Most software purchases start with a problem. The pipeline isn’t visible enough. The sales team isn’t following up consistently. Marketing can’t tell which campaigns are driving revenue. The problem feels clear, the solution feels obvious, and the purchase gets made.

Six months later, the problem is still there. Sometimes it’s worse. The software is running, the team is using it to varying degrees, and nobody can point to a specific moment where it stopped being the answer. It just quietly didn’t deliver what was expected, and now there’s a contract to honor and a decision to defend.

This happens more often than most leadership teams want to admit. And in almost every case, it traces back to the same root cause: nobody defined what success looked like before the purchase was made.

Why Success Gets Left Undefined

Defining success before a software purchase feels like an obvious step. In practice, it rarely happens with enough specificity to be useful.

Part of the reason is that the evaluation process tends to focus on features. The vendor shows a demo. The team asks questions about functionality. Someone builds a comparison spreadsheet. The conversation stays at the level of what the tool can do rather than what the business needs to accomplish. And by the time the contract is signed, the clearest thing anyone has agreed on is that the platform has the capabilities that were demonstrated, not that those capabilities will produce a specific measurable outcome.

In a recent episode of The Fast Slow Motion Podcast, Fast Slow Motion principal account executive Max Bevan framed this as one of the most important questions a business can ask before any implementation: what is the definition of success? How do we know objectively that this was a good investment? What does done look like for this engagement?

Without answers to those questions, there’s no way to evaluate whether the tool worked. The implementation ends, the vendor celebrates the go-live, and the business is left to figure out on its own whether anything actually changed.

What a Useful Definition of Success Looks Like

A useful definition of success is specific, measurable, and tied to business outcomes rather than platform capabilities. It answers the question: what will be true in the business six months from now if this implementation goes well?

That might look like a specific improvement in pipeline visibility, a reduction in the time it takes to follow up with inbound leads, an increase in the percentage of deals that move through each stage consistently, or a clearer attribution model that shows which marketing activities are driving revenue. The specifics will vary by business. What matters is that they’re defined before the implementation starts, agreed upon by the people who will be responsible for achieving them, and measurable enough that everyone will know whether they’ve been hit.

This kind of definition also forces a useful conversation about whether the tool is actually the right solution for the problem. If the goal is to improve lead follow-up speed and the current issue is that reps aren’t logging leads consistently, the problem may not be the platform. It may be the process. A new tool won’t fix an adoption problem. Defining success upfront surfaces that distinction before the purchase is made rather than after.

The Difference Between a Feature Evaluation and a Strategic One

Max made a distinction in the episode that’s worth sitting with. There are two kinds of software evaluations. One is a feature matrix comparison: which platform has the capabilities we need, which one has the best AI tools, which one costs less. The other is a strategic evaluation: what are we trying to accomplish, how does this tool support that, and how will we know if it worked.

The first kind of evaluation produces a purchase decision. The second produces an implementation strategy. And the difference between those two things is significant.

A business that buys software based on features tends to treat implementation as a technical exercise. The platform gets configured, the team gets trained, and the expectation is that adoption will follow. A business that buys software based on a strategic evaluation treats implementation as a change management exercise. The platform gets configured around the process, the team understands why the tool is being introduced and what it’s supposed to do for them, and adoption is planned for rather than assumed.

The first approach produces a lot of expensive underperforming software. The second produces platforms that actually change how the business operates.

Building the Success Definition Into the Contract

One practical way to hold a software purchase accountable to a definition of success is to build that definition into the engagement from the beginning. That means documenting the specific outcomes the business is trying to achieve, getting alignment from the vendor or implementation partner on how the platform will be configured to support those outcomes, and establishing a review cadence that measures progress against them.

It also means being honest about what the business needs to do on its side of the equation. A CRM implementation that’s supposed to improve pipeline visibility requires the sales team to log deals consistently. If that adoption isn’t happening, the tool isn’t going to produce the outcome. The success definition should include the internal behaviors and commitments that are required to support it, not just the capabilities the vendor will deliver.

When a business goes into a software purchase with that level of clarity, the evaluation process changes. The questions asked in the demo change. The criteria for choosing one platform over another change. And the implementation that follows has a much clearer target to aim at.

What to Do Before the Next Purchase

For businesses that are considering a new platform, or reevaluating one they already have, the most useful exercise before making any decision is to write down a specific definition of success.

Not what the tool will do. What the business will look like when the tool is working. What metrics will improve, by how much, over what timeframe. What internal processes need to change to support that outcome. What the team will be doing differently six months from now if the implementation goes well.

That exercise often reveals that the problem isn’t the software. It’s the process behind it. And that’s a much cheaper thing to fix than a platform migration.

Listen to the full podcast episode here.

Related Resources

• The Revenue System That Pays for Itself
• Your CRM Is Expensive and Your Revenue Is Still Unpredictable — Here’s What’s Missing
• The Difference Between a Sales Process and a Revenue System
• How to Build a Revenue System That Holds Up When Growth Gets Hard
• Why Your Best Sales Months Are Hard to Repeat