For many people reading this book, this chapter could be called “Working with Yourself,” because as the only paid person, the title “executive director” describes you, as does the all‐encompassing title of “staff.” Nonetheless, even if you are a sole staff person, you may find this chapter helpful in avoiding mistakes once your organization is big enough to hire someone in the development role. Some organizations are lucky enough to have one or more volunteers who devote themselves to fundraising, being in essence unpaid staff. If you supervise people in this role, you will want to review this chapter. But mostly, if you are a development director working with an executive director, this chapter is about you.

The executive director can be the development director's greatest ally or biggest challenge, but rarely anything in between. The job of the development director is odd in the sense that you report to and are accountable to the executive director, yet your job includes organizing the executive director's time efficiently with regard to fundraising—which means telling your boss what to do. To work effectively with an executive director requires discussing early on in your tenure how the executive director wants you to present the fundraising tasks that they are to carry out and how the executive director intends to be accountable to that work. Here's how an ideal working relationship between an executive director and a development director would play out.

At the beginning of the year, the executive director and the development director create a draft fundraising plan. The development director may do most of the work on the plan and then bring it to the executive director to discuss, but the executive director is familiar with it and believes it is the appropriate plan for the year. These two staff go over the plan in great detail with the board leadership, such as the fundraising and finance committees. Board members' suggestions for changes are incorporated, then someone from the board presents the plan to the full board, ideally receiving enthusiastic buy‐in (or at least willingness to do the job) from the full board. The development director feels supported by the executive director in all efforts to work with the board. The executive director sees the development director as a partner in the financial future of the organization—a junior partner perhaps, but still someone to turn to for advice and whose counsel and instincts can be trusted. If not friends, at least these two see themselves as strong colleagues, interested in each other's opinions on a wide variety of topics related to running the organization.

Some coworkers develop this relationship naturally. They are usually people who are competent, not competitive, and not controlling, more committed to the mission of the organization than to their own ambition, and able to delegate tasks and share information. Each appreciates the strengths and talents of the other, and they have complementary skills. These people are not without their struggles or disagreements, but they are able to be straightforward in conversation and listen to each other, and they are willing to take the time to work things out.

People who do not naturally subsume themselves to the work of the organization can still have a strong working relationship if they put in the effort. These are usually people who are competent but can be controlling, who are committed to the mission of the group but desire personal recognition, who are so overwhelmed with tasks that they have trouble sorting out what can be delegated and what cannot, and who keep information to themselves more out of sheer inability to find the time to share it than any real intent to conceal. Again, honesty in communication and a commitment not to harbor resentments will help this be an effective relationship. It is also important to note that chronic overwork with no praise or recognition of effort can cause anyone to become difficult to deal with.

DEVELOPING A GOOD RELATIONSHIP

Unfortunately, there are far too many situations in which the relationship between the executive director and the development director does not work. We discuss here the most common reasons a productive relationship between executive director and development director fails to occur.

• The executive director's successes eventually mean that the organization grows beyond their ability to run it. Rather than admit that they have reached their limit of competence, the executive director becomes more and more controlling, even secretive, and may actually shrink the organization back down to a size they can manage. This dynamic is particularly prone to occur with executive directors who were founders of the organization.
• The executive director has been at the organization too long. They feel tired and have lost enthusiasm for the work, but they stay in the job because they can't imagine what to do next, or are afraid they won't find another job. Mediocrity becomes the standard of work. Other staff, as well as the board and volunteers, follow the lead of the executive director and exhibit the same mediocrity.
• The executive director is sensitive to criticism, even defensive. They create a work environment in which only total loyalty to them is acceptable, and questioning their decisions or directions is perceived as insubordination. Creativity is squelched.
• The executive director is afraid to ask for money and will not help with fundraising from individual donors. Often this fear is disguised as “I can't deal with a bunch of little gifts. Let's just get a foundation grant.”
• The executive director may recognize that fundraising is an important part of the job but fails to make it a priority. The executive director will say such things as, “I'm going to get to that,” or “We need to find a better time to discuss this,” or “I have a lot of other things on my plate.”
• The executive director doesn't trust the board members or wants to retain power, so does not share decision making with them. Few if any boards will actively engage in fundraising if they are not involved in policymaking and other board activities, so the board is of little use in fundraising.
• The executive director is threatened by the development director's knowledge of fundraising and feels that their own lack of knowledge will be perceived as incompetence. They continually belittle the development director's ideas or ignore them altogether.
• The executive director's job is too big. They work between 60 and 70 hours every week, which means they are often at the office on weekends; they rarely take a vacation (and even then they respond to email and send work‐related texts); although they will protest that they do not, they expect the same effort from the other employees. Such people do not realize that they simply disguise the cost of doing business, and they wonder why they have high employee turnover.
• The executive director, slightly embarrassed that the organization needs money at all, wants the development director to bring in the cash, no questions asked. The director is continually asking, “How are you doing?” “Are you meeting your goals?” “What's your plan?” These comments make clear that the executive director does not consider fundraising their responsibility.

