To Manage or Not to Manage?

Deciding whether to remain an individual contributor or to pursue the managerial or executive path is the cross roads all successful people eventually have to face. This can be a pivotal career choice, one that can have a profound impact on your professional satisfaction and growth. It's a decision that often comes with a unique set of considerations, and I'd like to share a story from my own experience in the tech industry that might shed some light on this decision.

Very early in my career at HP, I knew I wanted to climb the executive ladder. While I was a very good individual contributor and a successful sales rep, my calling was to lead a sales team. I myopically focused on a path that would prepare me to be a VP of Sales or Chief Revenue Officer. In 1999, I was given the opportunity to create a team of 8 sales reps across the US. The following year, I was asked to double the size of the team as well as assume responsibility for Canada. After another successful campaign, in 2002, I was tapped to take over the US PC business during the most interesting time of my career, as HP was acquiring Compaq. Being asked to integrate 2 very different cultures, businesses and processes while growing revenue and market share was challenging, frustrating, invigorating and rewarding. The success in this role helped me get the North America Server business job, a role I held at the time of my departure in 2008. My team of 62 was responsible for $2.4B in revenue and all indirect (channel) routes to market. From my own managers and executive leaders, I learned to create a culture that was self-managed, focused on team goals and dedicated and committed to each other’s success.

In 2008, I left HP to take the role of VP of Sales at Dasher Technologies. Our revenues in 2008 were about $26M and we had 3 sales people. 3 of our clients represented 80% of our revenue and profit. This was a far cry from the job I left at HP, but gave me the autonomy to build a team, create and drive a vision and establish a fresh culture. By the time I retired in 2020 as President, our revenues had grown to $175M, we had 20 sales professionals, an entire marketing department, over 30 engineers and a stable of business development reps spread out across 4 offices.

I share this backstory to help illustrate why I made the decision to pursue a leadership role, not only at HP but also a bigger role with more responsibility at Dasher. Every step of the way, I knew I could make a larger impact and difference in the business if I had a bigger team. While I might exceed quota myself, why not try to help a team over-perform?. More importantly, by having some influence over the career paths of my team, I am proud to say that many people who once worked on my teams have achieved status and goals that far outweigh my own, and I’d like to think I had a little bit of impact on their trajectories. I genuinely enjoyed watching others make money, get promoted or accomplish their dreams. Whether they chose to be account managers, VPs or CROs, each carved out their own definition of a successful career based on what motivates them. I’ve helped many people evaluate their situations and make a decision on their path.

In a previous blog, I talked about the 6 things that might motivate you: money, praise, promotion, power, fear and education. While compensation is certainly very important, I believe I chased power because of what I could do with it. With power and title, in particular at a big company like HP, I knew I would be in a position to positively influence lives and careers and leave a bigger impact on an organization. Of course, not everything is glamorous in leadership roles. Managing people and their expectations and experiences in the work place can be exhausting, trying and frustrating. There is always something going sideways and always someone on the team dealing with some drama. Their problems become your own. There’s a lot to be said for being inwardly focused and being the master of your own success or failure. Corporate politics and bureaucracy can be where dreams go to die.

I know dozens of very successful and satisfied people who chose to be individual contributors for their entire careers: real estate agents, stock brokers, sales reps and entrepreneurs to name a few. For most, money is the overwhelming motivator and they find roles that are best suited to avoid company politics.

I believe your path can be distilled down to a few simple decision points:

1. Passion and Expertise: I considered how much I truly loved leading a team, helping individuals achieve their goals and creating a team dynamic. I made a good living as a sales rep, but I also knew that stock options, higher income and other benefits would come with the territory of pursing the corporate ladder and since compensation would align with my own passion to lead, management was a logical outcome.

2. Leadership Skills: I carefully and impartially assessed my leadership skills and potential. I had experience leading small teams and projects, but managing an entire group or company was a different ballgame. It was important to evaluate if I had or could develop the necessary leadership skills. It is important to note that influencing people not on your team is every bit as important as steering your own group. Not to be overlooked, I also chose 2 great mentors who helped coach me along the way, were brutally honest about my shortcomings, helped steer me through challenging times and provided solid, informal leadership training.

3. Impact: I thought about the kind of impact I wanted to have. As an individual contributor, my influence was primarily within my domain of expertise. As a manager, I'd have the opportunity to shape the direction of the company, mentor employees, and contribute to the overall strategy. By taking on a team, and being responsible for a larger team, group, division or company quota, I could impress upon the employees the vision and path we had to pursue.

4. Work-Life Balance: I considered the potential shift in work-life balance. Management roles often come with increased responsibilities, travel, longer hours and considerably more stress. I thought about how this would align with my desire to spend time with my family, family and hobbies.

Most professionals will come to the fork in the road between IC and management. For many, there will be several decision points and based on where your career stands, you may change your mind. Many individuals find immense fulfillment in managerial roles, relishing the opportunity to lead and shape organizations. It's a matter of aligning your career choices with your passions, skills, and long-term goals. For others, the flexibility and autonomy of being an individual contributor as well as the reduced stress that comes with leadership roles is more attractive.

So, if you're contemplating this decision, I encourage you to take a similar introspective journey. Reflect on your passion, your leadership potential, the impact you seek to make, and how it aligns with your broader life goals. Remember, there's no one-size-fits-all answer, and the right choice is the one that resonates most with your unique aspirations and circumstances.

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