installer and still do the paperwork at night

Battery installations grew so quickly after the Cheaper Home Batteries Program began that more than 457,000 were installed in its first 12 months. In many installation businesses, the owner or the senior electrician does the quoting, design checks and compliance paperwork after hours, because nobody else knows the jobs as well.

That knowledge is exactly what an agent needs written down. Until it is, the business can only grow as fast as one tired person can type at night.

What this means for you

  • Write the quoting and paperwork steps once, the way you would explain them to a new office manager.
  • Hand those steps to agents, and check their output each morning for the first fortnight.
  • Keep design approval and electrical sign-off with the licensed people who answer for them.
The short answerThe delegation trap is when a capable person, or a capable agent, does a task themselves because it is quicker today, even though handing it on would build the team's capacity. Coordinating agents fall into it too, doing specialist tasks themselves when they have enough context. The fix is a written rule to brief and hand on, and the discipline to send output back for changes.

Three slips in four days

My agent team has a coordinator. Its job is to take requests, write a brief and route each task to the right specialist through a shared task board. Over four days it skipped that job three times.

First I asked for a research brief before a meeting. The coordinator had the context, could see roughly what the answer would be, and did the research itself. Next came a research question on a new method, with the same result. Then I asked for a piece of writing and said explicitly that the writing agent should do it. The coordinator wrote it.

Each piece of output was fine, which is why the problem took me a while to see. Meanwhile the specialist never owned the task, the board had no record of it, and the coordinator got no better at writing briefs.

The manager on register one

Anyone who has worked in retail has seen this. A queue builds at the front of the store on a Saturday and the manager jumps on a register. It is the quickest way to clear the queue, the customers are grateful, and it feels like leadership.

If it happens every Saturday, though, the roster never gets fixed, the casuals never learn to call for backup, and the manager spends the busiest day of the week scanning items when they should be running the store. Most of us who have managed people have done some version of it.

Harvard Business Review makes the same point about first-time managers. Many people are promoted because they are good at the task, and that strength gets in the way once the job becomes getting things done through others.

My coordinator had the same problem for the same reason. It was capable, it had context, and doing the task was the shortest path to an answer.

Why it costs more with agents

The ceiling is higher. A manager who will not delegate limits a team of six. An agent boss who will not delegate limits a team that could run many tasks at once, overnight.

Microsoft’s Work Trend Index describes the agent boss as someone who builds, delegates to and manages agents. Delegation is part of the definition. Skip it and you have one very fast assistant.

There is an organisational version too. BCG’s AI at Work 2025 found about half of companies are moving from using AI for productivity to redesigning workflows around it. Redesigning a workflow is delegation at scale, because it means deciding who, or what, owns each step.

How to break the habit

Write a rule that runs before the task. I added a line to the coordinator’s standing instructions that names the habit and the alternative: “Do not do specialist work yourself. Write the brief, put it on the board, and let the owning agent pick it up.” The slips stopped.

Treat briefing as the coordinator’s main job. A coordinator earns its place by writing good briefs. The same is true of the manager on a Saturday, whose real job is making sure there are enough people on the registers.

Send work back for changes. When an agent’s output falls short, give feedback and ask for a revision. Every time you fix it yourself, you are back on register one.

Talk about it in training. Most AI rollouts assume capable people will work out how to delegate to agents. Many will struggle, for the same reason strong analysts often struggle in their first management role. Say it out loud: “You will want to do this yourself. That is the habit to break.”

Try this week

Pick one task you do every week that an agent could own. Write the brief: what is needed, what good looks like, the format and the limits. Hand it over and touch the output only to give feedback.

Time how long the brief takes. That is what delegation costs you, and it gets shorter every time, the same way a good roster gives a store manager their Saturday back.

Next in the series: the confidence trap, on what happens when an agent sounds certain and is wrong.

Your first move: wealth management

Ask three advisers to track one week of their hours. Find the preparation tasks they did themselves, write the brief for the biggest one, and hand it to an agent from next Monday.

Your first move: retail

Choose one administrative task every store manager does each week. Write the brief, hand it to an agent across the territory, and on your next visit ask each manager what they did with the hour.

Your first move: healthcare

Pick one document clinicians write every day, such as referral letters. Write the brief, agree the clinical check, and measure the minutes it saves over a month.

Your first move: product engineering and manufacturing

For two weeks, ask senior engineers or buyers to note every time they rewrote an agent's output. Turn the three most common reasons into changes to the brief.

Your first move: new energy and trade services

Before you write tonight's quotes, write down how you write them. Let an agent draft tomorrow's quotes from that brief while you check its work.

Questions readers ask

Why do good performers struggle to delegate?

They were usually promoted for being good at the task. Doing it themselves is faster in the short term and feels safer. Handing it on means accepting a slower, less certain result while someone else learns.

How do I stop an agent doing tasks it should hand on?

Write it into the agent's standing instructions: brief the task, put it on the shared board and let the owning agent pick it up. Then review what comes back and ask for changes, so you are not tempted to redo it yourself.

Does this apply to people managing agents?

Yes. Most people's first instinct is to fix an agent's output themselves. Each time they do, the agent learns nothing and the person stays the bottleneck.

Sources

  1. Learning to Delegate as a First-Time Manager, Harvard Business Review, June 2024
  2. 2025: The year the Frontier Firm is born (Work Trend Index), Microsoft WorkLab, April 2025
  3. 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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