Ways To Be Let Down in Sales

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For over a decade now, I have survived what I think is a relatively successful career in sales. At times it has felt easier than other times, but all things considered, it has never truly been easy. I am unabashedly a sensitive person, and sales is full of rejection. I have received many more “no’s” in my career than “yes’s,” something I have had to get used to over time. Any salesperson who tells you otherwise is a liar, or they work somewhere like Salesforce or Google where I imagine it cannot be very difficult to sell people on using a CRM or email.


To be fair, buyers are wary of salespeople, who are often stigmatized as manipulative and not really looking out for someone’s best interests. The worst salespeople are indeed very overt that they are selling you something. A good salesperson should make the sale feel natural and warranted.


I recently sat down to get a pitch from Westin Vacation Club. One of the first things the sales rep asked me was whether I was actually serious about the presentation because I looked very young. Throughout the presentation, she made condescending remarks about my various travel being the result of not being promoted at my job, and insinuated that I probably could not afford the package she was selling. The reality is, I could easily have afforded the timeshare, and I travel so much for work because I care about seeing clients and it makes a very real difference in my financial reality. But she lost me early on not really listening to what I was saying and making unfounded assumptions about me just by looking at me. You’ll see why I mention that later.


We are all salespeople in some way. With our significant other, we are often pitched about making plans we had not planned for, or we receive critical feedback we might get defensive about. A teacher is selling education to her students. An employee in the bank sells his boss on his work and that he is the right candidate for the promotion. And when you go to buy a used car, surely enough, there is a gentleman there who may or may not tell you what is on the Carfax.


Salespeople are overtly salespeople. I think this causes people to tense up in interactions with sales reps in ways they would not otherwise in the various other, more subtle moments of their lives when they are being sold on something. And that tension can sometimes lead buyers to act in unexpected ways. Let’s face it: the barriers are higher, the walls come up, and in the back of the buyer’s mind is the reality that the person staring across from them has an objective that may or may not come with the best intentions.


In my experience, it is inside salespeople – the “cold callers” and “appointment setters” – who have it the worst in terms of how they might be treated by a buyer. There are a variety of reasons for this.


First, inside salespeople tend to be more junior and earlier in their sales careers. For whatever reason, I’ve found that this empowers people to belittle them more. I remember early in my career that I did a lot of direct selling to much older enrollment and admissions professionals at colleges and universities. Whenever I showed up to their campus, it must have been a huge disadvantage to me at the time that they realized I was so young. How could they take me seriously? What did I know that they did not?


Second, inside salespeople have generally built little to no relationship with their buyer. This may make it a lot easier for a buyer to shut them down in a hurtful way. It is much more difficult to be rude or angry with someone who has spent a lot of time getting to understand you and your needs, someone who has become a consultant to you and is trying to make things better. Generally, some level of rapport and trust has been built at that point. This may seem counter-intuitive: it is often the people we know the best who have the capacity to let us down the most, but in the sales world, it’s much easier to hide behind a computer screen and belittle someone you hardly know who is beginning their career.


I’ve found this to be the case in some very disappointing ways. One of my inside sales reps a few years ago was trading emails with someone in IT at a credit union in New York. He was clearly trying to make her run in circles for his own amusement, so I asked her to CC me on her reply so that I could help us get to a “yes” or “no” on whether or not he wanted to meet with us. I asked him a question, and his reply was a video that he made himself about him using Google to answer the question I had asked. He was trying to make some sort of point that I was too stupid to use Google, and must have spent at least thirty minutes of time out of his day making the video so that he could try to ruin our days. Another time, someone told one of my reps (a college student doing a co-op with us) that he should consider another career and work on his English. For this individual, English was his second language, so the comment was fairly racist and unnecessary.


It’s always shocking to me when people who hardly know each other have the wherewithal to make things utterly personal so quickly. Not being listened to or being spammed can be incredibly frustrating, but we hardly ever know what it’s like to be in the other person’s shoes. Maybe they don’t know any better. Maybe their leadership team is too aggressive and giving bad coaching, putting undue pressure on their sales reps. Maybe they are just having a bad day. I get contacted all the time by inside salespeople. When they do something great, I tell them, and I ask them for their manager’s email so I can tell them as well. I was that person once on the other side of the computer screen. So I have also been the person countless times who gets sniped at, thus when I don’t like the way a rep is handling something with me, I don’t tell them they are stupid or that they should consider another career or work on their English. Instead, I try to give them direct feedback about why their approach bothers me. It might not be pleasant for them to hear, but it’s respectful. I don’t mean to sound “holier than thou,” but we would all be a little better served to act that way instead of thinking of the condescending comment du jour before hiding behind our keyboards.


