"For some people…there seems to be a worry that this is turning us into a more risk-averse organization, because it feels slower to execute things that make so much sense to the person who's proposing the idea."
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Priya (name changed at interviewee’s request) is a VP of Operations at a nonprofit think tank focused on sustainable food systems. She has been at the organization for 3.5 years and in her current role for 2.5 years. The organization has approximately 115 employees.
“For some people…there seems to be a worry that this is turning us into a more risk-averse organization, because it feels slower to execute things that make so much sense to the person who’s proposing the idea.”
Priya joined the organization in 2022 as part of a deliberate wave of hiring. Following a major revenue increase around 2021, the nonprofit think tank entered a period of more intentional investment in internal capacity and systems. They brought in director-level talent to mature the organization, and Priya was one of them.
Before that wave of hiring and intention to mature processes, the organization had operated in classic startup mode. Individuals wearing many hats, never taking vacation, making decisions without rounds and rounds of consultation, because the fallout wasn’t as great if things went awry.
“Getting buy-in was not a time-consuming effort for a change that you wanted to manage.”
The growth meant the organization could invest internally—revisiting compensation benchmarks with the goal of having salaries fall, on average, at or above the 75th percentile for comparable nonprofit roles; expanding the finance team to support a more complex organization; and building out functional areas held together by individual heroics. But long-tenured colleagues describe nostalgia for earlier-stage flexibility. Where individual decision-making authority meant if you thought something made sense, you could just do it.
“Now I think it is a more complex organization, so you have to tread much more carefully. Even something like promoting a high-performing team member—that is a very fraught decision if you don’t consider many other factors.”
A year into her tenure, Priya’s supervisor shifted roles, and she inherited the VP of Operations title along with new functional areas including HR. That stretch assignment—being thrown in to figure it out—mirrors how she’s learned throughout her career.
Which creates an interesting tension with how the organization develops its managers.
The organization runs monthly supervisor trainings on everything from administering maternity leave to giving feedback to implementing equity practices. They’ve built an open-door culture where people can schedule meetings across levels without fear of hierarchy. But Priya sees a persistent gap between training and application.
“Some things just take time and muscle memory to be able to do. Even if you do a training—we’ve done trainings about how to make decisions, how to get buy-in if you’re doing a cross-organizational initiative—within a few weeks, you’ll see that people are not actually doing the things that we trained them on.”
Maybe, she reflects, none of it is ever as good as just having to work through the actual thing.
The challenges vary by level. Early managers struggle with the boundaries of their ownership—how far they can push something forward without additional input. At 115 people, there aren’t endless opportunities for promotion, and mid-level leaders wonder about their career trajectory. Senior leaders grapple with strategic direction, with impact analysis revealing they’re doing too many things.
Newer managers face a different problem: fielding questions from direct reports without feeling confident to cascade information down.
“I have a huge desire for people to understand the logic all the time. If they could only hear me explain this, then it would make sense. But depending on people’s life experiences and what they see in their day-to-day, the same information lands so differently.”
If she could give any resource to managers, Priya would give them a thought partner—someone to bounce ideas off of. Not for right or wrong answers, but for the gut-check.
“One of the things I do when I’m feeling super stressed is I try to make my problem not just my problem. If I can bring somebody else in so now it’s like both of our problems, then that has helped me a lot.”
Her advice for leaders walking into a maturing organization: resist the pressure to immediately clean things up. Create space to learn. A problem that has existed for a while doesn’t need an immediate answer.
“You have to be willing to throw out what you did and not think that it makes you less intelligent or helpful to people if these things just don’t work all the time.”
And remember that the messy middle lasts longer than you think.