Customer Indecision: Why Your Enterprise Deals Stall, and How to Unstick Them

I was a recent guest on the Presales Collective podcast, on a problem that drains more pipeline than any competitor ever will. The episode was framed around customer indecision.

That is the symptom. The cause, and the thing I spend most of my coaching hours on, is decision confidence.

Here’s where it all starts.

Value appears only when a buyer connects what you do to at least 1 of those 3 outcomes. Features, roadmap, a beautiful UI, none of it carries value on its own.

Decision confidence is what lets your champion walk into a room without you and defend, to a CFO or a board, why investing now helps their company compete better, operate better, or control risk better.

When this is present, deals move. When this isn't the case, your deals will die at the finish line, no matter how much everyone liked the demo.

That is the common thread for everything below.

01. What has changed about buying, and why indecision kills deals

3 things have shifted recently, and they've compounded.

1. Money has gotten tighter and scrutiny has gone up. Companies still have to grow, every business runs key initiatives across multiple departments, and every one of those decisions now sits under a microscope. Money flows where the attention goes, and when budgets tighten, people jockey for position.
2. The buying committee has grown steadily. With 10+ stakeholders in Enterprise purchasing decisions, expect them all to be lobbying for a slice of the same pie and arguing over which initiatives survive the next round of cuts.
3. The supply side exploded. Building software has never been cheaper. I joined a company in 2020 to find 3 legacy players and 2 serious competitors offering something similar to our software. Two years later, 2 legacy players and close to 25 competitors. Several matched us on features. 3 offered 80% of the capability at 40% of the price.

7 or 8 near-identical vendors in a single deal is now normal.

Put yourself in your buyer's chair. There's no clean choice between an old way and a new way. Many plausible options. Internal politics and budget pressure to navigate.

Transformation projects are still failing at around 70%. And a job potentially on the line for backing the wrong horse. You have sat in that chair yourself. The safest move feels like holding the status quo, or starting small, which stings after you have worked the opportunity for eighteen months.

Here is the part that matters. The real selling happens when you are not in the room. Indecision surfaces there, when your champion cannot defend an investment now and explain why your product helps the company compete, operate, or control risk better.

Result - you're in limbo.

02. Diagnosing value clarity versus organizational friction

Is a stalled deal a value problem or a political one? In most enterprise and upper mid-market deals it is both. They show up as different patterns, and reading them is half the job.

Every company of a certain size runs 3 stakeholder levels.

• Operational people live with the process daily.
• Managers, all the way to SVPs, own the KPIs.
• CxOs own the financial picture.

Value reads differently at each level:

• time for operational
• KPIs and resources for managers
• money for executives.

That maps to WHY, WHAT, and HOW. The executive WHY is how the company competes, operates, and controls risk better. The managerial WHAT is what each department must deliver. The operational HOW is the daily work.

A value clarity problem looks like this. The buyer believes you can improve a process or a dashboard, but cannot connect that to strategic direction or name the metric you will move. They like it. They cannot say why it matters now.

An organizational problem reads differently. People raise priorities, timing, ownership, past attempts that failed. Gartner's May 2025 research found 74% of buying teams experience unhealthy conflict during a decision. That friction has nothing to do with your product. It is internal dynamics and teams fighting over limited budget and attention.

Tell them apart by probing dependencies and pulling other perspectives into the room. What other teams does this touch? Who sees it differently, and why? Why has IT not built it in-house? Sharper context earns sharper questions. The aim is to map how their goals connect to the teams involved, who else is invested or opposed, and how each person benefits from what you do.

03. What actually makes prospects open up

The answer that earns 500 LinkedIn likes is "build trust." Thanks, that helped. Go deeper.

It is what they come to understand about their own business by talking to you. When a buyer sees their situation more clearly than they did an hour ago, they start telling you how things actually work, where the mess is, and what it costs them.

Get there by starting from first principles. Do not lead with what you can do. Arrive having understood what they are trying to achieve and how their processes run today, backed by a point of view from research, experience, and the market. Building that point of view is far easier than it was three years ago, so showing up empty has no excuse.

