Thinking about what could go wrong…


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Let’s face it, many (maybe most) “average” sales people seem to be incorrigible optimists. When assessing their chances of winning an opportunity they tend to err on the positive and anticipate the good things that they hope will happen.

But I’ve concluded that many top sales performers behave quite differently. Whilst confident in their abilities, they are much more inclined to anticipate what might go wrong in any sales situation, and to take proactive steps to mitigate the risk.

It’s hard to avoid the conclusion that it’s actually far easier and more productive to systematically identify and eliminate the risk factors in selling than it is to strive for “sales perfection” (whatever that Nirvana-like state might involve) …

The idea of eliminating avoidable errors is one of the key themes in Atul Gawande’s “The Checklist Manifesto” – the subject of a BBC Reith Lecture a few years back, and a book that I regularly refer to for inspiration.

Gawande is a Harvard Medical School professor, and at first glance his experience appears primarily relevant to the world of medicine and in particular to securing better patient outcomes. But it’s obvious that his findings have a far wider applicability.


He demonstrates how the use of simple checklists help to ensure that avoidable errors are systematically identified and eliminated. And I think it’s pretty clear, if surgeons and airline pilots with decades of experience are prepared to be guided by best practice checklists, that even the most experienced sales people (as well as the less competent ones) could benefit as well.

It’s obvious that some circumstances are completely beyond our control – even if some of them are, in fact, predictable. But in the remaining circumstances where we have some measure of potential control or influence, Gawande identifies two forms of error.

The first are errors of ignorance – we may fail because we only have a partial understanding of how the world works. The second form of error is “ineptitude” – the knowledge (or accumulated wisdom) exists, but we fail to apply it.

These errors of ineptitude are inherently avoidable, and yet we succumb to them more often than we would be happy to admit. We might not have personally been exposed to them, but our colleagues have and may have worked out how to master them.

Don’t get hung up by the term “ineptitude”. I don’t any of us likes to think of ourselves as being inept, but if we fail to learn from and apply the collective wisdom that exists within our organisation and amongst our peers the accusation actually strikes me as being a reasonable one.


That’s why I believe it is so powerful for organisations to collectively learn what can and often does go wrong in otherwise promising sales situations, and to collectively brainstorm and apply the most effective ways of eliminating, mitigating or avoiding these errors.

No-one thinks it is remotely sensible to continually repeat the same mistakes – and yet that is what most sales organisations of any significant size seem to do on an ongoing basis, unless they have embraced a collective approach to error avoidance.


Here are a just a few of the ways in which an apparently promising sales cycle can go badly wrong:

  • Failing to target the right organisations (or to even define what an “ideal customer” looks like)
  • Failing to target the right people – the potential power sponsors
  • Failing to recognise that our primary contact is not a power sponsor
  • Pursuing enquiries as if they are qualified opportunities
  • Failing to establish a clear problem/solution fit
  • Failing to recognise that an organisation is unlikely to buy from you
  • Failing to identify a clear economic case for change or a source of funds
  • Failing to establish urgency, or to recognise that it does not exist
  • Failure to identify, assess and engage all the stakeholders
  • Failure to understand the prospect’s decision criteria
  • Failure to understand the prospect’s decision process
  • Underestimating the competition
  • Failing to understand the priority of the project
  • Allowing things that you feel are wrong to go unchallenged

These are just the generic errors. No doubt there will be specific ones that are particularly relevant to your sales environment. No doubt some of your sales people will have learned (often through trial-and-error) how to recognise them, and how to deal with them.

Some may be challenges that everyone seems to struggle to master. But there’s no great merit in leaving these things to trial and error. The power of collective wisdom and experience must be allowed to prevail.


So here’s what I strongly suggest that you do…

Evaluate your recent wins, losses and no decisions, as well as your current sales opportunities. Encourage your sales people to look back and acknowledge where they now recognise that deals went wrong – where they were delayed, lost or where things simply didn’t go as planned.

As them to openly acknowledge and share their “if I knew then what I know now” moments, and ask them what they could and would have done differently if only they had known. Even amongst your top performers, I’d be worried about the apparent lack of self-awareness of any sales person that cannot recall such moments.

Individually and collectively, explore what they believe they could or would have done differently. Encourage them to suggest the questions they could have asked and the things they could have done to identify and eliminate these errors.


I realise that this approach must seem like an anathema to the remaining traditional sales organisations that thrive on a macho, no self-doubt, “always be closing”, “take that hill” culture, but I doubt that anyone that subscribes to that sort of thinking would have stuck with this article to this point.

But if you are striving to build a collaborate, collectively learning sales organisation, asking the question “what could go wrong?” could prove to be one of your most effective ways of systematically improving sales performance.

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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