A First Principles Guide to One-on-Ones (Part 2)

In Part 1 of this series, we have established that one-on-ones have the purpose of improving the quality of a leader’s direct reports and of their relationships with them, and that – despite the opposing practices of Jensen Huang and Elon Musk – the private dialogue between a leader and a direct report is the most efficient way to achieve this goal for most of us.

We will now determine how to design a one-on-one according to this purpose.

WHAT to focus on in one-on-ones?

What topics shall we focus on in a one-on-one? A plethora of articles, texts and references exist on one-on-ones, providing a broad range of suggestions, ranging from career development to operational topics, dealing with workplace challenges, goal setting, feedback, private discussions and motivational issues.

Unfortunately, none of this helps. These examples are not necessarily wrong, but they are just that, examples. Without a logical derivation, taxonomy or priority, they provide no guidance for their application.

One-on-one interactions are context-dependent. We’ve seen in Part 1 that the seniority of your direct report impacts how you can run your one-on-ones. But also your role, the maturity of your relationship with the direct report, and the current set of challenges each of you is faced with play a role. And all of these change over time. So we need some flexibility in setting the focus.

As a general rule, strict repeatability is great when your priority is to ensure conformity of outcome or standards over time and across individuals. This is the case when there is a stable and repeatable goal, e.g. when you teach fishing. Everybody who enters the class has the same goal and will have to pass the same exam to get a license. But there is no such conformity of outcome if you are the leader of a variety of individuals with different strengths and weaknesses and a different set of responsibilities. In such circumstances, adjusting the focus of an interaction results in far better outcomes.

But at the same time, we also need some consistency. Not only for the sake of efficiency and not having to reinvent the wheel for each one-on-one, but also because consistency allows us to observe how our one-on-ones develop over time and understand patterns across various direct reports. And consistency allows us to keep working on long-term developments and goals and accumulate improvements over time in a meaningful way.

Ideally, we would have a framework that provides a consistent set of topics and a logic that allows us to choose from these based on the relevant circumstances, right?

Let’s build one then!

Our first step must be gathering suitable topics. Suitable is what serves the purpose of the one-on-one.

By way of repetition from Part 1: The only way for a leader to scale is through their direct reports. It requires the direct reports to decide and act based on their own judgment but do so in alignment with the leader. This ability of deciding autonomously but aligned is based on two things: the quality of your direct reports (their capability and knowledge to make decisions based on existing or deductible patterns of thought) and the quality of your relationships with them (the swiftness, clarity, openness and robustness with which you can exchange views on matters and align when new patterns of thought are needed or the application of existing patterns is unclear).

Ergo, suitable topics must have the potential to improve the qualities (1) of the direct report or (2) of the relationship between the leader and a direct report. This is our initial search area. But I think we can go one step further: Because we’re all human, both of these aspects not only have a factual, but also an emotional side. This gives us a search area of four quadrants to populate with suitable topics.

Before reading on (inevitably becoming tainted by my thinking): what topcis can you think of?

Spoilers ahead.

Last Chance.

Ok, the ones that I can think of are these:

But this collection is not yet helpful. We cannot possibly go through all of these in each one-on-one. So, as a next step, we must filter and prioritise these topics (or any other you have come up with), based on these two qualities:

• - Importance: Does the topic matter enough to be a regular part of a rather frequent routine of the most limited resource a company has (the time of its CEO)? and

• - Suitability: Is the one-on-one the right and most efficient format to address the topic?

Let’s put my shortlist to the test. Starting at the upper left corner and moving clockwise:

Trust

Does it matter enough to be a regular part of a rather frequent routine?  

Yes. Nothing has a bigger impact on how well you work with your direct reports than the level of personal trust that exists between you and them. Because without trust, there can be no candour. Without candour, there can be no untainted, truthful exchange of opinion and information. And without that, it’s impossible to have productive working relationships or to form a high-performing leadership team.

Is the one-on-one the right and most efficient format to address it?

