His years as a database administrator taught Matt Henry, founder of Ascendably, that before he changed anything about a system, he sat down next to the person using it and asked them to show him how they did their job.
“It’s really important to stay curious, not make assumptions, and ask the team to show you how they’re doing something,” he said. “I can’t assume people understand how to click around in their system the way I understand it.”
That habit is at the center of how Ascendably diagnoses an organization. Before anyone talks about replacing software, Matt wants to see what is happening between the people and the tool.
Ideally, he would walk up to someone’s desk and watch them work. Sometimes they were using completely unexpected screens. Occasionally they had found something clever the whole team should know about. More often, they were doing it the hard way.
The fix wasn’t always training. “Sometimes I could teach them an easier way,” Matt said. “But other times I’d look at it and say, that’s taking you too much work, and I haven’t set up the system in a way that lets you do it any better. So I need to change your page layouts, your reports. Or maybe you can’t see a field I thought you could see, and I need to change your permissions.”
He can’t walk to every desk anymore, so he asks for the next best thing. “At least have them screen share. Show me how you’re doing your job today. Walk me through it.”
“What they were really trying to buy was: life is better,” Matt said.
That is the promise behind a software purchase. Executives chose to spend the money, and they told everyone it would make things better. When the software doesn’t seem to help, they feel responsible for that promise. For staff, “it might feel like a broken promise: we got this stuff, and our life isn’t better.”
The promise has a condition. “That promise only happens if the people skills are also invested in. You have to upgrade along with the software upgrade.”
When it breaks, people usually point at the system. When things get fixed, they point to the person who got it working. The software takes the blame, and a person gets the credit.
Some people turn the blame inward. “People may feel like they have good tools, but maybe they don’t know how to use them,” Matt said. “They will assume unexpected behaviors are their fault, rather than the system being misconfigured.”
That comes with real weight. “There are usually feelings of fear, anxiety, shame. I don’t know how to use the tools I’m supposed to be able to use to do my job. And maybe not feeling comfortable speaking up about that.”
The Human Stack™ is a methodology developed by Tim Lockie, and Matt implements it with clients, including Give Merit. Most people know the tech stack: all the software an organization uses. The Human Stack is what an organization does with its people: its culture, strategy, training, governance, and guidance. Both are needed to get outcomes.
Matt sees the same two halves in Ascendably’s own work. “One of them is the technology: software implementation, support services, maintenance. If you go to vendors, they can do roughly the same things we can. The other half of our practice is tech culture. We focus on the people who are using the technology, so that you as an organization can unlock the value of all the tech investments you paid for.”
Most organizations have only been shown one half. “100% of what they see out there is about the software and the technology, and the budget tends to be all on one side. When they can clearly see that there are actually two areas to keep in balance, they almost instantly can see the imbalance of where their attention and their investment has been.”
The Tech-Human Gap puts a number on that imbalance. It places both stacks on one line, with parity at the center, tech-led to the left, and human-led to the right.
A vendor can’t close that gap alone. Matt explains why with a gym. “There are lots of gyms out there. You can get a gym membership for 19 or 20 bucks a month, and they’ve got all this equipment. Until you hire a coach, nobody’s looking at your body and helping you decide: you’d benefit most from these three, ignore the rest, do them this long, this many times a week.”
A software company can show you how to use its product. It can’t show you how to use it in your situation. A coach can, and sometimes the advice is to drop something. “We may even find software where you can cancel that. You don’t need it anymore.”
In August 2024, after Give Merit’s CRM implementation, the assessment put the organization at −8, tech-led. The human elements Matt looked at, sustainability, accountability, and digital strategy, all scored below the tech elements of data quality, solution fit, and utilization, the latter meaning whether the tools are actually being used. “It was interesting to see that they felt their tech was ahead of their tech culture,” he said. “At the time it surprised me, and now I understand it.”
Give Merit’s executives rated the human elements lower than their staff did. “That’s because they know what’s actually in place,” Matt explained. “If there aren’t clear expectations, they can’t hold people accountable to them. And they’re responsible for making the plan, so if there’s not a clear plan, they know it.” Staff trusted that one existed. “I may not know the plan, but there’s a plan.”
Matt sees executive scores run lowest with other clients, too. “They’re harder on themselves, and less likely to take credit for where they are today, because they see the gap between today and where they want to be.”
At Give Merit, the leaders were self-aware and open, and nobody was shocked. “It still helped clarify things for everybody,” Matt said. In larger organizations, the gap can stay hidden simply because “there are typically enough layers that it doesn’t make it to everybody.”
Either way, the results told him where to look. “They tend to indicate this is an organization we can help.”
By July and August 2025, Give Merit’s gap had moved to +5, human-led. The Human Stack rose from 62 to 77, and the Tech Stack moved from 70 to 72.
What Matt noticed first wasn’t the score. “Anxiety was replaced with excitement and curiosity. No one was pushing new features onto them. They were pulling: I could really use this update in the system, it would help me do my work.”
His picture for it is the horse in front of the cart. “They were leading their systems.”
A diagnosis only matters if it changes how you work. Once an organization can see both halves, it looks at things differently. It asks where its money and attention have gone, and how much of what it already bought is sitting unused.
And if the answer isn’t more software, what does the work look like?
About the author: K. Malaine Carr is Ascendably’s Director of Marketing. She turns executive conversations into articles like this one.
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