An immutable enterprise sales fact: The larger the size of the deal, the higher the likelihood that it will go south or completely off the rails.  It’s not really a question of “if” your enterprise deal will go off the rails at some point during the sales campaign, rather it’s a question of “when” and “how many times” and how do you recover.

Let’s start by examining common reasons why there is a distinct correlation between the size of the deal and the likelihood that it goes off the rails or simply never comes to fruition.  It starts with the budgetary amount involved in the purchase of your solution.  The higher your solution cost is to the customer, the corresponding higher level of access to power that you will need to get involved in the decision and approval process.  Yes, the dreaded and feared Fortune 1000 company C-Level executive!   The challenge lies in the fact that most F1000 C-Level execs can only focus on 2-3 strategic multi-year initiatives at a time.

The epic sales failure is deluding yourself, your sales team and worst of all your sales leadership that your solution is well aligned to a customer’s strategic initiative when it isn’t.   How do you avoid this costly mistake from derailing your deal?  Ask the executive sponsor of the strategic initiative (e.g., CIO, CTO) how they would envision your solution fitting in to the overall solution and initiative that they are working on.  The follow up by asking the exec sponsor if they believe they can accomplish their overall strategic initiative without your solution as part of it.

The next common cause for large deals going south or never coming to fruition is that the sales team didn’t adequately address the risk.  There is a delicate risk-reward ratio involved with any technology solution decision.  All too frequently, marginal sales teams either don’t know how to address this properly or are afraid to bring it up.  That bell you hear ringing is the sales death knell that accompanies the enterprise sales campaign that didn’t properly address the risk with their customer.  There are various kinds of risk that you need to think through if a strategic initiative fails.

There are a diverse set of risks that customer consider when making an enterprise decision, such as personal risk, professional risk, financial risk, brand risk, scale, security, user adoption, etc.  Put yourself in the customer’s shoes and ask yourself relative to the overall strategic initiative, how can your solution and company help reduce the various key areas of risk for the customer and their key stakeholders. Then educate them as to how your solution and company will help them mitigate risk.  Don’t be that sales team that makes the excuse that the reason the deal never happened is that the decision maker or exec sponsor was gutless and afraid to make a decision.  Any good sales leader will hear that and know that 9 times out of 10 that means the sales team failed at addressing the key risk factors.

What is the number of people involved in your sales evaluation and decision process?  That is a huge factor that commonly sinks huge deals from happening.  Many sales teams focus all of their energies on the higher-level stakeholders and offend/ignore key stakeholders in the process.  Sometimes it comes down to one overlooked person that had a disproportionate amount of influence in the decision when looking at their job title.  I refer to these folks as the “alpha geeks”.  Many times they don’t have a lofty job title, direct budgetary authority or a large team of people reporting to them.  But overlook them at your own sales peril because the alpha geek is the trusted advisor to the CIO or CTO.  They typically are not incredibly vocal in meetings or communications.  They may ask one or two seemingly benign questions.  It’s analogous to the old EF Hutton commercials; “When EF Hutton talks, people listen.”  (

Lastly, you can’t underestimate change.  Change is painful and people tend to resist change.  If there is an incumbent technology solution or vendor that you are competing with, you need to embrace the underdog role.  Depending on the source, your sales chances of unseating an incumbent technology vendor or solution are approx. 20% or 1 in 5.  Great sales teams understand this and yet are not afraid to engage against an established incumbent in an account.  How they engage is very different in a green field sales environment.  Great sales teams always ask the tough questions…and they do it early and often in the sales process.  They expect the customer to convince them that the evaluation and decision is a level playing field with the incumbent.  In fact, they ask the decision makers and key influencers to provide concrete reasons why they shouldn’t go forward with the incumbent vendor or solution.  Their position is that they need evidence or proof that the sales opportunity is a sound investment of their companies’ resources and time.  Because they need to put their necks on the line with their executives and convince them the sales opportunity is winnable and not column fodder.

These are some of the common reasons that I see frequently causing huge deals to derail.  I’d like to see better sales coaching where front line sales managers are asking about these deal risk points on forecast calls and strategizing with their sales teams on how to position and guard against the deal going off the rails.  Instead of just asking about the dollar amount, when the deal will close and what is left to do to close the deal.  That begs for the forecast blindsiding conversation about the huge deal that went south at the end of the quarter!