The Two Buying Journeys Every B2B Sales Leader Must Understand

Not all complex B2B purchases are created equal. Yet many B2B sales organisations treat every opportunity the same way, applying a single methodology regardless of what's actually driving the customer's decision. This fundamental disconnect explains why so many seemingly well-qualified deals stall, why forecasts remain stubbornly inaccurate, and why sales cycles appear to be frustratingly unpredictable.

After analysing hundreds of complex sales engagements and reviewing the latest research into B2B buying behaviour, a clear pattern emerges: there are two fundamentally different types of B2B buying journeys, each governed by different psychological drivers and requiring distinctly different sales approaches.

Understanding this distinction isn't just academically interesting - it's operationally critical. Get it wrong, and sales organisations watch winnable deals disappear into "no decision" limbo or lose inevitable purchases to competitors who better understood what the buyer actually needed.

The Two Buying Contexts

Let me introduce two terms that capture this essential distinction: inevitable purchases and discretionary purchases.

Inevitable purchases are those where circumstances mean the customer must do something. Unavoidable internal or external forces such as regulatory compliance, technology end-of-life, supply chain disruption, contract expiration and so on create a compelling trigger event with profound consequences. The classic example remains Y2K: organisations faced a specific date when their systems might fail if they didn't act. The decision wasn't whether to do something, but what to do and with whom.

Discretionary purchases, by contrast, are improvement-driven. There is no internal or external force that will compel action. The customer could decide to do nothing and stick with the status quo indefinitely without immediate catastrophic consequences. The value proposition is based on future gains rather than avoiding mandated change.

This isn't about deal size or complexity - both types can involve seven-figure investments and year-long sales cycles. The distinction is about what's driving the purchase decision.

Why This Distinction Matters: The Psychology

Inevitable and discretionary purchases are driven by profoundly different buyer psychology, which in turn demands fundamentally different selling approaches.

In inevitable purchases, the customer has already answered the "why change?" question. Critical changes in the customer’s circumstances have done that work for you: a regulatory deadline looms, a critical system reaches end-of-support, or a supplier announces they're exiting the market. The decision to act is inevitable; the question becomes which solution and which vendor.

This means the buyer's primary fear isn't whether to change - it's making the wrong choice. They're anxious about implementation risk, vendor reliability, and solution fit. Research published in Dixon and McKenna's The JOLT Effect reveals that once purchase intent is established, customers care far more about not failing than about succeeding. They're scanning for reasons to doubt each option.

The psychological driver here is choice paralysis. With 11 stakeholders in the average B2B buying group (according to multiple sources) and 74% of buying teams experiencing unhealthy conflict (Gartner), these groups struggle to reach consensus even when they know they must act.

In discretionary purchases, the entire dynamic flips. Here, the customer hasn't yet concluded they have to change. They might acknowledge a problem exists, but they often also believe - rightly or wrongly - that maybe they can afford to wait. The status quo can be sustained for the moment, even if it's costing them money or competitive advantage.

The buyer's primary fear is making any change at all. Loss aversion - the psychological principle that losses loom twice as large as equivalent gains - dominates their thinking. They focus heavily on what could go wrong: "What if this disrupts our current operations?" "What if we can't get adoption?" "What if the vendor overpromised?"

This is compounded by what behavioural economists call defensive decision-making. B2B buyers typically believe the negative risk of a failed decision falls to them personally, while positive rewards accrue to the business. This risk-reward gap drives them to select the safest option for themselves (doing nothing), rather than the best option for the organisation.

The Buying Journey Differences

These psychological differences create distinctly different buying journeys.

In inevitable purchases, the journey is compressed and comparative:

• Recognition happens quickly - the event triggers awareness across the organisation almost simultaneously.

• Solution exploration becomes intense and parallel - the buying team researches multiple vendors at once, sometimes deferring first active contact with sellers until they are already well advanced through their journey and have a shortlist largely predetermined.

• Vendor evaluation dominates the middle of the process. Multiple stakeholders scrutinise options, often creating gridlock. Gartner reports that buying groups that reach consensus are 2.5 times more likely to report high-quality deals, yet most groups struggle to achieve that.