Before we can answer that, we have to address how one can build or work on trust in a one-on-one. This is not straightforward, because “working on trust” is not an objective in the sense of a planned activity or something that you can request. It’s a mindset. And you have to make a time allowance for it, because being in this mindset and acting in accordance with it will take time out of the meeting, sometimes considerably.

This mindset is characterised on one hand by genuine interest in the other person (which can mean that you stay with a topic for a little longer if it helps you to understand better) and an openness toward the other person that is both truthful and vulnerable (which can mean that you take time to share thoughts or to relate to things you hear).

Getting into this mindset takes practice (I’ve been at it for years, and it still eludes me at times). But for starters, take a couple of minutes before a meeting to make yourself aware and become positive about the fact that you will now spend time with another person to understand and relate. If you manage to do that, you will behave differently in a one-on-one. Not only will you become more eye-level in your demeanour, but you will also be (visibly) more relaxed about spending time on non-operational matters, and you won’t feel as much of a need to rush to the next topic. This creates the space for trust to happen, and it exudes interest and appreciation without words, which is a great basis for openness and building trust.

So, yes. The best way to work on trust is in a one-on-one setting, where you can make the space that trust needs.

And because you cannot actively “make” trust, but only create the conditions to let it happen, I will refer to this topic not as “trust-building” but as check-in space from hereon onwards. It’s better and more descriptive, and while it does not have to happen at the beginning of the meeting, I think it gets the point across that you’re deliberately setting aside time to hear how the other person is doing.

Verdict:

This is my number one topic for a fresh-ish relationship, and the number two if a good level of trust has already developed. Never lower, though. Like a private relationship, a work relationship needs attention to stay great.

Motivation

Does it matter enough to be a regular part of a rather frequent routine?  

Motivation is what drives people to expend their energy in the workplace. It’s important. More important than, say, the qualification of a person, because motivated, unqualified people will improve over time, and their motivation can be contagious. Qualified, unmotivated people, on the other hand... I know it’s apples and pears, but you get my point.

Motivation is highly complex, though. It’s a personal sentiment, and is impacted by many forces, not all of which are suitable for a one-on-one. I therefore distinguish between:

- Avoiding demotivation: Detecting signs of demotivation early and identifying its causes is super useful and usually does not take long. Check.

- Actively increasing motivation: Not in my book. Having the one-on-one demonstrates to the participants that they matter to you, which is usually a positive motivational force (and you will quickly get a feeling of just how much power it has, when you suggest decreasing the duration or frequency of the meeting) and also, a little praise goes a long way, but I don’t see motivation as something that should require you to regularly feed the flames. At least not the healthy kind of motivation. So I don’t think actively increasing motivation is a good one-on-one purpose. 

Is the one-on-one the right and most efficient format to address it?

To detect/avoid demotivation, yes, as the setting allows for openness. But if the cause of frustration is another colleague, the discussion must be quickly moved to a meeting with all the concerned parties.

Verdict:

It’s not a stand-alone topic for me, and more of a question that can be asked in the check-in space. Ideally, this is based on an observation “hey, I have noticed that you acted/did/said/behaved … is something the matter?”. An unrelated question along the lines of “How high is your motivation right now?” sounds wary and usually doesn’t result in much insight.

Private issues

Does it matter enough to be a regular part of a rather frequent routine?  

Personal life issues may affect work, and it’s good to be aware of them. Not so much because you can do much about them, but because you will understand current moods/sensitivities better and be able to give better impulses or feedback. Be aware of what kind of relationship you want to have, though.

I, for one, always wanted to understand any issues that my direct reports had, and I deeply cared for them, but I did not want to have a friendship-type of relation with them, because in my role, the company would always have to come first, while in my personal value system, friendship takes precedence over work. I simply did not want to put myself in a position where I would have to trade my values for my responsibilities or vice versa. When you’ve started a business as a group of friends, you don’t have that choice. It sucks, but if you’re the CEO, you will need to prioritise to do what’s best for the company over what’s best for your friend (you will do what’s best for the shareholder in your friend, but that never compensates). The best solution to this dilemma, I think, is addressing it early and proactively. But I digress…

Is the one-on-one the right and most efficient format to address it?

