Earlier this week, I met with an experienced and thoughtful, but highly conflicted, philanthropist. She had found an organization that was highly aligned with her values and was getting good results from its programs. She was a committed and significant donor to that organization. She was excited about the opportunity to continue to invest in this nonprofit, and was also eager to engage with its leadership on ways that her donation could drive the greatest results. Unfortunately, she was beginning to feel that the organization wasn't terribly receptive to her questions and suggested approach to make the program even better.

In particular, she recalled a long discussion in which she was poring through the program's results with members of the nonprofit's leadership and other outside experts. She believed that the rich data set clearly indicated that the program was effective with certain groups of people, but less effective with others. In her mind, the clear next step would be to shift the program's focus.

She was glad that the group seemed (in the moment) to grapple with the important questions about changing the program design, and nobody disagreed on the facts surrounding the conclusions. The post-meeting follow-up was slow, however, and didn't fulfill the promise of raising and dealing with this controversial issue among the board and senior leadership. Through subsequent interactions with senior leaders, she received positive feedback on her clear-minded questions and thoughtful approach. But still, no action was taken.

There are clearly some principles and best practices for philanthropists who want to engage successfully with grantees. Many are detailed beautifully in a Center for Effective Philanthropy classic entitled More than Money—click here for a summary.

But the hard reality is that she had followed many of these best practices. How would you advise her?

This week, Tom and Joel had the pleasure of being interviewed by Charlie Rose. As usual, Rose zeroed in on the heart of the matter at hand, in this case the six questions that can unlock philanthropy's potential.

I know you're supposed to love all your children equally, but Tom made a strong case for the power of Question 6. Asking "Am I getting better?" is a great test question—are you complacent or are you a learner? Do you brag about your victories or ask how you can do better next time? He cited Jennifer and Peter Buffet's NoVo Foundation, and you can read more here about their journey of trying a path, getting feedback from the field, and making hard decisions to course-correct over time. 

One of the most common related questions I hear is "How should I measure success?"  We've also provided a fun checklist that can help get you started.

I'd also invite you to view the full Charlie Rose interview.  We'd love to hear your reactions.

Last week was my sixth Harvard Business School Alumni Board meeting. It's a surprisingly diverse group of alumni, representing over 15 countries from Saudi Arabia to Nigeria to Brazil, and dozens of graduating classes and industries. Many have achieved significant financial success; others are fulfilling the school's mission of "educating leaders who make a difference in the world" by leading mission-driven enterprises.

Given the stereotypes surrounding business school grads, I was a bit surprised at how many board members not only cared about social sector issues, but also were deeply engaged. It took various forms: In terms of careers, many had been leaders within multiple sectors over the courses of their careers. In fact, our outgoing board chair co-founded the Global Philanthropy Group, which is dedicated to serving high net-worth philanthropists, after a career in the private sector. Many others are highly engaged in the social sector in terms of substantial board commitments and volunteer time, and had dedicated substantial time to fundraising on behalf of causes they cared about. And everyone was concerned about whether their philanthropic dollars–be they modest or substantial–were being spent well.

Despite the board's diversity, one common thread was the commitment to results and excellence in their social sector endeavors. Over the multi-day meeting, I got to ask my fellow board members my favorite question: "So, you're interested in X social cause. What does success look like?" Overwhelmingly, people responded with really specific interests: Charter schools. Disruptive technologies in healthcare rolling out across the developing world. Base of the pyramid business models. Smart grids. A competitive workforce in their geography.

At Bridgespan we've seen this trend play out time and again–the growing number of philanthropists who care about the results their dollars are creating. Philanthropists who are blending their dreams of a better world with the hard data and evidence required to make change happen. So now I'll ask you my favorite question: What does success look like in your philanthropy? If you're intrigued by the question, I invite you to read "Defining Success," which highlights a how a number of philanthropists are blending their dreams.

Since we launched Give Smart earlier this year, it's become clear that while philanthropy can be incredibly diverse, philanthropists who really want to get better results share common questions. They're seeking like-minded people asking those same questions. They're seeking plain-English answers, not philanthrobabble. They're looking for simple (but not simplistic) ways to move forward with practical, decision-oriented ideas. And when that's not possible, they're looking for inspiration and fellowship among other philanthropists tackling the same problems.

Last week, I had the pleasure of joining the CEOs of four large family foundations whose benefactors are highly interested in building a community among 20- to 35-year-olds. A new program had been created and its leaders (both the philanthropists and the management) were justifiably proud of a database they'd invested heavily in over the past few years (a database which had hundreds of thousands of accurate email addresses for their target group). While discussing important questions like who had the right to send out emails and under what conditions, the conversation quickly turned sobering when one of the CEOs said: "This is all interesting. But we all know that we have 12, maybe 18 months left on this data. How many mobile phone numbers do we have?" The room grew quiet as everyone nodded thoughtfully—contemplating the fact that for the next generation, text messaging is replacing email as the main method of communication. They agreed that while it was tempting to keep discussing emailing rights given the database they'd been supporting, they'd need to turn their attention to the new data challenges ahead, or they'd put their entire investment and strategy at risk.

In working with philanthropists for the past decade, it's become clear to me that there are many reasons that it's hard to get better over time: it's hard to define "success" for your philanthropy; it's hard to measure that success; it's hard to change behavior and keep holding yourself to a higher standard. But also it strikes me that there are two other, opposing pressures that make it hard to know when to stick with a strategy and when to shift course.

On one hand, there are endless neat ideas and new approaches floating around. One philanthropist friend was especially critical of her peers on this front: "It's like we're birds, and new shiny baubles keep turning our heads away from the seeds in front of us." On the other hand, there's the real risk of "path dependence"–the well-known psychological fact that we humans tend to keep going down a particular path even after it becomes clear it's the wrong one–simply because it's the path we're on.

So how can philanthropists navigate between shiny baubles and path dependence? One way is to be in deep conversation with others who have similar aims – fellow funders, grantees, and most important, the beneficiaries. What impressed me about this group of CEOs is that they started to shift their conversation from themselves ("but we spent so much money making sure this database had accurate emails!") to their beneficiaries ("how do they want us to communicate with them, now and in the future?").The real trick, of course, is how quickly everyone shifts their behavior to match the new mindset; whether they can start the process of putting data behind their hypotheses. For example, under what conditions does this group want to receive email, texts, facebook messages, or communication through myriad other vehicles, and how do they build their new communication strategy and database accordingly?

When facing daunting questions such as this one, we've seen that three practices can help: first, reflecting on the data that can help you make better decisions over time; second, ensuring your strategies are tied to your grantees' strategies and beneficiary needs, and finally, thinking about what needs to happen over and above what your grantees are doing to create the results you're seeking. For more detail, read "Getting Better Over Time." I look forward to hearing the practices that help you get better over time.