Tag Archives: leadership

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.

On Leadership: Some advice from my bottom rung

Not having spent any time in a core leadership role might open me up to criticism for this post. Some of you will say, “Well, it’s easy to criticize if you’re not the one leading. Easy post for you to write.”


I don’t rake in the big bucks from the C-suite or even middle management … but I have led teenagers across America and Italy without misplacing or killing any of them, coerced an entire class of middle schoolers to do Latin conjugations willingly, and directed several plays – a project management quest like few other experiences.  I’m not a stranger to making crisis decisions, organizing a complex system, or juggling conflicting personalities.

You might think that I’m just sounding off about pet peeves, but I genuinely believe that some of us sitting at the bottom of the organizational chart can spot leadership failures much faster than the executives. We’re the ones who have to make those crazy plans work, after all.

Here’s my advice for CEOs and organizational leaders, from my vantage on the bottom rung:

1.  You have two jobs as a leader.   The first is to figure out what your company or organization is doing (your mission) and make it clear and inviting so everyone gets on board.  Second you need to hire the best people that you could afford and then get out of their way.

Everything else follows from these two tasks, and if you screw them up, you’re probably making your underlings miserable.

2. Sometimes leadership means making the decision, often quickly without enough information as you’d like.  Sometimes leadership means stepping back so your managers and planners can step in and make the call about a problem, issue, or policy they’re better informed to decide.  Knowing the difference is why you get paid three (or more) times as the rest of us.

3. The people who do the core work of the organization know more than anyone else about the problems that need to be fixed, the solutions that could be implemented, and the long, painful history of failed attempts at change. Perhaps that information isn’t equal to an outsider’s assessment when it comes to solving problems or implementing needed changes, but any leader who tries to implement change without actually taking time to listen to the people in his/her organization is a fool.

4. You know that old saying about how leaders need to spend the first month or year just getting to know the organization before they change anything significant? Yeah. That one. It’s absolutely 100% true. And unless the building where your office resides is actually on fire, you ignore that wisdom at your peril.  If you start changing parts of a system before you really understand the system as a whole, you run the risk of doing a lot more damage than the problem you were trying to fix.

5. You need multiple viewpoints among your organizational advisors. You need dissension — not discord, not disrespect, not gossip or backstabbing or other expressions of human nastiness. But you desperately need people who will tell you “No” or “That’s a bad idea” or “Wait, have you considered this angle?” You can’t get that when everyone around you thinks alike. Or when you don’t bother asking.  You have a blind spot… and you need spotters for that.<

6. Employee morale is an expensive currency. Like most human capital, employee goodwill is very expensive to acquire and too easy to spend. Don’t blow it all in one place.

Your human capital – the people who work for you – are your most expensive investment. It makes no sense to forego giving your employees the best salary and benefits you can afford along with real authority in their job positions, meaningful professional development opportunities, plus as many non-monetary perks as you can squeeze in and a couple kick-ass holiday parties. Hell, it’s amazing what a piece of chocolate and a sincere thank-you means to the people in the trenches. Forget this, and see how bad it feels when your organization starts hemorrhaging employees to the competitors.

Find ways to make the most of those doing the work – for their benefit and for yours.

7. If you aren’t spending time with the people in your organization, how do you expect to be leading them?  If you don’t  know the people in the departments, if you don’t walk around visiting all the offices, how can you make decisions that directly affect what they do in good conscience?

Get out there. Be seen. Take 10 minutes every day to walk into a different office and say hi. Ask what people need to do their jobs better. Listen to their suggestions.  Be approachable and friendly.

I don’t care if you “aren’t a people person” or “don’t have time” … you aren’t going to cut me any slack if I fail to do my job with thorough knowledge and skill, so why should I cut you slack at yours? Put in the time.

8. You will always piss off at least some people with your course of action. Your goal is not to keep everyone happy. Your goal must be to do the best thing for furthering your organization’s work, and that means pissing off the correct people in that situation — the people who are holding you back.

Have the balls to do hard things well and make decisive choices without trying to be everyone’s friend. But don’t be a dick either. It’s a tough balance.

