Questions to Ask Yourself During Nonprofit Strategic Planning

Nonprofit GrowthDevelopment
Written By Sherry Quam Taylor
Image of nonprofit leadership team discussing strategic plans and practicing the James Clear quote - "When making plans, think big. When making progress think small."

I love this quote by James Clear. He's the author of Atomic Habits . . .

“When making plans, think BIG. When making progress, think SMALL.” —James Clear

Image of a quote from James Clear, author of Atomic Habits, "When making plans, think BIG. When making progress, think SMALL.

Frankly, I see this play out for good and for bad in the nonprofit sector. Check for yourself…

Questions to ask yourself to see if you’re making BIG plans…

❓Has our org calculated the REAL financial need to your entire Strategic Plan?

❓Is your team raising to your org’s true financial need (vs. a squeak by number)?

❓Is your team consistently pipelining donors 2-3 years out?

❓Can you easily answer the ‘what would you do if I gave you $1M?’ donor?

❓Have you put a few innovative initiatives in your future plans that honestly scare you a bit?
 

Questions to ask yourself to see if you’re making SMALL progress…

❓Does your team confidently lead donors for 6-24 months before the ask?

❓Do you make annual fundraising plans based on hours-to-dollars analysis?

❓Do you say NO more than you say YES to fundraising ideas that come your way?

❓Do you time block your day so that your Top 30 donors yield 75% of your revenue?

 

If you answered “YES” to all of these questions, you’re killing it. Keep on doing what you're doing!

 

Answered “No” to too many of these? It might be time for some realignment. If you want help with that in 2026, you can apply here.

Whenever you’re ready, here are THREE things you can do next:

👣 Follow me on LinkedIn where I share insider info daily — the same lessons I teach my clients about attracting larger gen-ops dollars and diversifying revenue.

🍎 Grab FREE Guides + White Papers — download robust resources you can use to push against the sector’s misconceptions, equip your board, and shift your team into High-ROI fundraising.

📈 Work with me to diversify revenue & secure the gen-ops gifts you need to grow. If you’re a business-minded nonprofit CEO with big growth plans but need to make charitable revenue from investment-level donors a bigger part of your budget, you can apply to work with me here.

Sherry Quam Taylor

Sherry Quam Taylor works with business-minded Nonprofit CEOs whose Strategic Plans require expansive budgets and larger amounts of general-operating revenue for growth. To become investment-level ready, Sherry helps leaders see their revenue potential and helps them see what may be blocking donors from giving in this way. Sherry’s clients know how to attract larger donors by solving the funding challenges at the root of the issue.

As a result of learning her methodology, Sherry’s clients become sustainable, diversify revenue, and know how to add significant amounts gen-ops revenue to their budgets. But mostly, their development departments and board have transformed into high-ROI revenue generators – aligning their hours with relational dollars and set free from the limitations of transactional fundraising.

Sherry attributes the success of her business to her passion for modeling radical confidence to the future CEOs in her house - her two college-aged daughters.

https://www.QuamTaylor.com
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