Then connect the dots up and down the organization. Most teams I coach grasp the operational level well. In 4 deals out of 10 they understand how the work ladders up to a KPI the VP owns. Almost none can see what happens between the VP and the executive level, and that is the dynamic that unlocks the money. You cannot make a credible case for change without it.

Collaborative whiteboarding is the tool I reach for most. You map the situation together. The questioning model I teach AEs and SEs surfaces the dependencies and reveals the one thing you most need to see in a complex deal: the convergence of influence, where the people and priorities that decide the outcome overlap.

This is also where I break with the prevailing advice on personalization. The instinct is to tailor everything to one senior person, and single-threaded teams aim it all at a single director or VP. Gartner's data is blunt about why that backfires. Deals that reach consensus are 2.5 times more likely to be high-quality. Leaders assume tailored content drives that consensus. It does not.

The real lever is relevance to the group: buyers who find the conversation relevant to the whole buying group are three times more likely to report a high-quality deal.

Personalizing hard for one champion underperforms, and it can deepen the very conflict that stalls the deal. Help the committee agree. Do not win one person and hope they carry the rest.

04. Building a business case your champion can defend without you

Let me clear up a misconception first. An ROI calculation or a TCO comparison is not a business case. Those are inputs. They are not the case.

One emotional truth sits under every enterprise decision: the Fear of Messing Up beats the Fear of Missing Out. FOMU over FOMO. The core of an enterprise sale is de-risking.

So here is the definition. A defendable business case is the story your champion carries into a room with a CFO and uses to explain, in plain language, why this investment should be funded now.

The contents follow the 3 levels. Open with the problem and how it aligns to company strategy, the executive why. Name the KPIs, initiatives, and operational constraints it moves, the managerial what. Bring the numbers, and do not stop at ROI and TCO, because CFOs and procurement also weigh Net Present Value, Internal Rate of Return, and Payback Period. Add customer proof. Close with a risk assessment and a change management plan, because the do-nothing scenario and the path through change weigh as heavily as the upside.

Teams get the timing wrong. You do not assemble this the week before close. All of it is the output of value discovery, co-created with the customer along the way. Hand a champion a finished case and they will struggle to defend it, because they never built the conviction with you.

05. How AEs and SEs should actually work together

Sales and presales divide work naturally. The bigger opportunity is not dividing it more cleanly. It is converging on what should be shared.

I will be honest about the culture. Open LinkedIn on any given day and you will find posts ragging on AEs for one thing or another. I am not holier than thou, I have felt that frustration from both sides. It leads nowhere better. AEs and SEs, and CS, Services, and partner teams too, gain far more by working closely.

Before you decide who owns what, agree on what you own together. Understanding the customer's business and the outcomes they need. Uncovering the key stakeholders. Mapping how those stakeholders are held accountable. Knowing who is bought in and who is on the fence or opposed. Building at least a rudimentary financial picture of the customer. All shared.

Who handles orchestration and who runs the technical conversations comes later, and most teams already know how that splits. The mindset shift is the hard part, and it is simpler than it sounds. Teams I work with produce results within two to three months, because a framework gives them clarity on what to solve for.

It is simple, but it is not easy. It needs leadership and vision. The teams that get there fastest have a CRO or VP who already understands this and points their people at the customer rather than the org chart. Get that right and the customer stops experiencing two disjointed conversations and starts experiencing one coherent story of value.

06. The key takeaway: financial fluency

If you take one idea from all of this, make it financial fluency.

Do you understand your customer's priorities over the short and medium term? Do you understand how what you sell moves money into the building or out of it? Every SE, every presales leader, and everyone in the sale should be able to answer that.

Get fluent there, and decision confidence stops being something you hope your champion has. It becomes something you build with them, from the first conversation to the last.

This piece grew out of my conversation on the Presales Collective podcast. Watch the full episode here:

I coach revenue teams to build decision confidence into every deal, and I work directly with CROs, VPs of Sales, and Heads of Solutions Engineering on exactly the problems above. If your best deals are stalling at the finish line, book a consultation and let us look at where the confidence is breaking down.