What did I do about the IT manager who seemingly has more time in his day to write snarky emails to vendors than doing actual IT work? I forwarded his response to me and the despairing, young sales rep to the CEO of his company. Based on the phone call I received from the CEO ten minutes later – so utterly embarrassed that someone had represented his brand this way – I trust that the issue was taken care of with Mr. Snarkypants.


One way that we have put some levity into this reality that life has some bad apples is to have a “Hall of Fame.” This consists of responses we have received from people that are just way over the top. But let me be clear about something – this happens very rarely. My team actually often gets a lot of praise for the professional and personalized approach they take to their outreach. As a sales leader, I love to hear this kind of feedback. But there are inevitably people out there who are having a bad day or just have it out for someone. When it happens, we put it in the Hall of Fame. This helps people to remember not to take things personally. It happens to all of us, and we might even all get a laugh that the college student is much more mature than the IT professional, at least in a professional setting. I can’t speak for what they do in their free time because it does not involve me most of the time.


While inside salespeople probably get the worst of it, it does not mean that professionals who are “higher in the food chain” are exempt from being let down. There are times in sales that require a good rep to be very direct with people.


For example, let’s say Tony is selling enterprise project management software to Bill. Bill has hemmed and hawed for a year now about buying Tony’s software, and Tony is starting to believe that Bill is not ready for any software at all. Tony decides to be forthright with Bill and tell him how he is feeling – that they have not made much progress, and he’s starting to wonder if Bill is ready for this. He even offers Bill an out, something to the effect of, “If you agree with me, let me know and I’ll make a note to stop contacting you, and we can revisit this when you’re ready.”


There’s no predicting how Bill might take this. Most of the time, it should invite a pretty transparent answer. After all, Tony has given Bill an out, which has alleviated any pressure that existed in the situation. But maybe Bill is having a bad day or is offended that Tony would insinuate that Bill has been wasting his time. The situation can escalate when in reality it should not have to.


I like giving people an out because it is much better to hear “no” than “maybe.” With a persistent “maybe” both sides are often losing, and certainly so if the “maybe” is coming from a buyer who really wants to say “no.” The reality is, we have a hard time letting other people down because we are human beings with feelings. This can make it very hard to say “no” to people because you don’t want to hurt their feelings. But in that situation, both sides are wasting time. The buyer is wasting time talking about a product they will never buy. The seller is wasting time talking about a product he will never sell. This is a lose-lose situation.


I like to be very up front about this and invite people to say “no” to me. That probably seems counter-intuitive, but it helps me in a few ways. First and foremost, I genuinely care about my customers and I want them to know that I am here to help them. If they understand that I am OK with a “no,” it helps them to see me for who I am – someone who isn’t just here to sell them something. It makes me less threatening.


More importantly, it helps me get to the truth. If I tell someone it’s OK to tell me “no” or that I am happy to circle back in the future, I will know they are genuinely a “maybe” if they reject that. The threat that you are going to pull your product off the table can sometimes be the wake-up call for a customer who is genuinely interested in your product and scared that you, the seller, are going to walk away from them.


And lastly, getting a “no” is productive for me because now I have taken an unproductive “maybe” out of my pipeline. This helps my forecasting and it helps me allocate my time better to customers who are ready today.


So, the way that I think outside salespeople get let down the most is by buyers who are afraid to say “no” or who are bad communicators in general. The best thing you can get as a seller is a customer who communicates well and transparently. At least then you have all the information you need to try to help the best you can, and even if it does not work out, you get valuable feedback. Selling is an iterative process, so that feedback is crucially important.


This blog is not intended to be an indictment on buyers. We are all buyers and sellers. Back when I sold to enrollment professionals, I often remarked to myself how I was selling a product to a buyer who was going to turn around and use the tool to sell children on enrolling in their colleges. Were they really any different from me?


So as in all things, we as human beings have our blind spots and sometimes we do not react the way we should have when we engage with others. Whether that’s quarreling over which movie to see with your significant other or how it goes at the used car lot, it’s really all the same.


There are two simple things I would hope others might take from this:


  1. Try to be a genuinely empathetic listener and do not rely on assumptions.
  2. Try to communicate as directly as possible so as to be respectful of other peoples’ time.


Easier said than done, but if we could all pull it off, we would probably brighten up some days and make our lives a lot more efficient.

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