Writing Tips for Leaders

The dedication ceremony for the Gettysburg cemetery in 1863 included a keynote speaker, Edward Everett, who spoke for over two hours. Abraham Lincoln followed with an address that lasted two minutes. 

Writing is an intensely personal exercise in expression. Professional writing, however, needs to focus on your audience. While you don’t want to appear impersonal, your focus has to be on inviting your audience to engage with your message. My goal is to help writers apply the lesson from the Gettysburg Address to more successful communication experiences. Enjoy!

Know Thy Audience

Educational leaders need to write to meet the needs of myriad audiences with differing needs and attention spans. With every piece, remember this one critical truth: it’s not about you. If your audience isn’t engaged, your writing means nothing.

Stay Current

Language changes and so do grammatical conventions. Underlining went the way of the typewriter. So did the rule about two spaces after a period. Diaereses (reëvaluate) look cool but are essentially long gone, and we seem to have followed our germanic linguistic cousins in making compound words out of everything possible1. Roll with the changes.

White Space

Open up a book and look at a page that has a solid block of text with no paragraph breaks. Now, find a page that is loaded with dialogue. Which one looks more appealing? Our eyes and brains love white space and find it much more inviting. Knowing that, keep your paragraphs short, preferably 2-3 sentences long (yes, I know this one is 5).

Be Direct

A landscape design principle dictates paving the shortest path between where people exit their car and the main entrance. If you don’t, they’ll take that route anyway. As writers, pave the path you want people to take. If possible, add lights. Get to your point quickly. A related process tip is that the first two sentences of any first draft will be awful. Expect to revise them.

Stay Strong

Avoid progressive verb tenses; they end in –ing and suggest a lack of confidence. Instead, use active verbs in present and past tense as much as you can. Also, every verb in our language suggests action except to have and to be, so look to propel your language with other verbs whenever possible.

Be Clear & Concise

It doesn’t matter if you know what you’re saying if your audience does not. One tip is to challenge yourself to use a noun after the word this. Another is to apply Stephen King’s logic that “the road to Hell is paved with adverbs.” If you use effective verbs, adverbs are unnecessary; to wit, consider the difference between “he ran quickly” and “he sprinted.”

Never Say Never

Avoid absolutes and other forms of limiting language. Never, always, everybody, no one, and the like tend to overstate and are rarely, if not never, accurate.

Simplicity Is Good

If you don’t know how to use a semicolon, then don’t. And don’t worry about it; few others know anyway. Simple punctuation, including avoiding unnecessary apostrophes, and language that doesn’t require a thesaurus are particularly helpful in writing to a wide ranging audience.

“You Never Get a Second Chance to Make a First Impression”2

Starting a piece isn’t easy, but remember that a lost audience rarely returns. I largely inhabit the email world and have some tips borne out of positive and negative observations. Inspired by a board member who reminds me of her affinity for bullet points, here are some tips on salutations:

  • Begin with a salutation appropriate to the audience. Use “Dear” or, if you’d prefer to sound less chummy, “Good Morning.” Avoid “Hey” unless you want to sound chummy.
  • Identify the person to whom the email is addressed. This point of clarification helps when multiple people are cc’d on an email and helps identify which recipients should respond. As a superintendent who is cc’d on 8,675,309 emails per day, I appreciate knowing when I’m expected to take action or simply nod appropriately.
  • Punctuate correctly. A salutation of a more formal or rigid message should conclude with a colon. Otherwise, a comma is fine.
  • Never, ever open with “Greetings and salutations.” To expand on that, never. I mean it. Never.
  • Similarly, at the end, keep your signature brief. Guess who cares about most of the information listed after your name? Actually, don’t guess. It’s probably no one.

Break Rules Intelligently

I’m the youngest of three children who were born within 39 months3 so this principle of wise mischief has been the cornerstone of my existence, and it’s relevant to effective writing. Don’t use a fragment? Please. Can’t start a sentence with a coordinating conjunction? But it works. Just apply the paprika rule: a little can spice up a dish, but too much will ruin it.

It’s not really a rule, but I recommend having fun as well. Sometimes we have to write difficult messages or items that we just can’t phrase the right way. What’s helped me is to loosen up by taking a walk (get away from the piece), say out loud what you want to say and then jot some notes, and depend on the kindness of good colleagues (I have an English teacher friend who is fearless with his feedback). If your prose feels constipated, the reading experience will be similarly uncomfortable. I’m not going to extend that analogy, but will encourage you to relax and have an authentic voice. 

  1. My favorite is the Dutch verantwoordelijkheidsgevoel (sense of responsibility) ↩︎
  2. I’m pretty sure this line comes from an old Head & Shoulders commercial ↩︎
  3. Yes, we’re of Irish extraction ↩︎

Merchant of Joy, Part I: Lessons from Elementary School Teachers

“Contrary to what we usually believe … the best moments in our lives are not the passive, receptive, relaxing times [….] the best moments usually occur when a person’s body or mind is stretched to the limits in a voluntary effort to accomplish something difficult and worthwhile.” -Mihaly Csikszentmihalyi

Premise: The secret to life is joy, which allows us to reach the ultimate goal of fulfillment. Both require work. Without persistent open-minded perseverance, neither can be achieved.

After teaching high school English for fifteen years, I thought all teachers were pretty much the same. The six years that followed as an elementary school principal very quickly taught me  that I was wrong.  In short, elementary school teachers are different. A quick summary:

  1. They work incredibly hard at things like planning for six subjects, updating bulletin boards, rationalizing with the irrational, and more that I hadn’t really considered.
  2. They communicate with the 20+ families on their rolls more in a month than I ever did with the 100+ on my rosters in a year, and it isn’t even close.
  3. A team of them could figure out world peace if you gave them a few hours of dedicated work time, a 42-minute prep and several pots of coffee. You’d have to construct the team like a boy band (The Super Organized One, The Elitely Calm One, The Frenetic Tornado of Productive Energy One, and The Sharply Intuitive Who Never Hits Reply All), but they’d get it done.
  4. They have empathy beyond description.