Yes, it’s the only setting that makes sense.

 Verdict:

Like Motivation, this is also more of a check-in space topic than a stand-alone one.

Feedback

Does it matter enough to be a regular part of a rather frequent routine?

A resounding yes for me. I cannot possibly go into the depths of why feedback is great and how to give and receive it well, but giving timely feedback on behaviour that you have noticed improves the development of the participant as a leader and a team player and also the relationship you have with them. This is where the one-on-one can also be about you if you invite feedback from the participant – just don’t make it the main point of the meeting.

Is the one-on-one the right and most efficient format to address it?

Talking one-on-one is the best way to exchange feedback. But there does not need to be feedback in every one-on-one meeting. Creating a habit of giving feedback is great, though, and I would wager that once you get into the habit, you will start noticing more stuff worth giving feedback on.

Verdict:

It’s in my Top3. But that’s not enough, because most of the weekly/bi-weekly feedback will be situational: “Hey, I noticed something in our last meeting with XYZ…”. Sharing these small observations is very valuable. But you should also have a more formal bidirectional feedback session with your direct reports 2-3 times every year to address the longer-running behavioural traits and developments.

Teaching/Mentoring

Does it matter enough to be a regular part of a rather frequent routine?  

This very much depends on the seniority and experience of the participant. Closing a relevant knowledge or experience gap will expedite the development of the participant, allowing you to delegate more relevant tasks at an earlier point in time. That’s time well spent.

Is the one-on-one the right and most efficient format to address it?

Yes – the best learnings are specific and therefore usually of an individual nature.

Verdict:

If the participant needs it, it would be high on my list. For more senior participants, it’s just something to be mindful of.

Career planning

Does it matter enough to be a regular part of a rather frequent routine?  

I am a big fan of Daniel Pink’s motivation theory, according to which “mastery” is a strong motivational driver. We all want to get ahead. It’s why titles exist. So this is an important aspect of motivation to be aware of. But as I already said above, I don’t think motivation is something that you should (need to) discuss on a weekly or bi-weekly basis. But do listen, if a participant actively wants to talk about their career, or you will create a flight risk eventually.

Verdict:

It’s not on my list. But it makes sense to have a yearly conversation about career advancements or personal developments with each of your reports.

Alignment

Does it matter enough to be a regular part of a rather frequent routine?  

Very much so. A leader can scale themself only by having direct reports that act autonomously and in alignment with them (see Part 1). So alignment is literally half of the requirements of a functioning leadership team, and a major reason why we do one-on-ones. But we need to clarify the term, or rather qualify it, because “alignment” is often used for an agreement or understanding that is too high-level to be meaningful. The quality or depth of alignment that we seek is determined by the information and understanding that’s necessary for a direct report to make decisions that work for you. This means that alignment often needs to be quite granular, sometimes down to a detailed operational level. It’s not enough to share the same goals; you also need to share the same understanding of how to achieve them: what are the most important steps, which principles and priorities guide the way, what problems exist, in what order do they need to be addressed, etc.

Going this deep with a direct report does not mean that you are micro-managing. You are not solving problems and making decisions for your direct report. You are preparing them so that they can do it without you in a way that works for you. That is a huge difference.

Is the one-on-one the right and most efficient format to address it?

Absolutely. Alignment requires bi-directionality at all times – talking and listening – and time to get to the bottom of things, where understanding dwells. This kind of intensive exchange between two people is at odds with a group setting. Also, the openness required from a participant to voice a dissenting opinion from yours and the intensity of discussing different points of view are much better achievable in a one-on-one setting.  

Verdict:

This is the number 1 topic on my list (number two only if the existing trust between you and the participant is yet underdeveloped or in shambles, in which case trustbuilding is No. 1, see also above).

Goal setting

Does it matter enough to be a regular part of a rather frequent routine?

