Before the Dashboard

Why the foundation comes before the fancy stuff

Jess Skylar with Jess Steele


Long Story Short

You can care deeply about measuring impact and still end up manually aggregating spreadsheets and clicking around in three different analytics sources trying to find an answer. The fix isn’t more data — it’s better architecture underneath it. Check out the Data Infrastructure Toolkit if you want a head start on building the foundation.

Jump to How!


I’ll be honest — I move fast. I care deeply about metrics and measurement. AND I do not want to slow down to build the system or make the hard decisions about who tracks what, when, and how. Not surprisingly, this leaves things all over the place.

Part of it, I think, is fear. Like, if I get too specific too soon, I’ll get trapped into something that doesn’t work or doesn’t fit. But the longer I do this work, the more I realize that spending the time to build the right infrastructure actually creates MORE options — and gets all the hard questions out of the way before they become expensive problems.

At Helia, we kept coming up with lists of metrics we wanted to track and then realizing they were too hard to capture, not quite right, or — my personal specialty — I’d come up with new ones. (Which everyone loves, naturally.) Connie and Libby finally led the way to something more concrete: specific, reliable metrics for our key questions, and an actual dashboard to make sure we capture them consistently. We can always add on. But knowing there are consistent, reliable answers to the questions that matter most? Even before it’s fully in place, it already feels transformative.

Building the right data foundation up front, even when it feels slow and unglamorous, is what makes everything that comes after it trustworthy, usable, and powerful.

And I really felt the cost of not having it.

  • When I click to see if folks are reading our articles and the same article shows up four times in the analytics — and I’m manually trying to add and subtract the numbers to get something accurate. 
  • When I’m trying to figure out whether going all-out on LinkedIn is actually worth it in any way, shape, or form, clicking around in our analytics module with three different LinkedIn sources that I can’t tell apart.

Investing the time into what matters and why AND the infrastructure to build it is a massive industry for anyone doing any business online. And yet when we’re measuring the things that really matter — like, are we actually helping people? — we often just pull it together. Or track 50 things. Or manually combine.

Data infrastructure matters. And once it’s in place, it can go a very, very long way.


The person who builds the floor before the furniture

Jess Steele started her career as a high school health teacher — and from day one, she was watching programs come in and out of schools, trying to figure out which ones were actually working. Funding followed hype. Celebrity helped. And she kept asking: how do we actually know if this helps?

That question sent her back to school for public health research methods and into two decades of work at the intersection of data, evaluation, and systems — in education, behavioral health, and child welfare. For a long time, she worked on the outcomes and evaluation side, which she describes as something close to a therapy session: “You’re helping programs really dig deep and figure out what impact do we think we’re having, where along the logic model can we create really meaningful ways to collect data points to help us understand if we’re getting there — and then helping them visualize it and tell their story.”

But the more she did that work, the more she saw the same problem everywhere. The analysis was only as good as the systems underneath it. And those systems were almost always severely lacking.

Jess’s approach is to start by laying a true foundation with two questions — what do you actually need to know, and what will you do with it — and then building the data architecture to make those answers possible. Not a dashboard. Not a report. The foundation that makes everything else trustworthy and usable. Because without it, you can build something beautiful on top that means absolutely nothing.


The Key Takeaway

Building the right data foundation up front — even when it feels slow and unglamorous — is what makes everything that comes after it trustworthy, usable, and powerful. Most organizations skip straight to the dashboard. The ones that start with the questions? They end up with systems that can actually tell them something real.


Jess Steele’s Data Infrastructure Process

If you’re a “just tell me what to do, I’m ready to get started” kind of person (aka Helia’s COO Libby), jump straight to the Data Infrastructure Toolkit — it walks you through the full process, including:

  • A Data Strategy Conversation Guide (with the questions to ask before you touch a single system)
  • A Data Systems Inventory to map everything you have — official AND the shadow spreadsheets
  • A Data Ownership Map so nothing falls through the cracks
  • A Data Quality Assessment to see what you can actually trust
  • A Gap Analysis & Roadmap to figure out what to fix first

If you’re a “tell me why this works first” kind of person (aka our Founder, Jess Skylar), read on for the good stuff!


