Community Development Field

Why Leadership Pays

In previous blog posts (Why Evaluation Stinks), I’ve discussed how the fragmented nature of the nonprofit sector makes it very difficult to impose top-down, comprehensive evaluative frameworks. The primary problem […]

In previous blog posts (Why Evaluation Stinks), I’ve discussed how the fragmented nature of the nonprofit sector makes it very difficult to impose top-down, comprehensive evaluative frameworks. The primary problem is that even if you have two nonprofit organizations, each working with similar clients and conducting similar programs, the mix of supports from philanthropy, contracts and earned revenues will be such that the way they achieve their results will be unique. The nonprofit sector, operating as it does on the margins of the market economy, is forced to pull together resources higgledy-piggledy, and this mix varies so substantially for each nonprofit (and indeed for each year of its operations), that you really can’t draw comparisons easily between two otherwise similar service activities. 

In short, our twinkling field of a thousand lights are all very different. 

There is, however, an upside to this. Each organization cuts its own path to achieving its mission, providing us with a diversity of models and strategies.  Some succeed by focusing on a specific, artisanal niche where they excel, while others grow through horizontal or vertical expansion. But there’s one thing that all successful organizations have in common: they exhibit strong leadership. And when I say leadership, what I mean is that the manager or managers of the organization are considered trustworthy, intelligent, passionate and capable. They may also be considered tyrannical, obtuse, plodding, or distraught, but in their own way they get the job done and they get it done well.

As you well know, measuring leadership is a damned hard thing to do.  There are no leadership widgets produced as such. Or are there?

When I put my mind to it, I think there actually are.  While these vary as widely as any other aspect of the nonprofit sector’s activity, there are nonetheless tried and true strategies that most of us would intuitively recognize. Allow me to lay out a few.

Leaders have opinions and expertise, and they share them. Usually, the executive director or CEO is the person taking on this role, but many organizations effectively share this role with many of their senior staff.  Not only does this help create a buzz about an organization’s effectiveness, but the process of testing ideas in a public forum strengthens those ideas and exposes the presenter to new insights.  Being able to do this well requires a clear-eyed self awareness about the limits of the expertise you can share, and a willingness to be frank about what you know and don’t know. In any case, it usually takes several forms:


  • Using access to journalists and media, leaders work to become recognized voices with useful perspectives to offer in their area of expertise.  This is frequently complemented by self-producing publications, studies, reports and thought pieces aimed at explicating strategy or impacts. 

  • Leaders offer public testimony, especially in public budgetary processes, but also in the crafting, refinement or repeal of legislation that impacts their sector.

  • Leaders lend themselves as knowledge-based experts on event panels, committees, working groups, advisory boards, and even as sources for potential jobseekers doing informational interviews. 

Leaders also work to convene other leaders. Whether they themselves are actually in charge of the effort, or are providing additional resource (time, space, administrative assistance, planning, and outreach support) to make the convening happen. Typically, this means:


  • Organizing efforts to educate or lobby public sector leaders on behalf of the sector, and not simply on behalf of one’s own organization.

  • Bringing peers together to discuss latest trends, innovations, best practices, common challenges, or simply to build relationships.

  • Developing working groups that can more systematically develop approaches and strategies for coordinating resources, tackling tough issues, and creating a larger dialogue around key issues.

  • Leading or supporting training efforts on skills relevant to the sector, and insuring high levels of participation from members of their own team.

  • Developing strategies and special events that can address the needs of consumers at scale, bringing together stakeholders, peers and partners to accomplish the task. 

Finally, many leaders are recognized because they are effective at sharing leadership.  To be sure, there are many leaders who manage through force of will to hold all the threads in their own mind, and to run large enterprises based on their individual capacity and the ability to get others to follow blindly.  Over the long term, however, these strategies usually leave a telling wake of frustrated underlings, and can have very dire consequences when the leader leaves their post. Leaders that facilitate the leadership of their colleagues and those who report to them as a class tend to sow a sense of vibrancy, and have a much better chance of developing a legacy enterprise that will outlast their tenure. 

Leadership = Visibility = Cash on the Barrelhead 

There are many effective leaders who have no interest in self-promotion, and many others preoccupied with their public image. We've all seen both. Leadership and virtue are discrete, and I don’t mean to imply that some type of Protestant Work Ethic (e.g. – work hard and you will be rewarded) drives all decisions by supporters and stakeholders. But we also can’t deny that effective leadership both creates and reinforces visibility. In a world where stakeholders wish to be associated with well led efforts of good causes, they will also tend to be attracted to those organizations where leadership is cultivated and practiced. 

Building a leadership organization requires a commitment to taking on unusual challenges—probably the most difficult of which is getting comfortable with our own visibility. Leaders will be attacked and criticized. It's a fact of life. Leaders deserve it:  they are fallible human beings and no one does it right all the time. And leaders also don’t deserve it: despite their challenges they are willing to put themselves forward to lead the charge and take the heat. That’s a very tough thing to do. Protecting and promoting leadership is something that, frankly, we don’t do all that well as a society. 

Still, I believe that effective leaders take on the challenge of trying to understand and support the developing leader in all those around them.  Fleshing out strengths, pushing against challenges, setting “unrealistic” expectations, and trying to motivate their colleagues based on an honest insight into that person’s desires (even the desires that we ourselves can’t necessarily tell we want). 

The bottom line is that this impacts the bottom line. Why? Because in the absence of a comprehensive evaluative framework, funders are basically forced to bet the jockey.  I’ve seen this happen over and over. I’ve seen leaders come in and out of favor. We all have. But the mechanics are consistent, and an integral part of developing an organization over the long term.

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