After a difficult implementation, it's hard to trust vendors, or the selection process, again.
Many implementations leave teams with workarounds, missing features and systems that never quite do what was promised. That experience shapes how every vendor claim is heard and how every decision gets made.
That caution makes sense. But if you don't look closely at what actually went wrong, it can lead the next selection off course too.
Teams rarely walk away from a difficult implementation with a clear diagnosis. They walk away with a feeling, and it tends to show up in a few ways:
Overcorrecting. The team asks for more of everything: more stakeholders, more demos, more criteria, more reassurance. The process lengthens, and the decision still feels risky because the underlying doubt hasn't been addressed.
Rushing to escape. The pressure to leave the old system behind pushes the team to move fast, and the same shortcuts get repeated: thin requirements, a shortlist built from familiar names, a decision made on the strength of a demo.
Both reactions treat the fear as the problem. The more useful move is to find out what actually went wrong.
When an implementation goes badly, there's usually more than one reason. It's worth pulling those reasons apart, because only some of them come down to which system you chose. These six questions can help:
The first two are largely decided before a contract is signed. The others depend more on how the implementation is planned and run, although the questions you put to vendors and implementation partners during selection can surface them early.
Once you know what went wrong, write it down as requirements and as questions. A few examples:
This moves the lessons out of people's memories, where they harden into general wariness, and into criteria that everyone can see and score against.
After a difficult implementation, taking a vendor at their word is a lot to ask. A better way to rebuild confidence is to trust the process: requirements written down before any vendor is seen, every vendor scored against the same criteria, references checked, and one named person making the final call.
None of this guarantees a perfect outcome. It does mean the decision rests on evidence you can show, rather than on whichever presentation was most persuasive.
A team that has been through a difficult implementation often needs a perspective that isn't carrying the memory of it. Udder's Vendor Selection service offers that. We lead a structured process: defining requirements with you, assessing the market, running the RFP, and facilitating vendor presentations and comparisons, with objective scoring carried out by your team. We have no software to sell, and our methodology draws on real implementation experience, so we know where selection decisions show up later.
The decision stays yours, and your people contribute at every stage. What changes is that you aren't rebuilding trust in the process alone.
If the last implementation is still weighing on the team, a useful first step is to write down what you learned. Our free Requirements Starter Template (an editable Excel workbook) opens with a Business Context tab, where you can record what is driving this selection and what success looks like twelve months after go-live. You then work through the requirements, scoring each one Must have, Should have, Could have or Won't have, so the lessons from last time become the criteria for next time.
Choose With Confidence.