There are many variations on these themes, but these are the most common. If you are already working for an executive director who has one or two of these characteristics, it is possible to make a change in the staff dynamic, usually with the help of a coach or a consultant. If your executive director has several of these characteristics, it is more likely that you will need to find another job. To guarantee that you don't take a job where these dynamics prevail, make sure that you know what you have the right to expect from an organization and an executive director, and what they have the right to expect from you. Try to find out what the staff turnover has been, and talk off‐line to people you know who are in the organization or know people in it.

One of the best ways to develop good working relationships is to be absolutely clear about your job. Your job is to coordinate the fundraising function of the organization. You must ensure that all fundraising tasks are completed, one of which is to help the executive director complete their tasks. You lead by inspiring others to fundraise, and your job is to involve as many people in fundraising as possible so that the organization can raise as much money as it needs from as many sources as can be managed by you, other staff, and volunteers. You also set an example of being able to ask for money by soliciting gifts, but you are not the only, or even the main, solicitor.

Given that these are your responsibilities, the executive director should expect that both of you would work closely together to create the executive director's fundraising task list, and that the executive director would expect reminders about those tasks and would assume some accountability for completing them. The executive director in turn would expect you to provide needed support, such as talking points, donor and prospect information, strategy details, reports, and so on. Keep in mind that the executive director is the front person for the organization. Many donors will prefer to meet with that person rather than anyone else in the organization. The development director has to appreciate that the executive director balances many tasks, of which fundraising is only one—even if it is very important.

Sometimes the executive director will know a lot more about fundraising than the development director. In that case, the executive director should mentor the development director. More frequently, the development director knows more about fundraising than the executive director. The executive director should welcome this knowledge, recognizing that an organization hires staff partly because the executive director doesn't have the time—or necessarily the skills—to do the whole job. Many successful executive directors have used their development directors as mentors. While their job titles give executive directors authority over development directors, they choose to play to each other's strengths and to create a learning community. Generally, this attitude will be found all the way through the organization.

The development director's job is also to coordinate the fundraising efforts of the board of directors and other volunteers. You should have access to all board members and be actively supported by the executive director in your efforts with the board. Both of you should work closely with board members, particularly on personal, face‐to‐face solicitation.

Both parties should know how the other likes to work. Questions of working style should be talked out early in the relationship. Such questions include whether interruptions are OK; how each feels about editing the other's writing (because the executive director needs to feel good about everything that comes out of the office, all written materials should be read and edited by someone other than the person who drafted the piece); how much nagging about getting a task done is bearable; methods of dealing with conflict; the best way to hear criticism; and so on.

A good working relationship between development director and executive director starts with clarity and agreement from the beginning about what is and is not in each of their job descriptions. In the end, the people in these jobs need to function as much as possible as partners in fundraising and to see the board as an asset to be developed. As development director, be mission‐driven and know that your main loyalty has to be to the work of the organization. Know that you are not always going to see eye to eye with the executive director and that final decisions rest with the executive director. Above all, be honest and demand honesty in return. Your relationship needs to mirror the kind of relationships we want to see in the world: respectful, caring, nurturing, genuinely interested in the other, and joined in a mutual belief in something bigger than yourselves.