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Strategic Philanthropy

Ten Reflection Questions to Deepen the Philanthropic Experience

By May 30, 2023December 15th, 2023No Comments

While every philanthropic journey is unique, nearly every funder reaches points along the way where they feel more – or less – connected to the work they are doing. It’s easy to get bogged down in details and processes or overwhelmed by the enormity of the issues we seek to address. One of our roles at TPI is to help funders take a step back, reflect on their work, and set clear intentions for their work moving forward. We often build this in as an annual check-in exercise with our clients, to take stock and calibrate our work together. While this can be a very personal process, we have distilled some of the questions we use into an exercise for funders who wish to proactively and continually deepen their philanthropic experiences. 

If you feel like your philanthropic endeavors are on autopilot and want to reconnect with a real sense of purpose, I invite you to ask yourself the reflection questions below. Take your time. Be honest. Answer with your heart as much as with your head. Offer these questions to family members or to your board and staff as an exercise. There are no wrong answers. Where there might be indecision or different perspectives is often where you can learn about each other and become more intentional about your work. 

Reflecting on the Past 

  1. Among your accomplishments over the last year, which have been most personally meaningful? (Choose up to three.) What made you most proud? If your philanthropic teammates answer this differently, what energizes them most and how can you build on that? 
  2. What might have gone better or differently, in retrospect? Every program or relationship builds on knowledge, experiences, and perceptions that shift over time. What do you know now that you didn’t understand before? How should we make adjustments going forward?
  3. What did you enjoy most about your work engaging in philanthropy over the last year? If question one was about what made you proud, this is about what made it fun, what made you feel fulfilled or gave you hope. These tell us what fuels you and generates energy and connection to the work.
  4. What did you learn over the last year that you might bring forward? In addition to tactical lessons, there may be deeper observations. After all, every donor experience can offer different kinds of insight: into the lives of those most affected by an issue, into the fields of grantee partners tackling that issue, into the issues and systems you seek to influence, and into your own role in the world and your intentional and unintentional impact. 

 Planning for the Future 

  1. What parts of your philanthropic work are you most looking forward to next year?  Building on your answers in the prior section, what do you find most motivational?
  2. What goals do you want to set for the next year? Are there new focus areas or special projects you would like to explore? Or is this year more about continuing and strengthening existing efforts? 
  3. Do you want to maintain or increase your giving rate over time? Before you skip this due to budget limitations, play with the question a little. What could you do were you to shift you giving rate? Is there anything there worth considering, relative to the time horizons of the issues you are working on? There is no right answer to this, but donors often have more flexibility than they think. And while it is a separate question, keep in mind there are more ways to support a grantee or an issue than writing a check.
  4. How are you feeling about the size and scope of your grantee portfolio? Do you have a manageable number of partners that you can build relationships with, or do you feel scattered? Does your portfolio reflect your goals, or are you noticing misalignment or gaps that need more attention?
  5. How is your funding style shifting, if at all, based on your experiences partnering with grantees? As you more deeply understand the challenges in their work, and learn more about the nuances of their strategy, how do you view your role as their funding partner? How has what you’ve learned made you rethink how you support them in any way?
  6. Moving forward, how do you want to spend your time doing the work of philanthropy? What activities are most meaningful to you (e.g., developing strategy, learning from experts, collaborating with other funders, visiting organizations and partners, reviewing proposals)? And given your current responsibilities and bandwidth, are there things you want to do more or less of, and what are they? What can you delegate to others to optimize your engagement? 

Many funders overlook that last question, but it helps to be intentional with how you spend your time and effort. If the work is not sustainable, you might not sustain it. The more solid you feel about your direction and engagement as a philanthropist, about your role in the complex web that is any issue of importance, the better. What you do and how you do it is important. The more it means to you, the deeper your connection to helping to create change will be – the more rewarding and ongoing your journey will be.

I hope these questions are useful to help you “check in” on your own philanthropic path. If you found value in considering these questions and would like to take this process to a deeper level or engage others in a dialogue to shape the direction of your giving, TPI is here to guide you and your team along the way. Reach out!