
Not knowing the reason for not selling something. The client doesn’t tell you. Sometimes they give a reason but it’s a “smokescreen” – a legitimate reason that sounds good and spares your feelings but masks the actual reason. Having knowledge of the real reason you did not win the business means you can make a better tweak next time. Falsely attributing the reasons for why you lost the business can falsely inform a scarcity mindset and lead to bad outcomes.
Adding the right amount of value. As a great salesperson, I’m an educator in chief, thought leader, and product expert. When I meet with clients, I try to deliver value in each interaction. In these situations, I’m not “selling”. It’s painful to deliver value with some prospects and never land a sale or receive a referral.
Even though I expect it, I do not like the way it feels to not hear back from someone I reach out to in an email or by phone. It’s a rejection and though I know not to take it personally, I still do (a tiny tiny bit). So when I’m in hardcore sales mode and reaching out to a lot of people, it feels really vulnerable.
I hate being a second (or third) bid. I’m skilled at knowing when a prospect is truly interested vs. pumping me for information/expertise and not likely to buy. Sometimes we have to graciously run through the motions and provide a quote or a proposal to someone who may not be ready to buy. But if we don’t cooperate, they might not partner with us again.
As the seller, I don’t want to assume low probability of closing the sale because once I do, I know I’ll discount the opportunity and put less authentic effort into it…which virtually guarantees that I won’t close the business.
Talking too much. 70/30 is a good ratio of listening to talking, but what if I need to speak more to explain my product or prove that I have the requisite skills the prospect needs to make their decision. Push too hard, and you might offend. Push too little, and you might not impress. It’s a balancing act and it’s stressful (and fun).

Eli Howayeck (MBA, Kellogg School of Management), Founder and CEO of Crafted Career Concepts, is passionate about helping motivated people achieve their career, educational, or personal goals and helping businesses, large and small, overcome a variety of challenges facing their business.