No One Told Us! The Unspoken Challenges of Being an Executive Director

The challenges are real and the job is tough, but being an Executive Director has the potential to be life-defining and unbelievably rewarding.
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Being an Executive Director is an awesome job. So why is the turnover rate so high? Members of the Executive Director Boot Camp frequently lament the need for EDs to talk honestly about the challenges involved in running social change organizations. In order to help newcomers anticipate and avoid potential challenges, lets peel back the curtain.

Nine Challenges Executive Directors Face, And Rarely Complain About...

1.Your identity becomes intertwined with your job. As an ED, you can never truly "let go" because you represent something that is bigger than yourself, and your actions are tied to an entity whose reputation is yours to protect. The line between personal and professional blurs, and it can be hard to tell which relationships are authentically yours, and which are tied to your work. It's hard to separate the part of you that isn't XXX, Executive Director of YYY. The small piece of your mind that is always "on" creates a slow, subtle energy leak that eventually causes many EDs to fatigue. In order to sustain, you must carve personal space.

2.Your salary per hour is actually not very good. The job never ends, and every part of the role is legitimately important. Recruiting, developing and retaining talent? It's the most critical part of your job. High-level fundraising and management of key external relationships? Only you can do it. Ensuring the quality of your program? It's the bottom line. Being visible at community events? You have to show up. Responding to emails and requests in a timely fashion? Non-negotiable. But when do you sleep? Eat dinner with your kids? Focus on passions and interests other than your job? If you're always working, you lose a piece of yourself...and even if you are paid well in theory, it can be hard to put a price tag on sacrificing so many other parts of your life. As an ED, you need to understand your full job description so that you can knowledgably negotiate your salary and enter your role with eyes wide open. Advocate for yourself as strongly as you will surely advocate for your cause.

3.You will rarely be alone, but you will often feel lonely. Despite the social nature of their jobs, many EDs I work with remark that they feel extremely isolated. Even those who have very loving relationships with their board, key partner organizations, and staff members. Because of the power dynamics intrinsic in being the boss, it takes a truly rare, mature, trusting, co-invested space for an ED to actually be able to have friendships at work. It's essential to invest time in building an outside group of co-supportive peers. The long hours and exhaustion at the end of the day also make it hard to find/maintain a romantic relationship. Just keep in mind that the stronger and healthier you are as a person, the better you will be as an ED. Justify those date nights as an investment in your leadership.

4.It's exhausting to constantly have to inspire people. My EDs often lament about the energy they need to exert in order to recruit board members, motivate staff members, and woo donors to invest in their vision. When you breathe something to life and believe in it with all of your being, it can be downright offensive when people seem uninterested. Having to relay the same story over and over again about your vision, what problem you're solving, and why your organization's impact is worthy of note can be tiring. Conversations will bleed into one another, and it can be hard to remember who has heard a specific story or anecdote. You never want your pitch to get rote, and keeping that spark alive for the 400th time can be an exercise in personal motivation. Some EDs revise their pitch regularly to keep it fresh, and others give themselves a week off here and there where they are largely internal so that they can re-energize.

5.You will have to make tough choices. Sometimes, large donors or important community influencers will want to dictate decisions that you make, and you will need to choose between sabotaging critical relationships and doing things that would undermine the essence of your mission. Sometimes decisions will be loaded, and whatever choice you make will upset or disappoint a subset of your team. Sometimes you will sacrifice the battle to win the war. Sometimes you will make decisions without full information in order to act in a timely fashion. Sometimes you will have to fire people you love. Often your tough choices will be based on information that you can't share with others watching. Sometimes, good choices feel bad, and sometimes you will make bad choices and have to own them. Leadership at your level is hard, and the best true healer for this is time and perspective.

6.You will fail publicly. Regularly. If you're actually doing anything meaningful in your role, you are likely taking calculated risks, learning from them, and then making future decisions based on what you've learned. That means you're gonna have some loser moments where you make a choice and it blows up in your face. As you grow your organization, you will hire people for roles you never did yourself, you will learn things for the first time by doing them wrong, and you will change your mind and have to backtrack. Being in a visible leadership role is a wonderful thing, and learning graciously from the mistakes you've made is important for you, and for your team. If you haven't failed lately, ask yourself if you are being bold enough, willing enough to go for it, or if perhaps you're not being fully honest about your impact. Failure isn't the enemy. Stagnation is.

7.You will get thrown under the bus. As the top executive, you get public credit for the successes of your organization, even when the win had nothing to do with you, and even (or especially) if you pass the credit on to someone else. On the other hand, when things go wrong, even if they are completely out of your control, you are the visible dart-board. At times, even members of your own team may take shots at you. This is especially complex because deflecting criticism (even unfair criticism) can demonstrate a lack of humility or personal responsibility. It can be hard to take ownership for the tougher moments, but it is a critical act of leadership to be willing to speak the difficult truths, to shine a light on areas that need improvement, and to take responsibility for fixing them. EDs who genuinely view setbacks as opportunities to learn and grow set an important precedent for their teams, and make it easier for all members of the organization to handle challenging moments.

8.Sometimes you will not agree, but you will have to lead the charge. Your national/global organization may go in a certain direction, and you may kick and scream about it on the internal phone calls, but at the end of the day, as an organizational leader, you will have to lead your team to navigate the change. It is hard to be the representative of something you don't 100% agree with, but if you undermine your organizational direction, you will sabotage your larger effort. Some EDs choose to deal with this transparently, sharing that they don't agree, and doing their best to share the national/global rationale. Others choose to internalize the new direction in order to be a "team player", knowing they won't always get to make certain decisions. There are drawbacks to each approach, but remember, you have a choice, and the repercussions are yours to navigate as well. You're not a victim, you're a leader.

9.Even when it's time to go, it's impossible to leave. Because you are so committed to your organization's mission, (this is especially true for founders), and because your identity is so intertwined with your role, it can be extremely difficult to separate from your job. Many EDs worry that they haven't built a strong enough bench to leave the organization in a stable place, and they don't feel comfortable leaving because they are worried things will deteriorate. (Make a note - building a bench is something you should think about long before you ever want to leave your job.) You may feel pressured by outsiders who believe that if you don't stay in your role forever your contributions weren't authentic. This is unfair...you don't owe your entire life to anyone. It is wrong to negate someone's genuine contributions as they walk out the door in an attempt to dissuade them or others from leaving. EDs can set the tone for this by being genuinely appreciative for the contributions of their staff and board, and by treating any departures with graciousness.

The challenges are real and the job is tough, but being an Executive Director has the potential to be life-defining and unbelievably rewarding. Don't let the rough spots dissuade you from stepping into a leadership role - just go in with open eyes, and with a generous helping of resilience, perspective, and self-forgiveness. And when the going gets tough, know that there are so many others leading great organizations who are navigating the same challenges alongside you.

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