My Evolving Leadership Mistakes

Leadership isn’t a position or a title, it’s an ability and a desire to ignite and fuel an internal commitment from others to rally around a common vision.

It took me years and many mistakes to understand that.

Early in my career, I remember getting promoted to a management position and seeing it as a high stake, high pressure, sink or swim kind of moment.

It was a quick change (my responsibilities kicked in almost overnight), it came with no training or guidance and it felt like the weight of all my future mistakes had increased: anything I would mess up from then on would impact more than just me.

Adding to the pressure, I quickly started noticing a heightened level of scrutiny from many on my team (especially my ex-peers and now direct reports). It also felt like my own Management was carefully observing my every move to assess whether I was going to be a good leader or something else.

Being Knowledgeable isn’t enough

I remember thinking long and hard about how I should run my first team. All I knew was what not to do based on my own experience having never had a “good boss”. All I had dealt with at that point were micromanagers, bosses disinterested in coaching and people openly critical of my attitude but shy on guidance (I almost got fired once for not “looking more stressed out while at work”).

I figured that I should try instead to become the boss I always wanted to have: A knowledgeable one that knew more than most and was willing to share and teach.

So I went about doing that and quickly started hiring my own team while honing my technical abilities.

In my first year, I spent a lot of time teaching technical skills while hiring many new people and making a few mistakes along the way: I hired under-qualified bullshitters, fresh graduates that could never think outside the box, an ex-developer that took naps in the office most afternoons and even a guy that announced he had had a change of heart and wanted to become a police officer after spending 2 weeks with our Tech company.

I realized that being a knowledgeable boss willing to teach technical skills wasn’t enough to make a good leader.

I needed to become better at picking candidates.

People Aren’t Their Academic Achievements

I eventually stabilized the team and realized that the biggest mistake I had made was to focus too much on academic credentials and pre-existing technical skills as opposed to attitude and personality.

After a lot of trial & error and many insightful discussions with unlikely sources, I started seeing a pattern outside of a academic achievements which I since compiled into a list of 4 traits which, still to this day, I always try to seek in a new team member.

I refer to it as the G.E.O.S. criteria:

Grit: not easily giving up, having a tendency to increase effort when going against a tenacious obstacle.

Ethics: always doing the right thing when no one is looking.

Optimism: keeping a positive outlook even when things become tough. Pessimism solves nothing and is counter-productive.

Smarts: thinking fast and outside the box. Inventive and able to quickly solve problems.

To this day and based on my experience, any candidate scoring high in all 4 categories will end up excelling at whatever they set out to do (under the proper leadership).

Unfortunately, some of those qualities are very hard to assess in interviews and can be relatively easily faked by a deceptive person…

I still make hiring mistakes now and will more than likely make more in the future: the key isn’t to not make any mistakes but instead to learn to quickly recognize mistakes and adequately address them.

Rock Star Teams Don’t Manage Themselves

Surrounding myself with great new hires worked well and paid off quickly. They allowed us to grow and execute on our strategy faster than we had done before but we also ended up experiencing a fairly high amount of employee turn over.

My consultants would stay for about 1 year on average and leave to go work somewhere else.

They had no specific complaint about me, the team or the company: they left because finding another job was easy and quick and because they didn’t particularly feel connected to our vision or culture.

I realized I had done a poor job at creating a team culture and communicating our strategy in a way they could relate to or rally around.

The key here is that the actual goal of any given member of your team isn’t usually what they think it is:

We tend to think of our goals to be the same as what we are individually incentivized to achieve. If I am in Sales, my goal is to exceed my target; if I am Tech Support, my goal is to close tickets and get high scores on customer satisfaction; etc.

In reality though, the actual goal of any given team mate is to actively participating to the convergent vision of the company by leveraging their skills to the best of their abilities.

Think of it as a Team Sport: if you are a defender, your goal isn’t to block the opposite team from scoring... Your goal is to retain or obtain control of the ball in order to create more opportunities for your team to score.

In other words, you could be the best defender in the world (=do your job very well) but play with a team of talented but cocky and individualistic forwards and achieve none of the team’s goals.

If you didn't win the World Cup, could you blame yourself?

No, because you have no say in who is on your team and have limited influence on how individual members of the team communicate.

Picking the right teammates and creating an atmosphere ripe for collaboration and trust is the responsibility of the leadership team and the coach.

Even a team of high-achievers requires proper leadership to function well by creating focus, convergence and enhancing communication.

