For Milton Little, “Becoming a CEO was a dream realized.” But the decision to make the leap to becoming chief executive officer (CEO) of the United Way of Massachusetts Bay from his role as executive vice president and chief operating officer (COO) of the National Urban League was not one he made lightly: “In the COO job, you see the demands on the CEO, and you think about whether you want the additional headaches.”

Many experienced COOs of nonprofit organizations aspire to become CEOs or executive directors (EDs)^[1]. That said, these individuals are in a better position than most candidates to see that the top job has challenges of its own and that the two positions are very different.

Bridgespan spoke with a number of executives who made the transition from COO to ED. The consensus among this group was that the transition is a challenging one, but that there are ways to make it smoother and more successful.
 

Differences between the roles

While COO and ED responsibilities vary significantly across organizations, these variations tend to pale in comparison to the substantive differences between the two roles. It is because of the differences between the roles, our interviewees noted, that the transition from COO to chief executive can be challenging. They emphasized that both the people who make the transition and the organizations that hire them need to be confident that the candidate has the inclination as well as the skill set to accommodate the ED role:

• Concreteness of responsibilities. As compared with the responsibilities they had had as COOs, the EDs said that their new responsibilities tended to be less concrete, more big-picture, and further removed from the organizations’ front lines. As a result, a hands-on approach that may have worked well for them in the COO role ran the risk of turning into micromanagement at the chief executive level. One interviewee put it this way: “CEO is totally different from VP or COO—it’s not just a higher level of the same thing. The things you’ve always been rewarded for—getting things done, digging into an issue and finding solutions—are a problem. Your job [as ED] is to provide leadership, to create clarity around other people’s roles and responsibilities, and to keep your nose out of stuff whenever possible. You have to learn to sit back and let other people do the things that you’ve always done.”
• Emphasis on strategy, leadership, and external relationships. The transition from COO to ED usually entails a significant shift of focus from internal to external and from “doing” to communicating and leading. Lyndia Downie of Pine Street Inn moved from vice president—a program-focused position—to president. She said, “I spend a lot of time advocating for funding. I like the policy work a lot, but I am rarely involved at any intimate level in the programs, and that has been hard.” Jerry Hauser, who went from COO of Teach for America to president and CEO of the Advocacy Institute, identified the need to determine strategic direction as the most challenging thing about his current role and the biggest adjustment from his previous one.
• Responsibility, stress level, and schedule. Representing the organization publicly meant that the EDs tended to travel more and have more time commitments outside of the regular workday. In addition, they now had to answer to both internal and external stakeholders for everything that happened in their organizations. A number of the EDs—even those who moved into that role from very challenging COO positions—emphasized the increased burden of the ED role. Jim Schorr, formerly executive director of Juma Ventures, commented, “The ED role is worlds apart, even from being a member of the senior management team. It was impossible for me to grasp what the difference in scope of responsibility would be until I was in it.”
• Relationship to colleagues. The group also described how being “the boss” required them to develop a different relationship with staff. This transition was particularly difficult when the new ED was an internal hire and as a result had to take over supervision of people who were previously his or her peers. As ED, Schorr said, his interactions with staff  changed: “I [became] much more isolated—purposely, necessarily. You have to operate with the interests of the entire entity in mind and make decisions that encompass all perspectives. As a result, you can’t align yourself with particular people or areas of the organization. Not being able to get too personal with people at work is tough when you work basically all the time.” Isolation came in other forms as well. Kristen Ace Burns described her experiences as president of REDF (formerly the Roberts Enterprise Development Fund), “The board is my manager—but it's different from having a manager in the office on a daily basis, like I had when I was associate director. I found that this position is a little lonelier. Over time I've built a network of people I can consult informally, but it's still different."

