When I was a teenager, I went grocery shopping every Sunday with my dad and younger brother.
The three of us had the weekly excursion down to an exact science: Each of us would take a third of the list, grab a shopping cart, and meet the others at the checkout line 15 minutes later.
To an outsider, I’m sure we looked like a model of efficiency: a family that knew how to delegate.
But in reality, we had to lay a lot of groundwork before taking off on our respective missions. We needed to trust one another to put the correct items in the shopping cart. We needed to recognize the respective strengths of our family members: who could select the best produce, who was detail-oriented enough to grab ground cumin rather than cumin seed. If a particular item was too critical to mess up, then the person who added it to the list was responsible for finding it in the store.
The myth of simple delegation
“That person just needs to learn to delegate.”
Back when I was working in the research world, people used this phrase often to describe their chronically overworked co-workers—many of whom struggled to offload tasks to the eager, entry-level staff hired precisely to do those very things.
I’ve heard similar remarks across a variety of sectors, from higher ed to political organizing.
That judgment (or phrasing) never sat well with me, for it presumes the act of delegation is simple. In fact, delegating work is really hard.
For most organizations, delegation is nothing like dividing up a grocery list: it requires a careful assessment of what work needs to be done and the skills and expertise you have available.
And that’s the easy part. There’s a much deeper side to delegation, and I think that is where a lot of people struggle.
When it comes to complex tasks, the most effective delegation requires a mentor’s mentality: an investment in explaining not simply what needs to be done, but how and why. To delegate well, you’re not simply handing off tasks; you are also walking that person through your process and motivations.
And ultimately, delegation is also an act of letting go: letting go of your own vision for how something should be done, ceding it to someone else, and being ready to accept the results.
High stakes and low resources
These dynamics came into sharp focus for me a few days ago, when I facilitated a series of three community roundtables on the topic of “The Future of Nonprofit Leadership” for Madison Nonprofit Day.
Over the course of the afternoon, three big themes emerged:
- There was a wholehearted recognition of the need to make space for and mentor the rising generation of nonprofit leaders.
- When organizational leaders are pushed to the utter limits of their resources, it can feel impossible to carve out the time and space for mentorship.
- Early-career professionals are eager to take on new responsibilities and try new things, but they feel pressure to maintain the status quo and work within existing processes.
More broadly, when organizations are strapped for resources—and who isn’t right now?— they have little margin for error or experimentation.
When the stakes are high, delegating responsibilities to a junior colleague—who might get it wrong, or just do it differently—can feel like too big a risk.
The hidden cost of not delegating
How do we find the courage to delegate when the stakes are high? I’ll be honest, I don’t think there’s an answer that can be easily distilled into a few bullet points or a 5-step plan.
Perhaps it’s because the risks of not delegating, while less apparent, can be even greater than handing work off to someone else.
What risks? At the individual level: burnout.
And from an organizational standpoint, the risks are even greater: knowledge and skill silos, lack of succession planning, and rocky transitions upon staff departures.
Leaders change and employees move on. But by treating delegation as an ongoing practice rather than a one-time action, you’re making a solid investment in your organization’s future.
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