I first wrote a version of this in 2016, after our first fifty or so clients. We’ve passed a hundred builds since, and the pattern hasn’t changed. When I think back on the companies we’ve worked with, I don’t remember the specific problems that made them call. I remember the people — a leasing agent, an ER physician, a drilling engineer, an auditor, an A/R specialist, a CEO. All of them were in more or less the same spot: what worked for them yesterday was failing them today.
The systems every business runs on
Every day, the people in your business rely on a handful of systems to do, track, and manage their routine work. They fall into four buckets:
- Off-the-shelf software and SaaS. QuickBooks, Dynamics, Salesforce, HubSpot, Smartsheet, ServiceTitan, the industry-specific platform your vertical runs on.
- Spreadsheets. Excel, Google Sheets, and the shared workbook that has quietly become a system of record.
- Physical tracking. Whiteboards, clipboards, sticky notes, the binder in dispatch.
- AI tools bolted on top. New since the first version of this post: ChatGPT tabs, copilots, and the automation someone built on a weekend that now runs a real process.
None of these are bad. They’re how a business gets from zero to a few million in revenue without an engineering team. But as a company grows, they start to under-perform — more people, more regulation, more risk, more offerings, more locations. The question we keep asking with every CEO we work with is the same: how do you build systems that let the business keep adapting instead of holding it back?
The symptoms, by who feels them
Across all of those clients, the same problems kept showing up, and they showed up in three places at once.
Management
- Decreasing operational visibility
- Rising cost to acquire and serve a customer
- A constant need to hire just to keep up
- Shrinking margins nobody can fully explain
Employees
- Falling productivity — more time on the system than on the work
- Rising reporting requirements
- Three or four systems to work in, plus the spreadsheet that reconciles them
Customers
- Slipping quality
- Longer wait cycles
- Declining service and support
- More confusion at every touchpoint
What you’re left with is managers who feel a lack of control as sales and costs grow, employees who feel inefficient and micro-managed, and customers who feel ignored. In my experience, those are symptoms. The real problem is that the systems in your company are starting to break down and fail your people.
What it looked like for one client
A fast-growing student-housing operator knew two things from tenant and employee feedback: the leasing experience for prospective tenants needed to get better, and the workflow for their own team needed to get simpler.
Their constraint was the popular leasing and property-management SaaS product they ran on:
- The leasing module wasn’t built for student housing, where one unit can carry several leases.
- Renewals couldn’t be tracked per unit.
- The application process was paper, and none of it was trackable in the system.
- The vendor wouldn’t add features for large customers and offered no open API.
- Pricing was complex and climbing, with “convenience fees” charged to tenants and “processing fees” charged to applicants.
So the leasing agents did what people do. They started tracking signed leases and guarantor forms for each tenant group in a Google Sheet. It bought back some time, but most of their day still went to chasing signatures, hassling applicants for deposit checks, and reminding tenants to renew. Management had almost no view of the numbers that ran the business: units available, units leased, units pending, tenant count.
When we kicked off, we started by talking to the leasing agents. They were a gold mine. Because they were already working outside the system, they’d designed a simple, scalable workflow that was a great candidate for custom software — and didn’t depend on integrating with the platform the vendor wouldn’t open up.
Ten questions that tell you where you stand
We usually start with one-on-one conversations with employees, not with executives. The questions are simple:
- How many systems do you use every day?
- What would you change about the one you use most?
- Do you have to work outside of, or around, the system with spreadsheets or other tools?
- What part of your job takes the most time?
- Is there anything you do that’s a waste of time?
- Is there anything you do that’s duplicated somewhere else?
- Is your process or workflow written down anywhere?
- How much of your day goes to real work versus feeding the system?
- Have you seen a better process or system somewhere else?
- Do tasks ever get dropped or forgotten?
If the answers make you wince, remember: what’s working for you today will fail you tomorrow. Growth makes sure of it.
What to do with the answers
Start the conversation with your employees. The questions above are the whole first step, and they cost nothing.
If the conversation points at a system the business needs and nobody sells, that’s Custom Software Development + Design — and every new build we take on starts with a Validation, Design & Planning engagement, a fixed-fee step that tells you what it should be and what it will cost before you commit. If the problem is a system you already run that can’t keep up, that’s a different article: When your custom software stops working for you. And if what you’re hearing is “the process is fine, we just do it by hand,” that’s an automation problem — read about AI Office.
Either way, the people doing the work already know where the system is failing. Ask them.