Recently, I gave a small internal presentation to welcome a new team member. While sketching out my own path and how I came to be at Hennessey Digital, I got to thinking about how I’ve grown and how my responsibilities have shifted over the years. I’m in my (*cough* late) 40s now, so it’s no surprise that what I do now is very different from when I took my first full-time job at 21, but it was fascinating to think back on the evolution of a career over time.
My career evolution
As I looked over the past 25 years of my career, I observed that there were four main types of work I was doing, and their proportions had evolved over the years: learning, doing, managing, and leading.
In my very first full-time job after college, especially in the early going, I was learning far more than anything else. I was lucky to join a company with an amazing training program – a six-week “boot camp” starting on Day One! – and that set the tone for the early part of my career. To the company’s credit, it took learning very seriously, and I can’t even imagine how much money they spent to train us all for six straight weeks before we ever sat down at a desk.
Once I had completed the boot camp and started working, my learning was far from complete. I estimate that I was still learning about three times as much as I was actually producing (“doing”). Some of the learning was explicit, like more training on a software system or a business process, while other types looked more like an apprenticeship.
If you’re in your early 20s, you will probably not feel this way in the moment, but there will probably be a time when you look back on your early career and judge it not based on how much money you made, but on what you learned, what kind of growth opportunities you got, and the habits that you picked up for the rest of your career. What you learn at that point in your career can set you up for success over the next few decades, often in ways you can’t see until you’re far down the road.
To be clear, this is not an argument for taking on an unpaid internship or letting anyone take advantage of you in the name of “learning,” but keep the long game in mind. You probably have at least 40 years of work still ahead of you, so try to be as deliberate as you can about learning new things!
As I started to get the hang of things and needed less direction on typical tasks, I started doing the work more. By my late 20s, I estimate that I was doing the work about 50% of the time, and most of the rest of my time was still spent on learning.
Once your career is up and running, the learning becomes more and more “on the job,” in the flow of your team’s normal activities. Once I had demonstrated basic proficiency in certain areas – such as building an analysis model or making a presentation to management – my managers started to include me in more things.
If there was a big meeting happening, in my early 20s, I probably wasn’t even in the room. By my mid- or late 20s, my managers were more likely to say, “Scott, you should sit in on this meeting.” Even if I was a mere fly on the wall, I was learning thanks to the exposure.
Back to the doing: At this stage of your career journey, you’re producing a lot. You’ve become the master of a small domain, and people start to turn to you to get that thing done. Often your reputation grows, and more people seek you out to do that thing, and then one day someone will ask you to start teaching others how to do it.
I was in my late 20s when I was first asked to start training others. I didn’t become anyone’s direct manager right away, but I started to teach others what I knew and look for ways to help the company outside of my own team.
Once I did get my first direct report, I quickly learned that their success and failure largely depended on me, and it was my responsibility to make sure that they succeeded. At this point, I realized that being the expert on something wasn’t nearly as valuable to the company as making sure my small team could do what needed to be done.
A lot of fantastic individual contributors struggle with making this jump – they’re good at something, so then they’re put in charge of that thing and start leading people, and they hire or inherit people who may not yet be as good at that thing. When faced with this challenge, a lot of young managers will fall back on “I’ll just do it myself,” but that stunts growth for everyone involved.
This tends to be the hardest jump for anyone in their career because they have to unlearn so many habits and replace them with new ones. Is the team confused? Time to figure out a new process and new means of communicating. Is one worker falling behind? Get with that person and understand if they’re lacking the skills or commitment to succeed. Diving in and doing it yourself should be a last resort. Avoid over-functioning, as our CFO Michele Patrick says.
This tough transition is one reason why most companies deal with some amount of the Peter Principle – stars get promoted, but at some point, they’re being asked to do something very different from what made them stars. We think about this a lot at Hennessey Digital when we talk to our team members about their possible career paths – making the jump to the next level will always require team members to learn new things!
Today, I spend more time leading than managing people directly.
So what is the difference between managing and leading? Managing a team is focused on a lot of the “what” of the work – measuring progress toward goals, communicating with stakeholders across the company, fixing inefficiencies, and finding new ways to get things done.
Leadership defines a lot of the “why” and “how” for the team – Why do we do the work we do? How are we going to grow? Why is our culture important? How do we interact with each other, our clients, and our partners?
Managers most often directly influence their own teams, while leaders usually influence and motivate people across the organization. And this isn’t a strict “either/or” thing – lots of managers demonstrate leadership by bringing out the best in their people, and by inspiring others to take action even if those people don’t report to the manager. And every leader in a company spends some time managing their people’s work.
What has the change from managing to leading looked like for me? Whereas 10 years ago I would often say, “Here, do it this way,” I now come into conversations with Hennessey Digital team members armed with questions and prepared to do a lot of listening. The ideal outcome is when I can help my people arrive at the best way to tackle a challenge or opportunity, mostly on their own.
Don’t ever stop learning
Note that, in the above chart, “Learning” hasn’t gone down to zero. Even the CEO of a Fortune 500 company needs to keep learning and growing because they’re constantly faced with new challenges and opportunities. Career evolution never stops!
A couple of years ago, Jason Hennessey and I started working with an executive coach, Cameron Herold. The best thing about a good executive coach is that it’s rare to encounter a challenge that the coach hasn’t also gone through. Our coach has tackled big challenges, made mistakes, avoided other ones, and has basically “seen it all and done it all.”
Talking through a challenge with Cameron usually helps us see that it’s not as daunting as we thought. He also sometimes talks us down when we fall in love with one of our ideas too much. A great coach helps smooth out the highs and lows of running a business.
Jason and I also belong to Vistage, a peer group for people running businesses in all kinds of industries. Jason belongs to one Vistage group and I belong to another, and we frequently come back from our monthly meetings with great ideas on how to overcome a challenge or pursue a new opportunity.
Where to go from here?
When I close my eyes and try to imagine what my own “Learning – Doing – Managing – Leading” chart will look like in another 10 years, I think the evolution of a career will look fairly similar to how it looks now. For my part, I’m committed to always improving as a leader and finding ways to grow the people on the Hennessey Digital team. I’ve worked for some great companies with terrific cultures and caring leaders, and I love paying it forward!