A First Principles Guide to One-on-Ones (Part 3)

Part III – HOW to run a one-on-one

 In Part I, we’ve established the purpose of the one-on-one, and in Part II, we have created a framework that allows us to tactically prioritise topics across various one-on-one series in service of it. In this last part, we’ll put it all into action.

Congratulations, the bulk of the intellectual heavy lifting is in the bag. Now that the purpose and priorities of the one-on-one are clear, we can confidently proceed to determine the operational details. I’ll structure this section chronologically, as if you’d never had a one-on-one and are now setting one up for the first time, starting with the frequency and duration of all of the one-on-one series you will have, moving into how you can use a template to set up a particular one-on-one series, and finishing with some practical aspects of running a singular one-on-one meeting.

Setting frequency and duration

Before we can think about the frequency and duration of a particular one-on-one series, we have to establish your time budget for all of your one-on-ones. And best way to do this is by way of a calendar exercise.

The calendar exercise is a practical and basic routine that I believe is very helpful to do anyway every 6 months or so. In lieu of a full-blown guide for it, and in a nutshell, this is what you need to do:

You take the past 8 weeks of your calendar and aggregate any meetings or time blocks you’ve had into clusters. How you define your clusters is subjective, it depends on what you think are your most relevant blocks of responsibility, but as a start, you could base this on (what I believe are) the 4 core responsibilities of a CEO and break these down further where you need more granularity.

Choosing about 5 or 6 clusters usually works well, but there is no hard cap - whatever works for you.

That’s the easy bit. The hard bit is DECIDING, how much impact these clusters each generate for the company, and based on that, how much time you want to spend on each of them and then adjusting your calendar accordingly.  

In any case, and to give you an indication, I think that 60 minutes with each of your direct reports per week (if more junior/less familiar) or every two weeks (if more senior/familiar) is a healthy starting point. So, if you have 6 direct reports, 4 of which are experienced, and you have already worked with them for some time, and 2 of which are new to the company or your team and require you to spend more time with them, the math goes: 4x1h bi-weekly + 2x1h weekly = 4h per week. Net it’s probably closer to 4 ½ hours, factoring in that you will need a bit of time to prepare and follow up on meetings and that you will have other leadership-type meetings with your direct reports at larger intervals (Performance Review, Feedback, Career planning, see Part 2 for more details). 

You should not have more than 8 direct reports. If you do, it only means that you have not managed to find the right people or properly develop people into responsibility, and it will require you to spend too much time solving operational matters and not leave you enough time thinking about how you will shape the future of your company. Take it from a sinner: I had 16 direct reports at a time. That was stupid. I took great pride in my operational abilities, and it slowed us down. And it did not give me the time to work and engage with my team the way I should have.

This is no small amount of time, but I think it’s justified by the purpose: Time spent with the leadership team building trust and securing alignment will allow you to scale yourself, and it will make the organisation you are running a lot stronger over time (as established in Part 1).

However, if you need to cut down from that (temporarily, I hope), I have two suggestions for you:

• - Cut frequency before duration. Going from 60 to 45 minutes can be fine, but 30 minutes makes the meeting feel too rushed.

• - Cut senior before junior. When cutting the frequency, start with the most senior and trusted reports. If you know each other well, longer pauses will not require you to spend more time to catch up or warm up, and a senior will not have as much need for frequent feedback, guidance, alignment – and if you know each other well, and if there is a pressing matter, the senior will find ways to raise it with you between meetings. Don’t go below a monthly cadence, though.

So just for the sake of completeness, let’s say for our example-case from above that it’s fundraising time and because of that you feel the need to cut your gross weekly one-on-one budget from 4 to 3 hours for the next quarter or two: you could do that by putting the three most senior/self-directing reports on a monthly schedule, the fourth that needs a bit more operational guidance you keep on a bi-weekly cadence but cut the meeting time to 45min and the 2 juniors stay at 1 hour weekly. 3 x 1h monthly + 1 x 45 bi weekly + 2 x 1h weekly et voilá.

Shortening meeting durations or lowering frequencies will sometimes be met with resistance because it can feel like a degradation or de-prioritisation for the direct report. But if it needs to be done, it needs to be done, and a good direct report should and will understand this (particularly if you have a good basis of trust, for which this can be a bit of a litmus test). 

Designing a one-on-one series

With the time budget clear, we can move on to designing a particular one-on-one series, based on the topics framework we’ve created in Part 2.

This is something that you should do together with your direct report. And for this, a template is the perfect basis, because it allows you to carry the qualities of the framework - flexibility and structure - into a one-on-one series. It can look as simple as this:

The template will serve as an alignment artefact for you and your direct report. You will use it to agree on the (initial) focus of your one-on-ones, to remind yourself of it before a meeting, and to adjust how you run the meeting series over time.

But let’s not get ahead of ourselves. Let’s run the initial, template-populating meeting first.

