Complex B2B Sales is analogous to high stakes poker games. Full Disclosure: I love playing on line Texas Hold’em. My winnings are now at $575M. I started with $5K in free chips and haven’t paid anything for any additional chips. I often joke with my wife after a good day at the WSOP virtual poker table that we need to go to Las Vegas.

The single most important common denominator between the two is constantly assessing your odds or the probability of winning the hand or the deal. Math is simply fundamental to your success in poker and sales.

What are some of the key traits and attributes that make for a great poker player or a great high tech sales rep?

Patience: Complex B2B Sales (aka Enterprise Technology Sales) and poker require an. incredible amount of patience. In poker, you must play the hand/cards that you’re dealt. Often it can be quite frustrating in Texas Hold’em to stay patient when you’re constantly getting dealt crappy “hole cards” (the first two cards dealt to each player that only the player can see). You’re a competitor, you want to compete, bet, and win the pot.

In sales, the exact same challenge exists. It is incumbent on great sales reps to qualify out or fail fast. Great salespeople are highly competitive and hate to lose. And the bigger the stakes (e.g., the larger the deal size), the higher the desire to win. This is coupled with the fact that there is tremendous pressure on salespeople to build their sales pipeline and win the deal which brings in the revenue.

Discipline: Adhering to a qualitative process is paramount to your success in sales and poker. The parallel is having an Ideal Customer Profile (ICP) that delineates in great detail the demographic, company graphic and technology graphic data where you have a high probability for sales success.

In poker, you need to know the different winning handstrengths. As poker players, we all aspire to get a Royal Straight Flush hand that beats every other hand. Remember the importance of knowing the odds/probability?The odds for actually getting a Royal Straight Flush in Texas Hold’em is approximately 1 in 650,000.

Discernment: In my not so humble opinion, the most important skill that all great salespeople have is their ability to discern from their discovery process with customers. They are constantly trying to divine with the customer why their solution is the best fit for the customer’s needs. And they are sober and honest with themselves when they divine that they are not the best fit for the customer and qualify themselves out of the deal.

The same logic applies in Texas Hold’em. As the”community cards” (e.g., those dealt face up so all players at the table playing can see and use them in their hands) are rolled, the great poker player starts discerning what the odds are that they have a winning hand or not. And they are sober and honest with themselves when the probability of winning the hand is really low, they’ll fold their hands and cut their losses short.

Bluffing does not work in the long run: Smart customers in sales and smart players in poker will eventually call your bluff. You’ll lose the hand and the deal should you insist on trying to bluff your customers/poker players. And salespeople will likely lose their jobs if they insist on trying to bluff themselves and their bosses. As a long time Complex B2B Sales leader, I can personally attest to the fact that successful sales people are always honest and fully transparent about the status of winning a deal.

Marginal and poor salespeople think that by having happy ears and telling their Head of Sales that they are going to win that deal this quarter will make their bosses happy. And they would be… Dead Wrong! That’s the fast track way to getting yourself fired in sales.

Being a perpetual student of the game: One of my Cybersecurity clients CRO/Head of Sales would come to every new hire sales onboarding bootcamp that we developed and delivered and welcome them to the company with a thirty (30)minute talk. He never used slides and would just sit at the front of the training room and answer his new sales team hires questions. The #1 question that each new sales hire cohort would ask him was what was the single most important thing that he observed to be successful selling for his company.

He would always say the single most important thing that he observed in his top performing salespeople is that they were all obsessed with being a perpetual student of the game. He would go on to say that what he meant by that was that they would learn more about their customers and their customer’s business than any competitor salesperson would. Great poker players are always looking to up their game and yet are humble enough to learn from other great poker players.

There are huge ebbs and flows in the process: There are only four rounds of cards being dealt in Texas Hold’em. But each round of cards being dealt changes your probability of winning substantially. Just because you were dealt a high pair in your hole cards… does not mean that when all of the community cards have been dealt that you still have a winning hand.

The exact same logic applies in Complex B2B Sales. In an enterprise technology sales process, there are lots of different meetings/interactions with different key stakeholders. And they each have different agendas, priorities and things that are important to them. That’s why the average sales cycle length associated with a net new logo Complex B2B Sale can be 9-12 months.

Great sales teams conduct a post-mortem after every single customer interaction and re-qualify what their probability is of winning or losing.

Look for the blind spots and risk: In Texas Hold’em, I’m constantly monitoring with each community card that is dealt whether another poker player at my table could possibly have a straight or a flush. When that fifth community card is dealt face up, many times another poker player at your table just hit a straight or a flush that will beat your hand of three Aces. I’ll write another blog post on why I think three of a kind or trips should be ranked higher than a straight in poker someday soon.

Great salespeople are constantly monitoring the strength or weakness in the deal as they’re engaging with new key stakeholders, key influencers and decision makers. They are always on the lookout for deal. blockers or key stakeholders that prefer a competitive product or simply don’t like their sales team.

Good Selling!