10 Lessons in Leadership After 21 Years Alive

“A genuine leader is not a searcher for consensus but rather a molder of consensus.” — Martin Luther King, Jr.

I have always been fascinated with the influence that leaders can have on societies and individuals. As human beings and whether we like it or not, our lives are dominated by a complex web of hierarchical structures that control the way we think, behave, and grow over time. While often it is the systemic or organizational influence of these hierarchies that truly impact society, on a more individual level it is the people at the top of these hierarchies that we tend to be most concerned with.

I believe the definition of a good leader is somewhat subjective. What is evident though is that while a good leader can raise an organization to excellence, a bad leader most certainly can bring that same organization to its knees. Whether that organization is a local elementary school or the United States of America, being a leader means that you have the power to significantly impact human lives both positively and negatively. Whether this level of responsibility excites you or terrifies you, it should be taken seriously by anyone who has it bestowed upon them.

Over my 21 years on this planet so far, I have had the privilege of experiencing the pressure of leadership in multiple different settings. Though all those experiences were relatively positive, my many mistakes and failures throughout them have allowed me to construct this list of the top 10 lessons I have learned regarding how to be an effective leader. By publishing this list and making it public, I hope that I can do my part in improving the qualities of our leaders and thereby improving the quality of society itself. What I also hope is that I will be able to look back at this list in the future and be able to make changes or improvements to it. Leadership is something that can only be mastered through the type of experience I hope to gain in my years to come.

1. DEFINING YOUR EFFECTIVENESS

I’m putting this point first because it is the demon that has consumed me and that I’ve seen consume so many others before me. As a leader, you may not have a boss and you are at least in some capacity responsible for forming your own rules and standards. There is also probably a certain level of self-consciousness you have regarding how your team members are viewing you. The question is then, how do you objectively evaluate if you are doing a good job?

You could simply ask your team members how they think you’re doing, and if you’ve got a good team and fostered a good environment, they’ll be honest with you and tell you. The problem though is that often team members are only able to reference their specific role on the team, and therefore are essentially going to be basing their feedback on the state of their department (PMs, marketing, finance, etc…). The problem with this is that each of those departments themselves do not encompass the whole team. Those departments should all be working harmoniously to contribute to the final goal which is established by you.

The only way you or anyone else should be measuring the quality of your leadership is simply by asking, “Is the team succeeding or failing?” That’s it! If the team is failing, so are you. If the team is succeeding, so are you, it is as simple as that. This means that one area of the team could be struggling, but as long as you’re mitigating that correctly, so it doesn’t impact the team’s end goals, it doesn’t matter. You are still doing your job.

You will have aspects of the team or initiatives that you try to run that will fail. If not managed correctly then they will cause the team to stray from its goals and therefore you are failing as a leader. However, if managed correctly and those failures don’t impact the goals of the team…who cares? The ability to self-reflect and self-evaluate is crucial and it is a skill that you will develop over time.

2. EVERYTHING IS YOUR FAULT

You and the team will have multiple failures and successes throughout the term of your leadership. Whether these successes or failures are small like an underwhelming marketing campaign or large like a product launch, you will be the person that is overseeing it all. The funny thing is though that you will never be the person that executes on them directly.

If something goes wrong and it fails then ask yourself, “Was there something I could have done differently to make this not fail?” If your answer is no, then either an asteroid hit the earth or you’re delusional. For every person who executed something poorly, a leader is overseeing that execution, who is being overseen by someone else, who is being overseen by you. This doesn’t mean that you’re failing as a leader (See Point 1), this just means that you must take responsibility for that failure and plan out how you’re going to do it better next time.

If something goes well, then congrats, you set something in motion that created a positive outcome upon execution. This success is also your fault, and therefore you should be happy. But, as a leader, you can’t praise yourself. After all, you had nothing to do with the execution of that success. You must recognize the efforts of the people working under you, positively reinforce their good work and do all you can to frame it as a success for the team and a success for that individual. Your self-praise is nowhere in that equation and it never should be.

It’s sometimes hard to accept responsibility for failure, not claim praise for successes and put the interests of your team and its members over yours. However, it is doing exactly that which makes a leader strong, and it is for that reason that good leaders find their way to the top in the first place.

3. WEAK TEAM MEMBERS AND UNDERPERFORMERS

A team member is only as weak as you allow them to be. Remember, everything is your fault.

Let’s be blunt. You will have members of your team that underperform, frustrate you to all hell, lose your trust, and lose your respect — it is inevitable, so how do you deal with it?

Option 1: Your first assumption should be that there is a lack of communication, understanding, training, resources, or proper planning that you could have implemented differently that would have allowed that person to be more successful. I can’t tell you how many times I was frustrated with the performance of an individual and upon investigation, it turned out that there were easy steps that I could take to improve the situation and better the performance of the individual moving forward.