9. For leaders of religious organizations:  Believing in Providence is not an excuse or a substitute for planning well, knowing your market, counting the cost before you make big changes, and choosing to take measured risks.

It’s quite possible that God doesn’t give a damn about your organization, no matter how awesome your mission statement. “Kingdom work” may be your goal, but God might have other plans on His table.  Pray and trust, yes, but work twice as hard as everyone else.

10. The best leaders are servants. Jesus said so. Management theory has finally caught up with the “servant leadership” theme in the Gospels – complexity leadership theory, for example, sees the role of the leader to be removing the obstacles that prevent the team from rising to their fullest potential. The leader carries the burdens of leadership, like responsibility for key decisions and oversight of complex systems, so her people can achieve more than they thought possible.

Does this sound like a demanding list? You bet it is.

We cannot escape the reality that those among us who step into the roles of leadership, guidance, training, and mentoring are held to a much tougher standard.  The rewards are greater, of course.  But sometimes a view from the bottom of the org chart can do a lot to realign leaders to their core purpose.

The price of experience is arrogance

We adults have a bit of a problem.

I was listening to “Think Like A Child,” an excellent episode of the Freakonomics podcast focusing on the inflexible thinking strategies of adults and how we can all move toward the good habit of kids to ask tons of questions and expecting the unexpected.

Truth is, adults get tangled up in our own experience.

We’ve done it before, seen it before, tried it before, failed that way already. And the older we get, the more the weight of our accumulated experience crushes the impulse to think differently.

But it’s more than just an unwillingness to shush the din of past failures and successes shouting down the other ideas in our heads. I think we adults suffer from a bad case of experience-driven arrogance.

Granted, it’s a very humble arrogance. We clothe it in beautiful phrases like “You might be right, but….” or “I’m not saying you’re wrong, it’s just that…..” Or maybe we prefer our humble arrogance served straight-up like a good whiskey – as dogmatic rejection, or the tendency to jump too quickly to conclusions or leap into decisions before having all the facts necessary to make it a good one.

Scary thing is, the more successful we are, the more likely we are to cash in our experience for arrogance. If I ever achieve the status of expert, guru, or CEO, it will be so easy to justify stubbornness as determination, closed-mindedness as wisdom, or hasty judgment as decisive leadership.

I tend to snap to judgment pretty quickly, and I often come across as far more dogmatic than I actually feel. Both are habits I’m working to break (or at least bend into a more useful shape). Feel free to call me out. Really.

Children struggle against their own inexperience, and novice workers in any field are by definition inefficient. Those of us who have gone around the block a few times can bring a lot of great advice based on our deeper knowledge. We assess problems a little more quickly and a little more accurately. And that’s hella useful and truly awesome.

But arrogance is always ugly.  It’s a bad use of all that hard-earned wisdom.

Why does this matter? Well, for one, arrogance in a decision-maker often leads to bad decisions – decisions that don’t fit the situation because the leader didn’t take time to learn enough in the first place.

Second, arrogant people have blind spots that they cannot see — not until they’re willing to recognize that their own personal experience might not be sufficient grounds for moving forward. Everybody has blind spots. The trick is remembering that you have them, and finding people in your life who will be honest enough to tell you. Hold on to those people.

And third, arrogance prevents leaders from recognizing the value in alternate points of view. Often a business or organization has multiple people around with deep knowledge of how things work, why certain decisions were made in the past, or who holds real power to get things done. The organizational knowledge resting in the minds of long-time employees is worth so much  — yet a leader who’s relying too much on his/her own experience may not place much value in the voices coming from below.

To put it another way, we make better decisions and we’re more creative when there’s divergent opinion – even conflict. When everyone sees the same picture too quickly, the danger is that we might have missed the actual image.



I appreciate the people who, as leaders or directors or administrators, must confront hard decisions and the discomfort they cause.

It is the burden of leadership to pick up the awkwardness of change or hardship and clear a path for the people under their care.

Today, it’s cool & hip to distrust anyone in authority. That distrust isn’t unwarranted, but systems and institutions cannot function apart from trust. Leadership — and follower-ship — is relational.