The key to success in a job search is finding the right fit between your skills, interests, and disposition on the one hand, and the characteristics of the potential organization, role, and leadership team on the other. In in-depth interviews with chief operating officers (COOs) and executive directors (EDs) about the COO position [1], we found that, because of the tremendous variety in role definition across COO positions, finding the right fit is particularly challenging and important for COO candidates. While the COOs we interviewed sometimes were able to be effective in positions that were not an ideal fit, we generally observed that a better fit led to an easier transition into the role.

Fit with the general characteristics of the COO role

Although COOs vary considerably in their roles and responsibilities, there are a few key characteristics of COO jobs that the COOs we interviewed generally agreed anyone should understand and embrace before pursuing such a role.

The COO role, while a challenging leadership position that interacts broadly across an organization, is of course not the top job, and COOs often do a lot of their work behind the scenes. The United Way of Massachusetts Bay’s CEO Milton Little, who was previously executive vice president and COO of the National Urban League, said, “You have to remember that your name is not at the top of the stationery. You get all the headaches but little of the glory, and you have to have an ego that allows you to live with that.” While it is important that COOs not need constant ego gratification, they must also have the confidence to lead others, to act as agents for organizational change, and, if they are second in command, to step into the ED position temporarily if necessary.

Despite the fact that COOs tend to get less public recognition than EDs, for someone who is passionate about making organizations work well, the position can be very fulfilling. Little was attracted to the opportunity to run a large organization and “master all of the moving parts.” And Martha Mueller Cook, said of her role as COO of The Crittenton Women’s Union, “I like the mix of the strategic and the mundane, and it’s a great opportunity to have impact on an organization. Also, I’m physically here more than the ED, so it’s a real opportunity to lead and form the organization internally.”

Most of the COOs with whom we spoke had a large number and range of responsibilities requiring a wide assortment of skills and talents and an incredible ability to manage and prioritize. A good candidate for the COO job is not only someone who has these skills but also someone who considers the variety and complexity of the job to be one of its advantages.

Fit with the specific organization and role

Even candidates who have determined that they want to be COOs need to look hard at the specifics of the COO jobs they are considering. Beyond the basic fit issues any executive would face in considering a new position, the COO position poses particular challenges because of the level of variation in the role across organizations. Cook says that when she was looking for a COO position earlier in her career, she found that “some people were looking for a COO who was very finance literate, while others were looking for someone to transform the culture of the organization. These are very different kinds and you have to be clear which kind you are.”

A number of the COOs with whom we spoke said they had struggled with responsibilities that turned out to be quite different from what they had expected and only then realized that they hadn’t fully understood their roles when they accepted the positions. They stressed the importance of understanding their own professional strengths and interests, the culture and needs of the organization, and the role and expectations of the COO at that particular moment in the organization’s development.

Fit with the executive director

Finding the right fit with a COO position also includes finding the right fit with the other members of the leadership team—particularly the ED. There is a lot that the COO and the ED can do to build a strong relationship, but it helps tremendously to start with a good connection. This doesn’t necessarily mean similarity, as the organization’s goal may be to find a COO with a skill set complementary to that of the ED. However, there must be some consensus about the most basic issues, such as mission and values. One COO we interviewed said that he knew when he was considering his current position that he and the ED would face some complex issues and wouldn’t always agree. However, during the interview process they established a precedent of candid conversation about difficult topics, and as a result he came into the job with confidence that they would be able to work together effectively.

How to find the right fit

Job seekers often make the mistake of assuming that determining whether or not a job is a good fit for them is largely the responsibility of the potential employer. Candidates have an important role in assessing fit, particularly at the executive level. Because the COO job is so complex and varied, COO candidates must take a particularly active role in this process. The key pieces of the process are:

• Know yourself. The starting point is knowing what you do well, what you find challenging, and what you need to be effective. Do you have the skills and inclination to play a leadership role in programs, or is your strength managing the administrative functions that support the organization? Do you work best with a hands-on supervisor or one who doesn’t intervene unless you ask? Are you someone who can provide the internal “glue” for the organization? Are you more oriented toward vision or implementation? Which of the things you are looking for in a job are must-haves, and which are negotiable? Candidates must think through these questions carefully. While it is important to do some serious self-reflection up front, it is natural for issues that come up in the job search process to further push and develop your thinking.
• Ask the hard questions about the job. Former Bridgespan Group Partner Kathleen Yazbak recommends that candidates “get out of sell mode” as early as possible and ask as many questions as they can about the position and the organization. Many COOs we interviewed said that managers and board members who interviewed them were surprisingly forthcoming during the interview process, including offering information about what they saw as the challenges they, the organization, and the new COO would face. When interviewers don’t offer all the information a candidate needs, it is the responsibility of the candidate to ask questions. Some of the most important questions can be sensitive and difficult to ask. For example, organizations often look for a COO to complement the skills of the ED; to determine whether a job is a good fit, COO candidates must find out what the ED’s strengths and weaknesses are, and how the COO will be expected to complement them. Getting this kind of information may not be easy, but a number of the COOs we interviewed reported that their challenging questions were well received during the interview process. Of course, in the end it is your decision what questions to pose directly to the ED and what to ask in other settings, depending on your own personal style and risk profile. Most COOs supplemented the information they gathered in interviews with additional due diligence performed through their personal and professional networks.
• Negotiate and set ground rules. A final technique that some COOs use successfully to promote a good fit with their positions is to negotiate and begin shaping the position while they are in the late stages of the job search process. When Melinda Tuan was interviewing for the associate director position with REDF (formerly the Roberts Enterprise Development Fund) in 1997, she did significant research on the organization and its key people. Based on what she saw as differences between her management style and that of Founder and then-ED Jed Emerson, she felt strongly that staff and portfolio organizations needed one clear manager. She proposed that that role be hers, and he agreed. Reflecting on her decision to undertake this negotiation before she had the job, Tuan said, “I saw that if I couldn’t negotiate a great working relationship with him, I couldn’t take the job anyway.” Janet Albert, former director of regional talent at The Bridgespan Group, noted that this kind of negotiation can be “an early indicator of how an ED will respond to your views, and it’s a way to begin to develop the trust and candor you will need to make the relationship work if you get the job.” COO candidates who are focused on finding the right fit can use these techniques to prepare themselves and to take an active role in the interview process. The COOs we interviewed reported that while most COO positions are challenging in various ways, COOs whose jobs are a good fit for their own skills and inclinations are well-positioned to take on these challenges and be effective and comfortable in their positions.

