This was originally published on my blog, where I often write about remote work, learning to code, and technology.
“The greatest leader is not necessarily the one who does the greatest things. He is the one that gets the people to do the greatest things.” – Ronald Reagan
I recently woke up with the realization that I’ve been leading a team for well over a year. What was once very foreign and daunting is still a work in progress, yet somehow feels manageable. Even, familiar.
As I reflect on my evolution in leadership, I can’t help but think of the early days; back when I had “no clue what I was doing”. What stands out is the troublesome perception of leadership that I started with, extracted from pattern-matching the “leaders of our day” (think Musk, Jobs).
I had mistakenly confused visionaries with leaders.
I’ve now learned that when these two are synonymous, an incredibly powerful dynamic is unlocked, but also that these two attributes can just as easily be mutually exclusive.
This realization has led me to further question, “What other misconceptions might there be about leadership?”. This article is my perspective on exactly that. But first, a story:
Being Handed Opportunity
Some people know that I lead a Publications team. To date, this has been one of the most amazing opportunities that I’ve been given. But what many don’t know is that I found myself leading this team of twenty at the ripe age of 24. And when I began to lead this team, I was by far the youngest of the group.
Many of my new teammates had a decade (or two) on me, and despite how much I wanted to believe that age was just a number, I could feel the apprehension. But how could I blame them? Now that I was in the “driver’s seat”, I too felt like an imposter.
Here’s the thing: when you enter a position where no one is going to assume you know what you’re doing, you need to work that much harder to prove that you do. So, I acknowledged that if I didn’t have all the answers, I better find them.
What I didn’t realize at the time was that the sheer act of acknowledging that I wasn’t born a leader and that I would need to learn leadership﹣just like any other skill in life﹣was a huge step in the right direction. But that in itself led me to a crossroads, or rather, a question: what makes a good leader?
What Makes a Good Leader?
The Internet is riddled with advice for people just like me, searching for queries like “what makes a good leader” (SV: 3600), “how to be a good leader” (SV: 9900), and “qualities of a good leader” (SV: 10500).
Unfortunately, many of the results are easy to process but hard to action. For example, how exactly does one “become a great communicator”? But what I find especially troublesome about these pieces of advice is that I think they paint a very narrow picture of leadership.
When I think back to some of my best managers, I never equated their ability to lead with always having a smile on their face or never faltering while leading a meeting. Similarly, their ability to “make decisions quickly” (or not), having a threshold number of years in industry (or not), or the strength of their conviction (or not), often didn’t correlate with their leadership ability or potential. These common conventions are found all over the Internet, but quite frankly, don’t always add up.
So as I apprehensively started leading, I took another approach. I made it my goal to learn how to be a good leader, iteratively. I read psychology books. I held discussions with fellow managers. I intentionally asked for feedback from those around me. I tried to distill the skills, attitudes, and choices that made my prior managers effective. Having had my fair share of good and bad managers, I wanted to at least try being the former.
I slowly, but surely began to understand that there are two types of leadership: “by consent” and “by force”. And even though leadership is often represented as a convoluted practice that few truly master, it’s really just a representation of human behaviour and cooperation. If you miss that, you will inevitably fall into the “by force” bucket and as Napolean Hill reminds us in his book Think and Grow Rich, “History is filled with evidences that Leadership by Force cannot endure”.
Over a year and a few stumbling blocks later, I have now formed a much clearer perception of how we can get to this state of consent.
The competent leader requires no "title" to give him the respect of his followers. - Napoleon Hill, Think and Grow Rich
Learning to Lead
At its core, I believe good leadership results from learning to lead. And in order to learn to lead, three key principles need to ring true. These pillars of good leadership don’t necessarily mirror what you’ll find in the hundreds of listicles floating across the web, but they are based on the principles of interaction and connection﹣not power﹣and thus I believe should always ring true.