Option 2: The underperforming individual has some sort of extenuating or unique circumstance that is preventing them from doing their job. In this case, the person’s role, the action plan, or the structure of the team may need to be altered to unlock the potential of this underperforming person.

Option 3: The individual is not on board with the goals, plans, or culture of the team and they need to be removed. If this is the case, then don’t waiver, just do it. It isn’t fair to you, the rest of the team or the underperforming member to keep them around. You will be doing everyone involved a favour by severing that tie immediately.

In any case, there is one key action that you as a leader should take to mitigate the impact of underperformers and hopefully prevent the presence of them: Communicate constantly with your team! Talk to them, listen to their thoughts, entertain their concerns and relate to them on a person to person level.

4. ACT THE PART

This essentially just means lead by example. Act how you expect your team to act. This may seem simple and intuitive, but it is easy to catch yourself slipping away from this rule occasionally. Whether it be in a meeting, team social or prototyping session, the number one thing that influences the attitudes of the team is your own. You’re going to have days where you are tired, stressed, irritated, sad, etc…. On days like that, it is your main objective to ensure that it doesn’t cross over to the rest of the team. Put your game face on and don’t give others an excuse to feel the same way. Act the part.

5. STAND YOUR GROUND WHEN NEEDED

This is a tough one to implement but very important. This tip comes down to the fact that you are the captain of the ship. Don’t get me wrong, it is always crucial to establish a team culture that encourages feedback, positive criticism, and disagreement. However, sometimes you will be put in a position where you are facing pushback or resistance to a decision that you know is best for the team. In this case, it’s time to step up and lead. Trust your instincts. You are in this position for a reason, you have planned out your goals and know what needs to happen to achieve them. The people that comprise your team, the people that are expressing disagreement or concerns, they’re also the same people that are trusting you to make the tough decisions, so make them. In situations like these, it’s your job to lead and own that responsibility.

6. OWN YOUR MISTAKES AND ROLL WITH THE PUNCHES

As the leader of a team of any significant size, you will make many mistakes and be criticized for them in some way or another. In addition to leading team operations, you are also responsible for completing the paradoxical task of binarily representing an organization made up of non-binary variables and stakeholders. This then leads to a complex concoction of politics, rules, agendas, relationships, policies, etc. which is now your job to navigate and manage harmoniously. Most of the time this is manageable, but sometimes you’ll get it wrong. Depending on the significance of your mistake you may be bad-mouthed, mocked, or questioned. You may get rumours spread about you, people angry at you and you may even have a few people threaten you in some way or another. This is going to happen. It’s happened to me, it’s happened to my partners, it’s happened to all the significant leaders I know, and it happens to everyone else who is responsible for leading a sizeable group of people. When this happens, own your mistake, don’t take anything personally, respond to it with class and composure, and never reciprocate the negative emotions of a team member. Stay humble, maintain integrity, apologize when you fuck up, and present your team with a plan of how you’re going to be better in the future.

7. LEAVE THE EGO BEHIND

Humility is one of the most important characteristics a leader can have. After all, being a leader should be a humbling experience. This point is simple and short. Your ego will be the number one thing that gets in the way of everything you do as a leader. Whether it’s not hiring someone better than you (which is the point of hiring), not recognizing valid concerns from others, or exploiting a team opportunity for personal gains, the ego is a toxic dumpster fire that needs to be constantly suppressed. This isn’t to say that you shouldn’t be driven by self-motivating factors, it would be silly not to acknowledge those in the context of your role. What it does mean though is that you should be constantly asking yourself, “Do I feel good because of the decisions I am making or am I making decisions because I like feeling good?” If it’s the latter, step back and check your ego.

8. DECENTRALIZATION CAN BE POWERFUL AND CHAOTIC

There is a reason why prosperous governments, powerful militaries, and successful organizations throughout the world adopt a decentralized operational model — because it’s powerful and it works. There is however a caveat, if it’s not done correctly it can ignite chaos and confusion in your team that is very hard to reverse.

