Lessons from Chess: why sales people need to think ahead


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When we observe a chess grand master in action (or an expert in any other similar strategy-based game), it quickly becomes apparent that they are not merely living in the moment but thinking several moves ahead. Pursuing the most obvious immediate move could store trouble up for the future.

The same, of course, applies to selling. The best sales people pursue long-term strategies – and they also give themselves options that allow them to anticipate and adapt to their prospect’s future behaviour.

Perhaps the best example of this is how top sales people adapt their strategies to their entry path into the prospect. There are really two fundamental paths: top-down and bottom-up, and the strategies that need to be adopted vary significantly between the two.

Of course, there’s an argument that you always want to enter an account from the top down by engaging directly with the ultimate decision maker from the start. It’s an approach that has been the subject of dozens of sales self-improvement books, but the reality is that even the smoothest of sales people often struggle to get an initial audience directly with a C-Level executive.

And as we’ll discover later, if sales people fail to plan ahead, the potential created by that initial senior-level conversation could easily get stuck in the mire of being delegated to a bunch of the prospect organisation’s “experts” who inevitably get asked to look at the idea in more detail.

There’s a different challenge involved when sales people enter below the level of the ultimate decision making authority. Sooner or later they are going to have to navigate a path to power – and it’s normally best to do so with the full support of their initial contact rather than risking conflict by trying to go around them.


Just like a chess grand master, successful sales people need to be thinking ahead, regardless of the initial point of contact.

Here’s how a successful C-Level first contact typically pans out: the executive is persuaded that the idea is worth looking at, but concludes that a detailed evaluation needs to be undertaken by their technical or operational experts elsewhere in the organisation.

Being delegated with a mandate can of course be very powerful, but if it is not properly negotiated up front this often leads to the project rapidly losing momentum. It’s probable that the “experts” will end up looking at the new idea through the lens of their current experience – and this is not always a good thing.

These expert evaluators often resent change being foisted upon them. They often lack the “Big Picture” perspective that got the C-Level executive so enthusiastic in the first place. And they often find it easier to identify reasons why the new idea wouldn’t work within the organisation’s existing environment.

This happens far more often than the “Selling to C-Level” evangelists typically like to acknowledge – but it’s a practical and all too-common consequence of adopting a top-down approach without planning ahead.

Faced with this predictable risk, experience suggests that the sales person must accomplish two critical things when their C-level contact suggests that the next step should be to meet other members of the prospect organisation:

  1. Pre-negotiate the sales person’s right to loop back directly to the C-Level contact once the conversation with the delegates has taken place, and
  2. Set the C-Level’s expectations that it would not be uncommon for his experts to at first report back that they have no need for the solution or that it would not be a good fit, explain that this is usually a function of the expert not necessarily seeing the “big picture”, and agreeing that the dialogue can continue regardless even if this is the initial response

Thinking ahead is also required when entering below the ultimate decision making authority. The goal here is help the initial contact see that it is in their own enlightened self interest to help the sales person navigate to the ultimate decision making authority and to the rest of the decision making team.

It’s usually easier to achieve this once an initial relationship of trust has been established with the initial contact. After that point has been reached, the agreement may flow naturally – but there are a handful of effective techniques that can be applied if it become apparent that a little encouragement might be necessary.

One particularly effective approach is to ask a series of business implication questions that are self-evidently relevant to making the case for change, and yet which the contact is unlikely to personally know the answers to.

Another useful approach can be to share stories of other similar projects, and to explain how the champions’ chances of success were dramatically enhanced by getting the executive and decision making teams on side.

No doubt there are other strategies that will work in your own specific sales environment. The key to making these “think ahead” strategies work is to identify what has turned out to be effective in your own organisation – and to identify the things your sales people wished in retrospect they had known or done to turn around a losing situation.

Gathering these collective experiences together, and coaching every sales person in how to apply them, can help to eliminate some of the most common avoidable errors in managing sales situations. If your sales people anticipate the future, and adapt their sales strategy accordingly, they can help to shape it. But if they only ever live in the here and now, they are likely to remain hapless pawns in somebody else’s game.

Republished with author's permission from original post.

Bob Apollo
Bob Apollo is the CEO of UK-based Inflexion-Point Strategy Partners, the B2B sales performance improvement specialists. Following a varied corporate career, Bob now works with a rapidly expanding client base of B2B-focused growth-phase technology companies, helping them to implement systematic sales processes that drive predictable revenue growth.


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