The Pursuit of Taller Hills: Lessons from Football and Product Management

Dion Almaer
Ben and Dion
Published in
7 min readMay 25, 2023

Management is a story of hill climbing. I started to reflect on this more while thinking about football management, a task that fits into more finite game theory.

NOTE: This was originally posted on my own corner of the Internet.

With a Ted Lasso season running, and Manchester City winning a third English Premier League title on the trot, I hope you won’t mind a discussion of the best league in the world. It has triggered thoughts on how timelines and risk aversion ties to management.

The premier league has 20 teams, and this season a record 12 managers have been given the sack. The stakes are particularly high due to the workings of the hierarchy of leagues in the english soccer pyramid, as shown above.

ASIDE: The term soccer was in fact invented by the Brits! It came from associated football vs. rugby football. I’m not just being a yank!

The Premier League is known for its fierce competition at the top of the table. However, there’s more at stake than just the coveted top spot. The top four positions in the league standings grant entry into the prestigious and lucrative European Champions League. Additionally, teams that finish fifth through seventh may qualify for the Europa League or Europa Conference, depending on various factors such as winning the FA Cup or previous Champions League winners. While there are numerous edge cases, many top places in the league are highly sought after, making for intense competition throughout the season.

Then you have the bottom three positions. If that’s where your season ends, you are doomed to go down a division, known as the Championship. Financially, your lose out on all that the premier league offers (TV rights et al), and it’s such a sudden drop that you get an parachute payment to help soften the blow. This leaves a small middle of the division that doesn’t have to sweat too much. Things were in fact so tight this year that teams in positions of 12 to 20 were all fearing a drop. Hence the firings.

Compare this to franchise leagues such as the NBA, MLS, MLB, or NFL. If you have a bad season you get to regroup for the following year and, in fact, you may even have incentives to do worse if it means getting better draft picks!

↑↑↑ This is Graham Potter. He only lasted 9 months at Chelsea before becoming one of the 12 to go. He was heralded when he left Brighton and Hove Albion, where he had built an amazing system. The recruitment was fantastic, and he had a flywheel that would follow this pattern: bring in new players for ~cheap => bake them into the system => other teams buy them for !cheap => repeat. I can’t tell you how often they would sell a great player for great money, and you would fear that the team would struggle… yet it seemed to somehow get better as someone would stand to be counted.

He joined a Chelsea operation where they had spent hundreds of millions of dollars, with long contracts (to get around the fair play rules), but weren’t playing like a team at all. No system to be seen here.

Picture yourself in Graham’s position. The clock starts ticking on day one, and you need to climb your first hill. There is pressure to show results quickly, and you need to find which players work well together, and under which system. 4–4–2? 3–5–2? What are the patterns of play? Do you use a low block? It goes on and on. So much money has been spent on the squad, and the individual players have quality, so expectations are sky high.

↑↑↑ This is Alex Ferguson, the best manager in the history of the premier league (or is it now Pep Guardiola? 🤔). His first few seasons weren’t great, but times were different and the Manchester United owners stuck with him and his system.

He could take time to explore the hills. How can he get the most from his squad? How can he recruit to fill the gaps and mould the squad to the system he wanted?

Without this time, todays managers are stuck having to quickly pick a hill and run as fast as they can to the top, with a huge probability that it is a very local maxima.

Another topic that every new manager will have is: do you go against the traditional style of play of the club you join? change it to your style? or create one that maps to the players?

↑↑↑ This is David Ginola, who personified the traditional swashbuckling style of play of Tottenham Hotspur. Despite the team not having won any silverware for several decades, the fans have still been able to enjoy exciting, entertaining end-to-end matches.

The last three managers to join Spurs have not followed tradition, and instead employed a much more defensive base. When the team sees success with this change, the fans will grumble but hold their tongue, but as soon as it isn’t working… look out.

Ok, enough of this footy talk, how does this apply to management in tech?

Just as I fear for how little time football managers get to find the biggest impact, I often fear the same in corporate life. You often see a ~2 year re-org cycle, especially when there are trade offs around focus.

Pendulums vs. Switchbacks

One common example is: when do you centralize a function vs. when do you group functions in a business unit? If you are in a function that feels the pendulum you are always waiting for the change. When don’t wrong, you feel like you are oscillating between two very known states without any learning.

When done better, it is more like climbing a spiral case, or switchbacks as swyx would say. This is where you take the strengths of each approach and bake them into the learnings.

Let’s take Developer Relations. When I rejoined Google in 2015, there was a centralized function. All tech writers reported through a functional tech writing chain. The same was true for developer advocacy, developer platform engineers, developer programs, partnerships, and more. Time was spent into solidifying what it mean to be great at these roles. On the flip side, if you thought of yourself more a part of the domain that you worked on, you weren’t as attached to the product and engineering world there. Consider yourself an Android expert as a Developer Advocate? Now you are in a hierarchy of DAs. How do the Android DAs, DPEs, Tech Writers, PgMs all coordinate? There was a special role to try to help bring things together. It was a tough role!

One of the first things I did was to switchback, and have one Android DevRel team, and eventually it went back into the Android product area itself to attach and integrate even closer with the teams there.

When joining a team as a new leader or manager, you have to make some decisions. After taking some time (hopefully!) listening the team, you will be working out what changes are needed. If you feel a rush to show impact, you may rush up that first local optima hill.

Through my own errors, I have learned to:

  • Listen to the natural feel for how orgs work at the company
  • Listen to the core problems your teams are facing, and think about potential solutions
  • Make some calls on what change solves real problems.

I am loathe to go against the grain of the company unless a) things are really broken with the approach, and b) I have a strong conviction that it’s time to actually create a new default for the company. I don’t want to flip flop, nor do I want to make changes that are surface level just because I am used to them.

If I was going into Spurs, I would very much lean into creating a Spursy team (hopefully breaking the mould of the losing!). When Manchester City got radically new management at the start of the 2000’s (and have allegedly done a fair amount of cheating I may add!) it was the perfect time to make a big change and create a new identity. The club needs to buy into this, and needs to allow the hunt for a better global maxima by giving the new leadership time.

The new manager bounce

One of the other reasons for the flurry of sackings is the myth of the “new manager bounce”. The theory is that the players will have some hope, and maybe will fight for their places more with someone new in charge. If the old manager had run out of ideas and left the team with no confidence, and the incoming manager has a series of fresh ideas, this can work! It doesn’t seem to be the case in practice.

Maybe the same happens in the office. I don’t know about you, but I feel like most of the reorgs I have seen are too frequent, and don’t occur when the ideas are dry. In fact, whenever you have a reorg you spend a lot of time revisiting items such as the strategy, the plan, and how you work. You require time to do the forming of the new way, and it takes time to get into your new stride. At times, a reorg has happened seemingly RIGHT when things were starting to click and execution was cooking with gas.

Too often real life feels like the CEO and the three envelopes joke.

Be thoughtful as a new leader, or a boss to a new leader, and make sure that everyone has the time to make sure they aren’t climbing the wrong hill.

/fin

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