Long Story Short
You’re about to make decisions about what to build, what to charge, where to show up, who to approach. Ten conversations with the right people will make every one of those decisions better, and it costs you a few weeks rather than a major budget line. Aylin’s DIY Market Research Toolkit has the questions.
Libby here!
Before I was CEO of Whetstone, I was hired to sell our teacher coaching platform to school districts. I believed in the product. I believed in the people building it. I had a list of districts, a phone, and a LOT of enthusiasm.
The problem was, I started in April. School district budgets get decided in March, so the window had closed.
Nobody told me, and I didn’t know to ask. So I spent months having great conversations with people who genuinely liked what we’d built. They’d get excited, I’d get excited, and then we’d hit the same wall every time: there was no line item for Whetstone in a budget. I could sell to the occasional school with a little discretionary money, but getting through a real district buying cycle took a full year.
At the time, I was sure it was a “me problem”. If I were sharper or more persuasive, I’d be closing. So I made more calls and got really good at a pitch that was never going to work in April (or May, or June).
Turns out it was a market problem, and it was completely knowable. Ten conversations with district administrators would have told me my real selling season started in the fall. Each one only needed two questions: walk me through the last time you bought something like this, and when in the year did that happen?
Here’s what I learned: you can’t out-hustle a question you never asked. The answers I needed were sitting with people I could have just asked.
The person who did it the expensive way first
Aylin Bell came to Helia through Collective Member Amy Omand. She spent 20 years at WestEd, a 1,000-person education nonprofit, in senior roles across strategy, business development, and organizational capacity building. A good part of that work was partnering with teams who had built something great and needed to get it to more people. One was a literacy PD program built on years of federal research. Another was a middle school math curriculum with real evidence behind it. Aylin’s job was figuring out how a district decides to say yes.
Early on, she did market research the “right” way. She ran a full RFP and hired a reputable firm, and got the whole methodology: a statistically significant survey, focus groups, interviews. It was really helpful.
Then the next project came along with no budget for a firm. The team still needed to understand its buyers, so Aylin started having the conversations herself.
She was happily surprised by how many people said yes. Folks were glad to talk once they knew she was trying to understand the field, rather than trying to sell them something.
Ten or so conversations got her pretty close to what the full study had told her, and they gave her more than the study did. She heard the answers firsthand, in people’s own words. She got remarkably honest answers about how things really worked, especially when she asked someone to talk to her “with your old superintendent hat on.” And she walked away with real relationships with the people she most needed to know.
(If you’ve ever talked to Helia Founder, Jess Skylar, you know this is basically her favorite line: Nobody needs a $200,000 landscape analysis!)
The Key Takeaway
People buy your offering when it meets a need better than whatever they’re using now. That’s true whether you’re selling a service, filling a program, recruiting volunteers, or asking someone to open a newsletter. Ten conversations will tell you what they’re using now, what it would take to get them to switch, and how the money actually moves.
Aylin’s DIY Market Research Process
If you’re a “just give me the template, I’m ready to get started” kind of person (aka me!), grab Aylin’s Interview Guide from the DIY Market Research Toolkit. It’s the real one she used.
If you’re a “tell me why this works” kind of person (aka our Founder Jess), read on. Here’s what we’re going to cover:
- Step 1 — Get clear on the decision you’re trying to make
- Step 2 — Pick the right ten people
- Step 3 — Ask how they’re handling it now, and what switching would cost
- Step 4 — Map how the decision actually gets made
- Step 5 — Listen for who you’re up against
- Step 6 — Look for patterns, and be willing to hear no
How Aylin’s Process Works
Step 1: Get clear on the decision you’re trying to make
You can have ten great conversations, leave with pages of notes, and still not know what to do next. That happens when the research wasn’t aimed at a decision.
So start with the decision in front of you. Aylin always writes a one- or two-sentence objective before she writes any questions. Here’s the real one from a math PD project: Gain an understanding of purchasing decisions, funding availability, and the competitive landscape for math teacher professional development; tailor marketing decisions accordingly.
There’s nothing in there about whether teachers want the PD or whether it works. Years of research and pilots had already answered that. The open question was how districts buy, so that’s all this round asked about.
Most rounds are answering one of two questions:
- What should we build? What the offering has to do, for whom, and within what constraints. These are open-ended conversations about what’s hard, what’s a priority, and what people are working around.
- How do we take it to market? Who decides, how buying works, and what else is competing for the same money.
In Aylin’s experience, teams spend years on the first question and barely touch the second. Write down what you need to learn and what you’ll do differently depending on the answers. Then cut any question that doesn’t serve that.
