10 Reasons Why You Can’t Outsell an Incumbent

It seems that nearly every time we (and our friends and colleagues) do business with a company, there is a problem and we must contact customer service.  It always seems to go bad, as reps are unable to handle the simplest of issues, don’t care, display no common sense, behave with incompetence and struggle to continue the conversation when forced off script.  My personal list of recent grievances includes:

  • Home Depot (finally resolved when I contacted the C Suite and they made sure my order was delivered without a fourth reschedule)
  • StubHub (unresolved. I gave up and will wait until early 2025 to receive funds from my tickets they sold)
  • Ferrari Pools (unresolved and we did it ourselves)
  • Chase Bank (unresolved and I gave up on getting them to refund a credit balance without a ten-day waiting period)
  • Federal Express (resolved and now the driver brings packages to the covered entrance instead of leaving them in the driveway to get wet)
  • Bloomingdales (unresolved and I gave up on getting a refund for incorrect shipment that I returned)
  • UPS (finally resolved when I contacted the CEO and two packages shipped but lost a month earlier were miraculously found and delivered)

Giving up simply means that getting it resolved to my satisfaction was no longer worth the time, trouble, emotional energy or principle.  My personal list of recent positive experiences includes only one company:

  • Taylor Rental (surprisingly helpful!)

My experiences seem to be consistent with most people I know.

Interestingly, most companies that reach out to us about their sales challenges complain that their win rates when attempting to win business away from incumbent vendors is quite low.  We know that most companies are failing miserably in the area of customer service and some aren’t even trying.  Given that the conditions are quite conducive for stealing business, it seems unbelievable to me that companies are struggling to succeed in this area.

There are a number of possible reasons why, but here are ten that quickly come to mind:

  1. Salespeople Have an Ineffective Strategy
  2. Salespeople Using the Wrong Tactics
  3. Sales Process is not Optimized for Outselling an Incumbent
  4. Salespeople Need to be Liked
  5. Salespeople are Not Comfortable Talking about Money
  6. Salespeople Not Qualifying Thoroughly
  7. Salespeople Not Taking a Consultative Approach
  8. Salespeople Not Selling Their Value
  9. Salespeople are Quoting/Proposing/Presenting Too Early
  10. The Messaging is Ineffective

Strategy is at the heart of the matter.  Watch this four-minute video about the proper selling strategy when there is an incumbent involved.


When the strategy is correct, the messaging can be perfected.

When the strategy and messaging are correct, the sales process can be optimized.

When the sales process is optimized, sales tactics will work effectively.

Stop winging it.  Stop struggling.  Stop losing.

There is an insane amount of sales development help available, including sales team evaluations, sales process customization, sales and sales leadership training, coaching and more.  If not from Kurlan, then get it from someone else. But please get it!

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