A few weeks ago there was a discussion in the Women in Tech community about the correlation between what kind of student you were at school and your tendency towards entrepreneurship. The original question was from an entrepreneur who was struggling to conform when she was at school (and now sees the same with her kids). She wondered if there is an inherent conflict between being a straight-A student (which requires, among other things, to adhere to whatever school needs from you and not necessarily the important stuff) and having an entrepreneurial mind.

I couldn’t address the general question since I don’t have data, but I did share my own story. I was a straight-A student and worked really hard to get there. One example that comes to mind was that when I was in the 6th grade I was about to get an A in all categories except in sports. The reason was that I couldn’t do a handstand and a headstand, which apparently were the qualifications from the Ministry of Education to get an A for 6th graders. It blew my mind because I can guarantee you that I was the most sporty student in school at the time. I was a professional swimmer, practiced for at least two hours (and usually more) every day, and was ranked 15th in the country for my age. How can it be that it wasn’t enough to get an A in sports? It was ridiculous. But since I cared about grades and wanted to excel, I worked really hard and learned to headstand. 

Generally speaking, I work well within organizations. It always has been the case. I never struggled with the little or big inconveniences that being part of an organization introduces. I served in the army (and almost stayed there for my entire career), and felt great as an employee in a variety of companies for almost 20 years. It was never a problem for me.

So how come today I run my own company?

Two things have changed: one is that I found my true calling in mentoring and coaching others. Helping product leaders and founders succeed had such a strong appeal to me that it made me get out of my comfort zone. The other thing that made it stick was that as I started I realized that I can contribute much more as an outsider than as an employee, partly because of the things that I dared to say. In retrospect, these were things that I needed to say as an employee as well, but my own tendency to work well within a company, my approach to authority, and my great skill of working well with others prevented me from saying them.

Nowadays, I’m coaching others to not make the same mistakes I did. Having the courage to speak up is one of the things that we are talking about in the leadership workshop that opens the CPO Bootcamp, for example. And trust me, I know firsthand that it does take courage.

Throughout our career as product people, working well with others was probably one of the most effective skills we all had to master. It was the only way to get results and make any impact at all. At some point, however, and especially as you become a product leader, this important skill is not enough. Moreover, if you rely on it too much, it can do more harm than good to your ability to succeed in your job.  

Have you crossed that line yet? Are you being too nice for your own good? Here is how you should be thinking about this.

Being Too Nice Prevents Any Real Impact

It’s a law in physics. Newton’s first law, to be specific: an object will not change its motion unless a force acts on it. In some cases, a mild force is enough – you raise a question, they agree to discuss it, you think about a new solution together and everyone’s happy. You gained both great collaboration and great results. But in other cases, this won’t do the trick. 

I’m sure you can think of at least one example where you tried really hard to change things, and it didn’t work. You couldn’t get them to agree with you (or even with each other) despite everything you tried. Now what? Think about how you felt then. My mentees often talk about feeling helpless, not knowing what to do next, and the default behavior for many of them would be to accept the situation as is and understand that their hands are tied. 

Taking additional action when you think you have done everything you could, often requires courage more than anything else. Even your view of what you could be doing is skewed by what you feel you can do, which creates an inherent conflict (you wouldn’t be thinking of doing something that you don’t have the courage for, but if you thought about it and realized it was the right thing to do, maybe you could have found the courage to act). 

Breaking this barrier, by the way, doesn’t always mean that you start yelling at people or becoming aggressive. But it does mean that you must be willing to act somewhat against your nature because your default behavior has only gotten you so far. We started with Newton, and we’ll end this with what Einstein allegedly said: “the definition of insanity is doing the same thing over and over again and expecting different results.” You get the point, right?

Your Job Is to Challenge the Status Quo

One of the things that can help you act differently than your natural tendency is the understanding that this is exactly what they want from you (whether they say it out loud or not, by the way). Every now and then I have a consulting customer where the CEO and the product leader (be it CPO, VP, or Head of Product) work with me together on a regular basis. They both participate in all of our sessions. Naturally, in these cases, the grey areas where their roles are overlapping become part of the discussion. There might be a bias here, but I have not once met a CEO who wants their product leader to simply conform with their guidance.

It doesn’t mean of course that the CEO doesn’t want the product leader to accept their guidance at all. They all have what they think is the right way to act. But they are open to being convinced otherwise (some more easily than others). Moreover, they expect the product leader to insist if they think the CEO is about to make a mistake. They won’t always accept it nicely or make your life easy in your effort to convince them otherwise, but they do expect you to work hard to convince them if you think they are wrong.

If you are like me, one of the traits that might have made you a great product leader is that you developed chameleon-like capabilities. You understand the organization around you and adjust yourself to work well within it. Pay attention to where it works for you, and where it starts becoming a problem. Some level of adjustment is usually required in order to be able to work well and make any impact (because you can’t fight them into change all the time), but too much adjustment is just as bad as no adjustment at all. It is even more dangerous since in most cases you won’t feel the backfire of it until it’s too late.

Authority Doesn’t Necessarily Mean Expertise

Another thing that took me a while to understand and I want to share with you here has to do with how you treat authority. I have a lot of respect for authority (thank you, mother 🙂 ). It took me way too long to understand that authority doesn’t mean expertise. In other words, to understand what might sound trivial in hindsight: that having a certain role or speaking confidently about something doesn’t always mean that they are right.

I don’t want to debate the general principle here, but rather speak about the specific implication for you as a product leader. As the top product person in the organization, your manager usually doesn’t have a product management background. Moreover, most of them never worked with a great product leader before, so they truly don’t know what to expect. Add to that the fact that product leadership is often a matter of thinking about things in a logical way, and it’s easy to understand why your manager and other people feel very comfortable talking about what you should be doing, although it’s not their field of expertise at all.

If you, too, respect authority, it’s time to test yourself to see if you have gone too far with it. I knew I did when, in a few separate incidents, I took what was purely bad advice despite my gut feeling. It took me a while to come back to my senses and reconvene, simply because it was given by people who behaved as if they knew what they are talking about. 

Following someone else’s bad advice is only one side of the problem. The other is that in face of authority I sometimes find it hard to speak up. As a consultant, I need to remind myself time and again that they hired me for what I had to say, and I would be doing them bad service if I don’t say it just because they wouldn’t accept it easily.

I wish someone told me that when I was an employee! Remember that they hired you, too, because they trust you to lead, and you will be doing a bad service to the company if you let your own respect for authority stop you from speaking up. 

One final note that might help you get out of your comfort zone: remember that when you do act differently, you don’t immediately become the other extreme. In other words, if you are on one end of the spectrum of being nice vs. being aggressive, acting differently won’t get you to the other end. If you are too nice and you start acting more aggressively, you will probably find a healthy balance. You won’t become all too aggressive as a result. Being nice is one of the traits you have, and it won’t go away. Now it’s time to develop additional tools to use on top of it.