Which choice sets athletes and amateurs apart? Athletes focus on training. Amateurs focus on playing.

Training is deliberate, often repetitive work to build or improve a specific skill. It is future-oriented.

Playing means applying existing skills in a competitive environment to win. It is present-oriented.

Training is why athletes remain competitive beyond the early talent phase and keep improving throughout their careers.

Founders are always at risk of not training enough.

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.

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-ones are the most basic type of meeting imaginable: two people talking with each other periodically. They are also the bread-and-butter artefact of leadership: a private, direct dialogue between a leader and a direct report.

Alas, from the perspective of a founder or CEO, they are quite the investment. You typically have more than one direct report, and your time is the most limited resource the company has (everything else can be sourced). By nature, the one-on-one does not scale. So there better be a good reason for you to take time for your direct reports individually and not as a group.

Europe is at a later-stage funding disadvantage compared to the US. There are a couple of reasons for this, mainly:

-  There is simply more money in the US Venture Capital (VC) ecosystem,

-  The majority of it gets deployed in later stages, in contrast to Europe and Germany, where the majority of investments are early-stage, and

-  Tier 1 US VC firms, in particular, have bigger funds, allowing them to sign a greater number of larger tickets.

This is an issue because while money cannot buy success, it can - and it does - buy growth. Usually by way of (growth) marketing, sometimes through M&A activity, and often through outsized talent acquisition or frontloaded organisational growth.

Delegating well is a superpower. It frees founders from some of their operational responsibilities, giving them much-needed headspace for strategic thinking and big decisions, it prevents them from becoming bottlenecks for their organisations, and it empowers their reports and gives them room for development. What’s more, everybody can learn it. It’s a skill, not an innate quality. But it takes some awareness and attention to get it right.

I guess most people would say that hierarchy is a necessary evil. I believe it’s more of a blessing in disguise. It is fundamentally helpful, but we often implement it in a very unfavourable way.

In any case, it has a very direct correlation with the question of being hands-on or being hands-off as a founder or CEO.

Paul Graham (the co-founder of Y-Combinator) recently published a piece called “Founder Mode”. It refers to a talk that Brian Chesky (the CEO and founder of Airbnb) gave at a recent Y-Combinator event and in which he reflects on what he has been told about running a larger company, how that advice has backfired on him and what he has chosen as his MO instead (there is no recording of the event but you can listen to this podcast in which Chesky talks about how he runs Airbnb).

According to the NYT, the talk of Chesky and the commentary of Graham have created quite a ruckus in Silicon Valley. The vibe reminds me a bit of the more positive reactions after Elon Musk took over Twitter and fired 80% of the staff. Regardless of that, their thoughts are relevant, so let me try to break the substance down for you.

Output is underrated these days. In most product-organization or modern-leadership-related literature the gist all too often seems to be something along the lines of: stupid/old organisations produce output, smart/modern organisations produce outcome. Take, for example, Marty Cagan (who is a well-known author and a founder of the Silicon Valley Project Group), where he compares (old) project teams and (modern) product teams, summarizing:In contrast, with the product model, we focus on products and outcomes. 

I think I know where this spin comes from and it does have merit– I’ll get to that in a second. But in my observations, it has an overshooting effect on product organizations to view output as an inferior or even outdated type of goal. I think this is a dangerous misconception. Output matters just as much as outcome. Particularly for a startup.

You’ve nailed the core strategy - now it’s time to drive it home. There are only two more steps to go: the Narrative which provides background and rationale to the choices made in the core strategy and the bridge which puts them into perspective with the business realities at hand.

The core strategy is the centerpiece of the strategy document. It is the purpose of a strategy to focus the organization. The core strategy is where this focus is defined. Everything else in the strategy document is just there to provide background, explanation, and tangibility to it.

The core revenue driver is the underlying mechanic or psychological law of attraction that has the biggest influence on the customer’s decision on where to spend their money in the market you have chosen to be competitive in.

The first Core Revenue Driver (“CRD”) that comes to mind is of course the product itself. Having the best product (by way of its features, quality, or design) certainly has a strong influence on the customer’s decision to spend their money on it. But there are other drivers that overlay with and sometimes eclipse the product as the core driver for the customer’s decision.

In order to focus a company’s efforts, a strategy must lead to a concentrated allocation of resources and talent on a macro level. But also it must align the (operational) decision-making in the company on a micro level. Both are necessary. Without alignment, a concentrated deployment of talent and investment is meaningless (well-deployed people doing random stuff). And if the operational decision-making is aligned but talent and investment are not deployed in a concentrated way the strategy lacks impact (people doing the right stuff but not enough of them).

Unfortunately, achieving focus while ensuring alignment can be tricky. Focus is generally achieved by less. The clearer and more single-minded a thought is the better it focuses. One sentence focuses better than two. Alignment, however, works the other way around. Because understanding is the key to alignment: the better you can explain something the better you can give the “why” to a decision, the more you can illuminate its background, the better you will be able to align the thinking and decision-making of others.

We really need to talk about strategy.

Having a strategy is almost universally hailed as a business necessity. Nobody wants to be caught running a business without a strategy, right?

So one would expect that a subject with so much significance is well-researched and defined and that there is somewhat of an educational standard for it. But that is not the case.

There is simply no broad agreement neither on the concept of a strategy (what is a strategy?), the purpose of a strategy (what does a strategy do?) nor the embodiment of a strategy (what does a strategy document actually look like as an organizational artifact). A lot of excellent management and leadership books leave the subject out entirely, or only touch it in an incidental fashion and with confusingly varied positioning of the topic ranging from purpose to planning. Also the relationship between a strategy and a plan – two very different things as I argue here – is unclear.

There are a lot of ways to think about what an organization is and how it operates. I don’t think that one is right and the others are wrong. What is important though is that any organizational development, any work on the organization itself, is based on an organizational strategy. Because improving an organization is a complex task and a strategy is the best way to deal with complexity. It is simply not possible to plan organizational change because you don’t control the people of which an organization consists. You can plan actions but you cannot plan the reactions. So instead, leaders must decide on an approach that they believe will have the biggest positive effect on their organizations, try it, observe, and adapt. They must decide on an organizational strategy.

Compared to the foggy use of the term strategy, the concept of a plan seems familiar and straightforward. Everybody knows what a plan is, right? And at first sight, a plan and a strategy have some things in common. Both look into the future. Both guide a company towards goals.

But here the commonalities end. A strategy and a plan are fundamentally different from each other in what they are concerned with and what type of problem they address (a) and how they affect the organization and interact with each other (b).