I consider myself fortunate to have worked in a wide assortment of environments. I’ve earned income everywhere from newsrooms and office towers to coffee shops and orchestra pits. But even with my varied background, it was quite a jolt to move from a position at Microsoft to teaching middle school.

At Microsoft, I was surrounded by engineers, designers and editors seasoned by long years in their profession, ranging in age from early 20s to late 50s. At my middle school, I spent my day instructing, assisting, cajoling and hopefully inspiring dozens of hormonal youths just learning what they were and what they wanted to be. Yet despite their differences, my Microsoft colleagues and my young students illustrated the fact that we’re all alike in so many ways.

People are invested in their language. My first months at Microsoft were a befuddlement of jargon — “DSAT,” “delta,” “deep dive,” and the innumerable mashups collectively called “TLAs” (Three-Letter Acronyms). I was pretty well lost until I figured out what the terms meant, but the more I became able to pepper them into my speech and writing, the more I was accepted as a peer.

Likewise, attempting to work with my middle schoolers meant learning their slang: “GOAT,” “lit,” “legit,” “bruh,” and so much more. While I didn’t actually use those terms much myself in my role as educator, understanding their use was key to decoding our interactions and communicating effectively.

People respond well to encouragement. No one wants to feel stupid. But like many environments, both Microsoft and middle schools are competitive places, with co-workers and classmates frequently pitted against one another for professional and social advantage. Unsurprisingly, there are plenty of people who will cut a peer down to size and smile while they do it.

In such an atmosphere, encouragement can feel hard to come by, and praise is worth its metaphorical weight in gold. In both the office and the classroom, I found that the best way to get the best work out of someone was to encourage their strong points — and minimize the negative feedback as much as I reasonably could. As a bonus, this approach was a good one for making allies out of both colleagues and students.


Everyone occasionally needs a reality check. As helpful as positivity is, there’s no substitute for telling it like it is when necessary. Students might fall behind in their assignments, or fake their work well without truly understanding it, or try to play video games surreptitiously. Co-workers might try to pawn tasks off on others, or routinely ignore deadlines, or … try to play video games surreptitiously.

It’s always good to try to make corrections gently the first time, but when poor behavior becomes a pattern, more strenuous interventions are necessary. And sometimes no matter what you do, resolving the problem will require escalating the issue to a higher authority, such as the manager or the principal.

Most people try their best. Someone’s work might not be exemplary all the time, or even some of the time. But in my experience, people rarely try to not do well. One of my students spent his evenings mostly alone while his single mother worked; another was a refugee striving to become fluent in English. One worker in my Microsoft office was pregnant and had unexpectedly lost her father; another was going through a divorce. In all of these cases, the work they produced wasn’t perfect — but they were trying their best, and they appreciated everyone who recognized that.

Whenever possible, it helps to assume there is genuine effort and good intent. That doesn’t mean you should settle for less than the best. But jumping to the conclusion that someone is just slacking off, and rendering judgment accordingly, seldom yields good results.

If someone’s work is lacking, work with them — and with their situation — as much as you feasibly can. If they see you’re willing to meet them halfway, they’re that much more likely to go the extra mile for you both now and in the future.