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What would you say is your biggest lesson over the entire span of your career?

I think one of the biggest key moments was learning to distinguish between deals I should pursue and ones I should drop.

You need to be thinking about qualification in your very first interaction with a prospect.


How do selling organizations overcome these frustrating challenges of long sales cycles?

First, you must follow an effective territory, account, and opportunity planning process that maximizes the likelihood that the deals you pursue are the ones you’re most likely to win. Having such an intuitive process that maps what you do best to the opportunities you’re considering pursuing also acts as your guide to ensure that you don’t embark on the deals that don’t match your profile. It sounds simple, doesn’t it?

But, such fundamental planning is often ignored or pushed aside by emotional attachment to tantalizing deals that should never have been considered. Clearly understanding what you do well and not so well and using that knowledge in account planning creates the best matches possible in the deals you pursue. Once you’ve done that effective planning, that due diligence to increase your odds of winning.


What can you do over that long sales cycle to improve your chances of success?

As the time passes, every action you take is being evaluated by the buying organization. These actions showcase your responsiveness, follow-up, and attention to detail, or lack thereof. Leaving the buying organization with positive impressions in these areas is critical because regardless of how capable, prepared, and sophisticated your competitors are, they might become just a bit forgetful as the long sales cycle continues. They might take their eyes off the ball. Perhaps they’ll completely miss a deadline or carelessly provide the prospect a boilerplate response instead of devoting the required time and effort to respond in a customized way. A wrong step at just the right time can leave the wrong impression, and the door open for your organization.

The key is to stay focused. With effective territory, account, and opportunity planning, you can establish which deals are worth pursuing. Then, trusting your due diligence, make sure your actions clearly illustrate to your prospect that you are fully committed and focused on the successful outcome for both parties.



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