Obstacle is the way: inside the COO's Playbook on standards, mistakes, and spotting future managers

Obstacle is the way: inside the COO's Playbook on standards, mistakes, and spotting future managers

Management

Meet Stefan, a Managing Partner and Product Lead at Eyes of Wonder, with experience across People, Support, and Operations.

He blends product strategy, customer psychology, and internet meme culture with equal enthusiasm.

Stefan calls himself the “John Wick from Temu” - under budget, sleep deprived, but still surviving through stubbornness and sarcasm.

Part operator, part strategist, part meme enthusiast, and definitely the guy who will help if you ask.

We sat down with him to talk about mistakes, leadership potential, decision-making, and why smooth careers are sometimes the most suspicious ones.


What’s a leadership mistake you made early in your career that completely changed how you manage people today?


In the beginning, I wasn't starting from setting standards. And I think that this is actually one of the most important things, because when you get a team, you believe in this very libertarian approach where there's no need for such structure. 


-> In reality, it doesn't depend on how big the company is, but it does depend a lot on the team and on the direction you want them to go in.

Once you set the direction, you need to be very careful with setting the standard for each person — depending on their level, what is the outcome that you actually want them to achieve based on their capacities.

 It doesn't make sense to expect from a junior the same level that I would expect from someone who's already super experienced. When I say standards, I mean what is accepted, what is exceptional, or what is bad and shouldn't be repeated again in terms of tasks, results, behavior. 

This is something I learned very early, probably in my second job.


How do you spot the leadership potential in someone before they become a manager?


I can't characterize it as a system, it's rather a series of behavioral traits. Usually, this person transitions very fast from the mindset of "I just need to do my tasks and move on" to shifting from their personal objectives to the team level objectives. 


  1. They understand the dynamics of how a team works, then transition to taking into consideration the goal of the function, and even tying it to the business strategy. 


This is the biggest hurdle I've seen in people - that mental shift from "I'm just in it for me," to understanding team dynamics and playing your role, then function level, and finally tying it all to business strategy. The more proactiveness that goes in this direction, the more it signals that this person is able to think strategically.


  1. The second point is whether they can separate the business mindset from the people mindset. 

  • The first part is just the ability to strategize or multitask in a complex context, but that doesn't guarantee you're going to be a good lead.

  • The second part is how you work with people — standards, systems. Because someone who aspires to leadership will not survive without systems thinking.
    You need to understand the dynamics of psychology, and the dynamics between multiple teams with different scopes working together toward one goal. You need to be a bit of a chameleon, because if you're only interested in your specific role, you can be an amazing specialist, but that will never guarantee you'll be a good lead.


  1. Finally, you need to have very strong discipline in the sense that, when you join or form a new team, people need to know two things: one, that you're capable, and two, that you're charismatic or trustworthy enough that they would follow you. Whenever people get a new team lead, they test the person —”Is there something I can learn from you?” and “Does this person have the capacity to give direction?” 

These two capabilities can be slowly learned but I believe they are necessary to go in that direction.


  1. You also need a good tolerance for risk, because as a lead you are a decision maker. People don't like decisions because they make them uncomfortable, and not everyone wants to assume responsibility for something that can go very bad.

    This is where strategy comes in — if you know what you're doing, if you do the research and your homework, it becomes easier to find alternatives, analyze them, and pick the best version, whether it's a project or a policy you want to introduce.


When someone on your team fails, how do you decide whether to coach them, challenge them, or move them out of the role?


Let me start from my mental model regarding making mistakes.

  • The first mistake is inevitable, people will make mistakes, and what matters is what happens after.

  • The second mistake can be a coincidence: they did something good, something less good, and the outcome suffers a bit. That's a situation where you want to check what people learned, and how they operate immediately after getting feedback or realizing what went wrong.

  •  The third time is no longer a coincidence — it's a habit.

So: when someone messes up because they're new or inexperienced, that's fine, they get feedback and support. When they mess up due to external circumstances, it's fine to correct and coach. But if this continues, meaning they don't exhibit learning from their mistakes or from feedback, it's slowly becoming a habit, and you might have a problem.


The second system I use is the three buckets — C players, B players, and A players. My strong belief, and it's counterintuitive to what traditional media outputs, is that you don't need everyone to be a top performer.

For C players, everyone needs to move one level above if possible. But if someone stays too long as a C player and can't contribute to the team or as an individual contributor, unfortunately you might need to replace them. If, however, they can move from C player to at least being productive and a B player, you can train them up to take on more difficult objectives. 

From what I've seen, only 10 to maybe 20% of people actually end up being top performers.

To directly answer the question:

 I coach when I see effort and interest.

I challenge in two instances — when they're ready to take on a challenge, or at the beginning of a role, if I have enough time to let the person swim — throw them in the pool and see if they can. But if the context doesn't allow it, I will not put team results in danger just for the sake of risk. Everything is calculated risk. 

I move someone out of the role when they don't contribute to the team or as an individual contributor — when they don't exhibit discipline, assertiveness, proactiveness. It really comes down to objectives. We base it as much as possible on data and reaching objectives or success dates. If I see someone's ambitious, I'll always give them something more difficult just to see where they are, if they manage something more complex, that's a strong hint they're capable of more.


What about the wrong person that you ever promoted? What lesson did you get from that?


My track record is actually very good in terms of people I promoted. I honestly didn't make a lot of mistakes with who I promoted to leadership or more important roles. I did make mistakes, however, with people I hired into regular positions. The thing is, an interview, regardless of how many calls you have, is not going to tell you someone's potential. You actually need to work with them for one or two months, see what they're able to do, and then you can make an assessment.


How do you personally grow as a leader, even having reached the C-level?


I constantly expose myself to problems that other people run away from.

My motivation comes from - and it's going to sound like a cliché, but I really mean it - smooth seas never make good sailors. Throughout my life, I've always learned more from failing a lot than from purely winning, because you need to see both sides. When people just win, the chances of being that exceptional are also a factor of luck. But experience comes from being in the gray zone. What I've seen is that people who come only from the winning side -  it's not really them who made the change. It was either someone else who came with the idea, or a team effort that implemented it. I'm very cautious with people who just always win.

I also like competition and I like to win, but only if I put in the work — meaning either me or the team figured something out, we move together in that direction, test different things, understand what works and what doesn't, and do it fast. If mistakes happen, we pick ourselves up and keep moving. But if all you know is that you tried something and it worked once, that's all you're going to add to your knowledge package. What if it doesn't work in a different company?

Besides being exposed to these problems, I learn a lot. I'm an eternal student. I don't see myself as capped or having already reached my potential. I really like being a beginner in new things because it opens my eyes to very different perspectives. Moving across different functions, you can learn some principles or a knowledge nugget that you can modify and apply to a different function and it just solves your problem.



What stands out most is that Stefan’s approach isn’t built around perfection or pretending leaders always have answers. It’s built around creating systems where people can actually grow. Sometimes through coaching. Sometimes through challenge. Occasionally through being thrown directly into the pool to see if they swim :)

And that probably explains a lot about the culture at Eyes of Wonder.
People here are trusted with responsibility early, expected to think beyond their own tasks, and encouraged to approach problems with ownership rather than waiting for instructions. It’s not always comfortable, but comfort was never really the point.

If you like how it sounds, explore our open roles and see what fits.