Balance Confidence with Humility

There is probably many different attributes of great leadership but none that is more impactful than finding a proper balance of Confidence and Humility.

Igniting and fueling commitments from others isn’t easy and cannot be achieved once and for all: it is a continued and relentless effort.

Confidence helps guide the ship and build trust throughout the team while Humility makes it possible for communication to flow more freely and for people to feel appreciated and safe.

Finding that balance is a key challenge of leadership because neither of those trait works well without the other: Confidence without humility is cockiness and eventually chips away at credibility while humility without confidence is uninspiring and invites divergence.

It’s also difficult to maintain throughout a career: When you first become a boss, it’s natural to lack confidence; when you get used to it, it’s easy to grow over-confident.

That’s why many first time managers are micro-managers: it’s a way to maintain a sense of control over a team.

That’s also why senior managers sometimes give the impression to their staff that they make decisions in a vacuum and do not listen: they grew over-confident over the years and instinctively think they know better.

Confidence and Humility are found in most people but rarely in equal amounts.

Make Yourself Irrelevant

The best boss I ever had knew what I was interested in and what my ambitions were (because he asked me regularly)... He also acted on it by challenging me on things that, even though they weren’t part of my job description, would prepare me to step up my game eventually.

If you want your team to grow, empower them and encourage them to do more.

What I communicate and many of the assignments I hand out to my team are calibrated on what I think each individual person is interested in learning and on the idea that I should little by little remove any dependency on me (especially for technical knowledge).

Focusing on making myself irrelevant has surprising benefits:

• I am effectively building myself a succession plan by up-skilling top performers (useful if my ambition is to also move up)
• My team feels appreciated and valued by being given more autonomy and more visibility
• My team is encouraged to communicate more freely

Correcting Future Mistakes

I have made many mistakes and I will make more: I am comfortable with that because over the years I have developed little tricks and reflexes that help me learn from them relatively quickly.

The Golden Rule is Bullshit

“Treat Others as you want them to treat You” — is an intuitive but misguided principle.

It breaks down when you realize that not all people tolerate the same things in the same amounts: Maybe you thrive in high pressure conditions and find it normal to reply to every single work email on weekends or maybe you feel comfortable being confrontational... But what YOU consider normal, is not necessarily normal to OTHERS. If you are in a position of authority, you should be careful to consider whether your own actions create unspoken expectations in your team.

Here is a much better alternative to consider:

“Treat Others as they want to be treated”

It implies that you need to spend time and effort trying to get to know your employees, what drives them, what makes them tick, what they find stimulating or frustrating. If you do it, you will get invaluable insight into your own team and better visibility on the things you are doing right and the things you are doing wrong.

Be mindful of The Curse of Knowledge

Deep technical expertise usually makes for terrible salesmanship.

Most people don’t realize it but once anyone has acquired advanced knowledge about something, it becomes very hard for them to remember what it is like NOT to know that topic.

Consequently, it makes it difficult for the expert to dumb down complex things and bring others to their level.

The bad news is that we are all victims and perps of the Curse of Knowledge. We have all used acronyms without skipping a beat and wondering if everyone in the room knew what they meant and we have also all been on the other side of that.

There is good news though: if you start paying attention to the curse of knowledge in others, soon you will start noticing it in yourself more often... and if you do, then you can make a conscious effort to explain things ever more clearly.

check out the article here for more information on this.

Don’t learn from decisions based on their outcome

Most decisions we make in our daily life have consequences that are not entirely dependent on the quality of our decisions.

We tend to think of our decisions being good or bad only based on whether they had positive or negative consequences. This is true simply because the outcome of a decision is much easier to measure than the quality of a decision.

Here is a hypothetical scenario to consider:

I witnessed unethical behavior at work and decided to report it. As a direct consequence of it, I was let go and lost my job.

Should the lesson be that next time I should just keep my mouth shut?

Obviously, no, I made the right decision by speaking up even though the outcome for me was negative. There is no lesson for me to learn here.

The opposite is true:

I decided to wage my entire life savings on lottery tickets and ended up winning 200 million dollars.

Most people would consider this a good decision because it resulted in extreme wealth but in reality it is a poor decision with a very positive outcome.

The only lesson here is that the outcome of a decision, whether good or bad, isn’t enough information to learn from it.

The careful assessment of the quality of a decision is just as important as its outcome, when it comes to learning from our successes and our mistakes.