I’ve written about this before, but as I look back on my career over the last decade, I’ve had remarkably few good bosses. In most cases, if I was lucky, I had a boss that I liked as a person. But only twice have I had truly good bosses.
The first was JP. I adore JP. I learned more from him than I can possibly say. And while there are some areas in which JP struggles as a manager, what JP does particularly well is be a leader. And aside from the great leadership he demonstrates for those who work with him, he inspires leadership among his staff.
The second is DH. It’s sort of amusing to me, because DH and I did get off to a bit of a rocky start and I had definite worries that we were going to be able to cultivate a functional working relationship at all, much less a good one. And yet, just about a year later, I can recognize that he has turned out to be precisely what I needed at this point in my career.
Part of why I learned so much from JP was because of where I was in my professional development at the time: I needed a sensitive coach whose strongest leadership qualities were the intangibles, and the emotional aspect of management with a strong emphasis on the interpersonal relationships involved in business.
At that point in my career, my needs are different. I have stopped being as emotional about work. I’m more disciplined. I’m more focused. I’m more aware of my boundaries and their importance — both of my role as a project manager and between work and my personal life. My focus is on actively making choices to help facilitate my growth, instead of accidentally careening from one learning curve to another courtesy of happenstance.
I’m more deliberate and specific in my choices and my needs, and what I need in a boss is someone who understands that, helps guide that, corrects me when I’m wrong, questions me, solicits my input, respects my judgment and incorporates my observations.
Now, in reality, JP did all of those things, too, but DH and JP have completely different personal styles and so the net effect is very different. In part it really is me just being in a different place in my life and my career, but a lot of it is them, too.
JP is very warm and fuzzy, very lovable, endearing; he cultivates an overwhelming desire not to disappoint him, at any cost.
DH is very caustic and analytical; he makes every effort to remain dispassionate, while still trying to do the best job possible.
Now, both of them have a lot of things in common, too: they are both very pragmatic and know which battles to fight and which ones to walk away from; they are both very observant and understand the critical subtleties of corporate politics; they are both very passionate about what they do and committed to doing it as best as possible; both of them are good at empowering the people who work for them to be strong leaders.
For me one of the hardest things about leaving ML was leaving JP. And one of the things that held such appeal about Massive, Inc. was that my boss there, DJS, had a personal style very, very similar to JP’s. And as much as I liked DJS, once I got to know him, it became clear that the areas where they did have similarities were limited to the personal side. DJS was technically exceptionally savvy, but he lacked the ability to inspire the leadership among his team that makes JP such an exceptional boss for whom to work.
Then, going to my next company, my boss was more of “one of the guys.” While I most definitely liked him a lot, his leadership skills had not yet evolved. His project management discipline was very solid, and his technical skills were good, but he completely lacked strong leadership skills.
And then there was my next job: I walked into an environment that, much to my surprise, looked more like my old start-up days than I ever imagined. A re-org not long after I walked in the door changed many things about that, and now they sit on the brink: not quite the immature organization that we used to be, but not yet a mature organization that we need to be.
DH is exactly the right person for me to learn from at this juncture: he’s been on both types of organizations, sees what changes need to take place, and what obstacles are in the way of that change. He’s pragmatic about how much can be done at any given point.
The thing that has me ruminating on all of this right now is an unfortunate turn of events: an opportunity at JBA has presented itself, and it’s one that I find tremendously appealing and which will give me the opportunity to grow my IT and Project Management skills in areas where I am most interested in growing. It’s a great opportunity within JBA, but the skill set is hugely portable and extremely leveragable in future roles at different companies.
The downside is that it would take me off of DH’s team. I’d have to report to a Director who isn’t as strong as he is in nearly as many areas. And while I am absolutely positive that I’d be in a position to continue to leverage him as a sounding board, I wouldn’t have as much direct access and I wouldn’t be working with/for him directly anymore.
This is proving to be a slightly more conflicting prospect than I originally imagined.
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