Step 2: Pick the right ten people
Ten conversations only work if they’re with the right ten people. This is where Aylin sees folks get vague, saying they’ll talk to “educators” or “our partners,” then calling whoever is easiest to reach.
Start with job titles. For the math PD research, that meant middle and high school principals, school and district coaches, curriculum directors, and district administrators. Teachers weren’t on the list. They were the users, and they matter a lot for whether something is good. This research was about how a purchase gets made, so it went to the people who hold the budget.
Here’s what that split can look like elsewhere:
| Area | Users | Deciders |
| Child Welfare | Caseworkers, foster parents, kinship caregivers | County child welfare directors, deputy directors of program, contract managers at the state DCF or DCFS, program officers that fund the work |
| Housing | Residents, case managers, property staff | Executive directors of housing authorities, Continuum of Care leads, city or county housing department directors |
| Re-entry | Returning citizens, reentry coordinators | DOC reentry directors, sheriffs and jail administrators, county reentry council chairs, and whoever holds the second-chance or workforce contract |
| Juvenile Justice | Youth, probation officers, facility staff | Chief probation officers, juvenile court judges and administrators, state juvenile justice agency directors, and county behavioral health leads |
Once you know the titles, there are more of these folks within reach than you’d think:
- Your network. You probably know people in these roles, or someone who does.
- Your team. Someone on staff used to be a superintendent or a program officer. Ask them to put that hat back on. You’ll get very honest answers about how it really works, especially from someone who used to have the authority to say yes.
- Your current folks. Customers, participants, pilot partners, and anyone they’d recommend.
- Your funders. A warm intro from a funder gets answered. It also shows them you’re thinking about sustainability.
- Cold outreach. Aylin is often surprised by how many people say yes. Ask for 30 minutes and offer something small, like a summary of what you learn or an invite to a learning community. Skip the gift card.
Most important: be clear this isn’t a pitch. You’re trying to understand the field. Aylin found folks really open to these conversations once that was clear, and she was surprised by how many people said yes. As we wrote in The Magic in Reaching Out to Others, people almost always want to be asked. (I learned the “not a pitch” part the hard way. I once used research calls to open a sale, and folks got off the phone fast. Never again.)
Step 3: Ask how they’re handling it now, and what switching would cost
“Nobody else is doing what we do.” Aylin hears this a lot. Your offering may well be one of a kind, and people are still meeting the need somehow, whether that’s another program, something a staff member built in-house, or a workaround nobody loves.
So ask: How are you handling this need right now? What are you using, how did you get it, and what’s not working? Then ask what would have to change for them to do it differently.
Switching always costs something:
- A district funds you, and something else doesn’t get funded.
- A volunteer gives you a Saturday they were spending somewhere else.
- A participant leaves a program they’re already in.
- A subscriber gives you ten minutes and a spot in their inbox.
Your offering has to beat the alternative by more than the cost of switching. You can’t know if it does until you know what the alternative is.
A note on pilots. Pilots are great for testing an offering. They also tend to run with folks who were already excited to do the work, and they’re often free. Someone who joined a free pilot hasn’t told you much about whether they’d pay for it.
Step 4: Map how the decision actually gets made
Someone has the power to say yes. Who that is, when they use it, and what has to happen first has very little to do with whether the person you’re talking to likes your offering.
Aylin asks about it directly:
- Walk me through the last time you brought in outside PD, from “we need this” to whether it worked.
- Who has authority to purchase? Who influences that decision?
- Does the board have to approve it?
- When in the year does it get decided, and how long from first conversation to signed agreement?
Each of those asks about something that already happened. People are much more accurate about what they did than about what they might do, so you get real timelines and real names.
The same questions work outside of selling. When do volunteers commit for the year? Who signs off before a partner org can say yes?
For institutional buyers, Aylin has seen it take one to two years from first contact to signed agreement. If your model counts on revenue in month six, you want to know that now. Sometimes you’ll learn something even better. If districts pay for things like yours through a specific state grant, you can ask to be written into that grant from the start.
Willingness to pay is the hardest thing to get a straight answer on. Aylin comes at it from a few directions:
- Start from the example they gave. What did that cost, and how was it priced: per person, per day, flat fee?
- Ask about the budget, not the number. Where does money for this come from, and how big is that pot?
- Do desktop research. Competitor pricing, past contracts, published budgets. Public institutions leave a paper trail.
And follow what each person knows. A teacher can tell you what works in a classroom but probably can’t tell you which budget pays for it. If someone doesn’t know the money side, skip those questions and ask about what they do know.
Step 5: Listen for what you’re really up against
Aylin likes to keep this one loose: What comes to mind when you think about PD in this area? The names people say first, without prompting, are who you’ll be compared to.
