Becoming a supervising lawyer: 4 mindset changes and lessons

There isn't a clear point when lawyers shift from a junior role to a supervising one. Somewhere between years 3 and 6 of my career, I went through that transition. There are plenty of guides on the "how-to" of becoming a supervisor (I've even written a few), but I wasn't prepared for the mindset change and self-reflection it takes to be a good one. In case it helps, here are some of the issues I encountered, the stories that guide my approach, and the lessons I picked up.

Issue #1 — "It'll be faster if I just do this myself"

When I became a senior associate, my partner warned me about becoming a 'hold point' for work. As juniors we get so used to doing the work ourselves that it's hard to start delegating — especially when we're the ones reviewing it. It's easy to think "it's faster if I just do it".

Story — "Who's got the monkey?"

There's a Harvard Business Review article, "Management Time: Who's Got the Monkey?". Tasks an employee brings to their manager are 'monkeys'. Often the employee brings a problem and the manager, instead of coaching them to solve it, takes it on — the monkey jumps to the manager's back. Managers end up shouldering many monkeys, which holds back their ability to manage, while employees never learn to handle the monkeys themselves.

Instead, the manager should keep the monkey on the employee's back, guiding and coaching them to "feed the monkey" themselves. Employees develop the right skills, managers focus where they add the most value, and bottlenecks shrink.

Lesson

There are times you have to take over a junior's work (tight deadlines and the like), but try to leave what's within their ability to them by:

• fixing a small part and giving specific feedback for them to fix the rest, instead of amending everything yourself;

• building timelines that give you time to review and them time to revise;
• providing guidance instead of answers; and
• having regular check-ins to deal with issues.

Whenever a junior comes to you with a problem, ask: does the junior still have the monkey, or has it hopped onto you?

Issue #2 — "I don't trust the juniors I need to delegate to"

In law firms, it's surprising how quickly some seniors label juniors as incompetent or lazy. A senior assigns a task, receives sub-standard work, gets frustrated, lowers their expectations, complains, or tries not to work with that junior again. The problem is this sets up a self-fulfilling prophecy — especially if that first sub-standard work came from poor instructions or unreasonable deadlines.

Story — "The Pygmalion experiment"

In a 1960s experiment, psychologists ran an IQ test on elementary students, then told the teachers that 20% were "high achievers". By year's end those students showed significantly greater improvement — but they'd been chosen at random; their actual scores weren't considered. The difference traced back to the teachers' expectations: increased attention, changed behaviour (more positive feedback, harder challenges, more support), and confirmation bias. So what happens when a junior is labelled "incompetent" off a few tasks?

Lesson

It stuck with me as a reminder not to underestimate the impact I can have on someone's career, and to:

• give clear instructions and set expectations;

• provide the right training and background for new tasks — an example end-product, or working through the first part together;

• take the time to give proper feedback; and

• hold off judging whether it's a skill issue (fixable) or an attitude issue (harder) until I've worked with someone for a few weeks.

Issue #3 — "I'll just teach them the way I was taught"

I once worked with a senior associate all the juniors complained about — a case study in bad management: harsh, personal feedback, intense time pressure, micromanagement. We assumed they just hated working with juniors. Over time we learned they genuinely thought this was quality mentoring: they'd been managed the same way and became a great lawyer, so they adopted the same approach. If juniors couldn't handle it, the thinking went, they wouldn't be great lawyers anyway. The problem is survivorship bias.

Story — "The bullet-ridden planes"

In WWII, Allied engineers studied returning bombers and found bullet holes concentrated in the same areas, so they added armour there. Survival rates didn't improve. A statistician pointed out they were only looking at planes that returned; the ones that didn't were likely hit in the other areas — so the armour belonged there instead. Survival rates went up. My colleague made the same error: focusing on their own success through intense 'mentorship' while ignoring all the juniors who were harmed or left.

Lesson

As we move into supervising, we need to reflect on the habits we picked up. Being a good lawyer doesn't make you a good supervisor. To avoid the same mistakes:

1. Get feedback — ask juniors what works for them and adjust.
2. Be flexible — different people need different support.

3. Prioritise learning — make mistakes part of the process, not something to fear.

4. Break bad habits — question the things you accepted as "normal" as a junior.

Issue #4 — "My feedback is really clear"

In my first year as a construction lawyer, I reviewed a couple of 300+ page contracts and drafted a due diligence report. My partner returned it with red amendments on basically every line. For days I thought I'd screwed it up and worried they wouldn't want to work with me again. After I made the changes and it went to the client, the partner said I'd done a good job — I'd picked up all the right issues, and they'd mostly rewritten it for their own style. The feedback was clear (every amendment was there), but I had no context to understand what was actually expected or missed.

Story — "Defects. Defects everywhere."

The best example of how important context is came when I engaged a building inspector to check a house I was thinking of buying:

Hi Jason, I've just finished the inspection. Before I send the defects report, I wanted to give you a quick overview. My job is to test every part of the house for anything that might be wrong, so the report will be about 40 pages and point out a lot of issues, which might look really bad. But overall the house is in really good condition, built well above minimum standards — one of the best I've inspected in years. Read the report, but remember it's written to set out only the negatives.

The report ran to 60 pages with 80+ defects. Without that call, I'd have thought the house was a complete dud.

Lesson

These remind me to add context whenever I give instructions or feedback:

• For a contract review, I might say I expect an accurate summary of all the key points, but not perfect writing style or a market-standard assessment — that's where I'll focus my review.

• With feedback, I point out what should have been in or out of their range of competence. A few amendments might be important and should have been picked up; a lot of changes might have been too technically difficult for someone new.