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4 Myths and Realities of Being an Executive Director

In October 2011, I was presented an incredible opportunity when the nonprofit I worked for announced they were opening another office in a nearby city and they had chosen me to lead the charge.

Within 30 days I had relocated and found myself in a role I had been neither planning for nor expecting: Leading a new team as Start Up and Interim Executive Director. Was I ready? Could I do this? Were they sure? While I’m not sure that you’re ever really “ready,” the experience was wonderful, humbling, and so revealing for me as a leader.

Here are a few myths and realities I’ve learned both by working alongside Executive Directors and by being one myself:

Myth: As Executive Director, I will need to be an expert in everyone’s job in order to lead and be effective.

Reality: While you may be the Executive Director, it is neither necessary nor possible to be an expert in each individual’s job. While you will be great, you will be unable to fulfill an organization’s mission all by yourself. You need your team and you need to clearly and consistently lead, manage, and inspire them.

With about 30 days notice before starting in my role, I spent time talking with other executive directors getting their advice and reflecting on my expectations and goals for my team. Once in the role, I focused on the people first: meeting 1:1 and as a team, learning about them, sharing about me, having dinner together. I learned long ago that if you don’t have your team (their trust, their respect, their hustle) you don’t have anything.

To get ready now for this role, understand your strengths and your work style. Attend as many trainings and workshops that explore leadership and management. Also, find a mentor or connect with other Executive Directors through mentorship groups.

Myth: I’m going to have to give up my whole life to be successful at this job.

Reality: No. You don’t. You can’t! The reality is, there will never be a day that all your work will get done; it will all be waiting for you when you come back tomorrow, right where you left it. Your staff, family, friends - they will all need you to take breaks, make time for yourself and turn the work off in order to be the best boss, partner, sister, etc.

I learned this lesson this personally when I had two family members pass away six weeks apart. I was unexpectedly out of the office and had to allow myself to go offline for my family and my team. It showed me my staff was capable and showed my staff that I trusted them.

Additionally, as a leader, it’s important that you model these choices so they know it’s okay for them to take time off too and have balance. For example, I watched a leader I admire set boundaries regularly as staff popped into her office often just to ask a “quick question.” She would ask them to send her a calendar invite to properly set time aside to have a focused conversation and protected her time so she was not taken off task.

What this looks like for you will vary, but right now, practice setting boundaries that make sense for your life and needs.

Myth: I won’t have to raise money - that’s what a development team is for.

Reality: As Executive Director you are the face of the organization and being a fundraiser is part of your job - even WITH a great development team in place. When I was a Development Director, I always prepped my Executive Director as she was heading to an event by asking her “What’s new?” so she was ready with a compelling answer about our work: a recent success, client story or an upcoming event.

To practice this now, read the local section of your newspaper to stay plugged in and regularly brainstorm your “what’s new” answer (big projects, upcoming trips) to share before attending social or networking events - even around the lunch table gives you a place to practice. Also, ask, “What’s new?” first and truly listen, chances are you’ll have the start of a meaningful connection before you even get an chance to answer for yourself.

Myth: When applying for the job, your experience will speak for itself.

Reality: Perhaps the best Executive Director I’ve known tells the story she learned (after she was hired) that when she was in the applicant pool for the job, the person screening resumes tossed hers aside. The hiring manager saw it and wanted to review it further, seeing a connection in the candidate’s prior team leadership and sales experience that made her a strong fit for the job.

To not get thrown out, you need to be very clear in connecting your experience to the job you are applying for, showing your results, and communicating your passion for the role and for the organization. While this is true for all positions, it's especially true for executive level jobs where multiple people will review your resume and, if hired, you'll have to engage with multiple stakeholders.

Keep this in mind when applying for the top job. Instead of a cover letter, try a pain letter, which will allow the board to already see you in the Executive Director role problem solving and understanding the current landscape. Help them envision you as the leader they need.

Of course there are other myths that get busted once becoming an Executive Director. The trick is to be humble, stay connected to the mission of the work and laugh every day - this is fun and we are lucky!

About the Author | Megan O'Leary has 13 years experience developing programs, fundraising, leading and serving in the social sector tech and education space. She is a proud AmeriCorps alumna and loves helping people connect to their strengths as leaders. She lives in Portland, Oregon and currently serves as the Chair of YNPN Portland.

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