Questions all COO candidates should ask

As discussed above, in some cases you may be able pose these questions to interviewers directly, while in others you will need to get at these questions in other ways. Which questions are appropriate to a given situation depends on the circumstances and the sensibilities of the individual candidate.

Questions about the position

• How are the position’s responsibilities defined? Is the position’s focus on program, administration/operations, all internal matters, or some variation on these portfolios? How might the position change in the years to come?
• What skills and qualifications must the COO have?
• What is the organizational/reporting structure? Is the COO second in command to the ED? Are there dotted-line/matrix relationships, and if so, how will they be handled?
• Has the organization had a COO before? If so, has the position changed? If the position is new, why was it created? Who initiated it? Who was resistant?
• What authority will the COO have? What decisions can the COO make alone, what decisions are joint between the COO and someone else, and what decisions are out of the COO’s hands? Whom will the COO supervise?
• What will be the relationship between the COO and the board? What role does the ED want the COO to play with the board?
• What will be the key challenges for the COO? Key success factors? How do the ED and other members of the leadership team view these issues? The board?
• What is expected of the COO on the part of the ED and others? How will the COO’s performance be evaluated? What are the criteria? Who plays a part in the evaluation? Are adequate resources available for the COO to carry out what is expected of him or her?

Questions about the ED and the ED-COO relationship

• What kind of a manager is the ED? What qualities does the COO need to thrive under this ED?
• Is the ED looking for a COO who will enable the ED to spend less time on internal matters? A thought partner? Someone to translate vision into action? Someone to “translate” between the ED and the staff?
• Is the COO part of a succession plan for the ED—either with the COO becoming ED or the COO helping to maintain organizational memory through ED turnover? What is the ED’s timeline in his/her position? What timeline does the organization envision for the COO?
• How does the ED envision the two working together? How will the two work to further define the COO role and build the ED-COO relationship? How will communication between the ED and the COO work?
• How open is the ED to working in partnership with the COO? To what extent does the ED understand and value the role of a COO? What will the COO need to do to gain the confidence of the ED so the ED can delegate important functions? Is the ED able to delegate and to let go of delegated areas adequately for the COO to manage them?
• On what issues and guiding principles does the ED think it is most important that the two be aligned?
• If one of the reasons for hiring a COO is to balance out some of the ED’s weaknesses as a manager, what are those weaknesses? Is the ED aware of them? Are they things that the candidate has the skills to do? Will the ED make room for the COO to do them?
• What biases does the ED have around the COO role (e.g. a fear that the COO might constrain the ED’s vision or that the COO will create unnecessary systems)?
• What are the expectations of the ED?

Questions about the organization

• What, if any, organizational changes are the ED and/or board hoping to make through the COO position? What obstacles exist to making those changes?
• What major strategic initiatives is the organization undertaking or planning to undertake? What will be the COO’s role in them? What does the ED want to achieve over what timeframe?
• What are the ED’s key concerns about the organization’s future? The board’s concerns? The staff’s concerns?
• What is the financial health of the organization? If the organization is in financial distress, what are the plans for turning the situation around? What role is the COO expected to play?
• Who are the strong drivers on the board? What significant board initiatives are in progress and planned? What changes are coming? What is the relationship between the ED and the board? Does the board effectively support the ED? Does the board effectively challenge the ED and provide checks and balances?

Questions to ask yourself (as part of the soul-searching process)

• Do you have the necessary skills and temperament (see above) to be a COO generally? To fit with a specific COO position you are considering? What resources can you access to fill in the gaps (network, mentors, etc.)?
• How do you envision yourself working with an ED? What are you looking for in a supervisor? A mentor? A coach? A colleague? How much autonomy do you want and/or expect? Do you work best with a hands-on supervisor or one who doesn’t intervene unless you ask? What are your expectations of an ED to whom you report?
• Are you interested in becoming an ED at some point? Do you feel that you could step in as an ED on an interim basis if necessary? What do you envision as your timeline in a COO position?
• Are you comfortable being second in command (or being on a par with other senior managers, depending on how the position is structured), and doing a large proportion of your work behind the scenes?
• Do you have the skills and inclination to play a leadership role in programs, or is your strength managing the administrative functions that support the organization?
• Are you someone who can provide the internal “glue” for the organization? Are you more oriented toward vision or implementation?
• Which of the things you are looking for in a job are must-haves, and which are negotiable?

Footnote

[1] Since January of 2004, Bridgespan and its members have been exploring the chief operating officer (COO) role through regular gatherings of executives in the co-pilot seat in their organizations for broad-ranging conversations about their work. In addition, we conducted a brief electronic survey of 23 COOs and a series of 16 in-depth interviews about the COO position with nonprofit COOs and EDs representing a diversity of organizational growth stages, budget sizes, funding sources, geography, missions, and individual backgrounds and tenures. In our interviews and survey, approximately half of the 34 responding organizations created the COO position more than 20 years into their operations.