On the last Monday of October, the staff of a small nonprofit community music school sit around the folding table in the room where the beginner piano class meets on Thursdays. There are five of them: the executive director, the program manager, the development coordinator, the front-desk lead who also runs the school’s social accounts, and one faculty member who agreed to stay after her morning lessons. On the whiteboard behind them, someone has written “OCTOBER” in blue marker and drawn a line down the middle.
October was the school’s busiest month of the fall. There was the open house on the first Saturday, with instrument petting zoos for small children and a string quartet on the front steps. There was the adult beginners’ class launch. There was the fall student recital. And there was the first push of the year-end scholarship appeal, which the development coordinator sent out by email in the middle of the month.
Everyone at the table has opinions about how it went. The front-desk lead thinks the open house was a huge success: the photos were shared more than anything the school has posted in a year. The development coordinator isn’t sure: the appeal brought in gifts, but she didn’t see many new names among them. The program manager has a waitlist for Saturday morning lessons and empty slots on Tuesday afternoons. The faculty member says, quietly, that two of her new adult students have already asked whether they can switch to evenings.
This is the moment the calendar topic is about: look at what October taught us and plan next steps. It’s also the moment most organizations get wrong, not because they don’t learn anything, but because the learning never turns into a plan that someone else can pick up and follow.
There are two common ways a month-end review goes sideways.
The first is that it becomes a celebration or a post-mortem, depending on the mood in the room. If the open house felt good, the review is a list of thank-yous. If the appeal felt thin, it’s a list of worries. Neither produces a decision.
The second is quieter. Once you know how something turned out, it’s very easy to believe you could have seen it coming. Psychologists call this hindsight bias: the tendency, after an event, to overestimate how predictable the outcome was. People selectively remember the information that fits what they now know, and they have a real need to see the world as orderly. In a staff meeting, hindsight bias sounds like “We should have known the open house wouldn’t bring donors” or “Obviously adults want evening classes.” Those statements feel like lessons. They’re usually just the outcome, restated as if it were foresight. And because they feel obvious, they don’t get written down as a change to the plan.
The fix isn’t to stop looking back. It’s to look back with a structure that separates what you meant to do, what happened, and what you’ll do differently, so that the lesson lands on a specific part of next month’s plan.
One of the most useful structures for this comes from an unlikely place. In a Harvard Business Review article called Learning in the Thick of It, Marilyn Darling, Charles Parry, and Joseph Moore describe how the U.S. Army uses after-action reviews to learn while operations are still underway, not just once they’re over. The practice they describe is less about a meeting and more about a discipline: being clear about what you intended, honest about what actually happened, curious about why, and specific about what you’ll carry into the next round.
For a small organization, that translates into four plain questions you can put on a whiteboard:
1. What did we intend? Not what we hoped would happen in a general way, but what each October effort was supposed to produce.
2. What happened? The facts, with their sources, before anyone explains them.
3. Why was there a difference? The causes you can actually see, not the ones that feel obvious now.
4. What will we do the same, and what will we change? Each answer attached to a specific part of next month’s plan.
The authors’ point that matters most for a nonprofit is that the learning is only useful if it’s applied to the next action. A review that ends with insights but no change to the plan hasn’t finished its job.
Here’s how the four questions played out on the whiteboard.
What did we intend? This is where the room went quiet for a moment, because the honest answer was “a few different things.” The front-desk lead had wanted visibility. The program manager had wanted new students for weekday slots. The development coordinator had hoped some families would become first-time donors.
What happened? The open house was well attended and widely shared online. A modest number of families signed up for trial lessons, most of them for Saturdays. Almost none of the families who came appeared among the scholarship appeal donors later in the month.
Why the difference? Because the open house was designed for awareness, and it did that well. There was nothing in it that asked a family to take the next step toward giving: no story about the scholarship fund, no student who could say what the scholarship had meant, no simple way to stay in touch beyond following the school online. Awareness and a donor path are not the same thing. Awareness is people knowing you exist and feeling good about it. A donor path is a sequence of steps that moves someone from “I came to your event” to “I understand what my gift does” to “I gave.” Many nonprofits run excellent awareness events and then wonder why giving doesn’t follow. The event did its job. The path wasn’t built.
