Leadership I learned from 5 years in business to help lead better
May 30, 2023
Have you ever grown anything? A plant? A child? A business?
Did it work out?
Growing things is hard and filled with lessons. This week we celebrated growing a business to 5 years old. It was a rollercoaster and we have the battle scars to prove it. Leadership growth is similar - it is easier when someone shares some lessons learned.
5 years feels like a milestone worth celebrating. 5 years of learning, growing, and making mistakes. But also probably the five most rewarding years of my life. I gave up the typical corporate GM role, inspired by the concept of moving around the world, working in cafes and coworking spaces, filling my cup with new cultural experiences and riches, and finally ending up basing our business in Mexico with team members in Europe and Australasia.
In that time, much like having a child, we have learned more lessons than I can count. I see direct linkages between running a great business and great leadership. I share these, not because they are some kind of hack to better leadership – you can’t hack this journey. What you can do is leverage the wisdom of others who have made mistakes and learned from them.
Lesson 1. It doesn’t matter how much you study it, there is no substitute for getting out there and experimenting.
Before 2017, I spent nearly every year of the 2000s studying something. Academia, coaching, project management, soldiering – you name it. I was a serial learner. When I became a business owner, all of this learning served me well in terms of knowing how to think like a senior leader, and being able to connect with leaders in my client organizations. At the same time, having an MBA didn’t really prepare me for the reality of actually doing it.
The thing is, leadership is the same. You can go on leadership courses, read about leadership, watch leadership videos and talk to others about leadership, but unless you start to try new things and learn what works and what doesn’t, your improvement will be limited. You can't get fitter without going to the gym. My tip is to be more curious about one thing at a time. Run weekly experiments and learn quickly as you go. The leader who tries and learns will always outperform the leader who sticks with the old ways.
Lesson 2. There will be a lot of people who try to bring you down. Leave them in your dust.
I was lucky to have an incredibly supportive group of people around me to help me with my transition to a new way of working. I think some people thought I was crazy to leave a stable, “safe” job which saw me heading toward an exec role before the age of 40, but I still remember the messages of support and encouragement I got from some key people in my life.
There will also be people out there who want to take advantage of your enthusiasm for their own gain or will try to limit your growth – perhaps because they are intimidated by your magic, or not adapting as fast as what you are showing potential for. There are others who might not understand why you're changing.
My advice – put as much distance between yourself and these people as possible. Focus on your team and serving them. Communicate clearly and often on your why and the purpose of the changes you are thinking about. Your focus should be to give your team all the support they need to do their best work to get incredible results. That support will differ for each person so make it your business to find out and deliver it. Don’t worry about the naysayers. "Do you" and the best version of your leadership each and every day, and watch the naysayers fade away.
Lesson 3. Action eats perfection for lunch
Too many people who start businesses spend hours refining, tweaking, and fettling their offering until it’s “perfect”. This has one of two outcomes:
1) It stops you from releasing anything to actually get any feedback and make improvements.
2) You put so much of yourself into something until you think it’s perfect that when you do release it, feedback can sometimes be a blow to your ego.
The same thing applies to leadership. If you wait until your strategy, plan, or idea is “perfect”; which normally means waiting too long. This means your team is left unclear. They also don’t focus on the big issues because "The timing isn’t quite right". Or, "We just need to let things calm down and then focus on the big issues later”. Wrong! These are precisely the issues standing in the way of your team performing better.
My advice – don’t wait for the perfect moment, idea or time. Create a space in the calendar, explore the issues and collaborate with your team to come up with the best workable solution. Set the team running with all the clarity you can provide, and support them by being an icebreaker – running in front of them clearing the path.
Also, remember that the spaceship to the moon was only on course for 2% of the time. The rest of the journey was a series of micro-corrections to land in the right place. The days of 3-year plans (or even 1-year plans) are gone. We now work at a faster tempo so take action and experiment towards perfection.
Lesson 4. You have to be able to trust those around you
Much like those people who try to hamper your progress (see above), being a business owner is a process of trial and error in who you can trust. Most of us don’t trust because we prefer to do things ourselves. When in reality, we actually do too much and should be empowering those around us who are keen to prove themselves, build a career and gain development.
When we start the Ways of Working program, we introduce the 3 pillars of game-changing teams. Actually, one pillar is more important than the others - trust. Without trust, communication and performance don’t work. If you are going to focus on one thing as a leader, it should be building trust with your team. If you don’t know-how, or even what trust is, that’s not unusual. We have a tool to help you assess the depth of trust in your team with each person and then show you how to build it – practically.
The result – is more time for you to focus on what really matters to you and your business. Not to be worrying whether you will have to work this weekend, be called into your boss's office for “the chat” about performance, or that your team keep leaving. Trust builds results and it also plugs the leaks.
Lesson 5. Connecting with others on the same journey is important
From the time I was in the Army, I have liked to be part of a tribe. Somewhere that people who are interested in similar things to me can connect. It’s a great garden in which to learn and grow because inevitably there are people who are further along their journey than you. Initially, this was the digital nomad tribe as part of Intrepid and then Remote Year. Then I spent a long period with the Thought Leaders Business School. Now it's a new tribe called BBD and a coaching group.
A year ago we started our WoW Global Leadership Mastermind to offer support to leaders who are looking for somewhere safe to share ideas, pick up tips, and feel part of a supportive community. Leadership has never been more challenging so having somewhere to check in with others is essential if you want to make progress. Often our own leaders are too busy or overloaded to offer this support and growth. Adding to that, most leaders have not been trained in leading hybrid teams, so perhaps you aren’t getting what you need from your manager. Either way, our community is open.
So that’s it – 5 lessons that will help you lead better. If you’d like a part 2, send me a note as I had to narrow this list down a fair bit and have lots more lessons I learned the hard way I’d love to help you avoid!
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Speak soon,
Jimmy
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