Trustward is a mission-driven accounting firm that provides fractional CFO and accounting services specifically for nonprofits. The Trustward team serves as the outsourced finance and accounting team for nonprofit organizations that don’t need a full-time finance person but require strategic financial leadership and day-to-day accounting support. Steven Weir is the CEO of the 20-person firm.
Steven spoke with us about his journey from running a nonprofit without any business operating system to successfully implementing EOS® with his growing finance firm, and how switching their EOS software from 90io to Strety transformed their team’s adoption and daily use of the framework.
Can you tell us about your experience before EOS®?
After working in finance at Capital One for many years, I ran a nonprofit for five years and did not have EOS® or anything like it. I was constantly feeling like we weren’t progressing, and we weren’t dealing with everything we needed to deal with. The energy was high, but we weren’t moving in a strategic direction. I eventually ended up doing a strategic plan and having some engagement with that. But even then, it didn’t quite feel like we were attacking things well.
When I left the nonprofit and started my own business serving other small businesses, that’s where I started to see EOS® in action. I saw a number of businesses that were succeeding so much that they surprised me. And when I got in there, I realized they were using EOS®, and that was the thing that was driving them forward in a pretty powerful way.
How did you approach self-implementation of EOS?
I joined this accounting firm, and there was a partner who has since retired. He and I did Level 10s every Friday. That was it. We didn’t do anything further than that. We used OneNote as the software for the Level 10 meetings.
But it was good in that it got us together. We didn’t always agree on everything, and it got us together once a week, forced us to talk about issues. So that felt good. And we did that for about a year and a half.
Even a little bit of EOS implementation was pretty good, I think, and helped move things forward. After he left, I just moved to regular leadership team meetings once a week, without the L10 structure, but I knew I wanted to get back to more EOS.
So when we had someone join as COO and I told him, “I want us to self-implement EOS. Can you do that?” And he spent a decent amount of time working on that in the beginning, but then he got busy with clients and billable work, and it sort of slowed down. We actually had a Scorecard that was really good and helped us, and even influences how we do things now. So we had a really good Scorecard. But that was it. We didn’t have it all – it wasn’t super formal.
What made you decide to work with an EOS Implementer?
I knew engaging an EOS Implementer was a good idea. The delay was financially driven. I met with all the implementers around town in Richmond – there seems to be three or four and one remote as well. And I decided who I wanted.
But I had to weigh the cost of engaging an Implementer with the fact that I had just bought the business. I was just trying to survive. They say year one after you buy a business, just try to survive. So I was just trying to survive, but I had it in my mind that an EOS Implementer could bring tremendous value. And then after year one came year two, and it was like, “Okay, we need to do this now.”
What steps did you take with your leadership team before moving ahead with a more formal implementation?
I went around and talked to the team who would be implementing it, made sure they were bought in, made sure they understood what it was. There was one horror story that one person knew about an EOS® implementation that went really badly. And I asked, “Why did it go badly? What’s different about us? Do you think it can succeed here?” And once I got that information out of them, we realized it was a really different situation, and this would be fine here.
So then we went through the EOS® process last summer. We’re on probably meeting number six of having a facilitator. And even before this last meeting I thought, “Maybe we’ll cut the facilitator and we’ll just go off on our own,” because they say 18 months is how long it should go. And then after this last meeting, everyone was like, “Why in the world would we ever cut off this facilitator?” We want JJ to be with us for a long time.
What’s the biggest difference between self-implementation and working with a facilitator?
With self-implementation, we just didn’t do it all. It’s really as simple as that. We didn’t have the vision, we didn’t have the core values. We just didn’t have it all implemented. So it didn’t work as a coherent whole where our values connect to 10 years, three years, one year, 90 days, Issues — it didn’t work all the way through. So we had Issues, we didn’t really have connected To Dos. We had L10 meetings. The meetings were better than nothing, but to have an Implementer changed everything.
Facilitation is not in my primary skill set in general. And it’s very hard to do when you’re the boss. It’s different when JJ is asking the team a question versus when I’m asking the team a question. Sometimes, honestly, I’m annoyed by the questions that get asked and the answers that people give, but it’s still better than me dominating, and gets more truth and value out of the meetings.
What challenges did you face rolling out EOS® to your whole company?
The leadership team was really bought in, so we could use the tools and we understood what it all meant. But last summer, it was time to move it from just a leadership team to the whole company. We have about 20 people, and the EOS software we had been using, 90io, wasn’t well integrated. It didn’t make sense.