Then:
- If they use something now: what, what else did they consider, and where does it fall short?
- If they don’t: why not? “We tried something and it didn’t stick” and “we’ve never had budget for it” are very different situations.
- Are some kinds of organizations more likely to say yes than others?
Back this up with desktop research on pricing and positioning. The conversations add something the desktop research can’t: how people talk about the alternatives in their own words. Your messaging has to answer that language.
Step 6: Look for patterns, and be willing to hear no
With about ten focused conversations, making sense of it is simpler than people expect. Look for themes that repeat and check them against your desktop research. Weigh answers by who gave them, too. Someone who has run the purchasing decision knows more about it than someone who hasn’t.
Then use what you learn to make small, concrete decisions: which conferences to attend, what to lead with in your materials, who to prioritize in outreach. Watch whether they work, and adjust.
Sometimes the answer is no.
Aylin worked on a science PD program that teachers loved. It changed how they taught, and it moved student learning, which most PD never does. Then they talked to district buyers. Science PD was the last thing districts paid for. Reading and writing got funded first. Everyone agreed science mattered, and there still wasn’t money for it.
So earned income wasn’t the right model for that program. The team went back to foundations and government funders. Learning that early saved them a year or two of building sales and marketing capacity around something that was always going to run on grants.
When to do this Yourself vs Bring Someone in
Most of this you can do yourself: writing the objective, building the list, sending the outreach note, and having the conversations. It takes a few hours of prep, the calls themselves, and some curiosity. You also come out with ten relationships that nobody else can build for you.
Consider bringing someone in if:
- You’re too close to it. After two years building something, it’s hard to hear “we’d probably stick with what we have” as information.
- People won’t be straight with you. Partners, funders, and fans may soften their answers, and they’ll often tell a neutral third party more.
- You’re the bottleneck. Ten conversations plus making sense of them takes real time, and it’s the first thing to slip when you’re also running the org.
- You’ve done the research and you’re stuck on what it means.
- This feeds something bigger, like a strategic plan or go-to-market strategy, and you want it built into that process.
If You Want Help
Aylin Bell works with education and youth development nonprofits to help develop and implement strategies for scaling their impact. She spent 20 years at WestEd, a 1,000-person education nonprofit, in senior roles across business development, strategy, and organizational capacity building, where she brought in more than $50M in competitive proposals and grew the organization’s earned income lines.
She’s a good fit if:
- You’re trying to diversify revenue and want a partner who’s actually built earned income lines inside a nonprofit
- You want quick, practical market research, the version that informs a real go-to-market strategy
- You need a strategic plan, retreat, or board convening led by someone who has run these inside a large organization
- You’ve got an ambitious, cross-functional project with no obvious owner, and you need someone who will carry it through implementation
Connect with Aylin!
Try it Yourself
Aylin’s DIY Market Research Toolkit
- Aylin’s Market Research Interview Guide: The real 16-question set Aylin used to find out whether a school district would actually buy a math teacher PD offering.
- Build Your Own Interview Guide: A fill-in-the-blanks worksheet that adapts Aylin’s structure — objective, targets, questions, outreach note, and tracker — to any sector or offering.
Questions to Sit With
- Who actually uses your offering, and who actually pays for it? If those are two different groups — and in the social sector, they usually are — can you describe the second one as clearly as the first?
- How are the people you’re trying to reach handling this need right now, without you? If your answer is “they’re not,” how sure are you?
- What would someone have to give up to choose you instead? Money, time, the thing they’re already using, the comfort of not changing anything. Name the actual cost.
- When was the last time you asked instead of assumed? And what were you assuming?
- If ten conversations told you people won’t buy this — would you actually change course? Or would you look for a reason the research was wrong?
- What decision are you about to make on a guess that ten conversations could make on evidence?
Not sure Aylin‘s the right fit? Talk to Helia directly!
This article comes from a coffee chat with Aylin Bell in August 2026. These conversations form the heart of the Helia Library — because we’ve learned the most from doing and from talking with other doers willing to share their wisdom. We don’t need to start from blank pages or do everything alone.
As always, take what’s helpful, leave what’s not, and make it your own.
About Aylin
Some of Aylin’s favorite projects have been close collaborations with leaders and teams passionate about an idea, a service, or a product, working on how to grow it and run it well. She loves translating across functions, keeping impact at the forefront of the work, and finding creative and resourceful ways to get things done.
She spent two decades at WestEd, where she led the organization’s first agency-wide strategic plan, built and grew earned income lines, and restructured programs. Earlier in her career she was the COO of a KIPP middle school.
Work with Aylin
