Sales Fails: 9 Avoidable Mistakes We Can All Learn From

Before we get into sales fails -#RevSummit17 was an unforgettable event that brought together B2B marketing and sales leaders from around the globe.

With their hard-hitting advice it’s easy to forget that the biggest winners have often had the biggest #fails.

We asked #RevSummit17 speakers to share their most memorable sales and marketing #fails — because learning what not to do is a great complement to learning what to do.

Sales Fail #1 – Lack of Prioritization

Tonni Bennett, Terminus

When I was a sales rep at Pardot, there was one quarter when I almost did not hit my quota. Looking back, my mistake was a lack of prioritization and understanding of what a late stage opportunity actually is. I focused on drilling accounts that had been in my pipeline the longest, who I’d had the most conversations with, but I was focusing on accounts that were never going to move forward. These were tire kickers. I learned that I needed to ask the right questions in my sales process in order to better understand which of my accounts had the strongest use cases and closest potential timelines for implementing the project. That’s where I focused at quarter end moving forward.

Sales Fail #2 – Pricing Woes

Amit Bendov,

It’s that moment when a prospect instantly accepts your proposal. Now you know that you have underpriced your solution :).

I was running sales for an early stage cloud startup. These were the early days of inside sales and the perception at the time was that you can only close smaller deals over the phone. So most of the deals we were closing at the time were in the 25K-30K range. I was determined to test the limits.

And then I got a lead that I knew is going to be my six figure deal. Large company, funded project. A 100K deal would be nothing for them. So I quoted them $126K. Like a good startup, we didn’t even have a solid price list at those early days 🙂 But I left some room for negotiation, so that I will not end up with a six figure deal.

Long story short, I got on a call with their procurement person. He starts going over various parts of the proposal asking for clarification on terms and conditions. Nothing major. But in the back of my mind I’m still waiting for the bloodbath when we get to the last section: pricing.

And then he asked me: if we pay cash, do we get a discount? This is often a trick question negotiators use to try to get a first price cut. So I responded carefully: “I’m not sure, how much do you want?”

“1/4 of a percent” he responded.

I thought that I did not hear well. “How much?”

“1/4 of a percent”

And that was it!

“Shoot! I should have doubled the price.” Or maybe triple?

The key takeaway is that the limits are more likely in your mindset than anywhere else. Ruthlessly test your assumptions, and don’t be afraid to test and fail, if the upside is important.

Sales Fail #3 – Lead Management

Dayna Rothman

“One of my first B2B marketing/sales roles was at a small tech company that built a CRM software for property managers. We were going to Chicago to meet with some prospects, so I helped plan a prospect happy hour at a local Chicago bar. This was the first event I had ever planned, so I was super nervous and mentally unprepared. At the event we were giving away these orange swag bags with branded items to everyone that came to the Happy Hour. And because this was back in the day before ipads or anything like that, when people came into the bar I got their business card. And where did I put their cards? In one of the orange plastic bags. So, I was handing out orange bags and putting the leads in orange bags. I am sure you can guess what happened.

At the end of the night, my boss asked me for the lead bag. I went to go get the bag of business cards and it was nowhere to be found. I searched everywhere to no avail–I had clearly handed out the orange lead bag to an event attendee instead of the swag bag. Disaster. I had to tell my boss that I no longer had the bag–and that was the only way we would know who attended this event. He was beyond angry.

In a panic, we decided to send an email out to the original invite list and offer a gift card to whoever handed over the lead bag. Luckily, someone came forward with the bag and gave it back to us. Miracles do happen!!

What did I learn? A) always keep your leads close, b) make sure you have a backup event registration method, and c) Pay attention and don’t be a dumb a**.

Sales Fail #4 – Lack of Preparation

Matt Heinz

Years ago, I showed up at a prospect meeting completely unprepared, couldn’t remember who would be in the room and hoping I could wing it.

Turned out I had met with that company two months prior, had pretty much forgotten everything that meeting (even though I had notes in CRM with all the details), and began to recite the same initial thoughts on their sales and marketing efforts they had already heard.  

Would be easy to chalk it up to too many meetings and not enough prep time, but that’s unacceptable. Suffice it to say, I didn’t win the business.

Part of my early morning routine now is to review my day’s schedule to ensure I’m prepared – briefed on key attendees, reminded of any history we have, prepped with whatever documents or information I need during the meeting.  

Sales Fail #5 – Lack of Focus

Julia Stead, Invoca

In the past we underestimated and undervalued the time and attention it would take to properly compile a list of target contacts for a trade show campaign. We spent lots of time debating the messaging and the offer, but ended up scrambling to put together a contact list and confirm details. As a result we had low response rates and lots of junk interest. We’ve learned to spend the majority of our time and resources focusing first on the list, then the messaging, and very little time on the actual offer. It’s getting the right messaging in front of the right person that is most important.

Sales Fail #6 – Harsh Rejection (But Perserving)

Shep Maher, guidespark

When I was 22, I had a sales call in Pittsburgh with the CFO of Mellon Bank. Mellon Bank, since acquired by Bank of New York, was founded in 1869 and at the time was one of the largest publicly traded banks in the US. I was selling a service that allowed publicly traded companies to webcast their quarterly earnings calls, thereby providing investors with more transparency.

This was a couple of years prior to Sarbanes-Oxley and Regulation Fair Disclosure – so companies were not legally obligated to do this. When the CFO fully realized what I was pitching, he promptly tossed me out of his office. I was embarrassed, shocked, and ashamed. I think if Rudolph the Red Nosed Reindeer got a look at how red my ears were as I crawled out of that office, he would have been quite jealous.

While we did eventually win Mellon Bank’s business, that was not what made this sales call such a great learning experience.  What made this such a great learning experience was that I realized that a 22 year old kid, who knew next to nothing, could land a meeting with one of the most important C-level executives in the country.  All that it took was a mix of persistence, elbow grease, creativity, temerity … and an ability to relate your value proposition to the challenges that exec was facing.  I learned that while you might not win every deal, you could get to the table with quite literally *anyone*.  No matter how too important, busy, or high and mighty your target audience might seem, if you are fearless (or you can swallow your fear) and you have a strong ROI, you can convince them to take time to hear your story.

Sales Fail #7 – Being Too Salesy

Bastiaan Janmaat

My biggest sales fail is that for the first year of building DataFox, I was too salesy. I always dove straight into a product demo! I was so excited about what we were building, and lacked the sales experience to know that it’s essential to deeply understand the customer’s needs first. We hired our first sales rep from Salesforce and he put me through what felt like an intensive sales bootcamp to whip my need-finding in shape! 🙂

Sales Fail #8 – Too Many Emails

Sangram Vajre

The epic fail was when people don’t respond to you, I would send more emails. I learned that I should rather pick up the phone and talk to them. Emails are reactive and phone calls or face to face conversations at events are real.

Sales Fail #9 – Too Humorous

Richard Harris

I once changed my elevator pitch to be “more humanly humorous”. I found out that while it might work in a social setting it does not work in a formal business discussion.

I had about 4 deals go from what I thought was great to ice cold.

I switched it back and the pipeline started growing again.

Nathan Lippi is VP Growth at Letter Friend, a company that helps sales development teams hack sales with real handwritten letters sent straight from Salesforce.

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