I remember watching the larger team try to jump in, and realizing that at this point, I had been working with EOS for two, maybe three years, so I knew all the language. I knew how it worked. I had overcome all my initial objections, and I was in. But these are folks who were just starting it for the first time, and things like Issues and To Dos and Headlines and Rocks — it was this whole other system that wasn’t integrated with anything else they worked on, and it didn’t make a ton of sense to them.
How did you discover Strety?
I had heard from our EOS Implementer that there were some other systems out there. So I asked him what other systems were out there, and he mentioned Strety. I met with somebody from your team and they said that unlike 90io, Strety was built by software developers who know how to integrate things, know how to create visual stuff that makes EOS® more compelling and engaging for people.
To be honest, I kind of thought it was baloney. I was like, “Okay, I’ve talked to 100 software salespeople. They always say stuff like this.” But then I got in and that’s exactly what it was.
Strety is well integrated — I got to use it in Teams, which is really helpful. I could create things really quickly. It was a big upgrade in software, which allowed for a lot faster adoption by the rest of the team.
What are some specific examples of what you noticed in the way Strety is built vs 90io?
To give an easy example — one of the first things our team got onboarded onto was the Level 10 Meeting. And the first section of the L10 meeting is the segue. You go into 90io and you have a segue, and it’s basically a blank screen. If you’re trying to get people to confirm they’re logged into the meeting, and they’re like, “Am I in it? I don’t see anything.” “Yeah, you’re in it. There’s nothing.” It’s just a hard way to start.
But in Strety, it feels like somebody identified: “Hey, we should actually have something we can do in this segue space.” And so Strety has the Icebreaker click-through in the Segue section, which sometimes we use, sometimes we don’t. But it’s was one of those things that made me say, “Okay, this person understands that if I’m going to be in a meeting software, I need to say something. It can’t just be a big blank screen.”
What’s different about using Strety versus 90io for your EOS implementation?
90io was a login that didn’t connect to anything. You basically had to go into 90io to operate. And if you left it, nothing connected there. Whereas what Strety has done is made it so I can live in Teams, assign people things, and they get notifications in Teams.
There’s external integrations in Strety that I like, and then also there’s the internal talking-to-each-other things I like. So now we’re starting to use the Project functionality inside of Strety. I can connect a Project to a Rock, or I can create a Project and create a To Do, and I can choose what space I want it to be in so I’ll know what meeting we’re going to review that To Do in. There’s a lot of connection and also flexibility.
What integrations in Strety have you found most helpful?
We just put in the Asana integration because I have a client who uses Asana. We don’t use Asana, but the client does, and it’s really nice that I can just connect it really easily. And we’re about to integrate HubSpot, which is where we manage our sales process.
With the client that uses Asana, they’re in the middle of this audit process for their whole organization, but there’s some finance elements to it. They’re able to manage the entire audit project in Asana and I collaborate with them from Strety.
Instead of having to go into Asana and get my tasks all the time, I can just push the To Dos they make for me in Asana into Strety. They show up on my list with the rest of my work, and then I can do them, and then mark them as complete in Strety, which they will then see as completed in their Asana project.
With Strety, I can collaborate with my client on their complex internal projects — and I’m able to instantly see what’s relevant to me.
How else has Strety helped you with client management?
We do nonprofit outsourced accounting. Generally, you’re looking at organizations that just don’t need a full-time finance person at all, but they have an executive director who is not a finance person. So they’re looking for us to come in and do it all, like everything from presenting strategic reports to running payroll and logging things into QuickBooks.
We can usually do it for cheaper than a full-time person, and we can offer multiple skill sets that you’re not going to find with one single full-time person usually. And we can scale up and scale down, based on how much stuff they need. So it’s almost like accounting and finance as a service.
We have one client where we’re actually having them as external users on a Team in Strety. We are basically the outsourced accountant for those clients. We meet with most of our clients every week. We talk through what their Issues are, and we do a ton of work for them that we can capture in To Dos. So it’s helpful to have a list of Issues, of To Dos that we need to accomplish and talk through, and for our clients to have total visibility and transparency.
How do you structure client teams differently in Strety?
The challenge with managing clients in Strety is that they don’t know EOS®. So all of the EOS® tools and vocabulary — To Dos, Issues, L10s —what is all of this stuff?
If you look at our leadership team in Strety, we have every EOS® tool and the additional tools Strety offers: L10 meetings, Rocks, Scorecards, To Dos, Headlines, Issues, People Analyzer™, Messages, Surveys. We have it all.
But if you look at our client team, I’ve winnowed it down. I basically got rid of everything except for Meetings, To Dos, and Issues.