I would start the meeting by asking the direct report a couple of questions first before looking at the template to make sure their thoughts are captured fully and to establish that their thoughts matter, and that this meeting is about finding out what works best for both sides, and not to follow some pre-determined scheme.

Good open questions to ask are: What would be the greatest value for you to come out of a one-on-one with me? How much alignment, feedback or guidance do you seek, on what specifically? Are there any particular topics that you would want us to cover? What else do you expect from the meeting? What has worked for you in one-on-ones you’ve had in the past? What has not? To what degree have you been responsible for conducting the meeting in the past, and how did you prepare for it?

Share any thoughts you might have on this. Then, share your thinking. Talk about what purpose the one-on-one has for you and what you want to focus on. This may all sound a bit mundane, but taking some time to establish the purpose and reflecting on what you want to achieve by meeting once every week or every two weeks really increases the intent and the quality of what you get from these meetings from the get-go.   

Then talk through the template and adapt it jointly so that it suits both of you. If, in doing so, the times allotted to the purposes you have both identified as relevant exceed 60 minutes (or the duration that you have allotted for this particular one-on-one series), start cutting selectively (it’s much better to prioritise than to cut equally or proportionally across all purposes). Then make use of the notes section to highlight subjects you want to pay particular attention to, or to agree on goals (if any, but if there are, also note down the review periods for these).

Lastly, set out the meeting frequency. Again, it’s your time budget that sets the limits for this, but it’s also worth listening to why your direct report might think they need more time with you and re-evaluate if you’ve been presented with new considerations.

Finally, put the participant’s name and the creation date on it, and you have a working document and an agreement that you can both relate to.

A finished template for a one-on-one with a new CSO might look something like this:

With this done, fix the schedule for the next 3 months. Try not to reschedule.

After 3 months, have a review session. Have you had productive meetings? Did you roughly manage to stick to the priorities and periods over time? If yes, do you want to continue like this? If no, do you want to adjust them or do you want to commit to more meeting discipline (and how will you hold each other accountable)? Did you reach the goals you had set in the notes or did you clarify what you had highlighted there (if any)? What has worked particularly well for you? What has not? Do you want to (or need to – see below) adjust the meeting duration or frequency?

Then start the next 3-month cycle.

Running a one-on-one meeting

A good one-on-one needs to centre around the current and the relevant. Each meeting, most of the time, should be about what matters now. Anything else will feel terribly contrived and administrative. Basically, any one-on-one starts with the question: “What is the most important thing for us to talk about today?”.

So why again the template, you ask? Because as much as it’s important for each meeting to be relevant in the now, it is important to have a clear frame for the kind of “current and relevant” that you want to talk about (and in particular to not transform the one-on-one into an operational problem-solving meeting - see Part 2). The template serves to guide you through a series of one-on-ones with consistency and purpose. It does not determine the details of each particular meeting.

In conducting the meeting, the following 3 simple rules have worked well for me:

Preparation

The meeting uses valuable time from some of the most expensive employees of the company. Not using it efficiently is a crime. So both participants should be required to come prepared. If you have one rule for the meeting, this is it. For the direct report, that might mean that they are required to send you an agenda of topics that they want to talk about a day before. For you, it means at least taking 5 minutes before the meeting, looking at the template and the agenda (if any) and reminding yourself of the priorities. If you’ve made notes of the last meeting, have a look at them too, and ask yourself what matters to you today.

No phones / Note taking

We’ve established in Part 2 of this Series that making space for trust to develop is paramount for the value of the one-on-one. And nothing prevents this space from becoming present more thoroughly than giving the impression that you have more urgent things to attend to, which is exactly what you convey if you look at the screen of your phone, or even have it lying next to you face down. So both participants should be required to leave their phones out of sight.

Laptops have a less devastating effect, but it’s also better if they're not present. It simply creates a different stage for both of you to connect.

How to do note-taking? What has worked well for me is not to write down anything in the meeting, but to take the last 5 minutes of the meeting to jointly revisit any actions or to-dos that were discussed in the meeting and write them down in Slack/email/Notion/ whatever else you use to prepare and track the meeting. If you feel that you need to take notes in the meeting, use pen and paper and digitalise them now.

As often as possible, take a couple of minutes after the meeting to reflect on it and to note down any additional observations or epiphanies you’ve had. This is part of the preparation for the next meeting.

Listen more than you talk

This is self-explanatory, but if you’re a bit like me, not easy to do. Write it down as a self-imposed task in your template and remind yourself of it before the meeting. Ask yourself after the meeting if you did it well, and you’ll get better at this.

And with that, I conclude this guide. It’s been a lengthy journey, I know, but I felt the need to build out a solid, principles-based derivation of what the one-on-one is about to give it the clarity it deserves and - hopefully also - to give you reason to feel confident in pursuing it with purpose. May you have great one-on-ones that take you and your leadership team to new levels of excellence. Good hunting.