At the veggie market on the corner of Jamaica Avenue and 216th Street in Queens, NY, my dad showed me how to pick a pineapple. He said, “It just has to smell like a pineapple and feel right, then it’s good to go.” I nodded in agreement, like I wanted him to really believe that I was following him and that I understood this wisdom.

Inside, I was thinking, feel right? What does that mean? Feel hard? Soft? Heavy? Prickly? How long do I have to hold it? What should a pineapple smell like? Fruity? How fruity?

If I asked him too many questions, it would feel like his wisdom wasn’t delivered clearly, and this might be the last lesson at the deli I would ever be invited to; so, I kept nodding.

But why do some people feel so much pressure to pick the right piece of fruit? Or order coffee just precisely right, while others have zero risk adversity? And how does this deliberation in choice affect building trust in your school community, when the pineapple farm feels like it’s burning in flames, and your community is looking to you to ease the conflagration?

These past months of leadership at The Young Women’s Leadership School in Astoria, NY, in the shadow of COVID-19, have been nothing short of medal-worthy in the greatest champion round of the leadership Olympiad. At a grade 6–12 all girls secondary school with girl coders who can beat MIT freshmen and teachers who can design, collaborate, solve, and QUESTION at every turn, it’s been nothing short of exhilarating and exhausting.

It’s involved reams and reams of guidance documents, discovering updates from Twitter and Channel 4 news, hitting the reset button on agendas, programming, polls, hosting town halls only to revise plans within minutes with the delivery because more reams of guidance documents, which have been newly revised, show bold and unread in your inbox.

And in the midst of this leadership journey, where the winding roads meet Lilliputians and you can’t imagine ever getting back home, you have to just pick the pineapple and trust your gut.

In my own humble journey during this time in a NYC landscape, here are tips I’ve discovered as I navigated the pineapple farm and found an opportunity to build trust.

1. For the most part, disregard the color of the pineapple (or at least its appearance, as things are not always as they appear).

The appearance of your staff’s silence, or the appearance of something in writing, doesn’t tell you much about what’s underneath or behind it. Not all teachers or staff members will be ready to share fears, personal traumas, physical or mental health challenges, nor will they appear (or want to appear) weak or in need. It’s up to you to recognize that, more than likely, deep paralyzing fear exists among the whole school community. And fear at this time is not a bad thing—it’s rather the most human of all the things we can feel.  So embrace, be patient, and respect boundaries.

2. Instead, give it a squeeze… (Step into the front lines, get your hands dirty, and be real about it)

If your staff is wondering why you’re not stepping into the lobby handing out devices or in the cafeteria working through the bag lunches, that’s a bad sign. Rather, you should be modeling and leading from the front lines. Don’t expect your teachers to do anything you’re not prepared to do yourself. And most importantly, be prepared to yield slightly with every question asked. Use that question as a post sign, to guide you to your plan (yes, keep to-do list items) to create a safe space for your community.

3. … As well as an inhale (Filter through the muck, and make your team first, second, third, and last).

Put your blue light blocking glasses on, take a deep breath, and start filtering through the enormity of the policies. Do so just enough to navigate with the grain, but not so much that you can’t live in the grey. It should smell aromatic, with the scent of fairness, humanity, and empathy. If there’s no scent, this is an indication that you’re not ready to place your team first. If you’re getting lost on page 98, section 4, left margin, take off the glasses, go for a walk, and hit your reset button. Remember the adage that culture eats strategy for breakfast.

4. Feel its heaviness in your hand (Use your power for good, Glenda).

Weight is another consideration when selecting the right pineapple. As with many decisions, the heavier the fruit is, the better. The heavier your decisions—the more important—generally the higher the opportunity to step forward and give space, time, flexibility, and understanding its due space.

5. If all else fails…

If you’re stuck and can’t figure out how to reach your community or bring them together, here’s what to do:

  • Keep your promises
  • Be consistent
  • Listen

*Not necessarily in this order.

What determines when risk feels small or big? Remember the movie Along Came Polly from the early 2000s? Polly was a salsa dancing, ferret-loving free spirit and her counterpart, very directly opposite, was the risk analyst, Reuben. Be a Polly and just pick the pineapple.

Dr. Allison Persad is the principal and lead learner at The Young Women’s Leadership School in Astoria, NY, and a NASSP 2019 Digital Principal of the Year. Follow her on Twitter (@apersad).



Leave a Reply to Dr. Barbara McKeon Cancel reply

Your email address will not be published. Required fields are marked *