On Leadership

The action of leading a group of people or an organisation.

It’s difficult to think of a world without leadership. It’s an inescapable part of our everyday existence. Whether it be the laws defined by our governing leaders or the delivery requirements set by our senior management teams. It’s everywhere, all around us. It dictates our interactions in a vast number of settings on a daily basis.

There’s many opinions on what great leadership is or in fact what even exemplifies the qualities of a leader. Given my own varied experiences, mainly in the startup world, I felt it was time to voice my thoughts on the matter.

What is leadership? I mean really. What is it? A bullet pointed list every would be “leader” feels the need to piece together that normally ends up on LinkedIn or Medium? The opinions of political delegates, based on what they deem the embodying qualities of a “leader” should be? Or maybe it’s just the loudest person in the room, in which case I’m in the running too.

From the moment we’re born, to the day we die, we’re experiencing some varying form of leadership. As infants our parents set an example as to how we should live our lives. When we’re in the playground, one of the other kids tell us what we’re going to do for the rest of recess. Teachers educating us, so we can thrive in this world and hopefully one day make it just a little bit better. Appointed bodies attempting to better our daily lives, but perhaps sometimes falling short.

There are many examples of how we lead. Most articles and discussions are usually fixated on the professional context and this one will be no different. While it would be ever more interesting to hear about leadership outside of the working world we’ll have to leave that one for another time.

What is a leader?

What are three words that come to mind when you think leader?
Charismatic, driven, selfless

That’s something or thereabouts that I usually default to. And to play devil’s advocate against my own thoughts for a sec… I don’t really believe charisma is a necessary part of all leadership. Is the government charismatic? Probably not. Does it need to be? Probably not. I want to know government has the ability to lead our country but I don’t look to them for inspiration (I look to society as a whole for that — maybe that’s naive, who knows).

Charisma is a quality I gravitate towards as I think most others do. The ability to inspire people through words and actions is immensely powerful. In film context, we hit the third act and at this point the protagonist begins passionately delivering a page long piece of dialogue which should in fact rally the troops and help them find the courage to overcome the aliens… or something like that.

In the real world, it could be that the actions of friends, colleagues or partners implore you to to do the same as they do or focus on the thing that interests you the most in life.

I can remember moments when I experienced this first hand from some of my past colleagues. Usually in high pressure environments and sometimes when we thought we were on the verge of failure. Yet somehow these people pushed me, drove me in ways I couldn’t do myself. When I think back. The leaders were not appointed, they emerged, and we valued them that much more because of it.

A leader who is driven. It feels pretty self explanatory. If someone is in the driver’s seat, I want them to have their foot on the gas peddle. There’s nothing worse than being at a standstill because the guy in charge has no desire to move forward. We’re not talking about decision making, it’s really about whether or not someone is “all in” and willing to put in the work.

A leader should be selfless. You want someone who’s putting the mission and the team first rather than their own agenda. There’s this notion of “managing up”; a method by which you can present yourself in the best light to advance your career. I’ve seen it used incorrectly by weak leaders, finding a way to put a positive spin on everything, taking credit for the achievements of the team and never conveying reality to their superiors. It’s essentially a form of politics played by those who put themselves first. Being selfless is about putting the team first, empowering them and sharing credit for the work.

Aside from the qualities mentioned above, a leader should be confident in their abilities, be thoughtful about their words and actions, have some self awareness about how others perceive them. They should be steadfast in the face of adversity. Understanding and empathetic towards others especially in difficult times or when mistakes are made. A leader should be capable of inspiring and elevating their peers.

While it sounds like I’m evangelising what it means to be a leader, truth be told, it’s what the people need, it’s what I need.

In the work place

Management is not leadership

It’s common place to identify managers as leaders. In many cases authoritative figures are in positions that require them to possess leadership qualities, but I would argue that a manager doesn’t have to be recognised as a leader. While it’s ideal for someone in such a position to embody those qualities, in larger companies it’s less urgent. In bloated orgs, there’s a need to maintain order, this is where managers thrive, utilising process and control. In smaller leaner places, startups for example, individuals are the vital sustaining lifeblood, having a much greater impact on it’s direction. In these cases, a manager without leadership characteristics could be fairly detrimental to the overall success of the company.

Leadership in the workplace. What immediately comes to mind? Team leads. Founders. The CEO. What else? Those are all fairly visible players and we’d expect something of them. What of those in lesser known positions, never privy to boardroom discussions or strategic meetings, unable to play a role in the decision making process. Groups or individuals most often referred to as a “resource” are what drive execution and in doing so essentially lead by example. In turn, inspiring others within the organisation to do the same.

