Skipping straight to the point, here’s the agenda:

1. How are you? Life is full of peaks and troughs. Where are you at right now, and what’s the trajectory?
2. Anything you want to brag about? Professional or personal!
3. What’s one thing we could change about work for you that would improve your life?
4. What have you been putting off? What is concerning you?
5. Are you fulfilled by your work? Are you getting the support you need?
6. What are your long term goals? Are we helping you achieve them?
7. Is there a skill you would like to develop, or a qualification you would like to obtain?
8. How are we doing against our agreed actions? Do we need to set new ones?

Each question is important, the order matters, I’ll break this down further later on.

Where this came from

A few years ago I received feedback from my team that one-to-ones weren’t really working for them. The adhoc chats, taken as needed, had failed to scale with the growth of the team and business.

I’d dialled them back from an originally weekly frequency, we met in person each Monday back then, as I found hours of back-to-back talks brutally draining.

That feedback was a wake up call that I wasn’t sufficiently serving my team and nascent department. With only further growth in the future, I needed to work out something that worked for the team, but also for me.

What are one-to-ones for?

A big part of what I aim to achieve with Cronofy is providing an environment where people can do their best work and achieve the personal growth they are looking for.

By enabling people to do their best work, we create a high performance team, which can then be used to create more high performing individuals through modelling.

As a manager, this can be most influenced by eliminating friction in the day-to-day, and coaching on longer term individual- and collective growth.

One-to-ones form a key part of that function as taking a regular step back from the day-to-day to ask questions about the environment, their successes, their progression, in order to keep a collaborative eye on all those things.

Forming an agenda

With a goal in mind, I chose to dial down the frequency, but counter by dialing up the intent. I choose a monthly frequency as, particularly when it comes to growth, this felt like a period of time over which someone could make progress and need to re-evaluate.

More frequent than that and there was little chance for meaningful change between. We already had a six-monthly review cycle in process and so this felt complimentary to that cadence; providing 5-6 check-ins, focussed towards growth and the removal of friction, between reviews.

There’s room for more frequent “how are you” catchups between, but this is the meeting to remind and focus people on their personal development.

An agenda is important for two reasons:

1. It allows both parties to prepare.
2. It ensures nothing important is missed.

Breaking down the agenda

In the early days there was a fair bit of iteration on this agenda to zero in on something that worked well. It’s been settled for a couple of years now spread throughout other departments of the company too.

This is a breakdown of the agenda, and the purpose to each question.

How are you? Life is full of peaks and troughs. Where are you at right now, and what’s the trajectory?

You are speaking human to human, you want to find out what’s going on in their life. If there’s anything in the background you need to be aware of or can potentially help with.

This also gives you both the opportunity to ease into one-to-one mode with a bit of a catch up.

Anything you want to brag about? Professional or personal!

I like to get people to realise the positive outcomes in what they have done. Some work takes longer than expected and they can focus on that, but there’s still been value delivered to customers and that needs some celebration.

You may have to provide some examples of this to begin with. Set the benchmark of what is brag-worthy with them, or simply get people to start noting brag-worthy things they are doing.

This also helps seed history for both of you when it comes around to review time.

Use your curiosity here. You’ll be hearing things that they are self-identifying as being examples of their high performance. Why do they think of it as high performance? Was there something they did differently in that situation? Are there practices that could be translated or replicated in future work?

What’s one thing we could change about work for you that would improve your life?

This is where you can find problems you can help with as a manager.

Anything highlighted here is significant enough friction in their work that you want to get to the bottom of it. People cannot perform at their best if they feel they are being held back.

There may be issues with team dynamics, working hours, desk setup, and so forth. We give a lot of automony to our employees but some people, especially new employees, need a nudge of “buy what you need on your prepaid card” or “that would be a great topic to bring up in the next retrospective”.

Of course, sometimes you will need to take charge rather than empowering them, but I tend to try and help assist people in solving problems themselves. Either approach requires you find out what problems they are having first.

What have you been putting off? What is concerning you?

These questions can heavily overlap with the “change” question, but opens the table for problems where they may not have a solution in mind.

Examples might be:

• I’ve been meaning to book some personal development days but not gotten around to it
• We’ve been working on X for a while and I’m still not confident in that area

This tends to bring up topics where you can do some coaching, or problems that you may want to raise with the wider team.

You will often find they know what needs to happen. However, anxiety often prevents bold actions that can help the team either improve or retain their current level of performance.

There’s often a growth opportunity lurking in these situations which you can open up for them.

