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Why Your Sales Team Needs Situational Awareness and Selling Skepticism

Why Be a Selling Skeptic

Prospects are engaging sales professionals significantly later in a buying cycle, no doubt due to the proliferation of digital content marketing, highly immersive and AI-enabled websites, and direct off-channel references and review sites. This makes it more difficult for the less experienced sales professional to inform and influence a purchase decision.

More often than not, once a prospect has identified a business issue, considered options with their stakeholders, received at least tacit budget and resource approval, and made decisions about how to proceed—all before a salesperson has made their first presentation—it is quite difficult for that salesperson to convince a buyer to retreat in their buying process and reconsider decisions already made. The buyer controls the sales process, and the sales professional is resigned to compete on feature/function, price, and references. Today’s sales methodologies tend to ignore these realities in a buyer’s digital-first journey.

Another lens through which to view this conundrum is to understand that a prospect invests in solutions under only three possible business scenarios: 1) Run the Business, 2) Grow the Business, 3) Transform the Business. The sales professional must then view every opportunity in their pipeline with these scenarios in mind.

Having Situational Awareness

If a sales executive is selling to a net new logo, where they don’t already have an established business relationship, then by definition the sales campaign must be different than a campaign targeting an existing customer relationship. Likewise, if the prospect already has a solution, even with an identified business, technical, or personal pain, the seller needs to consider which prospect business scenario they are approaching. Add-on and upsells to existing clients are no different, and may have the extra burden of vendor fatigue, which the account manager will need to consider in their strategy. However, too many sales methodologies, with their various tactic and strategy terminologies, fail to differentiate between these playing fields. One-size-fits-all sales processes don’t account for the three scenarios mentioned above.

Sales executives, and by extension sales leaders, need to have a situational awareness capability in their selling tool bags. Without understanding their buyer’s situation, they will often be unaware of the dynamics in the prospects’ decision making, and thus will miss forecasts, lose deals they could have otherwise won, and ultimately will be average in their chosen profession.

Quality Over Quantity

When a prospect buys from a seller, they are making a personal commitment, at some level, to the seller, which may impact the buyer’s career. If the buyer is attached to a successful solution implementation, they grow their own credibility, influence within their organization and career prospects. (This is not the same as a purchasing agent buying a solution, who’s own credibility is about gaining favorable terms and decreasing spend.) This can be greatly magnified in the cases where the land-and-expand revenue strategy originates from the seller, when the second purchase can be 2-3x the initial order. In high-volume, transactional selling models, where it takes just a few meetings to make the sale and move on, it likely is quantity over quality.

Thus, the quality of the seller’s deal cycle, vs. the quantity of deal cycles, can be a better gauge of the seller’s skills, than other less obvious metrics. Sellers who can implicitly identify value, both to the buyer and to the vendor, tend to be the sellers who consistently overachieve. The sales metric which best reflects quality over quantity is forecast accuracy.

The reality in today’s digital selling world is that buyers (and influencers) engage at different times with sellers—and for different reasons. Some are researching, others are executing a buying plan, and some have too much free time. Sellers who can make a qualified determination (and have situational awareness) sooner rather than later in a deal cycle will have a more value-oriented and quality pipeline than their peers. Put another way, quality is not just ROI or dollars saved, but can have a personal impact on the various influencers in the buyer’s and seller’s respective organizations.

When a Deal Is In Process

Once a decision is made (not whom to buy from, but to fund a purchase), often without the influence of a sales professional, sourcing a solution and managing an implementation project is often delegated down to a manager or director level. It often comes with a list of criteria the manager, who self-identifies as The Decision Maker, is expected to follow as they evaluate potential solutions and vendors. When a sales professional receives an unsolicited RFP, for example, they know they are already quite late to the buyer’s playing field.

64% of SaaS and technology buyers report that this is when they actively engage salespeople. And almost half of these buyers only contact sales to request a proposal, feeling they already have all the information needed to make a decision, not wanting to be ‘sold’ to and take precious time from their work associates. The clear implication is that the sales professional will struggle to have the strategic discussion with an executive, even though their company sales process requires them to do as such. Not to mention the expectation from their sales leader, who always asks if they have met with the decision maker. The sales professional is squeezed between the buyer’s buying agenda and the seller’s selling playbook.

When the delegated-to buyer does engage with a sales professional, it’s often round-robin with at least three vendors. In today’s remote-first work environment, it’s a Zoom meeting with multiple people, who may or may not be paying attention. The sales professional is not developing a personal relationship, which they often feel is their own secret selling sauce. The buyer, on the other hand, perceives everyone can compete fairly, and they feel they are doing their best on behalf of their company by creating competition and driving down the price. The buyer feels they already know what they want, and why they want it, all without the influence of multiple sales professionals confusing the issue.  

The average sales professional who engages with an opportunity at this point will only have a 1 in 3 chance in winning the deal. Worse, their forecast will often slip from the close date the buyer says they must buy, and inevitably the deal value will shrink over time. Buyers today are very sophisticated and know well that SaaS software selling is very time bound. This always works to the buyer’s advantage, when the seller has not been able to establish the business value of their solution to the executive driving the purchase. (Don’t confuse the buyer with the executive driving the purchase, as they are most often not the same people.)

Open the Escape Hatch or Retrench

Every sales professional runs into these sorts of scenarios, there’s just no way around it with today’s vast digital marketing capabilities. The very best sellers are completely honest with themselves, and reflect this thorough deal examination in their deal reviews and forecasts. They are skeptics, with a keen sense of emotional distance (which is quite difficult, because most sellers have a very high Emotional IQ.) Just the same, the very best sellers can determine, with the help from their leaders, if they are likely to win and maintain favorable deal terms, or should consider losing sooner and moving on. Not every deal is worth the sales professional’s time and energy. Some opportunities are best considered with an eye toward getting out sooner than later, while the quality opportunities, where the sales professional has evolving situational awareness, healthy skepticism, and the customer’s personal value identified, are where the time should be invested. Value is not just ROI or dollars saved, but can be personal impact to the various influencers in the buyer’s and seller’s respective organizations.