It takes significant effort to start a startup. It’s not for weak of heart and not something everyone is capable of. Being a founder immediately puts you into that leader category in my opinion. As time progresses and the company scales, there’s a need to hire other leaders who can share the responsibility and focus on specific aspects of the business. This usually evolves into a team of C level executives running the show, also known as the leadership team. The group’s responsibility is to manage day to day operations, scale growth and ensure the business thrives. They’ll normally head up specific divisions; finance, product, business, marketing, etc. In most cases people are hired based on past experience in similar positions. It’s imperative when hiring for these key positions that the individuals be thoroughly vetted. Never hire based solely on a resume.

Of course no leadership post would be complete without something on the CEO.

Chief executive officer. Captain of the ship. Commander in chief. Leader of the free… too far.

If there’s anyone that should embody the qualities of a leader, it’s the CEO. We look to them to ensure the company’s long term success. It’s not about micro-management, it’s about focus on the vision, maintaining a high level overview and keep the momentum rolling forward. Often you’ll hear the phrases, “The CEOs job is to play defence, it’s the team’s job to play offence”… or, “The CEO has one job, to ensure you don’t run out of money”, or even, “The CEO defines the culture and sets the tone”. I believe it’s all of the above and more. The CEO is the face of the company, nobody should be more invested in making it a success. I think some of the most successful CEOs are those with an intuitive understanding of product, how it should evolve, who the target demographic are and what it takes to reach critical mass and beyond. While the team is aggressively trying to nail targets in the here and now, the CEO needs to keep the team motivated and focused while also thinking two moves ahead, anticipating future issues; competition, regulation, market conditions, etc.

Former CEO of Twitter, Dick Costolo, shared some very interesting thoughts on the topic of being a leader at TC Disrupt 13. A paradox, “As a leader you need to care deeply about your people without caring about what they think of you…. managing by trying to be liked is the path to ruin”. Watch the full video here https://www.youtube.com/watch?v=Tbpd6vVdNQ0

Being transparent and honest with the team are key. Sugar coating the truth or telling people what they want to hear, will only hurt the company. It may feel good to know that your employees like you as a person but that doesn’t mean they respect you and it damn sure doesn’t make you a good leader. A good CEO needs to understand the difference between being liked and being forthright.

The good

Leaders emerge through selfless acts

Good leadership comes in many forms. Not everyone possesses the same qualities. In fact you’ll find many great leaders have some obvious weaknesses but make up for them with unparalleled strengths.

Elevating those around you. The ability to inspire and empower others is part of what sets leaders and followers apart. Whether it be leading by example or finding ways to acknowledge and motivate the team. Great leaders help others be the best they can be, to thrive and push beyond their limits and attempt to reach their full potential.

Actively communicate. Be transparent, honest and open. The foundation of any great relationship is built with open lines of communication and by being forthright. You cannot lead in isolation, it’s an act committed through action and interaction. Something that requires building and maintaining relationships. You would not hide problems from your spouse; don’t hide issues from your team. When key decisions are being made, let everyone know, it shouldn’t come as a surprise. Provide regular updates about the state of play.

Knowing what you don’t know. Being self aware enough to know that you don’t have all the answer is a strong quality to possess. Combined with humbleness and humility, allows one to maintain an open mind, seeking answers from others and working collaboratively to succeed.

Trusting in the team. You can’t do everything yourself and micro-management doesn’t scale. The greatest companies in the world were built by teams, not individuals. While it’s your duty to lead and have a great vision, it’s vital that you trust in the team and their ability to rise to the challenge.

Selflessness. One of the greatest forms of leadership I witnessed was in my first company. During the 2008 recession our business was hit hard. Cash flow was tight and the outlook bleak, but rather than layoff a number of people, the management team took pay cuts to ensure everyone kept their jobs. Very few in the company were aware of this. Selflessness does not demand recognition.

In contrast I’ve seen the complete opposite happen where executives have maintained their very lucrative salaries while large percentages of the work force were let go. In this situation a good friend and senior member of the team volunteered to be made redundant so that others would avoid losing their jobs. A rare selfless act.

Empathy. A good leader has the ability to read a room and gauge the emotions of others. They understand the needs of the team and have the desire to help. They’re able to put themselves in the customers shoes and ultimately deliver on their needs. It’s just as much about non-verbal communication as it is about listening. To be truly present when with people and genuine with your words and actions.

The bad

Talk to me when you have a C-level title

We’ve all probably experienced more bad leadership than good. It comes in many forms, sometimes indiscernible from poor day to day management and other times hitting you in the face like a bad smell.

Slow decision making. A way to subtly kill a company. Where every action is questioned or hesitation and uncertainty bleed into one’s thought process. It may feel easier to wait and see, hoping something will change and improve the status quo. Then maybe you won’t have to make a decision at all. Fear breeds uncertainty which results in slow decisions which inevitably leads down the path to mediocrity. The fear of making a wrong decision, the fear of making things worse, the fear of being held accountable.