Like mentoring, it depends to a large extent on the seniority of the participant.

Goal setting can have three functions: (1) providing motivation by giving a reachable, ambitious target, (2) measuring progress/success, and (3) ensuring clear priorities.

All three can be relevant when your direct report is an individual contributor or a junior manager. But they become a lot less relevant as your report matures. Or at least they should, because when a report develops into a manager or leader role, their area of responsibility increases. This brings about that personal goals become less important and get replaced by team, area or company goals (which should be set by way of a prioritisation or planning process to allow the company to work in lockstep and not in an isolated meeting). Likewise, their personal progress or success gets replaced by the measurement of the success of their team or area.

If your direct reports are still relatively junior, it’s fine if you are setting goals with them. But work towards not having to do that in the future. If your direct reports continue to be dependent on your goal-setting to do the right work, they are not good enough for the responsibilities that you will need them to take over as your company grows.

Is the one-on-one the right and most efficient format to address it?

Yes. Similar to alignment, this requires openness and candour. It also requires the participant to be able to honestly say “no” or “too much” or your relationship will derail. Even so, you will probably need to think about making individual goals transparent for all of your direct reports. Because if they don’t know what their peers are working towards, they will collide with them.

Verdict:

It’s not on my list, but if you have a lot of junior/individual contributor reports, it is a high priority.

Operational matters

Does it matter enough to be a regular part of a rather frequent routine?

We need to clarify the scope of what we are talking about first. None of the purposes we’ve already covered are included here. Alignment, mentoring, teaching, goalsetting and feedback, all deal with the operational, at least to some degree. But all have the goal to enable participants to grow and make decisions themselves, and so, excluding these, what remains is more immediate. It’s finding out what is going on and deciding what to do about it on the spot.

Distinguishing between the former and the latter can sometimes feel like walking a pretty fine line. A sentence that starts with “In this case I would do …” can be mentoring or alignment, but it could also be a directive. So which one is it? Answer: it depends entirely on what you want it to be. This is important to understand: the difference between leadership and (micro) management lies a lot less in your choice of words than in your (inner) attitude. Whether you want to enable the participant or are focused on a particular outcome when you say a sentence like the one above, it will be felt by the participant. I have unsuccessfully tried to clad my will for something to happen exactly like I wanted it to in elegant words that I thought would make it sound like I was merely giving good-willed advice. Avoid my mistake. It does not work.

Is the one-on-one the right and most efficient format to address it?

No. The one-on-one is about the participant and about your relationship with them, and solving operational problems always steers a meeting away from these goals, because the operational has a huge pull and usually feels urgent. Find another meeting for it.

Also, if the problem, its solution or the implications of either do not lie exclusively within the area of responsibility of the participant, a meeting with all relevant or concerned participants will be much more efficient. To say it with Jensen Huang: make sure that  “everybody heard the reasoning of the problem, everybody heard the reasoning of the solution”, and can voice an opinion too.

Verdict

It’s not on my list.

Participants Performance

Does it matter enough to be a regular part of a rather frequent routine?

It matters a lot, but not on a weekly or bi-weekly cadence. If you notice something that really concerns you, by all means, voice your concerns in the next one-on-one, but other than that, I think you should rather have a more formal performance conversation every 3 or 6 months.

Now, having worked through these topics, our framework takes shape as follows:

To design a greenfield one-on-one series for a senior direct report, start by looking at the topics at the top left and move over to the lower right. If nothing particular comes to mind that would require adjustment, stop at the top three topics (Check-In, Alignment and Feedback), apply a weighted timeslot distribution such as 30/20/10 and start from there. Likewise, for a more junior report, start at the lower left and move towards the top right and focus on Check-In, Goal-Setting and Mentoring (in that order).

In reality, though, I believe that it’s better to use this framework only as a starting point, and agree on the focus of a particular one-on-one series with the respective direct report in a kick-off.

 We’ll cover this and a couple of hands-on tips on how to actually run a meeting in Part III.