People pleasing has always been a part of my DNA (are you feeling seen?). When I was growing up, I asked myself, “Who do I need to please?” The answer was clear: EVERYBODY.
My parents were at the top of the list for sure, and teachers mattered a lot too. Actually, when I was young, if I caught a whiff of someone, anyone, who didn’t like me, I would do everything in my power to change that.
I’m not particularly proud of this, but in hindsight, it’s the absolute truth. Family dynamics are pretty central to the whole people-pleasing thing. Some families operate from this place of strength – who gives a crap what others think of you. Many other families, my own included, were driven by what other people thought. So I grew up in a family where people pleasing was valued.
And I was damned good at it. Maybe it even led me to nonprofit work. I can help people and change the world – the ideal spot for a people pleaser!
Or not…
Now, why the heck is this important in leadership? Well, perhaps you already see the error in my ways, or perhaps you think this trait might serve me well as a leader, especially as a nonprofit leader. There are so many stakeholders to consider, and you can’t really ignore any of them. You must care what people think.
Eventually, I learned that the true failure is trying to please them all. You can’t. I had to break this habit real quick when I became a nonprofit leader.
I now consider myself a recovering people-pleaser. Here’s what I mean.
Choosing a board chair or board president is one of the most important choices in a nonprofit. It ought to be done by the board with critical input and partnership from the Executive Director/CEO. Select a board lead whom the staff lead cannot work with at your peril. It’s one of the biggest mistakes I see nonprofits make.
There was a moment at one point in my career when the next person in line to be board president was someone who met all the usual criteria: he was engaged on the board, he gave, and he fundraised. He even seemed to be caring more and more about equity (he was white), which was a “must have” for the organization.
Then, he sent an email to a staff member of mine, a black woman, chastising her, ordering her to do things (she does not and did not report to him), and generally not respecting her expertise and role. In this action, he showed how he really felt and how he operated.
When I spoke to him, there was no apology.
In truth, I was still poised to support him, sort of on autopilot. My team, specifically the women of color on my team, asked me to pause and make a different choice. It was not easy, but it was obvious what I needed to do to walk the walk and actually support the racial and gender equity I cared for.
In the end, it mattered more to me that the women of color on my team – who I deeply respected – thought I was making the right decision, than if he did. He was indeed disappointed, and I was ultimately okay with that.
See, as a brand new Executive Director of a nonprofit I cared deeply about, I realized there was no way around disappointing some people. As a leader, you realize that almost every decision will please some and displease others.
So what to do? Well, here are a few suggestions:
Start with YOU and then with your org’s mission
First, have a real heart-to-heart with yourself. What is most important to you? What are your core values, and what do your heart and your head tell you should matter the most? If you are a recovering pleaser like me, do not be tempted to ask other people their opinions about these questions. This is an inside job, and I recommend you do it solo, ideally as early as possible in your life and leadership journey.
I also recommend that when you get to leading a nonprofit, you look at your values, look at the mission of the organization, and see how specifically they line up. Both your values and the organization’s mission are critical factors in making the best decisions.
For me, community and justice are deep values. If I do my best to root myself in – and connect my decisions to – these North Stars, I know I’m on the right track.
Decide who you are okay disappointing
The example I gave above was by no means the only one. I led an LGBT organization, and if you can’t tell by the acronym, the LGBT community is diverse and multifaceted, so are our opinions. I had to decide early on that gay, lesbian, or bisexual folks in the community who wanted us to ignore or reject the transgender community would be disappointed with me and my leadership. I could not, and would not, please them. This one might sound easy, so let’s try a harder example.
Consider power carefully
Your board and your biggest donors hold a lot of power. As the staff leader, you ignore these folks at your own peril. But. And. There is a real danger if they are the only groups you consider or if you always privilege their opinions. It’s tempting to do this, but if you do it at the expense of the people with the least power, you will fail yourself and your mission.
Trust me.
I learned this lesson most deeply as a white leader around the racial reckoning. I realized that if my “at the time” majority white board and white donor base thought we were doing well on this issue, but my majority people of color staff thought we were not, the staff was actually the group whose opinions I needed to consider more deeply.
If I had ONLY allowed myself to be guided by the opinions of the most powerful, I would still be lost, and so would the organization.
Consider peers whom you respect
This is often underestimated, but Executive Director, Nonprofit CEO jobs are unique, and they can be quite lonely. The people who truly understand what it’s like are usually not your friends or family. They are peers, but more specifically, peers you respect. These folks were another North Star for me. They understood the complexity of the community, the region, the role, and if the ones that I thought were doing an amazing job thought I was doing a crappy job with something, I listened. There is so much to learn from peers you trust and respect.
Don’t be tricked into an “either/or” configuration when the choice can actually be “both /and”
Now, don’t get me wrong, if you are a recovering pleaser like me, then you will be tempted to think that every decision can be “both/and” and satisfy all. This is usually false.
However, it is also true that our world likes to divide and make us choose when we don’t actually have to. Everyone has heard the phrase “divide and conquer,” and it feels like we are surrounded by this mindset right now in the U.S.
My organization had a women’s event that we had been running for many years. There were a handful of lesbian women who felt that we had begun focusing too much on trans women and the transgender community at this event, and ignoring them. This is a good example of how we needed to do both. I could not choose between these two communities that I deeply loved. I tried to strike a balance, and sometimes I feel like I succeeded, and sometimes I failed.
I went to this event recently, having not attended in two years, and I must humbly say, the new leader of this organization struck the balance perfectly. It was the definition of “both/and” in a way that was powerful and beautiful. Lesbian women were highlighted, trans women were spotlighted, and all were lifted up by the magical event. It can be done!
The bottom line is decisions are not easy when you are running a mission-driven organization – lots of opinions, feelings, and passion. But if you are leading one, that’s WHY you were hired, to make these tough calls, with grace and grit and integrity. So decide what your values are, understand who you are willing to disappoint, and choose wisely. The world needs you.
