Playing the sales game like a blackjack dealer

I’m walking into a casino with friends for the first time in almost a decade. The lingering scent of cigarette smoke is familiar but makes me cough. We sit down at a blackjack table. I’m apprehensive because my skills are rusty. I remember the gist of the game, but I’m uncertain of the intricacies like when to split or double.

The dealer shows a 6. I have 13.

Sensing my hesitation, the dealer says “the book would say to stand.”

To my surprise, the dealer helps all of us beat their own hand and win. Waves of confidence wash over me as the dealer offers guidance each hand we play.

Blackjack newbies like myself might initially think the dealer’s goal is to win as much as possible for the casino (their employer). But no, the dealer’s intent is to make you feel comfortable with your own decisions so that you keep playing the game, even if it means the casino loses in the short-term. Because in the long-run they’re more likely to end up winning anyway.

Playing blackjack as a newbie is a lot like being a buyer of business software. While the dynamics of blackjack and business of course differ significantly, both involve decision-making under uncertainty.

In fact, there are so many variables and intricacies that buyers face when making decisions in today’s business environment, I would argue it is harder to be the buyer than the seller. For example, buyers have to navigate:

  • Multiple vendors and options to compare
  • Budget approval and competiting priorities
  • Aligning with other stakeholders and getting executive buy-in
  • Ensuring IT security, legal risk, and industry compliance
  • Presenting a business justification to the CFO
  • Implementation and change management
  • “Will my boss hate me?”

According to a study by 6sense, the average buying journey for a solution consists of 4 external vendors to evaluate and 10 internal stakeholders voicing their opinions.

As marketers and sellers, we can guide buyers in their journey by recognizing these challenges and shifting some of our focus from advertising our products to helping people feel more confident in the choices they’re making, just like a blackjack dealer.

As part of the go-to-market, we know our products’ features and benefits. We know “what” the market is buying from us and why. But how intimately do we know “how” our customers buy? What’s happening behind the scenes during their buying journey?

We might question why a sales deal isn’t moving faster or why a buyer ghosted us. Is it because they chose a different product or is it perhaps because of analysis paralysis or a fear of failure?

While sales enablement is the process of helping sales teams close deals faster, buyer enablement is the art of helping buyers feel confident and comfortable in the decisions they make.

It’s not uncommon for buyers to engage salespeople while having a pre-conceived notion that the seller just wants close the deal and get a commission. Proactively addressing the concerns outlined above can help you position yourself as a trusted advisor. Here are some actions you might consider:

  • Mention common alternatives of your product proactively. Help the buyer feel a sense of control. At the same time, share why your product is different or better. Share advice even if it’s unrelated to your product.
  • Ask questions about their organization’s strategic and financial goals, and identify and how your solution aligns and contributes to its success.
  • Loop in leaders from your own company, such as your founder, and offer to connect your c-suite to theirs.
  • Provide third-party security validation, clear privacy policies, and transparent terms and conditions.
  • Document a business justification collaboratively with your point of contact using both quantitative metrics (ROI) and qualitative anecdotes. Help your point of contact manage up.
  • Provide written checklists for deployment, and offer implementation assistance and training, both remote and onsite.

By adopting a mindset similar to that of a helpful blackjack dealer—by setting aside the “deal” and empathizing with the complexities that buyers have to navigate—we can replace apprehension and fear with confidence and comfort in the buyer’s decision-making process.

Transparency, empathy, and unbiased guidance can go a long way in earning trust, keeping buyers at the table, and building a lasting relationship where everybody wins.

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