10 Things That Drive Executive Directors Nuts

toughest things about being an executive director

My glass? Half full. As far as I’m concerned, running a nonprofit is a joy and privilege.

But I’m also a realist. These jobs are hard. You throw your heart and soul into educating, advocating, feeding, lobbying, sheltering – the list goes on.

During my time as an Executive Director, the toughest thing for me was the enormous responsibility I felt.

There was this therapy session. So why are you here? My therapist (who was wonderful) had one of those voices that’s supposed to calm you down. But I was so riled up, her voice could not even make a dent.

I cut to the chase. I really like to help people. It’s part of my DNA. And for the most part I think it is one of my finer qualities…. And probably because of this, I just took a job running a gay rights organization. But I’ve gone overboard. Now I feel like I need to help all the gay people.

Over eight years, I had days when the responsibility felt crushing and I developed some go-to strategies for when I was having a bad day.

Today I offer you my take on the top ten toughest things about being an Executive Director. And because I cannot contain myself, some color commentary and maybe an antidote for each.

10. When a Donor Prospect Says No

There was this trip to San Francisco early on in my tenure. We were broke, but we secured three meetings. Each was going to be a $25,000 ask.

I brought my 9 year old daughter with me on the trip and a friend took charge of her while I had these meetings. I went 0 for 3. Back to the hotel, Scout asked, “So how did it go?” When I told her I was empty handed, she was pensive for a moment and then she asked, “Did you tell each of them how nice they looked?”

This strategy had not crossed my mind. But I laughed long and hard and I never again went on a donor ask without complimenting the prospect on how nice they looked.

9. When Something Goes Horribly Awry

It’s the most solemn moment of your annual gala. Over 2,000 people in the room. A victim of a hate crime is honored. A standing ovation. Solemn music is queued up.

Or so you think.

And then you can’t believe your ears. Frank Sinatra singing New York, New York. You turn to your wife and calmly whisper, “I’m going to get fired tomorrow.”

Turns out absolutely no one even noticed. No idea how that could have been, but just know that sh*t happens. And it is very rarely the end of the world.

8. When You Can’t Decide How To Spend That Big Fat Year End Bonus

While I recognize that this does not happen nearly often, I wish for each of you reading that one day, this one makes your list.

7. When You Can’t Hit Payroll

You’ve seen it coming and tried everything. Of all the emails I receive, this one is the most heartbreaking. Just remember. It is not your fault. And secondly. It is not your job alone to solve it.

Be totally transparent with your staff. Get your board chair to call a special meeting. Open that meeting by saying, “We are in this together. Our work is so very important and it is our people who do it. I need your help. Let’s look at both revenue and expenses. Together.

6. When Your Board Has Disappeared. Like Vanished

It happens. I like to say that the official insect of the nonprofit board is the cricket. Because E.D.’s send out emails, make phone calls and that is what they hear. The sound of crickets.

Please be sure you are communicating in a way that is a) not filled with a list of things you need to nag them about and b) includes something that allows them to touch the work – a story they can share and one that inspires them.

Reduces the cacophony of crickets. I promise.

5. When Literally Every Decision Feels Like It Matters So Much

Just after college I worked in customer service. If I screwed up, maybe the delivery was late. Not the end of the world.

But in the nonprofit sector, it feels like there is absolutely no margin for error.

There is. Honest. Think of yourself as a juggler. A very good juggler. You just have too many balls. Remember that the object of the game is not to keep every single one in the air. You actually can’t. The object of the game is to make intentional decisions about which ones to drop. Stop, prioritize and drop. And then repeat.

4. When You Have To Fire Someone You Were Sure Was a Rockstar

You thought she was perfect. And you have tried everything to help her. You’ve probably tried everything twice because you are someone who believes deeply in helping people.

So you’ve waited too long. Two thoughts for you if this one rang a bell. First, don’t try everything twice. Once is just fine and the longer you wait, the more the work suffers. Second, dig deep and consider the interview process. Include anyone who was involved in a thoughtful debrief (at least 30 minutes). You need to be sure to learn from making the wrong hire. Were there red flags? Pink ones? Did you ignore them? What did you miss?

I generally find that a debrief unearths clues, signs that pointed to the exact issues that led to the termination. Next time, don’t ignore them.

3. When the Responsibility of the Job Crushes You

As I mentioned, this one was very tough for me. I know I am not alone.

You sit at your desk and feel the weight of the world on your shoulders. Like the “man behind the curtain” in The Wizard of Oz (the technical term for this is “imposter syndrome.”)

You are waiting for the real and qualified leader to walk through the door. Grab your phone and turn the camera on yourself (assuming a mirror is not handy) and repeat after me. “The board believed I could do this job. This week I did _____ and it had real value. I can do this.”

And then go find some work to touch. Answer a phone call, meet a client. And just take it one person at a time.

2. When You Run Out of Kleenex

When I moved from the for-profit sector to nonprofit, I had no idea. Fifteen years in corporate and not a single tear.

In my office I had a nice pen holder, post-it notes, pictures of my kids. But Kleenex? Nope. And then I began my work as a nonprofit Executive Director. Within two day (maybe less), a staff member sat in my office to explain a problem and I watched in stunned silence as the staffer started to choke up and then actual tears. I felt like I had arrived in an alien land. With not a single Kleenex. I would not be caught gaping like that again without supplies, so the next morning I brought in a box of tissues.

Good thing. That morning, I got down to business. I hit ‘print’ on a solicitation letter to a significant prospect. The letter had to go out ASAP; we were short for payroll (see #7 above). I pulled the letter off the printer. There was not one but two typos. I had wasted a piece of letterhead. We couldn’t even afford letterhead. I was overcome. I burst into tears.

I grew to understand that the passion your team feels about the mission is essential to your organization’s ability to have real and lasting impact. And so except for tears that came with firing someone (see #4), I came to really appreciate the need for Kleenex.

1. When You Simply Do Not Know Where To Start

You are absolutely paralyzed. You are reminded of the job interview when a search committee member said with excitement, “You’ll get to do everything in this job!!!!”

She meant it. And you took the job anyway. And now here you are staring at “everything.”

My antidote for this condition: First pick one thing on your list that really can wait. Secondly, pick a thing on your list that someone else can (or should) do.

Third, call your favorite board member, volunteer, staff member or donor. Take just five minutes to tell that person how grateful you are for what they do for the organization.

Next, grab your phone and take another five minutes. Scroll through your photo stream and look at the faces of the people you love. And be reminded that they love you back.

OK, now you are ready. Pick one thing you absolutely need to do and get to work. The world is counting on you.

Are there others that drive you nuts? Tell us about them in the comments below.