How to run Successful 1-on-1s
How well do you really know your team?
Hey team hapy Tuesday!!
Big update from HQ, we’re opening up Custard today to another 50 teams, which feels so crazy/exciting that we’re already on the full second cohort. I can’t wait to meet some of you inside.
Eventually, Custard will be open full-time, like most tech products. But right now, I’m making a very intentional choice to grow it sustainably.
I’ve got an incredible audience ready and waiting to buy. I could open the floodgates today. But I’d rather build out our support, onboarding, and tech properly first, so that everyone who comes in gets an exceptional experience (not a rushed one).
But today I’m coming back around to my FAVOURITE topic… The 1:1
We cannot escape them as managers. Infact, they’re one of the single most important levers we can pull to improve our culture.
However, the traditional ‘appraisal’ system is wildly outdated and if we don’t switch it up we’ll get left behind. Instead, we need a system that runs seamlessly to understand your team, so you can continue to challenge and fulfil them at work.
Luckily for you, I have spent years testing and refining this system, experimenting with the questions, the frequencies and more, so it’s now literally plug and play ready for you to start using.
Today I’m laying out my 4 step 1:1 system, and I’ve linked out an agenda below so make sure you scroll to get those.
The mistakes
I train leaders inside some of the planet’s most successful organisations, and the mistakes I see over and over are:
The 1:1 turning into a regular status update, or just a task check-in, without making the space to talk about deeper stuff
The manager cancelling
Assuming our team's priorities are the same as our own (eg. You want promotions & pay rises, but they prioritise creativity or rest).
Only doing ‘appraisals’ annually (Bottling up feedback, praise and general performance improvement work until it’s all way too late).
Just saying ‘my door is always open’ (This isn’t enough, our team naturally don’t want to ‘bother’ us).
The method
Each employee should have:
Every year - Salary Review
The annual review exists to make sure each employee is paid fairly and has a real space to talk through their wins and the reasoning behind them, so the leader has the full picture and the employee has the best possible chance of a fair outcome.
One tip: ask the employee to bring a short written case beforehand, covering their wins and impact, so the conversation starts from evidence.
But what if they ask for something I can’t give them? Transparency is your best friend here. Be honest. Set realistic expectations from the get go.
Every 90 Days - In-depth 1:1
A successful 90 day 1-2-1 is a space that is dedicated to, and properly used for 2 people to open and honestly discuss performance, personal development, and feedback. Both parties will prepare answers to each question
Every fortnight - 30 mins
No agenda needed here. Just some simple rules:
30 minute calendar entry, regularly occurring every 2 weeks
You (the Leader) can NEVER cancel it. The team member may, but never you.
No agenda needed, this is just space being held for you and your team member to bring anything important to you
Every day - Regular, unignored praise & difficult conversations
Challenge your team at the time, never bottle it up. Don't discourage emotion (It isn't weak. It shows that you care). And never, EVER ignore the difficult conversations.
What’s next?
It’s not actually helpful for you to consistently nurture each of your teams wishes & priorities, if someone prioritises spending time with their children, you shouldn’t be figuring out how they can do the school run, that’s on them.
But you need to build a workplace that creates a healthy and fulfilling environment for all, that works for your company and your values. Rather than having different rules for different people.
You need to KNOW these priorities, you need to ensure your team are consistently working on them, and you’re holding them accountable to pushing towards them.
So ultimately, you’re not pushing them in the wrong direction.
What do you struggle with most around 1:1s? Let’s chat in the comments
Peace,
H x
I have a team member that will agree they aren't meeting expectations in an area and then won't follow through. As a manager I'm finding it hard to keep track of when exactly they fall on the wagon and I cannot for the life of me keep them on track. It's causing other teammates to suffer.
Layering the cadence like this gives each conversation room to breathe instead of cramming everything into one meeting.
Protecting that fortnightly no-agenda call is a small habit that builds a lot of trust over time.
Keeping salary talk separate from daily feedback lets both conversations stay genuine.
This system really shines once the daily praise and honest check-ins become second nature, not just something scheduled.