What my bosses have taught me

Reviewing my working life, I realize that I’ve worked for some pretty awesome people. Competent, professional, relational — I can genuinely say that each of the bosses in my life taught me (or allowed me to learn) pivotal lessons that make me a better person (not just a better employee).

It’s been a useful exercise to take the time to write these out. Here’s what I’ve learned from the folks I’ve worked for in my three careers.

Side note: Yes, all of the people on this list are men. I’ve known incredible female colleagues and departmental managers, but none of them served as my “boss” in the way I detail here. I look forward to working for an amazing woman someday — or being a good boss for people under my care — thanks to the insights I’ve gained from my own career experiences.

The Early Days: Mr. Allen, library leader

Mr. Allen was my first boss, really. I’d done odd jobs for my mom and others but I got my first “real” job during college at the library. I started in periodicals and moved into circulation and student manager as an undergrad, seamlessly transitioning into a grad assistantship position in circulation during my master’s degree, and finally becoming the reference librarian for a few years after college.

Working reference was a heady rush of anxiety and adrenalin: all the excitement of a mystery or scavenger hunt plus a dose of my introverted fear of strangers and a 20-something’s lack of confidence. (What if I don’t know how to find the answer and look like an idiot?) 

In other words, a perfect first job for a young professional.

Mr Allen’s superpower was the ability to “read” people almost instantly. When he interviewed students for one of the many jobs in his building, he usually knew within a few seconds whether the student would be a good fit for the work and the culture there. He was never wrong. Never.

It was a large staff — at least 20 “adults” plus nearly 50 student workers — yet Mr. Allen managed us all with good humor, a love for playing pranks on unsuspecting graduate assistants, and an even temperament. I learned much working under him, but here’s what stuck with me:

Reason and Passion can both be powerful tools for persuasion. Learn which one will be more effective in any given situation, in getting your ideas heard.

Any time I brought a plan for improving some area of the library or reorganizing my job, Mr. Allen listened patiently, asking questions and giving me a full hearing before pointing out any weaknesses or obstacles. It was an important first lesson for me: there are good ways to present an idea to your boss, ways that earn you respect and a hearing. Usually those involve dispassionate argumentation rather than emotional pleas, tantrums, or manipulation.

It’s not that you can’t be passionate about your goals or opinions, but you’ve got to understand whether that form of appeal is going to work. I’ve seen a lot of people try and fail to get their boss to listen to them. I’ve rarely had that problem, because I learned early on how to present ideas to my boss.

Teaching: Two headmasters who created an atmosphere for success

I went from the reference desk into the classroom, launching a decade-long career in teaching English (and Latin and theater and some other things) to a lot of fantastic teenagers whom I still keep up with. But getting launched as a teacher wasn’t easy. Not at all. Probably the hardest job I’ve ever done, day by day.

But the work of a headmaster or principal is no cakewalk either, considering how many problems hinge on figuring out people — notoriously a diffiult material to work with.

I was privileged to work under two great administrators during my classroom years, Dennis and Joey.

Dennis had already been through the wringer at The School Which Shall Not Be Named, a bad experience for his first job as principal. By the time I came to work for him, he was mindful of what he’d learned the hard way, hoping to avoid building a school that was broken from the very outset.

A calm head during any confrontation will defuse the situation and allow progress. (Usually.)

Dennis was a rock-solid partner in a crisis, and if you’re a teacher, crises occur with terrifying consistency. Inexperienced newbies (like I was) mess up blatantly and regularly, generating unhappy students and upset parents. Even the most experienced educators (and we had several colleagues with 15 or 30+ years under their belts) will find themselves in difficult disagreements over how to handle a particular child’s needs.

Dennis never seemed to fear anyone. The angriest parent would find him calm, reasonable, and settled. The most petulant student couldn’t sway him out of his steady approach to discipline and daily life at school.

It’s not that Dennis didn’t care — he cared deeply for the school, his teachers, the students, and their families. But he was able to separate his emotions and opinions from the situation at hand, searching for a solution that genuinely benefited everyone involved. I’m sure much of it made him angry or frustrated, but he didn’t let that become his approach.

