A few months ago, we were in the last stretch of a deal with a large manufacturer. Two of us left in the room, us and a competitor with a product most analysts would call slicker than ours. By the old playbook, this was theirs to lose. 

What turned it was not the demo. Before that final meeting, my team had pieced together what the buyer’s environment actually looked like: a tangle of aging operational technology sitting next to a cloud migration that was only half done, and a recent acquisition that had quietly doubled the number of unmanaged devices on their network. Nobody on their side had spelled this out for us. We had done the work to understand it anyway. 

So instead of walking in with a polished demo of a clean, imaginary environment, we walked in with a view of what their first ninety days would realistically look like given the mess they were actually living in. The competitor showed up with a beautiful product tour that could have been for any company on earth. We won. Not because our product was dramatically better, but because the buyer did not have to spend three meetings teaching us about their own world before we could be useful to them. 

I have thought about that deal a lot since, simply because it is not an isolated story. It is the shape of how enterprise buying now works.

The Market Is Growing and Getting Harder at the Same Time

Here is the part that confuses a lot of revenue leaders. By every top-line measure, this should be a good time to sell enterprise software. Gartner’s latest IT spending forecast puts worldwide software growth at approximately 15 percent in 2026, with total software spend crossing $1.4 trillion.  The budget is there. The slowdown everyone braced for did not arrive. 

And yet most of us are watching deal cycles get longer, not shorter. There are more stakeholders in every conversation. Procurement, security, and IT operations all have a seat at the table now, and each of them arrives with their own questions. The money is flowing, but it is harder to earn than it used to be. 

That tension is the whole story. Spend is up, but the bar to win a piece of it has moved. 

The Question Has Changed

For most of my career, the central question in an enterprise deal was some version of “Can we close this?” You built the relationship, you ran a clean process, you showed the product in its best light, and you managed the path to signature. 

The question now is different. It is “Do we understand their environment well enough to earn the deal?” That is a harder question, and it is the one that actually predicts who wins. 

Buyers have changed because information has changed. The people across the table show up to a first meeting having already read the analyst reports, watched the comparison videos, talked to peers in their network, and formed a point of view. They often know our product, and our competitors’ products, better than we assume. What they do not need is another vendor explaining features. What they are quietly testing is whether we understand their reality well enough to be trusted with it. 

I have started to think of it as a shift from product and relationships to context and credibility. Relationships still matter, and product still matters. But they are table stakes now. The differentiator is whether you can demonstrate that you understand the specific environment the customer is operating in, before they have to explain it to you. 

Context is the new edge. The vendors winning the hard deals are not the ones with the best pitch. They are the ones who show up already knowing what the customer’s world looks like, and can speak to it without being walked through it. 

Why This Is Uncomfortable for Most Go-To-Market Teams

The discovery call that felt thorough five years ago can now feel like homework we skipped.  

The honest problem is that most of our sales motions are still built for the old question. We measure activity, pipeline coverage, and stage progression. We coach reps on discovery questions designed to get the buyer to describe their environment to us, in the meeting, on our timeline. 

But increasingly, the buyer expects us to have done that work already. Asking them to narrate their own infrastructure can read as a sign that we have not bothered to understand them.  

That does not mean discovery is dead. It means the center of gravity has moved earlier. The understanding has to exist before the conversation, so the conversation can be about what to do, not about what they have. 

This is genuinely hard. Enterprise environments are messy, hybrid, and changing constantly. Knowing what a prospect is actually running, rather than what they say they are running, is not a soft skill. It is an information problem. And the teams treating it as an information problem, something to be solved deliberately rather than improvised in the room, are the ones pulling ahead.

The Question Worth Asking Your Team

I am not going to pretend I have fully solved this. We are still rewiring parts of how we sell around it. But I am increasingly convinced it is the right thing to be rewiring around. 

So here is the question I would put to any enterprise sales leader reading this, and the one I keep putting to my own team: How well do we actually know what our prospects are running, before we ever walk into the room? 

If the honest answer is “not as well as the buyer expects,” that is not a small gap. In 2026, it may be the gap that decides which vendors get a share of all that growing spend, and which ones keep losing deals they thought were theirs to win.