Making an effective transition from COO to ED

The experienced COOs and EDs we interviewed were unanimous in saying that the shift from COO to ED can be a bumpy one. However, they also pointed to a number of practices that can help smooth the way. Their tips for COOs making the transition relate to every phase of the process, from the first recognition of interest in an ED position to day-to-day functioning in the new role:

• Build your skills while in the COO role. Whether or not an ED identifies a COO as his or her successor, the two can work together to prepare the COO for a future job as chief executive. With support from above, a COO can begin gaining experience in areas that are critical for the ED position but may not be part of the typical COO job, such as fundraising, communications, and vision setting. Burns reports that while she was associate director, the managing director worked with her to create opportunities for her to acquaint herself with the external side of the organization, through networking with other organizations and writing and speaking about REDF’s work.
• Seek opportunities to demonstrate leadership as COO. Christina Severin, who was promoted from COO to executive director of Network Health, a subsidiary of the Cambridge Health Alliance, took on some important and visible leadership roles—such as leading meetings of the management team—while she was in the COO position. These opportunities both enabled Severin to develop her relationships and skills and signaled to other staff that the previous ED had confidence in her as a leader. Severin emphasized the importance of this history in building up to the transition: “Because of everything we had done along the way, when the announcement came, people from the senior leadership team to the front-line staff said, ‘Of course it’s her, she’ll be good at that.’”
• Find the right ED job at the right organization at the right time. Like COO positions, ED positions vary tremendously, depending on the organization’s particular phase of development, the strengths and weaknesses of the other managers, and countless other factors. Among the most important elements of achieving a good fit is understanding the needs of the organization during the period when you hope to lead it and your own professional strengths and interests. COOs who fit the traditional COO mold may be most successful leading organizations that are in a phase of building infrastructure and systems, refining or even turning around troubled programs, or creating organizational discipline. Organizations that are doing major fundraising and growth or building their core model may require more communication and fundraising skills and/or entrepreneurial energy—strengths of some but not all successful COOs. Not surprisingly, internal candidates tend to be at a significant advantage in assessing their fit with the organization, whereas most external candidates need to do significant due diligence to attain the necessary understanding of the organization.
• Prepare yourself for changes in your colleagues’ perceptions of you. Melinda Tuan noted that when she was promoted to managing director of REDF, “Suddenly all eyes were on me. I was used to running meetings, but whenever Jed [Emerson, the founder and previous ED] was there, people would direct their comments to him. Suddenly he was gone and the focus was on me. Even though I knew to expect that, it was startling.” Others reflected on the fact that, even though they had come from other senior positions with significant influence, their words now carried more weight, and as a result they needed to be more careful in considering what they said. For example, Christina Severin reported that she had to adjust to the need to be constantly “on.” “I have to remember that although I don’t always take myself literally, other people do. Sometimes I’ll ask why someone has done something in a particular way that surprises me and I’ll find that they are responding to something I said previously. I have to remember now that people will interpret what I do and say with a new level of authority and seriousness.”
• In internal transitions, communicate clearly how your role has changed. Paradoxically, while new EDs are adjusting to this increase in expectations, attention, and authority, they may also find themselves dealing with colleagues who are stuck in old ways of thinking—especially when the promotion to ED is internal. Pine Street Inn’s Lyndia Downie said, “Setting ground rules early on about what wasn’t going to be in my purview anymore was important. I had to be really clear about saying, ‘This really doesn’t belong in my sphere anymore.’ I spent a lot of time with the program staff transitioning them to the new vice president.” Downie emphasized that she wouldn’t have been able to hand off her responsibilities confidently if she hadn’t immediately hired a strong manager into her previous role. When organizations aren’t able to do that, clarifying the new roles is much more challenging.

The career COO

Although many COOs want to become EDs and are able to navigate the transition successfully, the move is not for everyone. Because the two jobs are so different, they sometimes attract people with quite different skill sets, personalities, and profiles. Martha Mueller Cook, former COO of the Boston-based Crittenton Women’s Union, considers herself a “career COO,” because she has a passion for making organizations run well and is less interested in fundraising and external affairs. “What I really like,” she said “is to have someone figure out the external strategy and let me run with implementing it internally.”

What, then, is the growth trajectory for career COOs? For most, the key is to continue to take on new challenges. This can mean moving to a COO position at a larger or more complex organization, or to an organization with a structure that gives the COO more responsibility. Sometimes, however, COOs can find new challenges even without changing jobs. For Cook, that was the case in 2006 when her organization, the Women’s Union, merged with Crittenton, another area nonprofit focused on women’s issues. Although Cook left jobs in the past because they didn’t offer enough new challenges, as she looked at her organization’s plans for change and growth, she saw significant opportunities to stretch her own skills and remain deeply engaged in her work after the merger.