These principles are also non-negotiables, so once internalized, will create the right value system to guide leaders toward the right actions. And with the Pareto principle in mind, I believe that you can get yourself in the top percentile of leaders by simply embodying the following behaviour:
- Have humility
- Scrap any agenda
- Lead with through influence
When I reflect back on truly amazing leaders, there are very few things that seem to ring true across all I’ve encountered. And ultimately, it’s been their uncanny ability to bring out the best in others, through truly caring, having humility, and leading through influence.
Imagine a World
Before jumping in, I want to convey why I care about good leadership (and why you should too).
At the heart of society we find people. At the heart of people’s lives we find work﹣and a lot of it. In fact, the average American spends 90000 hours of their life at work over their lifetime, yet 80% are dissatisfied with their jobs. That’s over a decade of straight, continuous work.
It’s not a new concept that fulfilling work creates a happier society, while non-fulfilling or toxic work, destroys the psyche. While there are many inputs that go into making a job stressful or negative, a bad boss normally tops that list. In fact, 75% of employees report that their bad boss is the worst part of their workplace.
I’d like to imagine a better world. One where good leadership is the norm and where “kissing up and kicking down” is not tolerated.
“We needed help to create a world where bad managers are the exception, and the learning curve to become a good manager isn’t so high.” - Know Your Team
In order to get there, I think we need an updated view of effective leadership that corners on this idea of constant iteration. Leadership has never been and should never be viewed as a skill that people are born with or without.
And to access this ideal world, our organizations need to reprioritize.
We need to celebrate compassionate management rather than the next unicorn to have scaled quickly, at whatever the cost. We need to recognize that any organization, however successful, is made up of thousands of people pushing that vision forward. We need to recognize that good leaders lead people, not just a company.
I want to dismiss the bells and whistles that circle leadership books and pare it down to a few simple principles, that I believe action us towards that ideal.
And with that world in mind, let’s dive in.
1.0 Having Humility
“When I wake up in the morning, I always think about three things: What are my strengths, what are my weaknesses, and did I work hard enough yesterday” - Eric Yuan, Zoom (Glassdoor #1 Rated CEO)
Signaling Trust
When I started leading, my first instinct was to exude confidence. If I wasn’t always confident, how could my team have confidence in me as a leader?
I’ve now learned that confidence shouldn’t be the central point of optimization for leaders. Instead, it should be humility.
Humility is commonly defined as “a modest or low view of one's own importance; humbleness”.
If we strip out the negative connotation, it’s simply the ability to see yourself objectively; your good and bad qualities alike. Although you don’t often find leadership books calling for this underrated trait, I would argue that humility is a leader’s greatest asset.
Why is this?
Let’s start from first principles:
- Becoming a leader does not inherently make your ideas more or less right.
- Becoming a leader does not inherently make you more or less skilled.
When you become a leader, very little actually changes. Sure, you get a nice new title to toss up on your LinkedIn profile and maybe a corporate credit card. But you know what doesn’t change in that moment? Your skillset. Your intelligence. Your ability to make mistakes.
Unfortunately, when some individuals get promoted, their confidence skyrockets, despite no respective change in ability occuring. Moreover, many people utilize confidence as a signaling tool; a proxy for level of ability.
However, it’s important to understand that confidence does not promise possession of skill. Confidence that doesn’t match skill-level falls into two buckets: doubt or delusion. Both become detrimental when the delta between confidence and ability is unearthed by others.
A confident leader that lacks the requisite skills is much worse than the humble individual that can follow through. By faking confidence, you break trust between your team and are signaling that their perception of you is more important than a relationship based in reality. And since leading a team is all about influence﹣not illusion of control﹣you are destroying the very fabric of that.
More importantly, in this state of overconfidence, a leader is shielding themselves from the possibility of improvement. The precursor to ability is awareness and targeted effort, yet overconfidence blocks one’s ability to even recognize that there is more to learn.
