Cultivating Successful Executive Directors

“Dream jobs” can be a lot of trouble. Imagine that, after years of doing excellent program work for a nonprofit you deeply respect, the board gives you the executive director (ED) position. You are finally able to lead your organization in truly fulfilling its mission. But now it’s two years later, and you are miserable and exhausted.  The board is angry, the staff is demoralized, and the finances are a mess. You are ready to quit and vow to never serve as an ED for anyone ever again.”  This case study illustrates some of the challenges for Executive and Interim Executive Directors managing in the Non-Profit sector.



This story has been heard far too often. Inexperienced EDs are hired and are not able meet all the demands of the position.  In two to three years, they leave and the nonprofit organization must search for an ED again. This means energy and focus are taken away from the mission of the organization as it struggles to replace its leader.

Over the last three months, the author spoke with 22 Rhode Island leaders with a stake in nonprofit capacity building.  These leaders represent foundations, state agencies, academia, for-profit firms, consultants, and several successful executive directors. Several overarching themes emerged from the 20-plus hours of conversation. First, lack of ED capacity is a huge problem for the nonprofit sector. Second, EDs are in need of assistance in two key areas: peer support and an understanding of key skill sets. Third, support can best be provided through mentoring and a series of trainings/long term program such as a fellowship program. This concept paper will explore how the interviews addressed these themes.



ED capacity issues begin with the hiring process. Nonprofits typically ask their leaders to do complex, varied, and intense jobs for very modest pay. When hiring an ED, nonprofit organizations often face the choice of hiring a candidate with extensive experience but who commands a higher salary or an inexperienced candidate with great promise and enthusiasm but limited experience with and understanding of the demands of the position.  Occasionally the board decides to raise the additional funds and hire the more experienced candidate. However, many times the board does not feel that they can afford the more experienced candidate and are convinced that, with support, the inexperienced candidate will be able to do job.

 Interviews suggest that nonprofit boards often overestimate the ability of the ED candidate to gain the necessary proficiencies. To be successful, the ED needs passion, vision, strategy, an entrepreneurial attitude, and a host of skills. This combination of attitudes and skills are best developed through practice, but an individual who leaps from program work to the ED position has bypassed the supervisory stages in which they would be learned. As these EDs scramble to keep up with all the suddenly appearing demands, they often put in unsustainable numbers of work hours. Sometimes EDs are able to learn quickly enough to make a successful transition. All too often, EDs are worn out and drop out after two or three years of this pace.

 This capacity problem seems to depend on the size of the organization. Large organizations such as Planned Parenthood and the United Way have systems in place for executive leadership training. Large nonprofits also may have career paths within the organization to develop the leadership skills. Small and medium size nonprofits tend not to have any succession planning or the ability to create a career ladder that provides the necessarily diverse set of experiences.  In addition, there is not enough professional development for staff as a benefit.

 The problem of unprepared and inexperienced EDs has larger implications than failing to meet an individual organization’s mission. Several studies point to a looming dearth of nonprofit leaders.  By putting potentially strong candidates in ED jobs for which they are not ready, these promising individuals are demoralized and unlikely to fill the growing leadership gap.



Interviews consistently pointed to the loneliness of the position and the need for a cohort.  EDs do not have a peer set to complain to or to vent to or to ask for advice. For obvious reasons, they cannot talk to their staff, boards or funders about their problems. A cohort of other EDs would provide EDs with someone to talk to about the issues they face on a daily basis.  Peers are able to understand the problems that arise and are therefore better able to encourage and console.  Due to the intense time demands on EDs, any cohort building or networking opportunity must include a concrete educational component or takeaway for EDs to want to participate; this was determined after a previous attempt to provide EDs with such opportunities was unsuccessful.

 It became apparent during the interviews that the biggest problem most inexperienced EDs face is that they do not know what they do not know. EDs need to understand a wide-ranging mix of very specific skills, including:

>     Finance

>     Fundraising

>     Ethics

>     Human Resources

>    Personnel management

>    Legal issues

>     Strategic planning

>     Succession planning

>     Board development

EDs constantly face questions relating to these skills. How do you fire someone? How do you delegate an important task to a staffperson? How do you adapt to your new board chair? How do you prepare and present a budget? How do you show your major funder the effectiveness of your program? The inexperienced ED is often unprepared to answer these questions. The successful EDs who were interviewed knew the importance of understanding their limitations and how to find support to buttress those limitations.   One interviewee stated that successful EDs know what they do well and what they don’t do well; if he did not know how to do something, he would find an expert to help. Another worked tirelessly to build a board that could support her. All the successful EDs balanced a business mindset with a passion for their organizational mission.  All described their organizations as businesses and spoke of the struggle between “running the business” and doing the program work.


Long-term programs are better suited to build cohorts than short-term programs. Simple networking events or spot trainings tend not to create a trusted cohort, since it takes time and repeated encounters to build trust.  Long-term programs are able to build upon and reinforce the knowledge base. Long-term programs also enable better peer learning as the participants learn how to work with each other over time.

 Many interviews spoke to the importance of mentorship.  Seasoned professionals provide information on the intangibles that cannot be taught, such as managerial style.  Often a mentor can answer questions that EDs are too embarrassed to ask a group, even a trusted group. Also, a mentor could provide industry specific information and advice if there is a diverse mix of fields.


Fellowship program

Interviews discussed how a comprehensive, yearlong ED fellowship program could be an effective means of addressing the needs and giving support.  Such a program should provide an overview of the issues that EDs need to know as well as an understanding of how to obtain them.  The program would need to provide training on specific skills, such as reading a budget or preparing an employee handbook. The goals of such a fellowship program should include providing a:

>     Trusted cohort for the ED to turn to for consolation and encouragement,

>     Mentoring system of seasoned professionals to give advice,

>     General understanding of the skill sets that successful EDs must have,

>    Information on how to obtain expert assistance and build support, and

>     Enough training in concrete skills to help EDs through the transition period.


This type of fellowship program would complement and feed into existing training initiatives. Academia and foundations currently offer many good programs with specific use for EDs. The academic programs are excellent opportunities for in-depth study but require a higher level of commitment than most EDs can afford. (Out-of-state schools also face the challenge of convincing Rhode Islanders to travel more than 45 minutes.) However, they are a great resource for those EDs who are willing to invest in mastering a subject introduced in a fellowship program. The majority of foundation trainings are one-time offerings. But they are excellent and present an ideal environment for EDs to gain more information about a specific topic that they are introduced to in a fellowship program.

 Interviews identified two major challenges to creating this type of ED fellowship program. First is how to pay for the program.  The cost of a fellowship program would be related to its structure.  More participants would mean higher costs, but larger groups would also mean that there could be affinity groups. In the last 10 years, there have been at least three other efforts to develop nonprofit support centers but each effort failed since nonprofits were not willing to pay for the support. A fellowship program would need to rely on several funding streams, such as grants, sponsorships, and marketing resources.

 The second issue would be how to keep people engaged for the duration of the program. Lack of commitment to complete the program would undermine the cohort aspect. Leadership RI has been successful with its intensive year-long program, but LRI has prestige and a hard won reputation. The training program would need to demonstrate tangible rewards. Several interviewees felt that linking a training program to an academic organization could add the needed prestige.


Winning the “dream job” should be a wonderful opportunity, not a nightmare. Nonprofits exist because individuals are willing to invest their time and band together to address a real need. Collectively we need to support those leaders willing to invest their energy and passion and talents to achieving the mission and meeting the need.

– Alison Buckser, MP; Public Health Solutions

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