• Selection and risk mitigation become the final battleground. The purchase experience - how you make buying feel safe - becomes the primary differentiator. Challenger research confirms that purchase experience quality remains "by considerable distance" the most important factor in both winning deals and driving customer loyalty.

• The timeline is externally paced: there's a deadline, even if exact timing remains fluid.

In discretionary purchases, the journey is extended and sequential:

• Problem awareness can take months. The buying team may not recognise a significant issue exists, or they underestimate its impact. Research reveals that buyers change their problem statement an average of 3.1 times during complex purchases, and misalignment exists more often than not in how sellers and buyers perceive the core problem.

• Urgency development must follow problem awareness. Even when buyers acknowledge an issue, they rarely believe they must act now. This is where most discretionary deals die. The JOLT Effect research found that 40-60% of deals end in "no decision" - and 56% of these losses stem from buyer indecision, rather than a strong preference for the status quo.

• Solution exploration only begins once the first two stages succeed. And here's the crucial point: the vendor who shaped the buyer's understanding of the problem holds a massive advantage. Forrester's research on buyer behaviour confirms that 48% of first-time buyers enter their process with a preferred vendor already in mind - and more than nine out of ten ultimately purchase from a vendor on their initial shortlist.

• Justification and approval brings a dangerous moment: stakeholders revisit whether they really need to act. The flames of urgency that seemed so bright weeks ago now look more bearable. Other priorities compete for attention and budget. This is when weak deals collapse.

• The timeline is internally paced: elastic, frequently delayed, often abandoned.

The Four Questions Framework

The distinction between inevitable and discretionary purchases fundamentally changes how we must answer four critical questions that every complex B2B buyer must resolve:

Why change? (Why should we abandon the status quo?)

In inevitable purchases, this question is already answered by clear trigger events. In discretionary purchases, this is the salesperson’s primary initial task - and if they can't answer it compellingly, nothing else matters.

Why now? (Why should we act with urgency?)

In inevitable purchases, the timeline is externally imposed. Your role is to respect it and prevent rushed decisions that lead to buyer's remorse. In discretionary purchases, urgency must be constructed by helping buyers recognise that every month they delay results in escalating cost or risk.

Why you? (Why should we choose your solution?)

In inevitable purchases, this often appears to be the primary battlefield - vendor differentiation dominates. In discretionary purchases, this question is secondary. If you managed to successfully create a compelling case for change, you've already won half the battle.

Why trust? (Why should we believe you'll help us succeed?)

In inevitable purchases, trust centres on execution confidence and risk mitigation. In discretionary purchases, trust has two phases: first, "Can I trust your diagnosis of my problem?" and only then, "Can I trust your solution?"

The Critical Qualification Question

Here's where this becomes immediately actionable: the most important qualification question you can ask in any complex sale is which type of purchase you're facing.

If it's an inevitable purchase, you know that:

• The sale is being driven by a compelling trigger event or trend
• Your competition is other vendors, not inaction
• Your focus must be on confidence-building and risk mitigation
• You should apply JOLT-style approaches from first contact

If it's a discretionary purchase, you know that:

• Establishing a compelling case for change must be your first priority
• Your competition is the status quo, and not just other vendors
• Your focus must be on problem awareness and urgency before solution positioning
• You must qualify rigorously: if no compelling reason to act exists or can be created, you should move on

The Inconvenient Truth

Most B2B sales organisations don't make this distinction. They treat all opportunities identically, applying generic "complex sale" methodologies that were typically designed for inevitable purchases (with built-in urgency) to discretionary opportunities (where urgency must be created).

This explains why:

• Discretionary deals stall at 40-60% despite high engagement
• Inevitable purchases go to competitors who generated greater buyer confidence
• Forecasting remains unreliable - engagement doesn't equal commitment
• Sales cycles become unpredictable - two fundamentally different dynamics

The research is clear: buyer psychology, journey dynamics, and required seller capabilities differ profoundly between these two purchase types. Understanding which journey your customer is on isn't optional insight - it's foundational intelligence that should shape every aspect of how you approach, qualify, and advance every opportunity.

In my next article, I'll explore how sales organisations must adapt their approach, capabilities, and measurement systems to win in both contexts. Because applying the wrong methodology to a buying journey isn't just inefficient - it's the fastest way to lose deals you should have won.

This article was originally published on LinkedIn