I graduated from elementary school with a straight-A report card. I’m writing about it thirty-five years later because I needed to work hard for it, but not necessarily the way you would think.

I didn’t have a problem with any of the subjects taught – I got A’s in all of them. My only problem was gym class. The requirements to get an A in gym were to do a headstand and a handstand, and I could do neither. I was about to get an A-.

You might read this and think that it’s no big deal, and you are probably right, but you can only say that because you are not a 12-year-old perfectionist. I couldn’t stand that A-. Moreover, it felt ridiculous since I was a professional swimmer at the time, ranked #15 in Israel for my age group. I’m pretty sure I was the best sportsperson at school, let alone in my class. But still, I couldn’t do a head or handstand.

Being both a perfectionist and a fighter, I went to talk to my gym teacher. She agreed that it was ridiculous but explained that she couldn’t just rank me based on my performance at the swimming pool after school. After some discussion, I got her to agree that if I learned to do a headstand by the end of the year, I would get an A, even if I couldn’t do a handstand (which I knew was too far-fetched to even consider). 

And so, I needed to learn how to do a headstand. The teacher explained to me how I should practice and the different phases – they all made sense. There was only one problem: my parents hadn’t allowed me to practice against the walls at home. They didn’t want footmarks (which I fully get now as a mother of three kids). 

I needed to find a softer heart, which I did in the form of my grandmother. We went there every weekend, and she allowed me to practice my headstand on her door, which was easier to clean than the walls. I practiced consistently every week and proudly demonstrated my headstand to the gym teacher by the end of the school year. I got my straight-A report card.

Yes, I’m a perfectionist. Always have been and still am. But nobody is perfect, and I am surely no exception. So, how do you survive adult life, as imperfect as it may be, as a perfectionist? You have to learn to adjust. There are some places where I’m willing to let go, lower the bar, and forgive myself for doing so, and others where I stick to my high standards, whatever the price is.

Professionally, I learned early on that perfectionism can’t work in product management and even less so in product leadership. Our world is too complex and uncertain to always get it right. Here, too, I had to learn to adjust.

But just because you can’t always be right and things cannot be perfect doesn’t mean that it’s okay to err. You will make mistakes for sure, but not all mistakes are the same. If you want to be a great product leader, here are the mistakes you can and can’t afford to make.

Take Calculated Risks and Fail

Taking risks is the only way to win in tech. We work for the future, and since the future is unknown, there is no way to move forward without risk, and some of these risks will materialize.

In her book ‘Thinking in Bets’ Annie Duke shares that at the Poker table, when she is facing a certain situation, she needs to analyze the odds of her winning the hand for each move she can make. These odds are never 100%. If a certain move has a 70-30 chance of winning, and it’s the highest one, that’s the right move. But if it happens to be the 30% that means she loses the hand, she did everything right and still lost the hand. This is inevitable and is part of the game.

The same applies to product leadership. We need to take risks all the time, and if you are not willing to do so, you will surely fail. 

The way to go about it and still sleep at night is to understand the risk that you are taking and make an informed decision. I recently heard a quote that I really liked from Tomer Cohen, LinkedIn’s CPO: “We might be wrong, but we are not confused.” You will make wrong decisions all the time – but that’s only true in hindsight. In real-time, you must decide and bet on something (because not deciding usually means you pay a much higher price), but you don’t want to do it blindly or randomly. 

Understand what you are betting on – both in terms of the assumptions you are making that make it a good decision and the price you’ll have to pay if you choose the wrong path – and then decide. Doing so also helps you manage the risk later on since you can monitor your base assumptions as well as outcomes and correct course along the way.

You Can’t Know What You Don’t Know

Even if you try to eliminate the uncertainty and operate solely based on clear assumptions and facts, there would be things you’d miss. The uncertainty in our world comes not only from dealing with the unknown future or our constantly changing world. Some of the uncertainty comes from the complexity of the here and now.

