Editors’ note: This article, first published in print during August-1999, has been republished for Nonprofit Quarterly with minor updates.

So you just got that promotion you always wanted. You’ve been an Organizer Intern, a Junior Organizer and, finally, a Senior or Lead Organizer, and the board of directors of WKB (We Kick Butt) has finally named you the new Executive Director. You have your new cards, new nameplate, new (old) desk and new authority — so why are you so overwhelmed and unhappy? You may have been a good organizer, but can you make it as an Executive Director?

I have talked and worked with many good community organizers who have become bad Executive Directors. Why is this?

Organizations often hire and train community organizers in the mistaken belief that there is a career track from Junior Organizer to Lead Organizer to Executive Director. We believe that good organizers can do anything. I have heard people brag about so-and-so, their new organizer, who could probably build a spaceship if she put her mind to it, never mind run a little grassroots organization. Yet the pattern of a person going from great organizer to not so-great Executive Director has repeated itself too many times for me to think that it is just a fluke and not a systemic problem.

The transition from Lead Organizer to Executive Director is similar to the transition from Leader to Organizer. Both require a big shift of roles and the assumption of new responsibilities. Both have the potential to bring quick growth and development to the organization because of the person’s familiarity with the organization. And, both have presented many problems for organizations.

Good Executive Directors are expected to have not only great political leadership, passion and drive, but also administrative competence, financial acumen, and time management skills. These skills are often not compatible or complementary. And beyond all this, we want our Executive Directors to be able to manage staff, raise money and provide leadership to the board of directors.

Even under the best of circumstances, transitions are tough. Humans, being part of the physical world, are inclined to take the path of least resistance. Think of a transition you have faced recently either in your job or personal life, and the uncertainty and uneasiness it brought. You were forced to move away from a sense of comfort to something unknown. You may have been eager to face new challenges but you also had to be willing to let go of things that you were good at.

Transitions are tough on organizations, too, especially the transition to a new Executive Director, the most important paid position within an organization. This person can lead the organization to new heights or destroy it. Transitions are tough on the staff and volunteers, too, as they have to go through the process of building new relationships. And, they are tough on the new Executive Director, who will be closely scrutinized by all internal and external components of the organization.

As I see it, there are five key frustrations that new Executive Directors face. In the rest of this article, I cover each of these challenges:

  • Managing Staff — You now have to hire, fire, supervise and evaluate your peers
  • Fundraising — It seems all your time is taken with administrative work or fundraising, and that you don’t get to do the fun stuff anymore
  • Time Management — You are no longer responsible for only your time and work
  • Working with a Board — You didn’t think this part would be so tough
  • Personal Issues — Your satisfaction becomes tied to more abstract accomplishments

Managing Staff

As the new Executive Director, one of your most critical immediate issues will be building relationships with the existing staff. Whether you have come from within or outside the organization, you will need to earn the trust of the staff. As an internal choice, the dynamics of your relationships with your co-workers will change. You will now have the power to fire folks who were your peers, and you will have to evaluate their work.

Coming from the outside, you must build the trust and confidence of your new co-workers. You realize that your relationships will be influenced, initially, by the relationships the staff had with the previous Executive Director (for better or worse). If the previous director was well liked, you must avoid the desire to try to be the previous director. You must build your own trusting relationships with your new co-workers.

Additional issues may arise from difference in age, gender, race and sexual orientation. Deal with these issues directly and truthfully. Do not allow them to fester and explode in a way that may damage future trust or the organization.

As the Executive Director you will get the opportunity to hire new staff. Try to avoid the new-director temptation to hire people just like you: people who think like you, act like you, work like you, laugh at the same jokes, look like you — in short, people you are comfortable with. Doing so can lead to a lack of diversity in many ways. It is much more important to bring different skills to your staff and stretch yourself to learn to work with people who may not be just like you.

Dealing with staff discord will also be in your new job description. When staff people have issues with one another, rest assured the difficulty will come to you. You will be asked to be the mediator of all staff disputes. In doing so, you must set an example of dealing with all staff in a fair way. If you show favoritism to one staff person it will come back to haunt you. Your key resources are your people, but the buck stops with you.

A mistake I see many new Executive Directors make is not delegating work to other staff members. There are many reasons that folks don’t delegate, including the following fantasies (and my responses to them):

  • I can do it better myself — This may be true, but if you want to develop internal capacity you must train others to do the work.
  • They might make a mistake — They probably will, but that’s how people learn.
  • I might lose control — Good, others will take ownership of the organization and work just as hard as you.
  • I feel threatened when I give up control — Get over it.

It is primarily the responsibility of the Executive Director to build a positive work environment. Since the Executive Director sets the tone for the work climate, be aware of negative orders and feedback. A positive order is better than a negative one. Ask staff to work on a project, don’t command. Allow staff the freedom to do projects their way, even if it’s not the way you would have done it. Give both responsibility and authority. As supervisors, we often give responsibility for a project to a staff member but we do not give them the corresponding authority to make decisions when necessary so they can complete the project correctly.

Pay attention to how and when you give feedback. Do you give feedback only when people make mistakes or do you compliment folks when they’ve done a good job? Be aware of your body language when you talk with staff. Are you constantly fidgeting, looking at your watch or acting disinterested? This is another form of negative feedback.

Managing staff is a difficult process. As liberals, progressives or radicals, we like to believe there are no hierarchies within our organizations. But there comes a time when decisions must be made and it is usually the Executive Director who must make the decision. Even if you are uncomfortable with making staff decisions, as long as you make them in an open and honest way, treat people fairly, and seek input from others you will earn the respect of your co-workers.