“The most difficult subjects can be explained to the most slow-witted man if he has not formed any idea of them already; but the simplest thing cannot be made clear to the most intelligent man if he is firmly persuaded that he knows already, without a shadow of doubt, what is laid before him.” - Leo Tolstoy
The Antidote
Just like confidence, humility is indeed also a signaling tool﹣to the world and to oneself. But, the big differentiator between humility and confidence is that humility is actually tethered to one’s ability.
Humility is the antidote to overconfidence. With an accurate view of your ability, you are unlocking the door to actually improve.
And when practiced effectively, humility enables leaders to see themselves objectively; to acknowledge that their ideas are no more, but also no less, important than another person’s. In understanding this deeply, you are creating the right standard for rapport with your team.
Humility is confidence in what you know, not that you know. It’s not complete confidence, it’s representative confidence﹣the only type based in reality.
Humble leaders know they don’t have all the knowledge or answers and therefore they actively listen to learn. They also know their own limitations and that self-awareness helps them get better. - Orly Maravankin
Humble Confidence
All leaders should be striving toward a humble confidence; the keenest sense of awareness for their true capability. Humble confidence is in effect, self-realization, when the true antithesis to humility is ego or pride or arrogance, and perhaps at the worst end of the spectrum, delusion.
The beauty of humility is that it’s absolutely essential for developing all of the other skills or attributes that a leader should possess.
Seeking Feedback
If humility is the antidote to overconfidence, its partner in crime is feedback.
Once a leader has embraced the concept that they won’t always have the answers, it’s much easier to be authentic and vulnerable. Utilize your desire to improve as an asset, and bring your team along for the ride.
“Advice seeking is a form of powerless communication that combines expressing vulnerability, asking questions, and talking tentatively.” - Give and Take
Some leaders shy away from highlighting mistakes or requesting direct feedback, so as to not compromise people’s perception of them as a leader. Contrary to this belief, asking your team for feedback is often a net positive.
In fact, there is a set of research called the Pratfall effect, which suggests that exhibiting a lack of perfection can actually result in enhanced trust and interpersonal appeal, so long as you’re relatively competent.
So talk openly about your mistakes! Rid the stigma that always being right is better than always being reasonable. Embrace the transparent, unsurprising, and very human fact that sometimes you mess up, and that you’re totally resolved about it. By definition, if you’re working towards something difficult, mistakes will be made. If they aren’t, it’s likely that you aren’t taking enough risks.
Leaders need to learn to stomach the concept of risk<>reward, and be okay with the mistakes the must come with that. And in being transparent about these mistakes, people will respect you more for being an open book, rather than exuding levels of fake confidence.
This public introspection also enables your team to be more effective, by giving them a seat at the table. Ideally, you hired a bunch of smart, creative people to contribute to the mission, not just agree with your ideas. The best teams are dynamic in thought and if you are in full resolve about your own opinion, you prohibit that dynamic from flourishing. Malcolm Gladwell relates to this concept in his book Outliers, by reminding us that “planes are safer when the least experienced pilot is flying, because it means the second pilot isn’t going to be afraid to speak up”. The same is true with leadership. If your team is afraid to speak up, you better bet they won’t stop you from nose-diving.
In short, good leadership comes from those who actively invest in learning how to lead well, and without asking your team for input, you’ll never know if you’re moving in the right direction. It would be like designing a product without talking to your users. While it happens often, it rarely succeeds.
2.0 Drop the Agenda
“Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others.” – Jack Welch
With the strong foundation of humility, a good leader needs to take the next step and drop any agenda that may have once existed. As an individual contributor, people are often struggling to have their work seen or their voice heard. But once you transition into a leadership role, it no longer becomes about you. Your role is to prioritize the success of your team over your own. That is the most common thing that new leaders miss: your new role is not just a continuation of your old. You must completely realign your priorities.
And this is exactly what I mean by scrapping the agenda. Reversing your priorities such that your personal gain is no longer at the top of the totem pole. Without doing this, you will never be able to establish the level of trust that you need with your team.
