Executive Leadership: Success From Day One
Stories and Strategies for Nonprofit Leaders

I’ve been in executive management in the nonprofit world for over 22 years. Ten or more prior years of nonprofit middle and senior management. A brief and unhappy stint in the for profit world of health care. From these years, I have tales to tell. Some funny and some embarrassing or borderline horrifying, but most yield lessons…threads of knowledge…which eventually weave into wisdom. These are my stories.
In the beginning…
Nobody told me something critically important when I started my current executive management gig over 22 years ago.
All you know is all you know.
Had I realized the essential wisdom of this at the time, I would’ve done a much better job making my initial priority one of learning. I’m good at paying attention, asking questions, listening and learning now, but in the beginning, not so much. I thought I needed to hit the ground running to be a successful leader. I thought I needed to know everything or at least project a “know everything” level of confidence. This style might have been more important if the organization was in trouble, but it wasn’t. This was not a turnaround situation where everyone in the room needs the leader to know more than they do. I wouldn’t have been the best pick at that stage in my career for an organization in trouble anyway, but we were good. Financials were strong. There was an almost unheard of depth of tenure and skill throughout the senior management team. We were growing, almost without strategic effort. I was in the most enviable position (I realized later) of having the luxury to take my time and learn.
The better approach: Don’t pretend to know what you don’t know.
I would’ve been a competent leader without knowing, or pretending to know, everything. To think you know everything from day one looks arrogant…is arrogant. Looking back, I didn’t have the I’m better than you, obnoxious kind of arrogance, but I did have an “I’m pretty sure I know just about everything I need to know to do this job” arrogance. It kept me from seeking opportunities to listen. It also probably invited some occasional eye rolling behind my back. There were many things I did know in the beginning. And many more I didn’t.
I did know: The buck now stopped with me. I was responsible for the ongoing health and well being of the organization. I had been in another position for two years prior to taking the executive role so watched my predecessor do many things well and some things poorly. I learned some what-to-do and what-not-to-do lessons. I was also mid-career. I turned forty a few months after assuming the executive role. I knew I had solid experience. I had hundreds if not thousands of solid management decisions under my belt. I (erroneously) knew I was good to go.
I didn’t know: I was not good to go. I did not know the knowledge and skills I gained in other positions would need honing for any executive position and then further nuanced for this particular executive position. The essential truth is whether new to executive management or new to any specific executive management position, there’s a ton of stuff you don’t know.
If I got a do over, what would I do differently?
Here’s the thing: once in the top leadership role, you are responsible from that moment forward. It is important to demonstrate competence and confidence. It’s also important not to be an ass. No micromanaging. No talking over people. No failure to communicate. No behavior resembling self crowned royalty. It’s also, also important not to be a coward. No fear. No indecision. No hiding. No mixed messages. So, what would I tell my 40 year old self or anyone else new to executive management? Go slow. Over communicate for a while. Learn. Smile a lot. Go easy on snap judgments. Be nice.
Here are some practical, actionable strategies. These aren’t magic nor will they guarantee your ultimate success, but they will bank your odds in the right direction:
Tell the senior and middle management teams, or whoever the people are who make the majority of the operational decisions day in and day out, your main focus for 90 days will be to listen and learn. You will refrain, barring unexpected events, from making any significant changes to existing structure, policy, or programs.
This is important because if you go changing things before you more fully understand how the organization operates, which includes the organizational culture and individual personalities, you may find yourself needing to change the same things again in a few months. People will find this irritating and will not endear you to them as a thoughtful and organized leader.
On the flip side, if there’s an obviously stupid rule or policy you can confidently eliminate or change sooner than later, do it. A super rigid dress code for example. I know an organization whose dress code was three pages long. It made everyone crazy. There are enough challenges in nonprofit work without having to think too hard when you get dressed in the morning. Our dress code is “dress for your day” and it isn’t written down anywhere. People know how to do this without my help. It works 98% of the time. The only issue we ever had was with midriffs. We did have to change our unwritten dress code to “dress for your day but make sure your midriff is covered.”
Have an individual conversation with each person in senior and middle management in that first 90 days. My recommendation would be to go away from the office for lunch or coffee, budget allowing, or use a conference room or meeting space. Read: don’t do this in your new office. Describe these conversations as a chance to have a “soft”interview with each other, even if you’ve been there a while in a different position. These conversations are arguably more important if you have been there a while and have existing relationships with each of these people. The reporting relationships are now changed and everyone will have questions and feelings, maybe worries, about it.
You need to learn things you haven’t needed to really know in the past. What do they spend most of their time doing? Are there barriers to being more efficient? Is there training we should have but don’t? What kind of support will they need from you? What ideas do they have for better realizing the mission?
They need to learn things they haven’t needed to know about you in your past position. If you demonstrate good listening behavior, hopefully each person will ask the questions they need to ask to be at ease by the end of the conversation and excited about moving forward with you at the helm.
If you are new to the organization, the questions in both directions will be very similar but without the emotional overlay of having an existing relationship. Because you are new, your listening will need to be focused. The conversations may take a bit longer and may veer off track depending on how people feel about your predecessor…they may have a lot of stories. Be patient. Take notes. Redirect when necessary, but gently.
Note: Good listening means a relaxed posture, not opening your mouth or taking that intake breath while the other person is still talking, looking at the person speaking and not past them or above them. You don’t have to repeat back everything they say, but it’s always a good idea to use the old “what I think I just heard you say…” if you aren’t sure you understood their meaning. This lets them know you were listening. This kind of listening has limits if you’re having a one on one conversation with a talker. You may have to interrupt a talker to move the conversation along. If you do, wait for a breath and lean in a little saying something to the effect of “I’m so sorry to cut you short, but in the time we have there are a few other things I’d really like to get your opinion about. Is that ok?”
Establish a regular away from the office time for your senior management team to listen to and learn from each other. We, very cleverly, call ours “Directors’ meeting”. I came up with this idea shortly after becoming executive director, originally motivated by a need for us to not get interrupted every 15 minutes every time we tried to meet in our conference room. It has become sacred practice.
In the early years, we rotated meeting at our houses once a month. There was a distinct camaraderie and relaxed atmosphere, but now some live so far out the traveling became impractical. Currently we meet at one of our branch libraries. In Nashville, the libraries have free private meeting rooms of different sizes that can be reserved in advance. The one we meet in even has a dry erase wall.
The structure of these meetings is simple. Everyone reports out on the most relevant happenings in their department over the past month and raises any policy questions or ideas they want the group to consider. We also use this meeting to report on strategic plan goals and data tracking. It feels tedious sometimes when there are lengthy discussions on a topic not pertaining to every department, but I believe we’re better off when the entire senior management team has general knowledge about what’s going on across the agency.
Let’s recap. All you know is all you know. This will always be true. But as “all you know” grows, what I said at the top of this article is true. The threads of knowledge, gained through experience, will weave into the fabric of wisdom. You’ll be a better leader. You’ll have a stronger team. And as happens due to the work of nonprofits, the world will be a better place.