Fundraising

One frequent complaint I hear from new Executive Directors is they feel that all they do is fundraise. They are now spending the vast majority of their time in fundraising activities, something they are not always good at or comfortable with. Fundraising also takes them away from the fun stuff they used to do like organizing folks and doing direct actions. Many organizing groups don’t often have a full-time Development Director. If this is true of your organization, as Executive Director most of your time will be spent on fundraising.

To keep some excitement in fundraising, think of it as an organizing campaign. One tenet in organizing is, “We build relationships.” Similarly, all fundraising is personal and also involves building relationships, whether with foundation or corporate folks or individual donors. I have seen some of the most aggressive, in-your-face organizers become shrinking violets in a room full of funders. But the work has many similarities.

In an organizing campaign, would you submit a ten-page typewritten document to your target and expect them to meet your demands? No. Yet, as silly as this seems, this is what we do with funders and expect them to support us. In fundraising, think of the funder as the target. Do all the research you would do about an organizing target. Who else do they give to? What is their decision-making process? What is their background? You need to remember that most foundation program officers, even if their programmatic area is organizing, have little knowledge of organizing or may not have been very good organizers (otherwise they might still be organizing). Don’t hesitate to push, challenge, educate and organize funders.

As Executive Director of a grassroots organization, you can have a major influence on funding decisions of foundations and major donors. You should see in your role an opportunity to educate folks on the principles of organizing. Many funders are struggling to find ways to have grassroots folks involved in local decision making. Organizing is a natural avenue. If organizing groups are not represented on foundation grantmaking bodies or having conversations with major donors, those dollars will go to other groups that are not involving grassroots folks, do not have democratic processes, and are not trying to make systemic change.

Time Management

As an organizer, I could always put in more time to catch up on work. As an Executive Director, I don’t have that luxury. Executive Directors need to be more effective with their time. It doesn’t matter how much time you’re putting in if you’re not effective. Also, you are no longer managing only your own time and work, you need to be constantly thinking of all the other staff members’ time and work and how they interact.

Every new Executive Director should have a calendar system. Whether you use the fanciest or cheapest calendar system, the important thing is that you open it. You would be surprised by how many people scrupulously write every appointment and meeting down in their calendar, then forget to check it. I recommend you also conduct weekly check-ins with staff to go over schedules for the week and prepare for major activities. These do not have to be long formal meetings, but quick informative sessions are helpful. Another good practice is to conduct regular staff retreats. About twice each year you and your staff should get away from the day-to-day work and do some longer-term planning. This is also a good time to check with staff on burnout and job satisfaction.

Here are two general rules in time management that will stand you in good stead:

  • One minute of planning saves three minutes of time
  • It takes more time than you think to do the things you like, and less time than you think to do the things you don’t like.

Working with Your Board of Directors or “Can’t we all just get along?”

If there is one area that new Executive Directors underestimate in terms of amount of work it is working with their board of directors. It is surprising that like-minded people can have so many disagreements. New Executive Directors often feel that their board is the worst board that ever existed.

Keep in mind that the transition of Executive Directors is very difficult for board members. They have usually built their loyalty to the previous director and they may be worried about whether they made the right decision in hiring you. But remember, too, that they want you to succeed.

Find out who your natural allies are on the existing board. Who are the folks that are going to support your initiatives? Who are looking to you for leadership? These are your core supporters. You want to build your board around this leadership group and bring in new people who will be
loyal to you, but will not be afraid to challenge you.

One mistake I’ve sometimes seen new Executive Directors make is to want to make wholesale changes in the board as soon as they come on. They want to fire the current board or at least the vast majority of the members. This will lead to much unrest for the organization. A better strategy is to find out who the deadweight is on the board and gradually ease them out. This includes founders when necessary. No need to make enemies when you don’t have to. Thank people for their time and build your own board.

Personal Issues

In organizing, you could always tell if you’d done a good job by the number of people at an action, the development of a leader, or winning your demands. But, as Executive Director your satisfaction becomes more abstract and comes from accomplishments that take longer to see. Often, you may not see the fruits of your labor until you leave the organization.

Your problems in the job are both short- and long-term. They include not only whether you have enough money to meet this year’s budget, but worrying about funding sources for next year and the following years. You need to consider if you can hire a new staff person before the existing staff gets burned out. Or whether you should continue to rent space at increasing rates or invest in the purchase of your own building. These are just some of the issues that Executive Directors face.

As a new Executive Director it is important that you know your strengths, but also recognize your weaknesses. You will be pushed into a number of jobs that you do not want to do and are not trained to do, yet they have to be done. You will have to pass on things you like to do (and do well) but can’t or shouldn’t do. You are the vital link up and down the organization. Staff, board, and donors often perceive the organization through the actions of the Executive Director. Don’t be afraid to show your weaknesses, admit when you’re wrong.

Making the Transition

For the Individual — It means giving up roles you’re comfortable with and taking on roles you’re not (yet) comfortable with.

For the Organization — It means being financially sound so as to not put undue pressure on the new person and being aware of power dynamics (such as in the transition from a white Executive Director to a person of color in that role).

For the Board — It means having a strong Executive Committee in place that can provide support for the new director and act if the new director is not working out, and that makes sure that board turnover is held to a minimum.

For the Existing Staff — It means changing relationships with friends and building trust with a new person or a familiar person in a new role.

Studies have found that outstanding Executive Directors have the following four qualities:

  • They believe in themselves and have self-confidence
  • They believe in their ability to teach, train and to select
  • They have an ability to communicate expectations that are realistic and achievable
  • They believe that employees can learn to make decisions and take initiative

Final Thoughts

It is possible to balance your artistic, passionate side with an analytical, deliberate style, but it is hard work. Go to management training sessions (even from mainstream sources). Good directors are made, not born. You must accept that you are now in a different position and have different responsibilities. One of those will be to find ways for dealing with the stress and learning how to relax.