I’ve seen this a handful of times. The CFO walks into the kickoff meeting with a shortlist already prepared.

Three platforms that have been evaluated by the accounting team. The criteria were built around month-end close speed, chart of accounts flexibility, and reporting outputs they need to present to the board.

The operations manager, warehouse lead, and sales director are all sitting at the same table. The majority of their tasks have been manual for years because the current system is outdated and can’t talk to other solutions well. Here’s the kicker, no one asked for their input.

The CFO has done his homework, and the presentation is thorough. The scoring matrix is color-coded to highlight the pros/cons. Before you know it, six weeks later, the company signs a contract to move to the new solution.

Eighteen months after go-live, the warehouse is running a parallel spreadsheet system because the new platform handles inventory the same way the old one did. Nothing changed. The operations team had to adapt again. The sales team is still using spreadsheets to track their leads.

This did not go wrong at go-live. It went wrong in the room where requirements were built.

The Department Holding the Wheel Gets to Pick the Destination

When one department drives a software decision, the company normally gets a solution built for that department if they aren’t thorough in their requirements gathering. Accounting and sales are almost always the loudest voices in the room.

Accounting wants clean financials and good reports. Sales wants pipeline visibility and commission tracking. Both are legitimate needs, but in a company that runs on operations, those two departments only represent a fraction of the people who actually live in the system each day.

If operations isn’t considered, the receiving dock is left still using clipboards and the production floor isn’t able to see a digital work order schedule. They are still printing off packs.

The solution fits the driver. The rest of the company adjusts to figure it out.

What makes this dangerous is how invisible it is in the moment. Everyone in the evaluation room feels like they are being thorough. They are asking good questions, comparing features, checking integration capabilities. It looks like a real process. If the only voices shaping the requirements are the ones with the most authority rather than the most operational exposure, the requirements are incomplete. You are solving the visible problem for the loudest people and leaving the rest of the business to figure it out later.

They Were Not Siloed. They Were Strangers.

A few years back I was brought in to help a company select a new platform. Standard engagement. Before we got anywhere near a vendor conversation, I started running department sessions to map out their actual processes.

What I found stopped me cold.

Every department was running its own software. Nothing was connected except where it rolled up into the financial system. There were no shared tools but multiple platforms, selected for their own needs, with no visibility into what anyone else was doing.

Worse, nobody knew where the handoffs were between departments. When I started asking questions, it became clear that people had no idea how their work connected to the next team’s work. They had been operating in complete isolation for so long that they had stopped thinking about it.

Here is the part that really got me. Some of the software they were already paying for had functionality that could have served multiple departments. It was sitting right there, unused, because nobody had ever looked at the business as a whole.

When I started bringing this to light, the reaction was not relief. It was resistance.

Each department had built its own little world of tools and processes that worked for them. When I started talking about integration and shared systems and understanding the full data flow, the response felt a lot like asking kids to share toys they had never been asked to share before.

They were not trying to be difficult. This was just the culture. Every department for itself. What is best for us. Nobody thinking about the handoff.

Getting them on the same page in those early sessions was harder than any software selection I have ever managed because the problem was never the software.

The Closest People to the Work Have the Clearest View

This is not a radical idea, but it rarely happens in practice.

The warehouse manager who touches inventory transactions fifty times a day knows things about your data flow that no vendor demo will ever surface. The person who processes purchase orders knows exactly where the current system breaks and what a new one would need to do differently. The production scheduler can tell you in ten minutes whether a platform’s routing logic is going to work or whether the team will be building workarounds by month three.

These are not IT decisions. They are operational decisions that happen to involve software.

When you exclude those people from the evaluation process, you end up buying a solution optimized for the people in the room. There is also a secondary cost that does not show up in the implementation budget. When the people who use the system every day had no input in choosing it, buy-in is slower, adoption is lower, and problems surface later than they should.

Do This Before You Talk to a Single Vendor

Before you talk to a single vendor, you need to know where your business is experiencing friction. Not where your CFO thinks there is friction or where your sales director wants more visibility. Where the actual operational breakdowns are happening, who is involved, and what solving them would actually require.

That means talking to the people doing the work, the subject matter experts. Mapping the processes before you start evaluating the platforms gives you a great idea where things are breaking down or working well. This allows you to be honest about whether the problem is people, process, or software problem.

It also means the person steering the evaluation cannot be personally invested in one department’s outcome. Their job is to represent the whole business. Not the function with the loudest voice.

Most founders assume the department closest to the pain should lead the solution. That logic makes sense on the surface but closest to the pain is not the same as furthest from bias. The department that is most frustrated is often the one most likely to prioritize their own relief over the needs of the broader operation.

If accounting is driving your software selection, you are optimizing for accounting. If sales is driving it, you are optimizing for sales. Neither of those is the same as optimizing for the business.

Software shapes how your business operates for years. The loudest voice in the room should not get to make that call for everyone else in the building.