Leadership Lessons from Working the Crossword

For the last few months, I’ve been working the NYTimes Crossword as a way to relax, sometimes in the morning as I’m having coffee or sometimes in the evening with a glass of wine. If you’re an avid NYT Crossword worker, you know that the puzzles get harder as the week goes on. Sunday’s is always a bear (though my daughter swears Thursday’s is harder).

Later in the week, on the more difficult ones, I often have to sleep on them. I can’t finish until the next day. I often wake up and pull it up again as I’m having coffee. Words with random letters and mystery clues suddenly become clear and I can fly through some of the most difficult clues. And of course, solving those challenging words reveals other words and so the puzzle starts to almost solve itself.

Working a crossword is a mental activity. Not as challenging as, say, figuring out how to open school safely during a pandemic, but it still requires mental energy. Resting, sleeping, going for a walk or even doing another mental activity that’s very different helps restore that energy. You can come back to the puzzle refreshed and sometimes with a different perspective.

As leaders, especially during challenging times, it can feel irresponsible to take time for yourself, to sleep for a reasonable amount of time, to go for an hour walk. There’s so much to be done and, speaking for myself, a constant nagging feeling while I’m not working that I should be working.

I’ve been watching Twitter threads of educators, some that are classroom teachers and some that are principals or administrators. They’re exhausted. And they didn’t get their usual vacations. Some of the things they used to do to step away and refresh are no longer possible — a massage, getting your nails done, even spending time with friends and family. Everyday activities are harder, take longer, and are filled with anxiety. Going to the grocery involves wearing a mask, standing in line, avoiding close contact, bagging your own groceries, and wiping everything down when you get home. And then there’s a nagging feeling that maybe you were too close to someone who has COVID and doesn’t know it, and if you get it, will it be severe? If you don’t, will you pass it to your family and they might get it and it will be severe or fatal. That’s a lot to contemplate just to get your groceries.

But we have to find ways to rest, even if it’s just insisting on getting enough sleep, or taking one day of every weekend to not check email. The puzzle will start to solve itself if you can find ways to restore your energy.

I like the challenge of crosswords because they span so many areas of knowledge, everything from pop culture to science to geography. I’m always trying to expand my knowledge base and I pride myself on having some understanding of a range of fields. But still, my knowledge is limited. When faced with a clue I know nothing about, I immediately think, who else might know this. I’ve turned to my daughter for popular culture clues, my husband for science and 1970s tv shows. My mother is usually good for political history and the occasional French or Latin phrase.

Yes, being able to solve something independently can feel good, but it actually feels better to be supported by others, to accomplish something collectively. It also feels good, absent immediate collaborators, to feel part of a community. It’s been comforting to be welcomed and supported by area educators and administrators, people who’ve provided advice and information or who’ve had long conversations with me, simply because they wanted to help.

Former colleagues, fellow new heads, too, have provided an outlet for sharing information or for just listening as I’ve thought through a problem out loud. Leadership doesn’t happen in a vacuum and the support of others can not only provide possible solutions to problems but also a sympathetic ear and encouragement when you’re facing challenging situations.

A few days ago, after solving a clue, I said to my family, “Well, that book I wrote in fifth grade just paid off.” In fifth grade, I wrote a mystery that centered on African Sleeping Sickness. In order to write the book, I had to research the illness and learned that the tsetse fly is one of the main carriers. And I’ve remembered that fact for forty years. The tsetse fly was the answer to the clue “Carrier of sleeping sickness.”

We all have experiences, from old jobs, from school, from travel, and from reading that we can turn to for answers. Answers are not always found in the usual places. If you’re a school leader, you might keep up with education research and news, but sometimes, insights can come from far afield. A fellow head I know is learning about hostage negotiation and says it’s been helpful to him in his conversations with various community members because the crux of negotiation is about asking good questions. I’m currently reading about rocket science and I recently finished a YA novel about dress codes. Both of these have given me insight into how to approach different problems I’m working through.

As leaders trying to solve hard problems in the face of a situation that we can’t control, we can feel isolated and feel as if our usual methods of managing either are no longer available to us or aren’t working as planned. Rest and restoration, support from your network and community, and relying on varied experiences can all be part of your arsenal. Take the time to step back and find the resources you need to carry on. All the email will still be there when you’re ready.

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