The Mentee and the Manatee

Posted by in Life

I never asked to be a mentor. I never wanted—nor do I think anyone wanted me—to be one. But much like getting old, going to the dentist, or laughing at Sail Cat, you can’t really stop it from happening.

And as a jaded, hateful person, it was a lot more impactful than I imagined it would be. It wasn’t one of those life-affirming “let’s teach each other about people” situations like from every 90s sitcom, but you obviously learn a lot from the first time you do anything, and that includes mentoring.


For two years, I worked at, well, a company. It had some struggles coming to grips with growing from a Fuck It/Ship It startup to a Real Business, and I, both fortunately and unfortunately, was there for the entire transition. It wasn’t anything exceptional in that regard; every company that makes that jump has troubles.

On the list of things they did—other than transition me into a leading architect role—was stop hiring almost exclusively senior-level developers and start padding out the roster with junior programmers. That’s not to say they weren’t already there, but that they hired more of them. One of them was a fellow from Wisconsin.

He was Midwestern as cheese and just about as close to a male ingénue as you’ll ever see. He was also one of the greenest devs I’ve ever seen. Had I been there for his interview, I would have been surprised if he’d then showcased enough knowledge to get an offer. (He used to keep open when we chatted on Slack.) But like landing on the moon in Kerbal Space Program, wild, flailing reach usually smacks grasp square in the face sooner or later.

He eventually became more wolf than pup.

The Mentee and the Manatee


For the next year, he worked exclusively with me on my various endeavors. From a massively distributed web crawler to scratching out the foundation to new microservices, he was entirely ender my guiding hand. It was weird taking a seed to a sapling when I hadn’t even taken a seed to a sapling in literal, non-metaphorical terms.

In those dozen months, my philosophies seeped into him. He (and a few in the blast radius) absorbed probably more than was healthy from me. I was a strictly realist employee, never giving an inch to optimism and responding to every question like a hostile witness. But mixed in with all the weird, unsavory bits, some good slipped between the cracks.

Here are what I consider to be the gems.

  1. Good leaders don’t want to lead

    I never liked any person in a leadership position that wanted to be there. They dedicated too much (read: any) amount of their limited time and power to maintain their role rather than making sure they made the right decisions.

  2. Earn respect through results, not effort

    While primarily poised as a lesson in regards to non-technical roles, it applies to pretty much everyone. Giving it your all certainly is good, but when it ends in a mess or less, that’s worthless. That means talking big and often is a sign of being useless. (Say that in the mirror every morning, project managers and product owners.)

  3. Stupid questions are very, very real

    It’s a bit mean, but there very obviously stupid questions. You shouldn’t necessarily call someone out on it (that’s counterproductive and toxic) but that doesn’t mean you should respond to it either. Once you start answering them, you don’t stop. Because they don’t stop. They never learn.

  4. People want to look busy

    Attending meetings, sending emails, making calls. Despite saying the literal antithesis, people love looking busy because it makes them feel and appear more valuable. That means that if you are about to attend or call a meeting, initiate an email thread, or get on the phone, ask yourself if it is absolutely necessary. And if you are caught in one of those things, you should be able to reevaluate and leave to actually work.

  5. Programming is being an artist

    The answers to problems are objective, but the methodologies are legion. Code is ugly—brutal, even. But ideas and algorithms, the underlying fundament of your thinking, can be beautiful. You are carving away the emptiness of the editor and revealing elegance. Continue to hew until you have a lithe, impeccable chunk of brilliance.

  6. Leading is transparency

    Holding back from those working under or right beside you is folly. Don’t dwell on details, but don’t fall under the siren song of having secrets. Secrets, like looking busy, make people feel superior. Get people involved early and often. Not only do you have no idea what information is pertinent or potent to someone else, you never know where an insight will come from.

The Mentee and the Manatee


I have no idea which of those stuck. I don’t even know if I managed to encapsulate all of those notions either in my words or my actions, though some evidence would point to the affirmative.

The first few months were especially rough. It was like the first half of any buddy cop movie where it’s just two personalities trying to figure out how to squeeze any amount of juice from the pulp. It’s not that we didn’t get along (we’re actually good and fast friends) but making our time together efficient was a struggle.

More than the philosophies I tried to impart, the methods with which I tried to shove them into this awaiting puddle of cheddar-scented gray matter are revelatory.

  1. The Whiplash lesson

    In the fantastic movie Whiplash, J. K. Simmons’ character towards the end says, “There are no two words in the English language more harmful than ‘good job.’” And he has a point, though maybe not to that abusive extent shown in the movie. The point of a junior developer isn’t to be immediately effective and impactful but to learn to be effective and impactful. That means ruthlessly rejecting a lot of pull requests and saying try again.

  2. Say what you want, not how you want it

    Do you remember that old proverb about teaching a man to fish? Turns out development takes that step further. If you tell a junior dev how to do something, they’ll never understand why it’s done that way, and that’s far more important. Tell them what you want, they’ll give a shot, and then you tell them why it’s wrong. That’s how they learn.

  3. All sorts of reinforcement

    Continuous positive reinforcement is poisonous. Solitary negative reinforcement is equally virulent. What you really need is commensurate and escalating reinforcement. As more good work is done, more pats on the back are earned. But as more bad work is done, more slaps on the wrist. You don’t pick a strategy and go at it. You treat your ward like a real person, which means you react to them like a real person.

  4. Awareness is dangerous

    Once I realized I was mentoring this guy, it got in my head. The mechanics of it became shockingly apparent. Immediate and full understanding of Andy Roddick telling every coach to not coach him on his legendary serve hit me like a 140 mph cannonball. You can’t work your mentee like a science project. They know it and it feels promptly unnatural and alienating. Get it out of your head that you are teaching someone and just be the font of knowledge they need.

  5. Play the waiting game

    Don’t seek out to divulge lessons. Even if you see them heading down an egregiously wrong and wasteful path, just let it happen. Pull them out if they get too deep, sure, but let them get down there. You are not Batman, running in to save the day without anyone ever asking. You are 911. You only show up when they ask. And even then, it doesn’t hurt to ignore them every once in a while. Only once you start sinking do you swim.

The Mentee and the Manatee


In retrospect, I probably wasn’t a good mentor. Maybe I wasn’t even a decent one. If anything, I’m sure my mentee’s success is a testament to his desire to succeed and not my skills at teaching him.

It’s nice, though, hearing him talk about being a mentor and having his own mentee nowadays. I hear him talk about how he thinks a good leader approaches leadership and how he withholds his choice methods so his pupil can figure out his own approaches. It’s how I think.

And I’d like to think I did something right, even if I didn’t ask for it.