October 25, 2020

– This article is one in a series by Lee de Lang, Founder at Big Red Oak, about his learning experiences in leadership.


Tentative, dynamic, lonely, exhilarating, intimidating, rewarding, frustrating, uplifting.

Assuming a role in a leadership position can throw you into quite a mixed state of mind.

  • I don’t know what I’m doing; this is all going to fall apart.
  • I’m so proud of our team!
  • The path is so clear; why am I the only one who sees this? Why can’t we just get this done?
  • We did such a great job on this project: well done!
  • Where is the next job coming from?

A quick Google search brings up a multitude of leadership styles, and then a bunch of resources where you can learn how to become a good leader. The first question that pops up is: “What is good leadership?”. 

I’ve often wondered that myself.

Through years of shooting corporate videos, I’ve had a chance to peer into the intimate world of many leaders. I’ve filmed Town Hall addresses, press events, CEO messages to employees, pep talks, courageous conversations telling the team to pull up their socks. I’ve coached senior leaders when they break down in frustration because they’ve crumbled in front of a camera and beat themselves up for it ….” I can speak comfortably in a room full of people, but I have no idea why I can’t do this.”

It’s these moments — seeing so many leaders and leadership styles at work — that I instinctively draw from to inform my own approach.

While there are a lot of coaching services, formal education sources, books and blogs, webinars, eBooks and case studies available, seeing first-hand interactions and drawing insights from peers has been considerably helpful to me.

I recently took some time to chat with Lisa Stam. She runs a boutique law firm named Spring Law. In talking to Lisa, I found that our businesses were moving in similar directions; and she had some great ideas about leadership.

“Be self-aware. You need to know what you’re good at and what your business needs from you. You have to put yourself into a place where you are most effective.” 

Right off the bat, Lisa had emphasized the value of peer groups to exchange ideas. She had gone down the coaching route but found that she was explaining her business more than she was learning how to run her business. Leaders of any organization, of any size and across different types of industries, may all be facing similar issues with operations, HR, marketing, sales and business development. By looking to peers outside of your industry, solutions can clearly present themselves, or at least suggest another point of view to try. There is much to gain by sharing ideas in this format. Mixing among those who are bolder and more brash, or who have more aggressively grown their companies far beyond where you had planned to go, can lead you to a vision that you can adapt for yourself, and then push yourself even further.

There’s also another thought: “You can’t touch everything.” I think that it’s probably fair to say that anyone who finds themselves in a position of leadership has a desire to have control. As you scale up, though, it has to be delegated. You find the people who can support you. To move to the next level of leadership in your business you have to learn to “fire” yourself from almost every job that you currently do.

As the owner of Spring Law, Lisa wrote the manual for the company. As part of that initiative, she suggested writing out all the job descriptions from the beginning for the roles that she would assume, before firing herself from each as she moved up, leaving behind the roles that would need to be filled.

Regardless of the scale of the business, this mindset can lead to efficiencies in staffing and clarity of roles. And then, it can be replicated. Thinking of the business as a franchise, how can it be set up without you having to tend to its every need? Relying on the strength of good workflow, people and process … but just the right amount of process, because you can quickly fall down the rabbit hole there!

Still, there is always uncertainty. For myself, I’ve continually felt a need to look for people to help bear the burden of steering the ship, leading the staff and taking the business to where it needs to go. I have recently come to learn, though, that there’s no need for a security blanket. It’s the dedication of employees, together with their knowledge and skill sets, that can support business growth and allow faster decisions and more flexibility in the direction that the leadership wants to drive.

Lisa had offered the metaphor of the business as a bus. You have the right people onboard who want to go where the leader wants to take them. It makes sense. But I wonder if it’s more apt to think of the people not as passengers, but as all the pieces of the bus that make it run. It needs a strong and reliable engine; the wheels must be aligned and true; the chassis needs to be robust to support the bumps along the road; and the body protects us from the elements so that we are safe and comfortable. I guess the leader in this case is not just the driver, but also the mechanic who can make repairs and get everyone back on the road if there’s a breakdown. When you know that the components are the highest quality and mesh together really well, and there’s a solid driver and mechanic on board, you can rest easy, knowing that the bus you’re riding is sure to take you where you want to go.