I’ve had excellent mentors and managers in my career from whom I’ve learned a tremendous amount, sometimes through advice and more often through observation. But work is not so separate from the rest of life as many people believe or wish it to be, so career advice, or at least the lessons that stick with you and help shape your career, can come from all over and far outside the walls of your workplace. Keep your ears open!
One piece of advice that has shaped my career, impacting my actions and decision making on a day-to-day basis, is actually something my father shared with me in my very first year of professional work. He explained to me that “it is your job to tell your manager what they don’t know.” At the time the advice felt not only wrong, but also dangerous — how arrogant would I appear and how much offense would I cause by conveying to my manager the belief that I knew something they didn’t? In its simplicity, this advice shatters an extremely pervasive presumption of information symmetry between a manager and a report. It is very easy to assume that your manager knows all the things you know, after all, they’re the manager. It’s even easier to get frustrated with your manager when they don’t know something that you know, again, after all, they’re the manager. This is a mistake I continue to make in my career and also why I find this lesson so consistently valuable.
The reality is that organizations can’t function without delegation of work and, critically, of knowledge, expertise, and visibility. Failing to communicate upward because of a presumption of knowledge or fear of overstepping is an abdication of critical responsibility. In your career this responsibility starts with communicating facts and status, but as you get more experienced and senior, this same paradigm transforms into an obligation to share your best ideas, recommendations, advice, and warnings. And, as a manager, your job increasingly becomes more and more about creating an environment where everyone feels encouraged and rewarded for telling you what you don’t know … which is often that you’re wrong.
Another lesson that has stuck with me through the years (though never intended to be career advice) comes from my high-school English teacher. Some context is required though. When we would receive a new assignment, I would often ask many questions to make sure I understood exactly what I was expected to do; his response was always “you can do anything you want as long as you get away with it.” What became clear after more than a year with this teacher was that “getting away with it” was a really high bar. This advice wasn’t license to do anything we wanted, but rather a challenge to bring our own judgement to the ambiguity of a task, to take a risk, and to reach for something special. Many years later, at work, I found the lesson reverberating in my head every time I was confronted with a challenge that wasn’t fully specified. And years after that, as manager, I find myself saying this quite often to my team. Organizations, particularly fast paced start-ups, are full of unspecified problems and situations for which there is no precedent and no process or policy in place. For me, the mantra of this advice has always been a call to action and a belief that an unspecified problem is an invitation to be creative, to be bold, and to stretch a little past the boundaries of your authority; that you can take a risk and move forward and reach a destination even when there isn’t a path to follow.