That last point presents itself generally in positive ways, but occasionally manifests itself in their feeling deeply hurt. With my underwhelming emotional capacity, I felt limited in my ability to offer true support beyond listening. I’m typically a fixer but couldn’t fix that so usually I didn’t say much, but did make it a point to check in frequently.

Since they gently tolerated my overt nerdiness, I did, however, occasionally dip into my English teacher toolbox and talk about how the Greeks nailed the human condition in their tragedies. The often misunderstood concept of the fatal flaw was particularly relevant as it’s essentially the quality that makes us great, but when taken to an excess, can bring about our demise. The applicable traits are legion: stubbornness, pride, passion, compassion and lots more.

The tricky part of compassion and empathy is that they require us to treat our emotional front more like a screen door than a sliding glass door or the sturdier and more impenetrable option, a reinforced dungeon door. Beauty, joy, fun and more pass freely in and out though the screen door, but there’s an inevitable vulnerability that comes along with it. And I say it’s worth it.

What I often observed in elementary school classrooms was joy shared between unhindered children who know that the educators in the room care deeply for them. That’s the trick with high school kids, too: if they know you have their back, they’ll work for you and take healthy intellectual risks. But the intensity of nurturing the same group of kids for the entire day has to drain even the strongest soul, and yet I can attest to the power of kindergarten therapy (hang out in a classroom for 5 minutes and your day gets significantly better). 

So where do they find the energy to keep up? Joy. They start with the mindset that their calling is to shape learning experiences for kids. What’s next is letting the screen door approach work its magic. hey feel the elation of their students’ successes by listening to their stories, celebrating their moments and sharing in the breathless excitement of curiosity and discovery.

We’re looking at a new year in the education world (it’s mid-August as I write) and that provides a rich opportunity to resolve to be something even better than what we’ve been before. While no one really gets a completely clean slate (no tabula rasa, sorry), we do all get a fresh start each school year and we each have the opportunity to define how we want to assert ourselves in the days and months ahead.

Here’s my challenge to you: be a merchant of joy. Start the new year with a perspective that allows you to both feel and spread joy. Yes, by May we’ll likely start giving each other the stink eye when we notice who chews too loudly in the faculty room or always parks over the line next to your spot, but we can start from the best place. Easy? No. Vulnerable? Yup. Rewarding? Definitely. It starts with your mindset, demands commitment, and hopefully pays off both in the joy you receive and the fulfillment you feel.

Be a merchant of joy. Have fun and Happy New Year! 

Sand Castles & Struggle: A Leadership & Parenting Observation

This entry, my first in a while, was inspired by a casual conversation with my wife while walking on the beach in the Outer Banks. It really did unfold as described and then just stuck in my head as I felt there was something much larger than sand castles going on. I ended up writing a lot of this in my head on the drive home a few days later, and am really excited to finally deploy the word shambolic. Enjoy!

My wife and I enjoy morning strolls on the beach, which sounds like a cheesy line but is true. We talk about a lot and, really, nothing much at all while we dodge beached jellies, scan the horizon for dolphins and observe people enjoying the sun and surf. In our conversations, my success rate in expressing opinions with which she disagrees is close to 70% and a recent warm Wednesday morning added to that. The topic? Sand castles.

I noted that we were seeing more sand castles that morning (agreed). I then added that it seemed like the builders were more parents than kids (quiet disagreement). I waited a few steps and then summoned the courage to say, “That’s really not a good thing,” which elicited outright disagreement.

She’s a teacher so she’s well versed in the “I-do, we-do, you-do” continuum and countered that the parents were just being nice and helping their kids.

But in taking over the work, are they truly helping their kids? In the long run, I don’t think so.

I contend that our children’s construction skills, no matter how shambolic they might be today, should be reflected in what they produce. Their labor might not inspire passersby to gasp in amazement and take pictures, and might even dissuade you from snapping a few shots to post on social media, but at least the sand castle will reflect their work authentically.

For perspective, I’ve long advocated for the 10-and-10 Rule by which no school project can require more than $10 spent at Michael’s or 10 minutes of parent labor. When our kids were little, I also made it a point to compliment my wife on how much her work improved on dioramas she crafted for third son. I got away with the irony, but still believe that life has taught us that we learn by doing. More importantly, we learn by experience, which tends to consist of the mistakes we learn from.

On the beach, I took a gentle swipe about how our aspiring sand castle builders are being denied opportunity by well-intentioned parents and wanted to craft an argument based on a syllogism, which is that if A=B and B=C, then A=C.

My A=B logic is that struggle builds strength. The B=C is that we want our kids to become strong. Where the equation and explanation get a little messy and drift into applying negation, is that if we don’t want our kids to struggle, then we don’t want them to build strength. That’s problematic. Not intentional, but problematic.

Instead of framing that argument, I elected instead to read the room/beach and my audience, and opted to pivot: “So the Red Sox game was really exciting last night.” The experience of 26 years of marriage has taught me to cut bait.

Truthfully, I don’t care about sand castles, but am looking at a bigger picture of mindset and agency. I submit to you that we do well by allowing our children or the people we lead to endure the messy early stages of developing their skills. Be there as the safety net and provide a helping hand, but let them grow by doing the work to their own ability and vision. As they endure, we can guide them to become more durable and confident, and, ideally, celebrate in the brilliant sand castles they can eventually create.