Shoulda, Coulda, Woulda #15 with Rush
Nov 13, 2025
Shoulda’, Coulda’, Woulda’: Do You Love The Fight?
"What the hell was that?" You leave a call having tried a SAYA Sale. It doesn't work the way it was supposed to.
- What actually happened and why?
- I wish I woulda’...!
- Now that it’s over, what could I do?
Send me a selling situation you’ve encountered that didn’t go the way you expected. I’ll attempt an autopsy what could help you and others to avoid those pitfalls. 📧 [email protected]
Steve was a student/coachee from the dark ages. An entrepreneur who had built a small company – reasonably successful – and now was running a team of people helping him sell, develop and install custom software solutions. All four of his salespeople, like him, were pretty technical folks. They loved their “subject matter”, loved talking IT and loved helping people solve problems.
They seemed to work hard…well at least lots of hours meeting with other techies. The water fountain chatter (for those of you who have been in sales only since 2020, most businesses had an area in their office where people congregated to get water or coffee and often chat) was usually about how great their meetings were going and how their “customers” (not really; suspects or prospects) loved them and what they told them about the company and their presentations and technical knowledge.
As Steve eavesdropped, he was disappointed because:
- He didn’t hear many ‘selling’ related conversations. (like “they had a lot of pain”, “their budget made them a likely buyer” or “they said they’d say yes or no after I met with them this coming Tuesday”)
- Most of them seemed to like to talk…not ask questions and listen (which were skills they had been trained as part of their sales training.)
- Fact: They weren’t having enough new opportunities, nor were they closing business!
Seems like the sales folks are good people and very articulate, and the suspect/prospects seemed to love them. They just weren’t selling!
Thinking about Steve’s situation brought me to a point that had vexed me for decades as a sales force development guy…trainer, coach, consigliere to leaders.
The salespeople weren’t passionate about selling. They loved their subject matter (what they sold), they loved people, they loved telling people about themselves, their company, what they knew, their solutions (well telling them pretty nearly everything and anything) and they loved being loved!
What they didn’t seem to love was the fight!
In this instance the “fight” they didn’t seem to love is the selling process from “Hello to Thanks for the order.” Like the furniture builder who loved the accolades for the finished product but didn’t love all the “building” stuff.
If you are going to call yourself a professional salesperson, and be paid like a sales professional, you must love the art/science of selling as much as you love the subject matter (the solutions you sell). You must see selling as your craft. You must study and practice your craft. You must critique your use of your craft. You must find others who are vested in the craft of selling!
You must love the fight!
Note: I had little-to-no experience selling (certainly no training) before I owned my own business. For the first couple of years, I was often asked “What would you rather do: sell or train?” My answer was easily phrased, “Oh. I love to train!” The accolades, the basking in the glow of my trainees, the feeling of invincibility…sigh! One day early in my business's third year (we were actually making good money) I was asked “the question”. Before I could think about my response I blurted the truth. “I love to sell!”
I had finally learned to love the fight!