Navigating Strategic Planning and Board Engagement in the Digital Age

By Published On: February 19, 20244.4 min read

Boats and I have a complicated relationship. I can still remember my earliest experience as a middle school student on a whale watching field trip off the coast of Massachusetts. The weather was not ideal. The boat rocked incessantly. And for much of the afternoon, despite taking the recommended dose of Dramamine, my head was buried in a yellow plastic bag, miserably unaware of the pod of whales swimming along our starboard side. Hours later, I pulled myself together enough to venture out and see the vastness of the Atlantic Ocean, sorry that I couldn’t fully enjoy the day-long experience.

Whale Watching Boat

I find myself thinking alot about being in a boat as a metaphor for the challenges facing educational nonprofit leaders and those they serve nowadays (yes, I’m “going there” because the metaphor works, stay with me). The sea is vast, oftentimes unpredictable, and sometimes downright terrifying. At the same time, it can be beautiful and awe-inspiring, a reminder of endless possibilities. The boat, if properly crewed and supplied, can handle the choppiest of waters, give its passengers a memorable, valued experience and, ultimately, get everyone to their destination safely (even if some may have a more pleasant experience than others).

For non-profits, membership organizations, and state and local agencies in the education ecosystem, navigating the turbulent seas of change and uncertainty today requires more than just a sturdy rudder, a few trusted nautical maps, and yes, a Dramamine or two (though I still recommend taking them!). Propelling organizations towards a future brimming with efficiency, board engagement, and impact may require upgrading to a more powerful ship engine and the most precise and reliable GPS. If you’re looking to get more out of the strategic planning process and board engagement, my suggestion is to finally throw the dusty binders overboard and embrace the flotilla of digital tools for educational nonprofit leadership that can help steer you, your board, and your organization towards success.

Data-Driven Decisions: From Instinct to Informed Action

Imagine mapping your organization’s next strategic move without making use of the expansive ocean of data at your fingertips. It’s a risky gambit, at best—and potentially a huge disaster in the making for all aboard. This is where good data analytics tools come sailing in, whispering hidden insights by way of easily digestible charts and infographics. Analyze member demographics, engagement, fundraising trends, and industry benchmarks – these become the aforementioned GPS, keeping you on course and guiding you towards informed, mission-driven decisions that resonate with your members and stakeholders. While several AMS or CRMs have such native tools, there are also some great (and relatively inexpensive or even free) standalone tools out there like Tableau and Looker (previously Google Data Studio).

Board Member Development: Sharpening the Crew’s Skills

Much like veteran sailors (and educators), board members require continual learning and skill development to be effective leaders. Online learning platforms and virtual and in-person professional development opportunities are the critical training ground for board members as they immerse themselves in issues of governance, finance, risk management, and other relevant topics. Furnish your crew the knowledge and skills they need to keep the boat afloat and stay focused on the final destination, all while navigating the complex and often harrowing waters of today’s non-profit education landscape. There is an ocean liner’s cargo worth of great resources in this space, free or otherwise, beginning with ASAE, state-specific associations, and others. But regardless, make the investment in those you’ve entrusted with steering the ship.

Engaging Virtually From Distant Shores

For board members scattered across the United States and even the globe, bringing people separated by literal oceans together can be daunting or next to impossible. Technology, implemented properly, can bridge the divide, connecting board members to each other so they can continue charting the strategic direction of your organization without being in the same physical boat. Board portal software or a well-designed and properly maintained communication platform like Slack or Teams becomes your digital marina, securely housing Board materials, minutes, archived notes, and voting options. They’re also a wonderful way to build a culture of communication, keeping boards thoroughly engaged year-round, not just during the rare in-person meeting.

A Final Word Before Setting Sail

While proper implementation of technology can help with strategic planning and board engagement, it’s not without its challenges. Much like that upgraded ship engine or navigation system, there are costs involved. There’s also an inherent security risk whenever your organization’s intellectual property is in the cloud. And for some board members, it may take longer for them to get their sea legs and adjust to the new digital-first environment. In the end, be sure to keep humanity at the helm; after all, technology is a tool and not a replacement for personal interaction, intercultural communication, and critical thinking.

Wishing you fair winds and calm seas ahead!


Howie Berman, MA, CAE is a principal and co-founder of Learning Curve Partners, an independent consulting group which connects and empowers educators and education organizations to be leaders and lifelong learners in pursuit of their missions. Learn more at learningcurvepartners.com and follow this blog for more thoughts on the education space.

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