What will we do the same, and what will we change? Keep the open house. It’s the school’s front door, and it works. Change two things: next time, collect a way to follow up with every family who wants to hear more, and plan a separate, smaller moment for donors in November, such as a scholarship students’ informal performance, where the story of the fund is the point.
What did we intend? Fill open teaching slots, especially weekday afternoons.
What happened? Saturday mornings have a waitlist. Tuesday and Wednesday afternoons still have room. New adult students are asking for evenings.
Why the difference? Families with young children prefer weekends, and the open house was on a Saturday, so the families who came were Saturday families. Adults want evenings because they work. The marketing invited everyone to “come learn music” without saying which times were open, so demand piled up where it was already high.
What will we do the same, and what will we change? This is the capacity limit, and it belongs in the plan in plain words: the school can’t add Saturday morning teaching time without new faculty, and it isn’t hiring this season. So the plan for November is to stop promoting Saturday openings, and to aim outreach at the times that are actually open: weekday afternoons for homeschool families and after-school programs, and a pilot evening group class for adults if one faculty member is willing to teach it.
What did we intend? The recital was for students and families. The appeal was meant to start the year-end giving season.
What happened? The recital was full and warm. The appeal brought in gifts mostly from people who had given before.
Why the difference? The appeal went to the existing donor list, and that list is mostly longtime supporters. That isn’t a failure. It’s what an email to the donor list does. But it means the appeal didn’t reach the families who had just experienced the school at the recital and the open house.
What will we do the same, and what will we change? Keep the appeal to longtime donors, who deserve to hear from the school first. Add a separate, personal step for recital families in November: a short note from their child’s teacher, not a fundraising letter, that says what the student worked on this fall and how the scholarship fund helps other students do the same.
That’s the review. Now comes the part that makes it worth the time: a plan that the front-desk lead could follow if the director were out sick for two weeks, and that the board could read without a briefing.
A good strategy session produces four things, and the plan should state each one in a sentence.
One thing this season has to produce. Not three. For the music school, the November priority is: turn October’s new families into either enrolled weekday students or connected supporters. Everything else is secondary.
What the organization can actually handle. For the school: no new Saturday morning lessons this season, one pilot adult evening class if faculty agree, and no more than one new outreach effort per month, because the front-desk lead is also the social media manager, the registration desk, and the person who answers the phone.
That last limit is worth dwelling on. Small nonprofits often plan as if they have more staff time than they do, partly because the people who fund them expect them to run on very little. Ann Goggins Gregory and Don Howard wrote about this in the Stanford Social Innovation Review in The Nonprofit Starvation Cycle: funders’ unrealistic expectations about what it costs to run a nonprofit push organizations to underspend on infrastructure, including the systems they need to track whether their work is working, and the cycle feeds itself. A plan that names its capacity limit honestly is a small step out of that cycle. It tells the board what the staff can do well, rather than what they can do badly if everyone works weekends.
Where the effort goes, and where it doesn’t. For the school’s November plan: personal notes from teachers to recital families, a targeted invitation to weekday-afternoon trial lessons through homeschool groups and after-school programs, and the existing donor email. Social media continues at its current pace, but it isn’t asked to fill lessons or raise money.
How the school will know whether the plan worked, checked at the end of November. Not a vanity number like post shares, but measures connected to the priority: how many October families enrolled in a weekday slot, how many recital families responded to a teacher’s note, and how many first-time donors came from families the school met this fall. The measure doesn’t need to be large to be useful. It needs to be honest and tied to a decision.
This is the part most plans leave out, and it’s often the most valuable. For the music school in November: no second open house, no new social campaign, no promotion of Saturday openings, and no general “support the arts” appeal to the public. Writing those down protects the staff from good ideas that would quietly eat the month.
It’s worth saying clearly, because the two get confused. A proposal meeting is about what an agency will do for you. A strategy session is about what you will decide.
In a proposal meeting, the agency presents a set of services and a schedule, and you choose whether to buy them. In a strategy session, the work is forcing choices you haven’t made yet: who the next season is for, what it has to produce, what your team can handle, and what you’ll leave alone. The package comes afterward, and it’s scoped to those choices. If the session doesn’t produce a priority, a capacity limit, a channel choice, and a measure, the package that follows is a list of tactics, and you already have plenty of those.
