TTL 11
Stand for your principles, even when it’s not comfortable.
👋 Good Morfternight, this is Paolo Belcastro, with the eleventh issue of TTL: Tools & Thoughts for Leaders, your weekly leadership fix.
Today, we talk about those times when choosing the uncomfortable path, while not inevitable, is the best option.
Before going further, if you have time and unless you have already, it can be useful to read the post I published yesterday on the blog, “What the heck is going on with WordPress?”. It’s not a requirement, but it can help gather more context about what follows.
This is TTL, not paolo.blog, so I won’t comment more on the situation itself. Instead, I want to share a few thoughts about why sometime wishing for polished speeches and soft-spoken diplomacy is wrong.
Analogies & Metaphors
Let’s start by addressing the question of comfort, discomfort, and how heavily this weighs on a leader’s decisions.
We can use a relatively basic example from the daily life of a Product Manager: saying “no” to ideas to remain focused on what is important.
Everyone can easily say “no” to bad ideas, it doesn’t require any effort.
Saying “no” to very good ones, though —the things you would love to build— is so much harder, yet necessary. Surround yourself with a smart team, and most proposals you’ll hear will be excellent.
Try to execute on all of them, and you’ll be doomed.
Stepping up, let’s talk about Freedom of Speech. It’s easy to defend it when someone tries to censor the people you agree with. How hard is it, though, to defend it for people you abhor, who say things you deeply disagree with? Yet, that is the way.
The point I am making here, is that there are times when the right thing to do is not the one that makes you, or everyone around you, more comfortable. Instead, it’s the hard thing, the one that generates short-term pain, that is the right path.
Visionaries, and then everyone else
It is fascinating how hard it is for the average human being to imagine a distant future. Some, though, have this ability. It’s not just about imagination, or creativity, it’s a different skill. It’s about understanding deeply how the current systems work, identify immutable goals and separate them from the constantly evolving tools to reach them, then figure out which new tools will, in the future, help us attain those immutable goals.
It also works in the other direction: identifying early on the threats at risk of becoming existential; at a time when they still seem minor.
Think about climate change, and how obvious its consequences look now. Some scientist, though —one could call them visionaries— started looking into the possibility in the late 50s, and raising serious alerts as early as 1980. Their recommendations were full of sacrifices, they were uncomfortable, so we did not listen to them.
Finite and Infinite Games
(To learn more about this concept, you can check James P. Carse and Simon Sinek)
The difference between finite and infinite games is that in the former, the finite game, the players are trying to win the game. When that happens, the other players have lost, and the game ends. Then another game starts. There are countless games of that sort.
The infinite game, on the other hand, is unique. Players play with the purpose of continuing playing. The game never ends. Some players lose and leave the game, new players come in. The game goes on.
Business is an infinite game. This means that existential threats are infinitely more serious than non-existential ones. In most areas one can make mistakes, then course-correct. In some rare cases, not.
A particularly critical aspect of playing the infinite game is to encounter a player who thinks it’s a finite game, and focuses only about winning that one game and moving on.
They tend to play the game like pigeons play chess.
But, Paolo, where are you going with this?
I am glad you asked…
It’s truly simple, in fact.
There are existential dangers, threats that can bring down even a massive open-source project like WordPress.
Because the project is so massive, any existential danger will naturally also appear very remote.
Therefore, only someone with a very long-term vision will see it early enough to make the necessary corrections and avoid it.
But every action they will take will seem disproportionate, and most people involved will feel a strong sense of discomfort or fear.
Add to that an extra dose of transparency and sincerity, which translates into speaking like an imperfect human being, and not like a robot coached by lawyers and PR teams, and you get a perfect cocktail to generate anxiety.
Many, in the WordPress community, see through all this, and while they may not have seen the danger at first, can understand it when it’s shown to them.
Others don’t see the long term existential threat, they only see the present discomfort, and argue that ok, maybe the point is right, but things could have been done more diplomatically (I disagree, that would have failed).
Finally, there are all those, who short the project, playing the finite game, or worse, are manipulated by those who do.
History will say whether I am reading the situation right, or not, but I believe that most of the criticism of Matt Mullenweg I hear around the WordPress community these days is that he should have been more gentle with that abusive corporation, that he should have taken more time to explain, that he should let his PR or legal people coach him…
In a nutshell, that he is welcome to try to save WordPress, but he should do that while making everyone feeling comfy and cozy.
In conclusion
I doubt that would have the slightest chance of working.
Not that the current strategy is a guaranteed home run, of course it’s risky and there are many ways in which it can fail, but the comfortable path, would have been a behind-the-scenes dialogue between the two companies legal teams, with no involvement or contribution from the community.
Remember that this is about avoiding a long term existential threat for WordPress, the open-source project powering almost half of the web, and an ecosystem of thousands of companies and hundreds of thousands of human beings.
The whole community must be aware of what is happening, learn the facts, develop opinions, and eventually, collectively, win.
By choosing the uncomfortable path, Matt makes the matter impossible to ignore. It seems confusing and hard now because many uninformed voices create interferences, but eventually this will highly improve the odds of succeeding, and that, is worth a bit of discomfort.
Fortune favors the bold. Being a leader means taking the path with the highest odds of success, not the easiest one.
That’s it for today.
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Here on TTL, we dig into practical leadership tips and effective strategies, with a particular focus on tech leadership and managing distributed teams (that’s what I do every day, add me on LinkedIn).
Whether you’re steering a tech startup or leading a remote team, these insights are designed to help you navigate the complexities of modern leadership.
I also publish on paolo.blog and monochrome.blog
Cheers,
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