Are you fulfilled by your work? Are you getting the support you need?

Work is sometimes unfullfilling, but that shouldn’t be a long term state. For software engineers there are sometimes yaks to shave or unrewarding bug hunts that are a necessary part of the role. However, if someone feels they are receiving an unfair share of this burden, that’s something you can solve.

You can also coach them in finding fulfillment in such tasks, seeing the wider picture, reminding them of why such work matters. Sometimes there is an opportunity to experiment with a new tool or approach alongside the known tedium. A spoonful of sugar can help the medicine go down.

Even when finding their individual efforts fulfilling, they may feel isolated from the team. Beyond the obvious of them requiring more support than they are receiving, this can also signal whether they feel part of the collective.

What are your long term goals? Are we helping you achieve them?

A key part of longer term fulfillment and performance for employees is the sense that they are progressing their career at your company. As a manager you want to facilitate that progress the best you can, creating a long term, sustainable pace to their work.

Some people don’t have a clear idea of what their long term goals are. This can be a project that you work with them on. Helping them self-identify where they want to go makes for a development plan they can commit to, and makes it more effective as a result.

Even with a clear idea of where they want to go, even with the best will in the world, the company may not be helping them get there. If that’s the case, you need to know that so you can resolve it.

In the extreme case they may be looking for progression you cannot provide. You might not be hiring at a pace that creates the opportunity for them to lead their own team for example. In such situations you will want to have a candid conversation about whether their aspirations would be better served by another company who can offer the opportunities they are looking for.

It’s tough, but in that situation you’re likely losing the person anyway. Better for it to happen in an open and amicable way.

Is there a skill you would like to develop, or a qualification you would like to obtain?

Some elements of career progression can be tied to binary activities such as achieving a certification. Many others relate to more amorphous skills like “leadership”.

Using leadership as an example, as a manager and coach you can suggest areas of investigation such as books you’ve found useful on the subject. You can also facilitate practical activities like asking their team lead to get them more involved in the leadership of the team. For example, running the team’s next retrospective.

Either way, this question helps surface concrete actions that can be taken by them in progressing their career and making them more effective in their role.

How are we doing against our agreed actions? Do we need to set new ones?

Some issues flagged can be solved on the spot, others require further work. Many activities towards career progression work on a horizon of months. To make sure such things are not forgotten, we have a rolling record of actions owned by either myself or them.

It can be useful to assign a due date as well. Some activities are consciously deferred so the can receive more focus, and that’s fine, but you don’t want to lose sight of them entirely.

Pushing from multiple angles

There is some deliberate overlap from these questions, many push towards surfacing problems from different directions:

• What’s one thing we could change about work for you that would improve your life?
• What have you been putting off? What is concerning you?
• Are you fulfilled by your work? Are you getting the support you need?
• What are your long term goals? Are we helping you achieve them?

A broad “anything I can help with?” isn’t as likely to illicit a response, what these questions do is maximise the chances that you ask a question that fits a problem in the way they perceive it.

The worst drag on individual and team performance are issues you aren’t aware of. You can’t help with something you are unaware of.

In a similar way there is overlap within:

• What are your long term goals? Are we helping you achieve them?
• Is there a skill you would like to develop, or a qualification you would like to obtain?

Sometimes there’s clarity in the answers to one question but not the other. In an ideal world the two are symbiotic, the actions should relate to the overall goal.

If the goal is unclear, digging into the actions can help flesh out the goal. Similarly if the goal is clear, potential actions become more obvious. If there’s a mismatch, that can indicate the goal has changed, or the action isn’t the best thing they could be doing for their growth.

Don’t take “nothing” as a consistent answer

Hopefully, you’ll not have many problems to solve from month to month. In fact having none is the ideal state. However, whilst I don’t have a firm rule, if I’ve not even heard a grumble for a few months I pretty much force them to raise something.

There might be something that they feel is too trivial to raise, but that’s still an issue that exists and could grow over time. Highlighting it can avoid it ever becoming a signficant problem and impacting the performance of them or their team.

Sometimes you’ll find out there’s actually a big issue and they are the proverbial boiled frog. This should be rare, but it is possible and you want to know.

Growth and performance

Through this one-to-one framework, alongside collective practices such as retrospectives, we maintain a close eye on individual and team growth.

This framework has been effective for myself as a founder, and my team as a collective and individuals.

People feel heard, empowered, supported, and fulfilled in their day-to-day work as well as in their longer term career progression.

This creates and nurtures the environment necessary for people to do their best work, which leads to high performance.