There are better people to be telling you how to properly adopt and maintain a decentralized leadership model but, in my experience, these are the 3 key factors that are crucial to get right:

i. Make sure your objectives and the rationale behind them are strongly established and effectively communicated.
When you’re working under a decentralized model, you are trusting each leader at every level to act semi-independently to manage their portfolio effectively. This goal-oriented mindset will be hard for some people to follow but it makes it much easier if everyone has a firmly established and common goal that they know they are supposed to be working towards. It gives clarity to the lower-level leader and ensures that any plans they come up with and execute are moving towards that larger objective that you have established.

ii. Make sure that everyone understands the objectives of the other departments on the team and knows how important they are to your success.
Plain and simple…if one department on the team fails, the entire team fails. That is the nature of decentralization. It is your job as a leader to be constantly pulling puppet strings to make sure that each department is continuously operating well, and you must make sure that everyone else on the team plays their part too. The PMs must communicate with operations personnel and work together to complete their individual goals. This is the one that I’ve screwed up the most and have found the hardest to execute on.

iii. Prepare for some people to respond poorly to the independence and responsibility they’ve been given.
You are in this position because you are motivated, self-driven, confident, and strong. You like independence, you thrive under pressure, you like creating your narrative and you like the challenge and responsibility that comes with leading people. At the end of the day, you want to be a leader…a lot of people don’t. It’s easy to assume that anyone applying for or put in a position of leadership or independence would like it, but that’s not the case. Most people are going to hate that. It is crucial that anyone you put in a position of significance understands exactly what is required from them to thrive in that position. I’ve had a few experiences where we hired a person to fill an independent leadership role that they didn’t know they would hate. This can completely derail a team department and can be detrimental to your team’s goals, so make sure that it doesn’t happen.

At the end of the day, constant, straight forward and detailed communication among everyone in a position of significance within your decentralized model is the best way to get it to thrive. Always assume ignorance and always check in with your leaders.

9. CREATING AND SUSTAINING TEAM MOTIVATION

Like the decentralization section, there are many people more qualified than myself to be telling you how to ignite motivation in humans, but these are the top three methods that I have found most effective.

i. Establish a collection of quantifiable incentives.
One way of replacing or adding onto the incentive that a paycheck provides is to try to establish a few key incentives that are quantifiable and attainable for the members of your team. This can take many forms but some that I have found useful are advancement opportunities, social media shoutouts, personal development milestones, team awards, and personal acknowledgements of achievement. These incentives don’t have to be large or fancy. The presence of anything tangible or quantifiable that someone can work towards is a powerful tool for motivation in people.

ii. Create a sense of ownership and accountability.
One of the main reasons why someone becomes unmotivated on a team is because they feel like the contributions they are making are worthless or unneeded. Alternatively, they may feel like if they don’t contribute or perform optimally then it doesn’t matter because someone else is responsible for the success of the team and therefore, they’ll take care of it. As a leader, if you can constantly show or acknowledge how important the contributions of a person are, or let them know that they have the power to directly impact a team positively or negatively based on how they perform, that person will immediately become more committed and motivated to produce good work. This essentially is using someone’s ego to your advantage. You build the ego up and then create a scenario where, if a person doesn’t perform well, their ego takes a hit. That is a very powerful motivator.

iii. Wear your commitment on your sleeve.
This essentially just means lead by example. Everyone on your team will constantly be looking at you as an example of how they should conduct themselves. Use that opportunity to set a standard of expectation for the level of commitment and motivation you want your team to have. This means always conduct yourself with enthusiasm, drive, and a deep passion for the team. Stay late, put in extra hours and establish an expectation that others will do the same. This is easy but very important. One of the quickest ways for your team to lose confidence in you is if they feel that you are being hypocritical towards them. Do not give anyone a reason to question what your expectations are.

This will be something you struggle with in any team that you lead. After all, the fact that you are the leader of the team probably means that you care the most about it and that’s important to remember.

10. NO WORK IS BELOW YOUR PAY GRADE

This is perhaps one of the most important concepts to live by as a leader. You’ll see variations of this phrase in all sorts of different contexts, “You’re never above carrying the water”, “You’re never above mopping the floors”, etc…. This essentially means that when it comes down to it, no job or task is too small or insignificant for you to concern yourself with. Every position, job, and task has its place in the team and is important to its success. There should never be a situation where you are not prepared and willing to carry out a simple, shitty task that needs to get done. There will be circumstances where you are counting on someone to complete a task and they don’t pull through, or you might find yourself in a last-minute crunch to do something and you don’t have time for task allocation. In this situation, it is on you and only you to bear down and get the job done. This might take the form of spreadsheets, documents, administration, etc. It might take the form of sprinting from building to building or store to store looking for a cable adapter because you need it for a presentation that’s happening in 5 minutes. It might even take the form of having to pick up a project manager’s duties or put in CAD and other design work for a project team. Whatever it is, there should be no job that you give to someone that you are unwilling to do yourself, no task that doesn’t get completed because someone else didn’t pull through. Everything is on you. If something doesn’t get done, it’s because you didn’t do it or didn’t allocate it properly.

“It’s not what you preach, it’s what you tolerate.”

— Jocko Willink