Nobody hands you a manual when you hire your first person. There’s no orientation packet for “how to tell another human their work isn’t quite landing.” I got promoted from Boss of Myself to Boss of Other People with zero training, same as every solo owner who’s ever brought on a VA or a subcontractor. One day you’re just… managing someone. You didn’t apply for that job. You gave it to yourself.
My first attempt at a “performance review” was, honestly, a Slack message at 9:47pm that said “hey great work this month!” and nothing else. My second attempt overcorrected so hard I basically read my subcontractor a legal deposition. Neither one was useful. Neither one was fair. And both times I closed my laptop feeling like I’d failed a test I didn’t know I was taking.
So I built my own system, the same way I built my invoicing process and my tax-saving spreadsheet — by getting it wrong first and writing down what I’d do differently. This is that system. It’s not HR-approved. I am not an HR person. I am a person who pays two other people and needed a way to tell them the truth without it turning into a whole thing.
The annual review template is built for a company that isn’t yours
I tried, briefly, to Google “performance review template” and use one of those. Big mistake. Every single one assumes things that don’t exist in my business: an HR department, a compensation band, a “career ladder,” a fiscal year anyone is tracking. One template asked me to rate my contractor’s “cross-functional collaboration” on a scale of 1 to 5. My team is me, a VA named Priya who works 10 hours a week, and a subcontractor named Marcus who does my video editing. There is no function for them to cross with. There’s just: is the work good, is it on time, do we still like working together.
The other problem with the annual model is the word “annual.” Twelve months is an eternity when your business changes shape every quarter. If Priya’s onboarding process for new clients has been quietly broken since March, I don’t want to find that out in December during a stiff, calendar-invited “review.” I want to catch it in April. Waiting a year to say “hey, this thing isn’t working” isn’t rigor — it’s just procrastination wearing a blazer.
So I ditched the annual cadence and the corporate rating scales entirely. What I needed wasn’t a more sophisticated form. It was a smaller, faster, more honest habit.
Three questions, once a month, no scorecard
Here’s the whole framework. It fits on a sticky note, which is the point.
- What’s working — the specific stuff to keep doing exactly as-is
- What’s not — the specific stuff that needs to change, named plainly
- What’s next — one or two concrete things to try before we talk again
That’s it. No point system, no “exceeds expectations” language that means nothing to anyone. I run this once a month, for 20 minutes, over a call or a shared doc if someone prefers writing. Short enough that it never feels like a Big Scary Meeting. Frequent enough that nothing gets to fester for eleven months before someone says something.
Real example, lightly disguised: last spring, Marcus was turning around video edits fast — like, suspiciously fast — and the quality had started slipping. Color grading looked rushed, a couple of captions had typos that spellcheck should’ve caught. In the old world, I’d have sat on that until some imaginary future review, gotten more annoyed every week, and eventually sent a passive-aggressive email. Instead, in our monthly check-in, “what’s not working” was literally: “the last three edits had caption typos, and I noticed color grading feels quicker than usual — everything okay on your end?” Turned out he’d picked up a second client and was overbooked. We adjusted his weekly hours with me down slightly, quality went back up, nobody had to guess what the problem was.
That’s the whole value of doing this monthly instead of annually: you catch the overbooked-Marcus problem in month three, not month eleven, back when it’s a five-minute conversation instead of a “we need to talk” email that ruins someone’s Tuesday.
Saying the hard thing without torching the relationship
Here’s the part nobody prepares you for: giving feedback to someone whose rent you’re partially responsible for feels different than giving feedback to a coworker. There’s a power thing sitting in the room whether you acknowledge it or not. So you overcorrect. You either go so soft the actual message evaporates (“everything’s great, just, you know, maybe think about deadlines sometime? no worries though!”) or you go so blunt it reads like a warning shot.
The fix I landed on is boring but it works: specific behavior, specific impact, specific ask. Not “your communication needs work” — that’s vague enough to be useless and vague enough to feel like a character attack at the same time, which is the worst combination. Instead: “The last two client emails went out a day after you said they would, and I had to cover for it with the client myself. Going forward, if something’s going to be late, ping me same-day so I can manage it.” That’s not harsh. It’s not soft either. It’s just accurate.
I also stopped sandwiching bad news between two compliments, because everyone’s onto the compliment sandwich now and it just makes people brace for the middle part. If there’s a real problem, I name it directly, early in the conversation, and then we move into what’s working and what’s next. People would rather hear the hard thing in the first ninety seconds than spend a meeting waiting for the other shoe.
One more thing that saved me from being either extreme: I write the notes down before the call. Not a script, just three bullet points per section. If I can’t write the “what’s not working” bullet in one plain sentence, that’s usually a sign I’m annoyed about something vague and mood-based rather than an actual, fixable issue — and I go think about it more before I bring it to someone else.
The review has to go both directions
This is the part I skipped for almost a year, and it was a mistake. I was so focused on “how do I evaluate them” that I forgot the scarier, more useful question: how would they evaluate me? I’m the client. I’m the one setting deadlines, answering (or not answering) Slack messages, paying on time or not. My performance affects their work just as much as their performance affects mine.
So now every monthly check-in ends with me asking, out loud, not as a formality: what’s one thing I could do that would make your job easier this month? The first time I asked Priya this, she told me I send her tasks in four different places — email, text, a shared doc, and sometimes just verbally on a call — and she was tracking my requests instead of doing the work. That was completely on me, and I’d never have found out if I hadn’t asked directly. Now everything goes through one shared task doc. Obvious in hindsight. Invisible until I asked.
If you ask this question and get “nope, all good!” every single month, that’s not a great sign either — it usually means the person doesn’t feel safe giving you the real answer yet, not that you’ve achieved managerial perfection. Keep asking. Eventually something honest comes out.
The actual template — steal this
Here’s the exact structure I use, copy-paste ready. I keep one doc per person and just add a new dated section each month.
Monthly Check-In Template
- Date and person’s name
- What’s working: 2-3 specific things, named clearly (not “good job,” but the actual behavior — “client responses have all gone out within 24 hours”)
- What’s not working: 1-2 specific issues, stated as behavior-plus-impact (“X happened, and it caused Y”)
- What’s next: 1-2 concrete actions either of us will take before the next check-in, with a rough date attached
- Ask them: “What’s one thing I could do that would make your job easier this month?” — write down the answer, even if it stings
- Ask yourself, after the call: did I say the hard part clearly, or did I bury it? Be honest, this bullet is just for you
That’s the whole system. Twenty minutes, once a month, six bullet points. No rating scale, no HR jargon, no pretending you’re a Fortune 500 company with a performance-improvement-plan process. Just an honest conversation you have on a schedule instead of by accident, whenever you happen to be annoyed enough to bring it up.
I won’t pretend I run this flawlessly. Some months I show up to my own check-in with Priya having written nothing down, and it turns into a vaguer conversation than I’d like. But even a sloppy version of this beats the version where feedback only happens in a crisis, or never happens at all until someone quits and you find out in the exit conversation that they’ve been frustrated since February. Small team, no manual, still figuring it out — same as everything else about running this business. At least now I’ve got three questions and a sticky note instead of a Slack message sent in a panic at 9:47pm.