It’s nearly impossible to consider everything you need to. One person – be it the product, the CEO, marketing, or sales – can almost never know everything there is to know about whatever topic you are discussing. There are multiple perspectives to be aware of, meaning, by definition, you will have unavoidable blind spots.

But even if you can’t know everything, you can know that you don’t know and manage yourself accordingly.

Writing your assumptions clearly and debating them with your colleagues, managers, and stakeholders is a good start. Differentiate between assumptions and facts, and ask your partners to highlight and elaborate on what you might have missed.

Making the Wrong Recommendation

Now that you have all the relevant information and context, you can better lead to action. However, there is another type of mistake you might make even with great knowledge. 

As a product leader, the decisions you need to make are complex. I always say that it’s our job security. Let AI make the easy ones and leave us only the complex ones 😉.

Part of the complexity is because of the unknowns – both the future and the context. However, some of the complexity is simply because there are so many things to consider. There are often contradictions and trade-offs that you need to make. How can you tell which one is more important? It’s indeed complicated.

Sometimes, the complexity will lead you to the wrong conclusion. Generally speaking, you should build your claims like a proof for a mathematical theorem. Your statements should build one on top of the other until you get to the unavoidable conclusion, the Q.E.D. if you like.

But unlike math, where the set of rules is very clear, our claims come in many shapes and forms, and sometimes you will think about things the wrong way.

A mistake I see many product leaders make is simply leaving the decision to someone else. That’s not only not helpful (because you ask them to do the hard work of considering everything), but also is more prone to logical failures. If you only outline the complexity, you might miss things along the way.

The way to go about it is to force yourself to make a recommendation. When you do so, not only do you base your leadership, but it also forces you to think things through.

Since you might be wrong with so many things to consider, it’s important to review your line of thought with others. They will help you identify what you might have missed and conclusions along the way which are not necessarily true, and reduce the risk of leading in the wrong direction.

Big No-No: Sloppiness

All the mistakes we have discussed so far are due to the complexity of the world we live in. This is the world and you have to deal with it. Doing your best doesn’t mean that you will always be right. It’s natural and it’s part of being a leader in tech.

There is another kind of mistake – the ones you can avoid. Some things are 100% in your hands, and if you still make mistakes there you come out as unprofessional or unreliable.

Sloppiness is one such kind. If you want to base your leadership, you need to be trustworthy. And if your boss needs to babysit you to make sure you don’t make mistakes you can avoid, trust is the last word that they would use to describe your relationship.

Note that there is a major difference between sloppiness and involving others throughout your work. Avoiding sloppiness doesn’t mean that you can only share perfect, bottom-line artifacts. For example, in many cases, having a beautifully designed presentation is not essential since it’s just a means to share your ideas and line of thought internally. It’s also perfectly fine to share what you have up to now, even if there isn’t a clear conclusion yet. It is an important tool to bring everyone in the loop—partner with them to review your work and align on the next steps. 

But if you don’t get the details right, fail to do something you said you would do and don’t communicate on time, or neglect something that is within your responsibility, people will find it hard to trust your leadership.

It’s true even if they see it and get you to fix it before any real damage happens. It’s the seeing it before you do that is problematic. As a manager, whenever I see such a mistake, even if this specific one is fixed on time, I start worrying about potential other mistakes that I am not aware of. If I need to be there to make sure you do your work right in every little detail, you are a much less valuable employee than if I can know that you are on it.

Don’t Repeat the Same Mistake Twice

By now, we have established that everyone makes mistakes. So will you, it’s unavoidable.

However, a mistake is only acceptable and worth it if you learn from it. As a manager, I will happily pay the price of letting you fail as long as you learn from your mistakes. 

If you fail to do that (see what I did here?), you simply remain with the failure, and as your manager, I know that I will always need to keep a close eye on you.Made a mistake? Great! It probably means you are growing and dealing with something you haven’t done before. But don’t leave it there. Make it count to establish your growth and leadership over your mistakes and failures.