Are You an Enterprise Sales Grand Master?

Are you a sales grand master?  Could you be?

I love the stories of the chess master that can look at any set of player positions in a game and instantly know the best next move.  This is because they have seen (and remembered) thousands of board patterns, and the patterns that might follow the current one.

There is a lot of discussion about AI systems that can recommend to sellers the “Best next action” for their deals.  (Full confession - I’ve joined the crowd and am building one - more on that in a later post.)  The problem is that opportunity strategy is not as easy as chess.  And it’s not just twice or four times more difficult; it’s 10 or 100 times harder.  Checkout “Range” by David Epstein and his references to “kind” vs. “wicked” environments, and the fact that most of real life is not chess,  it’s much, much more complex.  Chess grandmasters have as many as 30,000 patterns memorized (of billions of possible moves).  But how many patterns are possible in a 9 month enterprise sales process, with on average 5.7 decision-makers and untold number of influencers on the buying side, and a similar number helping each selling team, plus partners, consultants, and old friends the CFO sees at dinner parties the night before they’re supposed to approve the PO that mention the great competitor that hasn’t even been considered!?

Trust me, I wish enterprise sales was like chess - an environment with rules, boundaries, a limited number of players with a limited number of allowed rules, an ordered process with clear starts/stops and a continually transparent scoreboard.

But, it’s not.   In fact, it’s the opposite - which is why I find it so hard, and frustrating - and amazingly fun.  But, if you’re paying attention to AI, there’s a lot being written about AI replacing enterprise sellers.  Actually, all sellers.  Apparently we have - at most - 5 years.  (If it’s any consolation, consultants only have 2.)  

I do believe that AI will take over a lot of tasks we do.  And will be a great thought partner on many others.  But I don’t think it will be able to think through all the options and patterns, and  instinctively know “we’re winning” or “we’re not” at the same level as an “enterprise sales grand master” (if there is such a thing).   And that is the actual issue.  Not everyone is at that level.   And an AI that was at 50-75% of that level would be really helpful. It would at least remind us of a few patterns and options we hadn’t considered - because if nothing else, they are complete (if you haven’t experienced this, pick one deal and put all your docs and call transcripts into Gemini Deep Research and ask for advice.).

But the opportunity we now have is to become a sales grand master - faster and at higher level than ever before.  We’re not because most of us don’t spend enough time thinking about deal strategy. We don’t step back, clear our head, draw everything we know on a whiteboard or scratch pad, and force ourselves to game out 10 or 20 different scenarios, and how we might respond, or take advantage of them.  Instead, we fiddle with our decks, update our call notes, argue over sales stages, rescore MEDDPICC, whatever.  And we rarely do this with just one or two other people on our team.  I believe one of the greatest breakthroughs AI could give us - if we use it properly - is doing all the menial tasks to free up our time to do the strategic thinking we’re not doing now.