Five things I’ve learned about leadership

Leadership is something that has always come naturally to me. I’ve written before about how I got my first leadership job in a call centre at the tender age of 19 – and I’ve managed people in some capacity ever since.

In this article, I wanted to share with you some of the things I’ve learned about leadership over the course of my career. I don’t profess to be any kind of expert – and I have no doubt made countless leadership blunders, so, as my dad says; if you want my advice, don’t take my advice. I’m writing this mainly because it helps me crystallise these findings in my own mind, and if it helps anyone else, that’s a bonus. It’s not the top five things you need to know about leadership; just five things I have learned that I value.

Seek input and counsel wherever you can

One of the things I find fascinating when I read or listen to the stories of great leaders is the anecdotes about who they turned to for advice, or just a friendly ear in a crisis. For me, I have a core of friends who, despite not working the same industry as me, are my sounding board for my frustrations, anxieties and philosophies. This is a nice safe bubble that lets me vent, preach or confide as much as I need to, without fear or favour. It is however, mostly an echo chamber.

When it comes to being in charge, it can be lonely at the top. Having a network of trusted and objective associates that you can count on to shout you down when you’re being irrational, build you up when you need support, or give you expert advice when you’re facing a challenge is an absolute requirement. I’ve found as an entrepreneur that having specific people I can turn to for advice on things like HR, business development, technology and strategy is like having an extension of my team – only better, because they’re outside the team and therefore, more objective.

Within the team too, I find that sharing little snippets of information from time to time with key people who’s opinion I value on specific issues is a useful ‘canary’ for some of my more tentative ideas. As I told the CEO of a startup I worked at; you don’t need to have all the answers just because you’re the boss. Having the questions is a great start.

Be open and honest with those you lead

Back in 2009 when I was working at a startup owned by a husband and wife team, I felt immensely privileged and empowered when they shared with us their advanced plans and even the current financial state of the business. Having worked at big companies, I wasn’t used to this level of transparency.

I remembered this feeling, and I’ve tried to carry it through my own leadership roles. I go to great lengths to ensure that people are kept informed about my plans. Yes, I can’t tell everyone everything – nor should I. But keeping a steady stream of honest information flowing to those you’re leading empowers them to work toward the same goals. There’s no point hiring smart people and then keeping them in the dark about what they’re working toward!

This particular philosophy has worked very well in recent years in the context of one-to-ones with team members. Having the courage to be honest – but not hurtful – can make the difference between someone pretending to be aligned with you, or identifying that they may not stick around. Critical insight to have into your team.

Be a servant-leader

This is a phase I’ve borrowed directly from the manual on Scrum – the project management methodology we use – and it’s something I’ve adopted as my personal style of management for many years.

A servant-leader looks for ways to serve those they lead. What can I do to help you achieve your objectives? That’s how I try to approach every interaction with my teams. One of the ways I do this right now is running twice-weekly technical clinics. I have a wealth of technical know-how and experience that, as the Managing Director of the company, I don’t always get to put to practical use myself. Being able to hold dedicated office hours for people to pick my brain on things I might know about has proven a useful way to put that experience to good use for my team’s benefit.

If you’re not technical, and you want to find ways to help your team, it can come down to doing a lunch run when they’re really up against it. If you can’t actually contribute to the technical effort, feed those who can! Above all, stay humble and show a willingness to open doors for your team whenever you can.

I’m going to end my description of this particular leadership quality with an important caveat that I’ve only really appreciated recently. Know when to be unavailable. You can be, and I have been, too willing to serve your team. This can make them too reliant on you, and hamper your ability to do your job. I have no magic solution for the right balance – but learn to recognise when you’re playing too active a role, and failing to provide enough good quality leadership. The people you lead need empowerment and freedom, and you, as a leader, need time and space to work.

Have out-of-body experiences

I’m not a spiritual or superstitious person; but out-of-body experiences are an important part of my leadership style. What I mean by this is trying to look at myself from outside my own head. Putting myself in the shoes of those who have to live with the consequences of my decisions is a powerful moderator.

I try to re-read emails I’ve sent to the team later when I’m out of the moment, to check how I came across. I seek feedback from people as much as I can – and it can be difficult to get objective input – but sometimes you can use proxies to make it easier for people to open up. For example, asking questions like “do you think there’s anything about our process we should change?” instead of “do you think I’m doing anything wrong here?”.

I’ve studied body language for years. Joe Navarro’s book What Every Body Is Saying is a great guide to get you started. I always look for the body language within the team when I have to break news, seek feedback, give instructions or manage difficult situations. This helps me gauge the real sentiment among them and I can work on mitigating any discomfort by spotting it early.

Practice empathic listening

A few years ago I read the awesome Seven Habits of Highly Effective People by Steven R. Covey, and one new skill I’ve been practising since is empathic listening. When you have a rant to someone, quite often their initial reaction is to give you advice. In reality, you probably don’t want advice. You want to vent. There are few things more infuriating than someone giving you advice you don’t want.

Empathic listening is the technique of encouraging the speaker to elaborate more on their sentiments by creating a safe environment to do so. When they say something like “This new process is a joke”, rather than saying “I know but we have to follow it”, instead try “Oh, the new process is causing you difficulty?”. You’ve identified what they’ve said, and essentially paraphrased it back to them in a way that forces them to elaborate without putting your own spin on it. You haven’t added anything new to the conversation, but you’ve moved it to a place where they can continue.

Often, we listen while continuously planning our own response. We are not listening with the intent of listening – but with the intent of responding. Listen purely with the intent of listening, and the speaker will be more inclined to open up – tell you what the real issue is.

Just keep paraphrasing back to them what they said each time, without offering your own narrative. Don’t give advice, don’t add your own point-of-view. Just keep drawing them onwards in the conversation. You’ll learn something and you might just help them resolve their issues, simply by listening. This is a powerful tool, that I haven’t yet mastered, but which I practice as often as I can.


My leadership education continues, and I practice and refine these five techniques as I grow. I’ll leave you with some of my favourite books that have helped me learn and refine my leadership skills.

  • Seven Habits of Highly Effective People – Steven R. Covey.
  • How to Win Friends and Influence People – Dale Carnegie.
  • The One Minute Manager Meets the Monkey – Kenneth Blanchard.
  • What Every Body Is Saying – Joe Navarro.
  • Lean In: Women, Work and the Will to Lead – Sheryl Sandberg.
  • Start with Why – Simon Sinek.
  • The Lean Startup – Eric Ries.
  • An Astronaut’s Guide to Life On Earth – Chris Hadfield.
  • Leading – Alex Ferguson.
  • The Infinite Game – Simon Sinek.

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