How Jess Steele and Insight x Design think about building data infrastructure


Step 1 — Start with the questions

Before touching a single system, Jess wants to know what you actually need to know — and why.

This sounds obvious. It is not obvious. Most organizations skip it entirely and jump straight to tools, dashboards, or whatever a funder asked for. And then they end up with data that answers someone else’s questions instead of their own.

“Lots of nonprofits, based on their size or scope, get stuck because they’re like, well, we can be scrappy — this funder wants this, that funder wants that, so we’ll just build systems to report against those. And then they’re missing the larger picture of what their program is actually doing.”

Here’s the thing about why that actually matters — and it’s something Jess learned watching her husband, a high school principal, bring program after program into his school. “The effectiveness varies every single year because of the person implementing it,” she says. “If you have a good person in that role, they could be running a mediocre program and the kids can still get phenomenal outcomes.” The instinct about what’s working is often right. But without data, you can’t see why it’s working, or where it’s not, or what factors are actually driving the difference. “Having the data gives you the segmentation and the ability to see — what are the factors that are making this successful? What are the factors leading to lower impact in that area? And that can be a really hard question to answer without it.”

The goal isn’t a perfect, complete picture of everything. It’s a clear enough picture to take confident next steps.


The fix is a data strategy conversation — ideally with leadership, before anything else. Not a planning retreat. Not a full-day workshop. A real, focused conversation with the following questions:

  • What are we trying to understand? 
  • What decisions do we need to make? 
  • What does good look like — and how would we know if we were getting there?

Jess runs these as individual interviews first — 30–45 minutes with executive and program leadership separately — and then brings the group together to align. The reason? People often have different answers. And surfacing those differences early is a feature, not a bug. 

“Do the individual interviews before the group session — always,” she says. “People tell you very different things one-on-one than they will in front of their colleagues, and you want to know that before you’re all in the same room.”


Step 2 — Audit what you have

Once you know what you need to know, the next question is: do you actually have the data to answer it?

This is the data audit — and it’s almost always more illuminating than people expect. Not because the findings are surprising. Usually they’re not. “The audit is rarely surprising to staff,” Jess says. “They usually already know what is and isn’t working. What it does is make the informal visible — the workarounds, the shadow spreadsheets, the data no one trusts.”

A real data audit maps three things:

The systems — Every place data lives in your organization. The official ones (your CRM, your database, your finance system) AND the unofficial ones (the 14 Google Sheets your program team is maintaining, the paper intake forms from 2019, the Gmail inbox where some of your referrals are living). All of it.

The ownership — Who is accountable for each data domain? Who’s responsible for day-to-day quality? If the answer is “no one,” that’s important information. Unowned data is unreliable data.

The quality — For each data source, how complete is it? How accurate? How consistent? And — critically — do the people who use it actually trust it? “Data that exists but no one believes is not useful data,” Jess says. “If your team is making decisions based on instinct because they don’t believe the numbers, that’s a quality problem even if the numbers are technically accurate.”

Here’s something worth saying out loud: you don’t have to bring every possible data source into the centralized infrastructure you’re building. The audit isn’t about cataloguing every system, spreadsheet, and inbox your organization has ever touched — it’s about understanding what you have relative to what you actually need to know.

Some leaders want every possible data source in there. But if you include everything, the cost in time and resources goes up — and you end up with a lot of data that isn’t actually helping you make better decisions.


Jess is direct about this: “Some leaders want every possible data source in there. But if you include everything, the cost in time and resources goes up — and you end up with a lot of data that isn’t actually helping you make better decisions.” The goal isn’t a perfect, complete picture of everything. It’s a clear enough picture to take confident next steps.

Start with the questions that matter most. Everything else can wait.