So then the question becomes, how do you establish trust with your team?
You need to ensure that your actions match your values. It’s a simple statement, but is easily overlooked in practice.
Jeff Weiner, CEO of LinkedIn, conveyed this by explaining that generating trust was foundational as he led the company through the early days, their IPO, and their subsequent acquisition. For him, trust was a function of consistency/time, both of which had no substitute in the “trust equation”.
Trust also comes from the combination of things:
- A belief that you have someone’s best interest at heart
- The confidence that you have the ability to help that individual
- Demonstrating the character that especially in tough situations, you will do the right thing.
At the end of the day, trust is a feeling. And in the case of leadership, trust comes from the faith that someone truly has your best interest at heart. That’s exactly why there can be no back-channeling. No kissing up and kicking down. No blaming.
"Trust is not an action or a resume, it is a feeling that others have about you.” - Matt Russell
"If a leader is a REAL LEADER, he will have no need to advertise that fact except by his conduct-his sympathy, understanding, fairness, and a demonstration that he knows his job." - Think and Grow Rich
People say that “leadership starts at the top”, and that’s because leaders need to enable their peers to operate from a place of 360° trust, meaning that trust is not unidirectional, but instead above, below, and lateral. That is exactly why if a leader is operating from a place of fear, it’s nearly impossible for them to lead effectively, because that trust is likely uni-directional, if present at all.
Part of “ditching your agenda” and enabling trust is to care personally (one of the fundamental pillars of Radical Candor) to the point that you are no longer sympathizing, but instead empathizing. Your team’s problems become just as much your own. The same is true for failures.
“Jeff explained to me that empathy is feeling what another person feels. Compassion is empathy plus action. It’s actually doing something to help the other person. In a work environment, this involves stepping back to be a “spectator of your thoughts” and taking time to understand others. We are naturally egocentric, meaning that we see the world from our own perspective. There is nothing wrong with this per se, but it means that we tend to expect others to behave just as we would and to get frustrated when they act differently.” - Eric Yuan
Although it doesn’t always come naturally, leadership is about learning to put yourself in the position of another. And any agenda is simply a roadblock to getting there, and thus must be completely removed from the equation.
3.0 Leading Through Influence
Leading vs Managing
“Leadership is about influence, not control. I am not the first person to make this observation, but it is worth repeating. The truth is that control is an illusion. You can’t control anyone, even the people that report to you.” - Michael Hyatt
We’ve experienced the types of leaders that are contagious. They inspire others to follow because they want to, not because they have to. They don’t just have their team’s consent, but also their enthusiasm; their belief.
The only way to attain this relationship with your team is to systemize positive behaviour. And the best way to systemize positive behaviour is to live by it. For example, the best way to motivate others to improve is to exhibit your own continuous improvement.
This is one of the key differentiators between leaders and managers. Leaders have people who follow them, as opposed to managers that have people who work for them. It’s hard to admire someone that consistently asks, without ever giving back, or at least proving that they too can deliver. Good leaders recognize that their ability to inspire is not based out of the things they say, but the things they do. By leading through influence, leaders not only make things easier for their team, but also for themselves, as their team will reward their acts of camaraderie with mutual respect and effort.
“When people want to follow you they will always give you their best; while, if they only follow you because they have to, they will always give you the bare minimum that they can get away with.” - Matt Russell
Talk Doesn’t Cook Rice
In practical terms, leading through influence means taking the time to understand exactly what your team does. It also means stepping up to contribute individually and not just hand out tasks.
This concept touches on a more significant takeaway that spans all work. As Napoleon Hill said, “The world does not pay men for that which they "know." It pays them for what they DO, or induce others to do.” The idea that some leaders expect that they should be paid or lauded for what’s cooking “up there” is ludicrous. Leaders, no different from the independent contributor, are responsible for driving value and should never feel above doing exactly that.
