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It's Lonely in the Middle - Six Ways to Thrive, not Just Survive, as a Nonprofit Executive Director

I decided to write this blog post because time and time again I hear from new nonprofit executive directors that their experience of starting their role mimics mine. When I first became an executive director, I was surprised to find out that there was an aspect of loneliness to the job.

It was the first time in my career I did not have a peer in the organizational chart to talk through issues with. The group of colleagues I had developed at that point in my career were not yet executive directors. Although they were supportive, they did not understand firsthand what I was dealing with.

I saw opportunities and obstacles on the horizon that were not ready for sharing – too many unknowns. My ideas needed to be more fully formed before bringing my board or leadership team into the conversation (I always say, ‘don’t start the roller coaster until you’re sure you’re up for the ride’).

After all, we have all been told more than once that your team wants to know what is going on, sometimes you may have little or none to offer up (I led through Hurricane Sandy, COVID and a host of less dramatic disruptions).

Sometimes you think you may be crazy. Is yours the only organization that faces these problems? Are you the only leader who cannot work this through? Are you the only person who has made such an obvious mistake?

Most importantly, I learned that I was not the “boss” in any traditional sense of the word that I had been raised with. Although I was depicted at the top of the org chart graphically, in reality I was in the middle – in the middle of many stakeholders that all had a vital interest and say in the work of the organization. Leadership was about bringing those stakeholders together around a vision, while also ensuring that they informed it.

So, as someone who thrives on collaboration and talking through his problems to get to the essence of an issue, what was I supposed to do?

I needed to move myself from “Lonely in the Middle” to a new way of feeling connected and supported as I went about a job that was structured in a way I had never worked before.

To figure out good strategies, I found it was very important to first gain some clarity on all of the different directions that demands and stakeholder voices would be coming from. Some of the ones I identified up front were:

  • Staff. Staff are the guardians of your mission, whether they work in program, development, finance, tech, or HR. They want their work to be facilitated by the organization and to be cared for in a way that shows just how important their work is. Beyond that, you have important human resources issues to attend to in order to ensure that your workplace is equitable and compliant with legal requirements. The needs of the team and the issues that some will come up against can be especially challenging because often confidentiality is of the utmost importance.

  • The People and Communities We Work With. This group is the reason your organization exists. Especially as organizations grow, it can be challenging to ensure that we leave time to hear firsthand from those who are most affected by our decisions. As executive director you should ensure there are regular touchpoints with the communities you serve. Further, you should ensure that other vehicles like surveys or focus groups are a regular component of your organization's practices and that your review of that information is frequent and the basis for discussions with your board of directors.

  • Donors. Those who contribute financially to your work or through in-kind support are champions who may not have time to engage in your mission but have a passion and commitment to the work you do. Because resources drive our ability to meet our mission, a good executive director typically spends no less than half their time building the organization's resources. The difficulty here is keeping our focus in balance, so that the donor voice does not drown out other voices. Listening to donors to the exclusion of other stakeholders is the beginning of mission creep.

  • Board. I have written a fair amount already about the importance of boards and our management of them. Because they hired you, do your annual review, and monitor strategy and governance, the board consumes a good amount of your time. You can see in this blog post how I recommend allocating time toward this work. One important part of their job that you must ensure happens is that they be well informed about the perspectives, needs, and requirements of all other stakeholder groups. How you use your time is often driven by board demand, so you need to partner closely with your board president to ensure that your board has a balanced view that enables you to also strike a good balance.

  • Similar Nonprofits. Organizations that are in the same orbit as yours are an important part of your management duties. Other organizations challenge us to understand best practices in our field, differentiate our services to avoid duplication, collaborate in advocacy, and provide valuable personal support to you as executive director. The days of looking at these groups as “the competition” should be far behind us.

  • Public. The general public demands that we be a well-run organization or have a great impact (however they may define these). At the same time, we have an obligation to build awareness for our organization to advocate for important mission-related issues. We invite the public into our work so that they can become involved and join one of the closer stakeholder groups in our orbit.

  • Compliance and Rating Agencies. Another demand that hopefully will not take much of your time is ensuring that compliance with government contracts or the rating agencies that assign us stars (which in full transparency I never considered a marker of success) do affect our public presence and, in the case of compliance, our cash flow.

That’s a lot to juggle. And it can be isolating for you as these passionate groups sometimes insist that they are the most important – as if success comes from prioritizing one group over another. You’ll get advice like “your board comes first” or “it’s all about the team.”

Of course, the opposite is true. Success does not begin with ranking your stakeholders. Your work is its most powerful when you strike a balance between the seemingly-competing needs and wants of your stakeholders – when everyone feels engaged, respected, and influential in helping advance the mission.

Managing this balancing act effectively requires you to:

  • Care about and balance the needs of your stakeholders; and

  • Actively pursue connections outside the organization to ensure you are not “going it alone.”

Here are six bits of advice to consider:

  • Maintain Good Boundaries. Connect with all of your stakeholders, but remember that they are your colleagues, not your confidantes. There is a fine line between transparency and oversharing. Reserve your concerns about the job itself or how you are managing your various constituencies for trusted colleagues or external coaches.

  • Plan Ahead. To make sure you are managing your stakeholders (and not the other way around), create a pie chart, designating what proportion of your time you want to dedicate to each stakeholder group. Then, spend two-three weeks observing how you actually allocate your time. Now, with a little bit of careful calendaring, you can refocus your attention. The flow of your year may necessarily move these proportions around, but being intentional will ensure that you do not ignore one stakeholder while being overfocused on another.

  • Build your Network. Local foundations or nonprofit capacity building organizations often offer learning cohorts or some support convenings for executive directors. Checking in with executive directors you already know can point you to one of these or, if a group of executive directors has formed its own group, you can find out about it that way. This is another great spot where an external coach can help you think through things.

  • Connect with Peers. Schedule time regularly (breakfast/lunch/coffee/Zoom) with peers you value. Groups are a great support, but once you find a few colleagues that you really connect with, make time for 1:1 meetings with them. I made time for this type of meeting at least once each month.

  • Hire an Executive Coach. For almost all of my coaching clients, balancing the demands of their stakeholders is core to our work together. Having a sounding board is nice, but also having the space to turn your concerns into concrete actions is invaluable.

  • Leave Work, Put Down your Phone. As you take on an executive role, the connections you have outside work become even more important. Being with the friends and family who shift your focus away from the competing demands of your work life ensures that you can be present in your work when you return.

The executive director’s life is an exciting one and can be satisfying and fulfilling with the right support in place – different support than earlier in your career. Once you are surrounded by trusted colleagues (and maybe a skilled coach), you can discuss concerns that are arising about your staff, board, funders, or community partners. You can also discuss how you are feeling about the role itself – how fulfilled you are feeling, how much longer you want to stay in the role, or how you are feeling about your own leadership.

For more reflections on the executive director life or to consider coaching, visit my website or follow me on LinkedIn.

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