And yes, this is where it can get a little politically interesting. In one project, the executive director wanted everything centralized — including the finance data from QuickBooks. The finance team had a different opinion. “The CFO was pretty much like, nope, this is ours, we’re holding it — totally understandably,” Jess says. 

Her move in those moments: come back to the questions. What are we actually hoping to do with this data? Do we have proxies that already get us there? What problem are we really trying to solve? It doesn’t always resolve the tension, but it usually moves it forward.


Step 3 — Build the roadmap

The audit tells you where you are. The roadmap tells you what to do about it — and in what order.

This is where most organizations want to skip ahead. “Many organizations want to jump straight to a dashboard or start using AI for analysis,” Jess says. “The roadmap helps build the case for starting with the unglamorous stuff first: definitions, ownership, data entry standards. That’s what makes everything else trustworthy and possible down the line. The goal is to move slow to move fast.”

A good roadmap is phased — usually across 60, 120, and 120+ days — and prioritized by impact and feasibility. Not everything can happen at once. And some things have to happen before other things can work at all.

One of the most important (and most skipped) items on almost every roadmap: metric definitions.

This sounds small. It is not small. Even a single metric can take weeks to get right — because agreeing on what it means is only the first step. Jess worked with a program that needed to define “solve time” for a case management system. The questions came fast: Does the clock start when someone submits an intake form, or when they’re assigned to a staff member? What if the staff member is in a different time zone? Do weekends count? What happens when someone goes on leave and coverage shifts? “That one metric ended up as a four-page SQL query,” she says. “And that was the right outcome — because the number finally meant something everyone agreed on.”

The goal isn’t just the definition. It’s cementing it within the infrastructure itself — so it doesn’t exist in ten different places, meaning ten different things.

Data that exists but no one believes is not useful data. If your team is making decisions based on instinct because they don’t believe the numbers, that’s a quality problem even if the numbers are technically accurate.


Step 4 — Build the infrastructure

Now — finally — you build.

And because you’ve done Steps 1–3, you know exactly what you’re building and why. You’re not adding systems because a funder asked for them or because a dashboard looked cool at a conference. You’re building toward specific questions, with specific owners, defined metrics, and a clear sense of what good data quality looks like.

What this actually looks like varies enormously by organization — from a simple centralized spreadsheet with clear ownership to a full data system pulling from multiple sources in real time. But the principle is the same: bring the right data into one place, clean it up, make it usable, and make sure everyone who needs it can get to it.

The clearest picture Jess can offer of what’s possible when the foundation is solid? Virtual Support Services at Think of Us — a program she supported for several years.

The program had four data sources: a case management platform, a phone call transcription tool, customer satisfaction surveys, and an internal resource database. Jess and her team built a centralized infrastructure that brought all of it together. What came out the other side was remarkable. But what stands out isn’t the dashboards. It’s what happened to the people using them.

The analysis was only as good as the systems underneath it. And those systems were almost always severely lacking.


Community responders — the staff supporting people navigating housing instability and crisis — used to spend significant time on a scavenger hunt every time they had a returning client. No centralized view, no linked history. Just clicking around hoping to piece together what had happened before. After the infrastructure was in place, when a returning help-seeker came in, the system automatically matched them to every previous interaction, generated a comprehensive summary of their history and key takeaways, suggested next steps, surfaced every resource that had previously been recommended to them and summaries from any previous satisfaction surveys they had completed  — all in real time.

“The administrative burden dropped in an incredible way,” Jess says.

The ripple effects went further. Managers started using data dashboards as the basis for every one-on-one — staff coming in prepared with their own metrics, their satisfaction scores, their response times. Conversations that used to be vague became specific. And the relationship with funders shifted entirely. “The team was able to be proactive with the type of data they were able to produce,” Jess says. Using AI layered on top of the clean infrastructure, they could answer questions like: over the past month, what emerging themes came up with help seekers? What gaps in services are people running into? What’s bubbling up that’s important not just for our program quality but for the whole state?

