Bosses, Best and Worst

One of my best friends told me several years ago, "I'd rather fill an average position with a great boss than a great position with an average boss." I had had very few bosses when she told me this, so I didn't really get it.

I do now, though, and I'd like to try to expand on that thought.

The Best

When I took my current job, I took it on a gut feeling. The competing offer, while laughable monetarily, was very tempting from a personal growth perspective, not to mention it would put me on a plane to Asia at least once a year—an appealing prospect for an ex-expat.

What really convinced me about CFX, though, was Juan, the CTO and now my boss. He was genuine, personable, obviously intelligent, but more importantly, he seemed almost aggressively empowering, eager to hand off huge pieces of the system to people who showed him they had the desire and the capacity to do a great job. He knew where he could be a good mentor, and he was also aware of his own limitations. I had never had the opportunity to work under someone quite so self-aware.

I took the job on that gut impression of him, and as it turns out, I was absolutely right. Working under Juan has been wonderful. It's also allowed me to better articulate why I enjoy it so much: In a nutshell, he has allowed me to be 100%, unabashedly me.

Here's how.


From my first days in the office, I was allowed nearly free reign over what I did. This was a little confusing at first, as I didn't fully understand the priorities of the operation, but I learned them quickly, and Juan communicated them to me at the right times.

As it turns out, though, Juan's management of my initial weeks was more nuanced than simply letting me sink or swim. He took a lot of time to ensure that I fully understood the context of the system and the business. He owned the errors that he had made thus far, allowing me to get past them, rather than getting stuck on them. He established boundaries not by setting them down, but by revealing them to me through solid arguments and in discussions in which I was a participant (sometimes even the winning participant), not simply a passive recipient.

As our relationship has deepened over the weeks and now months, he has firmly and publicly established himself as a colleague of mine, rather than a boss per se, allowing me to feel comfortable making my own strong arguments, having my own strong opinions, and equally comfortable in expressing my uncertainties. He has respected my decisions even when he hasn't fully agreed with them, and he supported them even to the extent of changing his own habits when necessary.


He has also been patient with me. A lot of what we're doing is messy. It's real. And I certainly don't have all the answers. In fact, in some cases, I've gone from wanting to completely destroy a solution that he spent weeks or months creating all the way around to recognizing that it was correct(ish) after all and deciding to push forward with it with only modest modifications.

He's given me complete latitude to do this. Furthermore, he's allowed me to poke around and try some unorthodox approaches that have been somewhat risky. Overall, these risks have panned out very well. But there have been some failures, and he has accepted those as part of the process of exploration that we're embarking on together as we reimagine the world of finance.


Finally, Juan has been frank and honest in all of our interactions. There have been times when he has been uncomfortable with what I've wanted to do, and his honest disagreement has allowed me to make concessions and compromise, when I might otherwise have grown resentful or defensive. He has never tried to flatter me; he has never kept important details from me to keep me focused on what he wanted. Instead, we've maintained remarkably open communication, and a two-way, on-going dialog that has allowed us to shape our work together and ensure for the company a more robust future than any that one or the other could have created alone.

All this has allowed me to embrace myself overall—to express myself honestly and passionately. I am a member of a team in which I can feel comfortable being myself, and that team was cultivated by a great set of partners who are now our great bosses.

The Worst

Fittingly, a few weeks ago, my previous boss emailed me, desperately seeking help with his website. "Boy, we're really under fire, Kael, it would be great if you could get this done in the next few days." Get what done? He hadn't even explained what he wanted.

This was typical. This was why I left.

My ex-boss had managed to create mess upon mess upon mess, and he relied on a small army of soft-hearted old acquaintences like me to constantly come in and clean it all up. Reflecting on my years working under him and on his team, I've been able to drum up a small list of things that made it awful. Without further ado....

Lack of Discipline

One of the most frustrating qualities of my former boss was his complete and total lack of discipline. He was immune to structure; irreverent to protocol. He was constantly chasing whims. He worked tirelessly, it's true, but most of what he did was an utter waste of time because it never fit into any coherent plan or strategy (short of a 20-year-out vision that wasn't particularly bound to earthly reality).

His lack of discipline poured out and infected the entire team. It was useless to try to do anything right because he would change what "right" meant at the last minute. We all got used to it, and we all stopped trying—poison to any growing venture.


It might be said that he practied anti-empowerment. There was a point about a year into my tenure with him that I actually went before him and admitted that I had never felt so unempowered. My ideas were privately commended by him and publicly ignored; my decisions, privately agreed with and publicly disdained.

This was manipulation. He dragged me endlessly through believable bouts of his own self-criticism, he showered me with compliments in front of important guests, he included me earnestly in high-level meetings, but it was all a show. His self-criticism was calculated to earn my trust. His compliments were payment in exchange for sacrifices that he had no reservations about asking me to make. And my presence in his meetings simply earned me a reputation for generating exquisite ideas that would never be acted upon.

The low point with him—and the one unequivocal example of true, dirty, inhuman manipulation—was when he altered the text of an email chain to make it look like he had included me in an important discussion that I had somehow not been copied on. (Suspecting he was lying, I asked the original recipient to forward me the chain and proved that he had altered it to include me.)


After 2 years working with him, I only began to understand the extent of the things I was kept from knowing. He had signed contracts with all kinds of people for all kinds of things. I would spend days creating a highly detailed budget with the little money we would get, only to find that he had secretly promised away half of it before it ever came through the door. And I would never know the full extent of the promises he made to get that money. No one would, often not even the people giving it (he had a remarkable knack for avoiding contracts).

This was infuriating. It was like playing a game whose rules you will never fully know. Any decision could be wrong simply because the game itself changed under you. He alone knew the final score....

Total Control

Perhaps the most insidious of his character flaws was his inability to disengage from decisions. He wasn't a micro-manager per se, but the result was the same: you would spend hours, or days, or weeks preparing something, then right at the end he would come in and insist on some change that brought the whole thing toppling down. This was bad enough in itself, but what was particularly damaging about it was that it was a self-reinforcing habit.

Because things would come toppling down, he would affirm that it had needed his help, and he would tighten his grip on future decisions and projects. At the same time, he would feign empowerment, sending you off with encouraging words about your brilliance and about how he was finally out of the picture.

Never did he fail, though, to own every single project and every single decision, even if it meant tearing down the original owner in dangerously subtle attacks on their self esteem. I suffered this more than once in my time under him....

Looking Forward

Needless to say, these two experiences couldn't be more different. And frankly, I'm glad I've had both. For all his awful faults, the bad boss taught me a ton—both good, useful stuff that I continue to employ today, and also some dirty tricks I can whip out to defend myself the next time I'm in some horrible intellectual street fight with a megalomaniac.

I guess everything's got it's upsides....

Anyway, suffice it to say that I now totally get what my friend was saying. The next time I'm on the job market, I'll be interviewing my prospective bosses rigorously, scanning for assurance of empowerment, patience, frankness, and respect.