I felt when it comes to communication and collaborating with our clients, everything was either a To Do or an Issue. There wasn’t much else there. I guess we could argue there’s some Headlines, but I don’t really want to introduce that to these folks.
This is another reason why I like Strety — I could remove a bunch of tools that I knew the client wasn’t going to understand, and keep the client team space custom and relevant to them.
What kinds of projects are you managing in Strety?
Here in Richmond, Virginia, there’s a large foundation, and every quarter they have board meetings. So we work on a quarterly board cycle, basically. I need to make sure the books are complete, which I have a bookkeeper who supports that. And then there’s always a thousand issues that come up, like there’s this board member who asked if we could fund this type of philanthropy, and so we have to look into that.
Right now, we’re trying to work on a project where we do grants — we give money to local nonprofits — but we’re also trying to figure out if we can lend money. Lending money is different. We don’t actually want to be the lenders. We just want to be the guarantors and have some other organization lend. So all this work goes into getting together for these quarterly board meetings and all these issues that come up.
We have some investors, and we have a company to invest their money for us. If they’re doing fine, then things are fine. But if they’re not good, then all of a sudden, we have a whole body of work to figure out why things aren’t going well, and talk to them and get their side of the story, and figure out the board members are who are going to be worried about it, and be proactive about spotting those Issues and calling them beforehand.
Another project is we need to increase our rates a little bit every year, just kind of an inflation increase, and we always forget. Three years in a row, no one’s gotten an increase. It’s starting to actually matter from a revenue perspective. So I created a simple Project board in Strety with To Do Lists for the emails that I need to draft, where every To Do contains how much the old amount was and how much the new amount is. Then I draft the emails, and move them to the list where they’re set to send over the course of October. And then once they’re sent, I’ll move them and assign them to Lisa, our admin, that on January 1, 2026, they need to be billed with the higher rates.
How has your team adopted Strety?
The leadership team who are really bought into EOS® and were already on 90io — they like Strety better. The rest of the people, certainly no complaints. And I can see that they’re engaging with the system, adding Issues, which is a great sign.
How has your EOS implementation evolved over time?
Now we’re fully in and it’s time to implement a performance management process, because we’re big enough where we need to do that. I worked at Capital One for a long time, so I was going to use the Capital One process. And JJ told me, “Well, EOS has its own quarterly conversation for performance management that’s probably in Strety.” And there it is — connected to everything else we have. So I’m fully bought in.
Why do you think nonprofits are good fits for EOS implementation?
I work with nonprofits, and I’ve run a bunch of nonprofits, and they all have this operating model that’s essentially: how charismatic and administratively skilled is the executive director? They really need something like EOS®. I think it would increase capacity so quickly.
The reason nonprofits are hard is because they have the regular things you have to do to run a business, and then three or four things on top of it. One of the things is, nonprofits have a board, which means you have all these stakeholders who need information. And then the other thing is, your goal is not easily defined as financial success. For-profit businesses obviously have other goals, but in the end, you’ve got to make money. That’s what you’re trying to do.
Whereas nonprofits — some organizations’ goals might die in three years because you solve the problem you’re trying to solve. And some organizations, it’s like, you’re doing big advocacy things that you hope impact things over time. But other times things are going backwards, and you still have to do the work, and it’s out of your control. That’s a huge challenge, and I think EOS® can help nonprofits continually work toward their goals, no matter how concrete they are.
What advice would you have for other business owners curious about implementing EOS?
What I’d say with implementing EOS is the amount of information feels so overwhelming — I couldn’t swallow it all at once. It took two or three years, and that felt like the right pace. I couldn’t get my head around every part of it and bring along the other people on my team all at once. So I say just bite off what you can chew. Any implementation — even a very small level of implementation — is better than none. But over time, try to get it deeper and deeper.
Also, the EOS® software really matters. I think Strety is really good project management software that, when paired with a good EOS® implementation, can really do what you would hope that a Monday or an Asana would do for your organization.
I’m using Strety now in the way that I used to want to use Monday or Asana, but I never really cracked the code on those. I never quite figured out how to use those in a way that was effective. And I felt like I was having to design these incredibly complex processes in order to fit in with the software. And now with Strety and EOS®, we’re going the opposite way. I have the process, it’s EOS, and so then the software built on top of that is really nice. It’s simple, and just works much better than designing complex processes.
Thanks, Stephen! To learn more about Trustward and their nonprofit financial services, visit their website. Ready to see how Strety can transform your EOS implementation? Start your free trial or book a demo to see how we can help your team adopt and thrive with the framework.