The California Department of Social Services (CDSS) started coming to them directly — trying to understand why people were having such a hard time navigating services on their own, where the gaps were, and what needed to change systemically. “Funders really, really liked that part.”

None of it would have been possible without the foundation underneath it.


When to do this Yourself vs Bring Someone in

Data infrastructure can feel so, so daunting. And Jess is the first to say it doesn’t have to be all or nothing — you can start with one project, one data domain, one question you’re trying to answer, and build from there. Her goal, as she puts it, is to “meet people there in the messy middle” — to help them figure out what they actually have, what they actually need, and what to do first without it feeling like an impossible undertaking.

The Data Infrastructure Toolkit and the data.org Data Maturity Assessment can get you surprisingly far on your own — especially the strategy conversation and audit phases. The maturity assessment in particular is worth doing first: it asks nuanced questions about your current systems and data literacy, and gives you a score that helps you see where you’re actually doing well (sometimes surprising!) and where you have real gaps.

But you might want outside help if:

  • Your leadership team has very different ideas about what you should be measuring — and the conversation keeps going in circles
  • You’ve done the audit and know you have problems, but you’re not sure what to tackle first or how
  • You’re trying to implement something technical (pipelines, data warehouses, automation) and don’t have that capacity on your team
  • You want to use AI on top of your data — for analyses, summaries, trend detection — and need the foundation to be clean and trustworthy before you get there
  • You’ve tried to build a dashboard before and it fell apart because the data underneath it wasn’t reliable

If You Want Help

Jess Steele and her team at Insight by Design work with organizations at every stage of this process — from the initial data strategy conversation all the way through implementation and capacity building.

They’re a good fit if:

  • You have data everywhere and no clear picture of what you actually have
  • You’re building toward something — a new program, a funder relationship, an AI pilot — and need the infrastructure to support it
  • You’ve been scrappy for a long time and are ready to invest in something more sustainable
  • You want implementation support, not just recommendations — someone who will actually help you build it

Connect with Jess!

Book a chat Email

Try It Yourself

The Data Infrastructure Toolkit

  • Data Strategy Conversation Guide — The questions to ask before you touch a single system
  • Data Systems Inventory — Map everything you have, official and unofficial
  • Data Ownership Map — Name who’s accountable for what
  • Data Quality Assessment — See what you can actually trust
  • Gap Analysis & Roadmap — Figure out what to fix first, and in what order
  • Data Maturity Assessment from data.org — A great first step if you’re not sure where you are. Nuanced questions, a score, and a clear sense of where to focus

Questions to Sit With

You made it through the whole framework. Before you close the tab — take 60 seconds with these. They’re the questions that tend to surface the real stuff.

  • If someone asked you right now where your organization’s data actually lives — could you answer in under two minutes? Or would it take a few emails to figure out?
  • Which questions do you find yourself answering manually every month that a well-built system could answer automatically?
  • Who owns each of your data domains? If the answer is “kind of everyone,” it’s actually no one.
  • What metric are you currently using that you’re not totally sure everyone defines the same way?
  • If you had clean, centralized, trustworthy data tomorrow — what’s the first question you’d ask it?

Not sure Jess‘s the right fit? Talk to Helia directly!

Book a chat

This article comes from a coffee chat with Jess Steele in March 2025. 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 Jess

Jess Steele started her career as a high school counselor, watching programs come and go and wondering which ones were actually working. That question sent her into more than a decade of work at the intersection of data, evaluation, and systems — in education, child welfare, and behavioral health — always asking the same thing: how do we actually know if this is helping?

Along the way, she kept running into the same problem: evaluation and analysis was only as good as the infrastructure underneath it. So she built Insight by Design to help nonprofits and mission-driven organizations improve their data infrastructure — starting with the right questions, building the foundation that makes metrics trustworthy, and offering hands-on implementation and capacity building when organizations need it.

When she’s not building data systems, you’ll find her outside with her daughters Simone and Nadine, always with a good playlist.

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Take what’s helpful, leave what’s not, and make it your own.
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