After Dennis left to take a position elsewhere, Joey became our new head administrator. Younger than I was by about 5 years, he forced me to get over my own predisposition to devalue someone with less experience than I had. But I learned a lot from his leadership, and we came to count him as one of our closest friends.

Joey followed two important maxims during his first year behind the desk, a strategy which quickly won us over to his side:

Don’t change anything until you understand why things are the way they are in the first place.

Joey walked into a small school with an existing structure and some obvious weaknesses. But it’s easy for new leaders to assume they understand why problems exist and leap toward solutions that won’t work because they don’t yet grasp the full situation, limitations, key players, and opportunities. 

Joey wisely set himself to follow all established policies and cultural norms without changing anything that wasn’t obviously broken. His goal during Year One was simply to learn everything he could about NCS, how it worked, and why.

Along the way, we gained a vital ally for accomplishing our mission, and he rapidly alleviated our fears that he was going to superimpose an alien agenda on the work we felt deep ownership over.

Relationships matter. Take time to be present, build bridges, and trust the people working for you.

Joey’s methods for building trust among his staff, many of whom with decades more experience than he had, involved listening, observing, and asking questions. His presence in the halls, classrooms, and events was positive and intentional; his interest in our methods and explanations was genuine. Upon this foundation he built up trust among teachers, students, and parents — “trust capital” that he soon had to spend when the unavoidable problems of a first-year administrator arose.

Many leaders assume their authority stems from some personal, unquantifiable aura they bring to the job. That’s not how it works. Do you want your employees to follow you and buy into your vision? Then take the time to listen and build relationships first. Apart from “trust capital,” leaders can only threaten or plead.

Communications: It’s the meta, stupid.

After a decade in secondary education, I stepped sideways into higher education, leaving behind teaching (at least for the moment). I took a job in the communications office of a small liberal arts college under Cliff’s leadership. A small team, we handle everything from PR to marketing to creative services for campus departments (to name a few of our responsibilities).

When I was interviewing for jobs, I received a similar interview offer from a much larger institution at the same moment I was interviewing with Cliff. In many ways, that other job is the one I should have pursued — the salary was larger, the benefits better, and the institutional resources much more available. But during my interviews with Cliff, I’d realized that his vision for office culture, work/life balance, and vocational mission was the one I wanted to be part of. So here I am.

We work with words. Every day, we take words (and often images) and craft them into messaging on behalf of the college. We seek to inform, persuade, diffuse, explain, encourage, disarm, and excite … for starters.

Sometimes, in the course of work, the communication tasks get really tough, perhaps because the answers are fuzzy, or the message is unwelcome, or the situation is too unclear to forecast much about the needs/attitudes of the audience.

Words are dangerous. They’re also powerful. Cliff is a master of nuance. He reads the “meta” like the rest of us read printed text. And if I’m the blunt Yankee in our office, Cliff is the careful diplomat, the one who weighs the effect of what is said and what is left unsaid.

Careful consdieration of the context and content for a message (or conversation) makes the difference between getting heard or being ignored. The higher the stakes, the more vital the preparation.

That sounds stupidly simple, but consider how rarely we practice mindfulness when preparing to speak or write or email. I tend to rush into a converstaion with ideas half-formed (it’s the peril of being an “external processor,” right?). Cliff may still be forming ideas, but he measures his words even then, considering effect as well as meaning.

While my motto is “reckless abandon” (not always, but sometimes) and “it’ll all sort itself out eventually,” Cliff’s is “listen first, talk later.”

I think I’ve been trying to work on that for as long as I’ve been able to talk. #lifegoals #stillworkingonit


I could list many more virtues from the people I’ve worked with over the years, but forcing myself to identify one or two big lessons has brought my these into a sharper focus. I am thankful that so many good people have been a part of my working life, shaping so much of how I see that part of my life.

So. What have you learned from your boss?

Cross-posted to my Medium channel.

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