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Losing is Easy…Winning is Hard!

I love this 40 second video by motivational speaker Eric Thomas:

Why did I open with this?


I was conducting a strategic selling training class, whereby we were reviewing active, $1M+ deals in the pipeline that participants brought to the training and felt they were in good position to win. Of the five opportunities they were working on through our first three weeks, they lost all five!


When reflecting on why they lost all five, it was typically one or more of the following:

  1. They didn’t establish relationships with the key decision makers

  2. They didn’t understand the key decision maker’s (“KDM”) critical concerns and objectives

  3. They didn’t understand the decision criteria and decision process

  4. They didn’t understand the political landscape

When I pushed them by telling them “It is not what you know that kills you in these deals, it is what you don’t know. You have to follow a structured repeatable methodology for uncovering what you don’t know.”


And then it came; the response that became the inspiration for this blog. One salesperson said, “Mike, I get what you are trying to teach us, but it is hard.”


I paused, took a deep breath, and said,“I appreciate that. Winning IS hard! Losing is easy,” and jokingly added, "It is clear, you have mastered that! Seriously though, winning takes work, planning, preparation discipline, process, and grit! Of course, it’s hard.”


Unfortunately, some people don’t want to do the work to be successful. That is why I opened with the video “Don’t be upset with the results you didn’t get from the work you didn’t do.


Those of you who know me know I want to win. I want to help my clients win. Trust me, I have had more than my share of losing. But with every loss, I looked in the mirror and said, “I was outsold, and these are the adjustments I am going to make going forward.” That makes each loss a “successful failure.”


I wrote a blog a couple of years back, “Five Reasons Why Non-Producers Don’t Produce.” They say they want to produce, but their actions do not match their words. Put simply, they don’t want to do the hard work.


Do you want to have success selling strategically to senior executives? You need a structured, repeatable methodology that removes variability from the sales process. It is that simple. You need a roadmap, and that roadmap should include:


1. An Opportunity Assessment tool—a checklist that qualifies each opportunity and the investment you need to make. It answers the questions

  • Is there an opportunity?

  • Can we win?

  • How do we align to win?

  • Is it worth winning?

2. Different sales strategies for different opportunities which include strategies such as:

  • Inside Track: Do we have a significant advantage in the eyes of the KDM?

  • Change the Game: Can we move the customer away from their current needs and help them understand their needs in a new or different way that benefits us?

  • Divide and Conquer: Can leverage a niche position or take on one segment or division to prove ROI?

  • Or implement one of two additional sales strategies…

3. Relationship Mapping

  • Are your relationships Competitive, Cooperative or Collaborative?

  • Are they with Key Decision Makers or Key Decision Influencers?

- Are they with support functions like HR or Procurement or are they with revenue generating functions like Sales, Marketing, Operations?


4. SWOT v. the Competition

  • How does your solution match up with the needs of the client?

- Relative strengths?

- Areas of weakness to mitigate?

- What changes or trends can be leveraged as an opportunity?

- What threats do our weaknesses expose?


Yes, winning is a lot of work. In every sales situation you are either on the inside or the outside. Cultivating solutions and relationships takes planning, preparation, and a strategically focused effort to get the prospect’s KDMs to see the value of investing time in you and your solution. Responding to cold RFPs is easy. Unfortunately, your win ratio is likely 7-8% based on research.


At Butler Street, we specialize in teaching companies how to optimize their sales efforts and resources to win multi-million-dollar opportunities the right way. Contact us to learn how we can help your team sell strategically.

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