Transitioning into Management? Prepare to Be Unprepared

An Apprentice in a CEO’s Body

A few years ago, I worked for a stretch alongside someone I’ll call Louis (not his real name). By all appearances, Louis looked like a world-beater on a path to the top. He was smart and had an outstanding work ethic. His undergraduate and graduate degrees were from top programs, and his resume had big-name company experience to add to his pedigree. More than once, I even heard other people refer to him as “the hardest-working man in the industry.”

It was only half-meant it as a compliment.

The subtext of their ironic compliment became clear after working with Louis. What his colleagues were really saying, in so many words, was, “It’s a shame Louis isn’t better at his job given how hard he works.”

It seemed crazy on the face of it. Louis really was one of the most prolific workers I’ve ever seen. I would have a brainstorming conversation with him at 6:00 in the evening, and by 8:00 the next morning he would already have a fifteen-slide presentation outlining his ideas based on the conversation. I can’t think of anyone else whom I’ve ever worked with who loved assignments that much. It would have been even more remarkable if not for the unfortunate fact that his ideas were often completely unworkable in practice. Louis had a habit of fixating on a solution rooted in business theory and then either ignoring or severely underestimating the human aspects that would allow it to work. When you advocate a provocative solution that requires people to make big changes in their worldview or behavior, you need to be a master of driving adoption of your ideas. It requires anticipating and guiding peoples’ emotional reactions more so than applying force of reason to win an argument. But rather than engage in the subtler aspects of persuasion, Louis instead vigorously defended his ideas based on their theoretical merit and dismissed practical concerns, which he regarded as trivial. It often made working with Louis exhausting and frustrating. I came away with the impression that his demeanor hampered his career progression, which is a shame for someone of his raw intelligence.

Not to play armchair psychologist, but my guess is Louis was a high performer early on who didn’t get enough coaching on how to transition from the apprenticeship phase to the leadership phase of his career. Anyone who goes through an intense apprenticeship phase to begin their career is at some risk of this happening to them too. Entry-level lawyers, consultants, bankers, software developers, marketers, and professionals in countless other categories usually begin their careers by working insanely hard on tasks assigned by their managers, with only a small portion of their work being self-directed. This layer of layer of smart, young apprentice talent is foundational to how most large organizations get work done. Worker bees at the bottom stay heads-down accomplishing tasks; Middle managers make sure the tasks fit into cohesive projects; Senior managers makes sure all the projects come together to accomplish a business plan. As a worker bee, the formula for career advancement can seem straightforward: outwork everyone. Before long however, that formula breaks down. Assuming they advance to the next stage, the people exiting the apprenticeship stage who don’t realize that the determinants of success are about to change can be in for a rough adjustment.

Prepare to Be Unprepared

The reason life gets harder for people who don’t look beyond their immediate tasks is because they don’t get any practice leading others and thinking big picture (they also miss out on opportunities to create more value for the business and themselves). They can get the first promotion or two by being an exceptional worker bee. But the brute force method is no longer adequate when the next role entails more than just getting your work done. Management and leadership roles demand more creativity, nuance and people skills than are usually required when you’re cranking away on your own. At a macro-level, the evaluation criteria for determining who advances evolve roughly as follows during a career in business (and yes, I'm oversimplifying for effect):

Worker bees who don’t know how to do anything but crank away are toast once they start being evaluated along dimensions besides their own productivity. This is why it’s so important that you deeply understand how you create value for others and for the business overall from the outset of your career. If you’ve internalized the connection between the immediate tasks you’re working on and the broader business outcomes, then the transition to management is considerably easier. Conversely, if you can’t explain to someone you manage why their job matters in a larger context, you probably won’t be an effective manager. You also won’t help your team members grow as individuals.

Some people figure this out on their own, and others are fortunate enough to have managers who prepare them to succeed in ways beyond being a great do-er. Those with mediocre managers exit the apprenticeship as productive but unimaginative contributors whose prospects have suddenly changed. They expect to keep getting promoted because they work super hard, but the pace of their advancement slows down as the rules of the game change. Unsurprisingly, people who find themselves in this position sometimes react adversely. They get upset when they see others advance whom they don’t believe work as hard as they do (because that’s their metric for contribution). Some blame politics or other institutional biases for the deceleration in their careers, or they get eaten up by the stress of underperforming. On the other hand, sometimes these people get promoted too quickly in an organization that doesn’t realize how unprepared they are to lead others. This is just a bad outcome with a bit more income. These folks turn into tomorrow’s bad managers, and the cycle of managerial abuse repeats itself for the next generation of worker bees.

Preparing yourself for the leadership phase of your career while you are still in the apprenticeship phase is one of the best, most important things you can do, in my opinion. The earlier you can prepare yourself for how the measures of excellence change as you advance in your career, the smoother your continued ascent will be. The disconnect between the qualities of a good “do-er” and what makes a good manager causes many young professionals to hit a wall when they start to move up, and it’s not hard to see why. Even the most intense apprenticeship phase can easily fail to prepare someone for the interpersonal demands of leadership. Most people aren’t naturally adept at navigating conflict, hiring the right people, making necessary but unpopular decisions, and managing through change. It takes practice to get good at these things, but people are given few opportunities to hone these skills until they are already in management roles.

Get Comfortable Being Uncomfortable

While the transition from do-er to leader may not be as overwhelming as beginning your career, many find it more uncomfortable. As you gradually take on managerial roles, your unwritten responsibilities change as much as your official ones. Managing people, means not only being accountable for others’ work but also being accountable to those who report to you. You owe them career development guidance and feedback on their work to help them grow professionally – all while still executing your own assignments. And while you can’t exercise as many of your people management skills until you have your own direct reports, you can exercise your thought leadership and organizational leadership muscles extensively even as a new hire. I argue it’s critical that you do as much of this as you can during the apprenticeship phase. The best way to prepare yourself for the demands of leadership is to start early, and you can exercise leadership whether you manage people or not.

The U.S. Navy SEALs have a saying: “Get comfortable being uncomfortable.” SEAL recruits perform most of their training activities while enduring extreme exhaustion, hypothermia, lack of oxygen, and other conditions that would cause anyone else to utterly cease functioning. SEALs cannot merely survive these hardships, they must remain at peak performance despite extreme discomfort and personal hazard to accomplish their mission. Now, odds are that no one will confuse your job with that of a Navy SEAL, but you also need to get comfortable being uncomfortable. The reason is that emerging as a leader in any organization does not just introduce the possibility of conflict, it guarantees it.

Leaders bring their own points of view on things that are important to the business. They all have opinions informed by their own knowledge, experiences, biases, and blind spots. When you ascend into a leadership role, assuming you actually try to make an impact and not just blend in, some of the points of view and experiences you bring with you will collide with other peoples’, and from these collisions conflict is born. I repeat: conflict is guaranteed to happen. Total conflict avoidance is thus an illogical and untenable career strategy. Sincere differences of opinion will arise between you and other people, and you need to be comfortable with that. Being a good leader, means making decisions you believe are necessary even though they may be unpopular. Making recommendations about whom to hire and whom not to inevitably spawns disagreement over not just individuals, but ideals. You have to be able to navigate the (completely healthy) conflict of business without it distracting you from your own mission and totally exhausting you. 

Communication and conflict navigation skills are as essential as your subject matter expertise as you start ascending the ranks. The best leaders aren't afraid to make waves, but they also know how to channel the conflicts that arise from their ascent into net positives for themselves and their organizations. Only the exceedingly brilliant can survive without these skills, but even they would be better off if they had them.