Slow decisions can also creep in when “process” is inserted into the execution path. Companies introduce hierarchy and complex reporting structures when someone decides they’re no longer a startup but a business. It’s a great way to lose sight of what’s really important.

Make quick decisions and don’t be afraid to change your mind when something doesn’t work.

Allowing personal vendettas to cloud your judgement. I’ve seen a few people in senior positions allow this to happen. They create subconscious bias which essentially means they stop hearing those people. Rather than setting personal feelings aside, they let it get the best of them. In the end only the business and their own reputation suffers.

Taking credit for other people’s work. I mentioned managing up earlier. You’ll usually see this sort of behaviour from those more concerned with their own career than the team or the company.

Ignoring opinions from a “resource”. I can’t count the number of times I’ve seen this happen. A person spends years getting to where they are, they paid their dues and now they don’t have to hear what anyone else thinks, especially not people doing the grunt work.

Question leadership

When I say jump you say how high

Are you a sheep? A lemming? Do you blindly follow orders? If I told you to jump off…. you get the idea.

Trusting leadership is important but they need to earn your trust. That’s not to say you should second guess every decision the CEO or your manager makes. That‘s a great way to destroy trust and respect, while also massively reducing the productivity of your team. Still, don’t be afraid to question the decisions you don’t understand or what you think might be detrimental to the long term success of the company. If you feel you have a better approach, speak up. Challenging leaders encourages them to better understand their own decisions.

Lead by example

Don’t just talk the talk, walk the walk

Good leaders set the tone, not only with their words but more importantly with their actions. They make sacrifices, in many cases which others aren’t even aware of. They play defence and allow the team to play offence. They take on the unglamorous tasks, the grunt work and unblock the team wherever needed.

An example of this is a tech lead. There’s no better way to earn the respect of your team than by rolling up your sleeves and doing the work along side them in the trenches. Whether it be taking on a bunch of bug fixing tickets or doing the monotonous API integration work. A tech lead does not shy away from the responsibility of being on-call either.

Knowing when to shut up

If you hear your own voice, you’re not listening

It’s less about you and more about everyone else. People are looking to you for advice, guidance and direction. Bestow your knowledge on them but not before actually hearing what they have to say. Dictating your opinions helps no one. The ability to listen, process and provide a meaningful response are qualities every human being should possess. Interestingly, a lot of the time people don’t really even want your opinion, they just want to know that you acknowledge theirs.

Don’t lose sight of reality

Constructive criticism vs tearing someone down

Empathy, a quality sorely lacking among many. At the end of the day remember, you’re dealing with real people, with real feelings and real emotions. With lives beyond the work. Treat them with respect, be patient and thoughtful.

When someone isn’t performing to the standard you expect or makes a mistake, think before you provide feedback. Does it help to echo a negative comment on its own? Would positive feedback along side thoughtful focus on the problem help? Is it possible to ask leading questions allowing the person to breakdown the issues themselves and produce a solution?

Eric Schmidt recently taught a session at Reid Hoffman’s class on Blitzscaling. It goes without saying that he is a brilliant leader and someone worth paying close attention to if you’re interested in being a great leader yourself. He provides a real world example of constructive criticism when an engineer built a free WiFi product at Google. Check it out here https://youtu.be/hcRxFRgNpns?t=41m10s.

In closing

What is a leader without followers? Just a person taking a walk.

We flock to those who engage us, who are driven, demonstrating charisma, ambition and confidence. Those capable of inspiring us to be greater than we thought we could be. And while the bold strong voiced figure is what we normally attribute to great leaders there’s also the individuals that give us what we need in a more understated fashion.

We lionise great leaders of the world but forget that they all had to go on their own journeys to get to where they are. Some littered with mistakes and learnings along the way. They say imitation is the sincerest form of flattery. I say, do not attempt to imitate others. Be true to yourself and your own leadership qualities will emerge. Walk your own path, experience your own journey.

I believe most of us know what leadership is and those qualities are understood by our gut instinct, but experience teaches us that there are also other parts that are perceived to be counterintuitive, inevitably leading to questions. Questions should be encouraged as it will either uncover impostors or strengthen our belief in them.

Undoubtedly, great leaders are not born, they are made.

Even the most highly praised leaders of our time had room to improve. If you’re in a position of a leadership, don’t be afraid to ask for feedback, in fact, you should encourage it. Find a mentor, someone who’s potentially been in a similar position that can provide an outside perspective to your current situation. Even great leaders need great mentors.

These are just a few of my thoughts on what it means to be a leader.

And now, I leave you with this last thought.

What is a world without leadership?