For a nonprofit, the session also has to test mission fit. Reaching more people isn’t the goal by itself. The question is whether the people you reach are the people the mission is for, and whether the path you build for them leads somewhere that serves the mission, whether that’s a lesson, a scholarship, or a gift.
To see how this looks in a different kind of business, picture a family chimney sweep and inspection company on the same Monday.
Their October taught them something different. The phones rang hard from the first cold night, and they were booked out for weeks by the middle of the month. Their ads, which started in early October, mostly added callers they couldn’t serve until December. Their review responses slowed down because the owner, who usually writes them, was on roofs.
Same four questions, different answers. What they intended was steady fall bookings. What happened was a pile-up in October. The cause was timing: they spent money on demand that was already arriving on its own, at the moment they had no room for it. This is one of the most common ways seasonal businesses mis-time spend. Advertising follows the season instead of leading it.
Their plan looks nothing like the music school’s. The priority is next year’s calendar, not this month’s: start inspection reminders and booking offers in late summer, when crews have space. The capacity limit is the number of crews and the hours of daylight. The channel choice is past customers first, by email and text, before any paid advertising. The measure is how full the late-summer calendar is before the first cold night. And what they will not do is run ads in October when they’re already booked.
That’s why strategy work shouldn’t be one generic template. A nonprofit’s plan has to protect mission fit and the donor path. A trade’s plan has to protect the crews and the season. Both use the same discipline, and they end up in very different places.
If your organization is about to look back at October and plan what comes next, a little preparation makes the session much more useful.
1. What each effort was supposed to do. Write one sentence per campaign, event, or appeal. If you can’t, that’s the first lesson.
2. What happened, with sources. Enrollment records, the donor database, the inbox, the reviews, the website report. Bring the facts before the explanations.
3. Your real capacity. Who is doing what, how many hours they actually have, and what’s coming that will take their time.
4. One question nobody has wanted to ask. Every organization has one. For the music school, it was “Is the open house a fundraising event or not?” Getting it on the table early saves an hour of circling.
5. A list of what you’re tempted to try. Bring it so the session can decide which of those ideas to put on the “not this season” list.
When the session is over, the package that follows should be something a team can use, not a deck to file. At a minimum, it should include:
1. The priority , in one sentence.
2. The capacity limit , in plain terms, including who is responsible for what.
3. The channels , with what each one is for and what it isn’t for.
4. The measure , with a date to check it.
5. What we will not do , written down and agreed.
6. A one-page calendar for the next month or season, showing what happens when and who owns it.
7. A short version for the board, a partner, or a busy season : a single page that someone could read in a few minutes and understand what you’re doing and why.
If a new staff member, a board member, or a seasonal hire could pick up the plan and follow it without a long conversation, the plan is finished. If they’d need you to explain it, it’s still a draft.
By the end of the meeting, the whiteboard had a new line under “NOVEMBER.” It said: weekday students and connected supporters. Below it were five short lines with names next to them. The program manager owns the weekday outreach to homeschool groups. The faculty member will ask her colleagues about a pilot evening class and report back next Monday. Each teacher will write a short note to their recital families, and the development coordinator will collect them. The front-desk lead will keep social posting at its current pace and won’t add a new campaign. The director will share a one-page summary with the board before its November meeting.
At the bottom, in red marker, someone wrote: “Not this month: second open house, Saturday promotions, public arts appeal.”
That’s what October taught them, turned into something they can hand to each other.
If your team is looking back at the season and wants help turning it into a plan with a priority, a capacity limit, a channel choice, a measure, and a clear list of what you won’t do, book a strategy session with WeKinnect. We’ll work through it with you and leave you with a plan your whole team can follow.
Photo by Med Badr Chemmaoui on Unsplash
Written By
Darlene Gagnon is the founder of WeKinnect Global Branding Agency. Guided by the core value of Service before Self, she works with entrepreneurs and family-owned legacy businesses. She focuses especially on restaurants, arts, and travel and tourism. Darlene writes on Branding, Positioning, Marketing Strategy, Public Relations, Storytelling, and Entrepreneurship. WeKinnect serves entrepreneurs and family-owned legacy businesses across restaurants, arts, travel and tourism, banking, home services, nonprofits, and the pet industry, and Darlene brings that same spirit of service to every piece she writes.
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