It is the nature of B2B selling that any given quarter as well as any given fiscal year is dependent on a handful of must-win deals. This is simply a manifestation of the Pareto Principle which is better known as the 80/20 rule or the law of the vital few. Where approximately 80% of the effects (bookings) come from 20% of the causes (opportunities).  This has been well documented in many human endeavors. You can see this type of distribution in a single sales territory, district, region, country and even the global corporation.  It is inescapable.

These are the deals that literally keep sales managers and executives “up at night”. When I discuss this with sales leaders (who readily acknowledge it exists) and ask them what they are doing differently with this “20%” or vital few, the answers range from nothing (because we can’t change the cause) to doubling down and giving each deal more attention. I certainly believe in giving these critical deals the attention they deserve, but I also believe they deserve a different type of attention versus doing more of the same. Let me try and break down the critical questions that, if left unanswered, lead to lost and slipped must-win deals, which in turn lead to those sleepless nights for sales leaders.

  1. Is the opportunity real?  Notice I steered away from the word “qualified” which leads to all sorts of contentious discussions on what qualified really means. I have my ideas, but will leave that for another blog. Suffice it to say, every sales leader should want verification the opportunity his/her team is pursuing is real. How will we know?
  2. Are we aiming at the right target? How do we know it is a $5M opportunity? Could it be $10M if positioned correctly or is it only $3M because of wishful thinking? Until the business is actually won and the deal is signed, we’ll never know the exact size, but we should know if we are aiming at the right target. And while we’re at it, why not make it a great deal?
  3. Can we win? I can’t think of another question that is more important than this one, and yet it is the one that doesn’t get enough attention – until it is too late. This should be one of the very first “go-no-go” questions that is definitively answered. Things change during a long sales cycle. It should also be revisited whenever anything changes.
  4. How will we win and why will the customer choose us? The answer to this question is not so much the activities the account team will go through (though they are important), but rather the actual sales strategy and definitive outputs like an irresistible value proposition. A critical subset of this question is when should we expect to win? Why does the customer care about that date?
  5. Is our proposal compelling? What should our proposal do for us? Does it effectively bridge the gap from selling to formal negotiations? How does it reinforce trust and make it easy for the customer to choose us? What choices are we giving the customer – if any?
  6. What are we uncertain about? How will we manage that? Complex deals always have uncertainty surrounding them. The bigger the deal, typically the more complexity. For instance, do we actually believe our customers are more aligned internally than we are? How many buying influencers are on the other side of the table? Does our team really have perfect information into this opportunity? As the saying goes, if we don’t manage it – it will manage us.
  7. Are we having the right negotiation? Your team can be expert negotiators but if they are having the wrong negotiation, the results can only be disappointing. This is the aim of many procurement organizations and something in which they have been trained.
  8. Are we negotiating the right way? “Your Price is too high…The competition is cheaper…Our budget is only…” are all typical negotiation tactics – and are basically saying the same thing. How the team negotiates; handles tactics and objections; and gets the deal done signals the customer they are working with the right company – or cause a lot of doubt to creep in. Even to the point of derailing a deal.

Notice, these question go well beyond the typical opportunity review – and they should as these are “must-win” deals for a reason. While the above questions focus on getting the must-win deal in the door, it is not too early to consider what we do after we win the deal.  After all, the job of our business is not just to win them, but also to keep them and grow them!

  1. Will this be a painless renewal? What should we be doing today to ensure the renewal is virtually automatic? Are there key elements of the deal that can help us do this?
  2. How can we easily upsell and cross-sell? If our selling motion is “land and expand”, are we landing on the right deal that will facilitate the expansion? What should we be doing today to ensure we are offered our “unfair share” of new opportunities with this customer in the future?

My plan over the next few weeks is to explore each of these questions in more detail in a series of blogs. I hope you’ll get value from it!

Good Selling!