Why enterprise technology fails and what collaboration-first organizations do differently
Last year, a mid-sized company spent nine months selecting a new enterprise system.
Fourteen people were involved. There were dozens of meetings, multiple demos, and a mountain of spreadsheets. Everyone agreed it was a “strategic” decision.
Two years later, most of the system still isn’t being used.
This story is so common that MIT recently reported that 95% of enterprise AI deployments fail to deliver meaningful business value. The applications work. The pilots succeed. But revenue doesn’t move. Costs don’t come down. Processes don’t really change. The ROI never shows up.
McKinsey found that the rare organizations that do succeed with AI don’t just install tools. They redesign workflows, change decision processes, and rebuild how teams actually work.
In other words, the problem is not the software.
It isn’t AI.
It isn’t features.
It isn’t even workflows.
It is collaboration.
We see the same pattern in enterprise software more broadly. Jon Hansen, citing Gartner, estimates that roughly 80% of enterprise system implementations fail to deliver their intended value. Different technology. Same outcome.
Most enterprise software is built as if agreement already exists.
In reality, agreement is the hard part.
Why RFPs Should Work
There can be tremendous value for both buyers and suppliers in using an auction process like an RFP to search the market for information and competitive alternatives.
Auctions are one of the great inventions of economic life. We use them every day in financial markets, digital advertising, telecommunications, and power markets. When they are well designed, they are brutally efficient at discovering both price and fit.
A well-structured RFP can help a buyer with a real problem:
- Compare genuinely different approaches
- Reduce haggling and politics
- Create a defensible, transparent decision process
- Get closer to the true economic value of a solution
When they are well structured.
Why They Usually Don’t
In practice, many RFPs collapse into a pro forma exercise in compliance.
Buyers rely on rules of thumb like “three bids and a buy,” as if three proposals constitute meaningful competition for anything more complex than a commodity. Internal coordination is hard. Gathering the data needed to articulate the real problem is harder. Executing the process with existing systems is often expensive and painful in its own right.
Suppliers resent the process because it often feels rigged. Buyers resent it because it feels bureaucratic and slow. Everyone ends up managing the process with a mix of email, spreadsheets, and half-fit enterprise tools.
The result is familiar:
- Endless meetings
- Late stakeholders
- Scoring systems that collapse under political pressure
- Decisions that get re-litigated
- Cycles that take far too long and cost far too much
Often there is no rigorous, structured way to evaluate genuinely differentiated proposals. The process fails to deliver value-for-money for anyone involved.
Most RFP processes don’t fail because the market is unclear.
They fail because the organization is.
A Familiar Story
Imagine a medium-sized company called Acme that needs to purchase a new marketing automation system.
The CEO and CFO sponsor the project. The CFO, Jill, is asked to run the buying committee. Because it’s software, she brings in Ted, the CTO, who assigns two people from his team. Jill also pulls in representatives from operations, sales, marketing, and engineering.
This is an important project. Everyone agrees on that.
Acme may or may not have a procurement professional involved. Until now, they have handled these large purchases as one-off projects using email and spreadsheets. But the company is growing, and these “one-off” procurements are now happening ten times a year. The old approach is starting to break.
Jill thinks this will take three months.
It will take nine.
And nobody will be completely sure why.
The Real Determinants of Success
In situations like this, success rarely depends on the tool alone. It depends on three things:
- The right partners
- The readiness of the users
- Clear, well-formed user stories
Get these right and the RFP almost runs itself. Get them wrong and no software will save you.
This is the part most procurement technology ignores.
The Right Partners Help … But Only If They Really Fit
Jill decides to hire a consulting firm, Sussex, to guide the process.
Good partners can be invaluable. They bring market knowledge, pattern recognition, and experience with both procurement and procurement technology. By reputation, Sussex has real credibility.
But Jill needs to be careful.
Many advisors arrive with a generic framework and a preferred enterprise solution, often one they already have a strategic relationship with. These systems may be far more sophisticated and far more expensive than what Acme actually needs at this stage.
You wouldn’t buy your college-aged child a Ferrari for their first car.
A mismatch here can easily lead to cost overruns of 100% or more. Worse, some very articulate consulting teams lack the domain depth their clients assume they have. When that happens, they default to generic approaches because they don’t understand the problem well enough to tailor the solution.
Jill doesn’t just need a partner.
She needs the right partner, collaborating in the right way.
Users Arrive with Very Different Levels of Readiness
The most important thing Jill can do, whether or not she uses a partner, is to level-set the team.
Not everyone on the committee is experienced with procurement. For some, this will be their first RFP. Even those who have participated before are often self-taught and only loosely familiar with best practices.
The goal here is not training.
It is education.
Training teaches people which buttons to push. Education teaches them why the process works the way it does.
That difference matters.
Educated stakeholders surface better data. They ask better questions. They help articulate a clearer problem statement and a more rigorous evaluation framework. This dramatically increases the odds that Acme buys the right solution and pays a fair price for it.
When people understand why they are doing what they are doing, collaboration improves and friction drops.
User Stories Clarify Value
The third critical ingredient is getting the user stories right.
A user story is a short, plain-language description of the value a user expects from a system. In Jill’s case, she needs to gather and reconcile user stories from everyone who will touch, or be affected by, the marketing automation platform.
This step is almost always under-invested.
The predictable result is that companies pay enormous sums for features nobody uses.
A good set of user stories cuts through internal complexity and forces clarity about what actually matters.
Good user stories:
- Focus the RFP on real needs
- Attract the right vendors
- Make evaluation more objective
- Dramatically reduce the risk of buying shelfware
Writing them is an iterative, collaborative process. It forces disagreements to surface early, when they are cheap to resolve.
Most organizations postpone these conversations.
They pay for that later.
What Success Looks Like
When these three elements are in place, the rest of the process becomes much easier.
Procurement cycles shorten because people are aligned. Evaluation becomes faster because the scoring model reflects a shared understanding of value. Much of the delay in modern RFPs comes from internal disagreement that surfaces far too late in the process.
Well-run RFPs also improve both solution quality and pricing. Good suppliers do not mind competing when the customer knows what they want. In fact, they prefer it. It signals that this will be a rational, professional relationship.
Most importantly, the company ends up buying a solution that actually fits the problem it has.
The Bigger Point
When companies end up in the 80% of failed enterprise implementations, or the 95% of failed AI projects, it is rarely because the software was inadequate.
It is because the organization wasn’t ready.
The irony of our age with its blizzard of new tools is that the answer is still the same:
Get the basics right.
Design for collaboration.
Invest in shared understanding.
Simplify wherever possible.
Tools don’t fix coordination problems.
Organizations do.
And when they do, the technology finally starts to pay off.
A Final Word
Sextant was built for exactly this problem.
Not to automate broken processes.
Not to accelerate bad decisions.
And not to impose a generic “best practice” template on organizations that don’t fit it.
Sextant is a collaboration and decision system that happens to produce RFPs.
Sextant’s collaboration-first technology is built to embody this philosophy in practice helping teams create alignment before they automate and make better decisions before they move faster.
It is designed to help teams:
- Build shared understanding before they lock in requirements
- Surface real disagreements while they are still cheap to resolve
- Turn stakeholder knowledge into structured, usable decision criteria
- And arrive at decisions that the organization can actually execute
In other words, Sextant is not a workflow engine.
It is a coordination engine.
We believe that when you design for alignment first, everything else gets easier: the RFP, the evaluation, the vendor selection, and the eventual implementation.
That is the bet we are making.
And it is the kind of bet that finally makes enterprise technology pay off.