You know what says, “I’m the boss”? Literally being a boss at what you do, not what you say. Your role as a leader is to inspire and enable your team to be the best they can be. The best way to achieve that is to lead by example; if you want someone to do something, do it first. Lead the goddamn way.
“If we could change ourselves, the tendencies in the world would also change. As a man changes his own nature, so does the attitude of the world change towards him.” - Gandhi
Make the Tough Calls
Life is filled with complication. As a leader, you can’t be there to make every decision for your team. So how do you ensure they’re making the tough calls when it matters most? By setting the example.
One of the toughest calls that a leader will need to make is termination. And often, who a leader chooses to hire or fire is arguably the most important call they can make for their organization. And if you are truly prioritizing your team’s success over your own, you need to base your decisions on what will drive better outcomes, collectively.
“On a dream team, there are no ‘brilliant jerks.’ The cost to teamwork is just too high. Our view is that brilliant people are also capable of decent human interactions, and we insist upon that.” - Netflix Culture Deck
For example: if there is a team member who is a great individual contributor, but is a jerk to the rest of the team, this is not okay. In addition to the intangibles, their impact on other members of the team almost always outweighs their individual contribution. In other words, an individual’s contribution cannot be viewed in a silo and if you’re leading the team, your action or inaction is a choice; a reward system.
“The actual company values, as opposed to the nice-sounding values, are shown by who gets rewarded, promoted, or let go.” - Netflix Culture Deck
If you choose to prioritize someone’s siloed impact over their net influence, you are signaling what gets rewarded. This is particularly important once you recognize that some team members are givers, while others are takers. Should you only account for the direct output of each individual, you are likely grossly underestimating the impact of the givers on your team.
| Siloed Contribution | Team Impact | Total | |
| Person A | +100 | -65 | +35 |
| Person B | +70 | +10 | +80 |
| Person C | +65 | -15 | +60 |
| Person D | +95 | +20 | +115 |
| Person E | +45 | +5 | +50 |
In the above example, you’ll notice that Person A may be the most effective when you isolate only for siloed contribution, but when you factor in team dynamics, their total contribution is the lowest. In some cases, the total contribution may even be negative.
“If you can recognize competition as a destructive force instead of a sign of value, you’re already more sane than most.” - Zero to One
I also have heard some leaders say things along the lines of, “They’re just too good individually. I wouldn’t be able to replace them.” My answer, although admittedly simple, is that you can. Being incredibly talented and a good teammate are never mutually exclusive.
"Great leaders make the hard choice, and self-sacrifice in order to enhance the lives of others around them. - Brent Gleeson"
In conclusion, if you want your team to bite the bullet and make the right decisions, especially when they’re hard, it’s your responsibility to do the same.
Setting a New Agenda
I recently listened to a conference talk, where the speaker asked the audience to “imagine a world without traffic jams”.
It was the sort of question that seemed arbitrary at first, but invokes a very vivid image of a better future. From that image, you can think backward and conceptualize what would need to change for the world to get there.
Now I want you to imagine a world without sh***y managers. A stark contrast compared to the reality we live in, but also not impossible. What are the steps that we need to take as a workforce to get there? What does that new wave of leaders look like? What must we no longer tolerate?
What I didn’t realize when I first started this journey into leadership was that I never needed to rule the roost. I just needed to have the right core values and the rest would take care of itself. It’s truly amazing what a splash of humility, trust, and honesty can do for your team and your company.
I believe this world can exist, but it takes a consistent look in the mirror for the leaders of today to learn to be the leaders of tomorrow.
If you liked this article, I would recommend the following books:
- Radical Candor (Kim Scott)
- Give and Take (Adam Grant)
- Originals (Adam Grant)
- Drive: The Surprising Truth About What Motivates Us (Daniel Pink)
- Think and Grow Rich (Napoleon Hill)
PS: Come join the conversation on Twitter.
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Top comments (3)
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I learned a lot from this perfectly written article.
Yes, long but worth every second of reading!
Thanks Steph 🌹
Thank you so much!