The WORST 3 Mistakes Salespeople Make

bad-sales-person-traitsI recently attended a Toronto Sales Hacker meetup. There were some great speakers who reminded me of some of the blatant mistakes we make as salespeople. Some of them are so obvious that we tend to overlook them.

Here’s a list of three mistakes I embarrassingly make.

1. Asking for the update

Sigh. I hate when I do this. You’ve been working on a prospect for a couple of weeks and there hasn’t been any real progress. How many times have you sent that quick, “Hey, hope you had a great weekend. Any updates?” which is then proceeded by a quick task in Salesforce to remind yourself to do it again in two weeks. The truth is, if this lack of progress has continued for a while, the prospect is probably not interested. I remember asking a prospect for useless updates for 6 months! Guess what? If they’re always telling you for another month, or next quarter, they aren’t really interested or a qualified buyer. Ali Irshad, VP of Sales at Top Hat was on point with this observation.

Lesson: Don’t waste time on your prospects with useless “update” emails.

2. Not disqualifying fast enough

Something that really resonated with me from Shopify’s Head of Sales Science (interesting title) Loren Padelford is the value of getting to a quick no. It’s much more valuable to get to a quick no so you can focus on the people that will say yes. How much time do we waste on people that will never say yes? A lot. At my last company, we never had a methodical process to get to a no. We’ve taken steps to correct that at Ideal Candidate.

Lesson: It’s just an important to get a no as it is to get a yes. Disqualify as much as you qualify.

3. Not listening

I have a tendency to describe all the awesome benefits of our solution before actually listening to the customer. The best salespeople don’t waste time explaining in the beginning and instead, ask the right questions to get all the relevant details needed to attack. And by attack, I mean provide information that shows value and how the prospect’s problem will be solved. Showing the customer how much easier life would be with your solution. Features and benefits rarely get a deal closed. Inferior products win in the market all the time because their value is better explained by salespeople. It’s easy to rely on flash and features to make the selling process seem easier. But you’re really just not listening.

Lesson: Pay attention and really listen to your prospect.

What are some other big selling mistakes I missed?

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Somen Mondal

CEO at Ideal
Somen is the Co-Founder & CEO of Ideal. Prior to Ideal, Somen served as Co-Founder & CEO of Field ID until it was successfully acquired by Master Lock LLC (a subsidiary of NYSE:FBHS) in December 2012. Somen’s leadership has helped earn Field ID a spot on the Profit Hot 50 and Deloitte Fast 50 Companies-to-Watch lists. In 2012, Somen was named winner of the Ontario Ernst & Young Entrepreneur of the Year award in the “Emerging Entrepreneur” category.


  • I totally disagree with your point 2 as a blanket statement. We are in the age of ‘Inbound Selling’ whereby prospects are running their own sales (buying) process and research shows they will make somewhere between 5 to 12 contacts with a salesperson before purchasing. Around 80% of salespeople give up on prospects after a maximum of 3 contacts, or, to use your term, “disqualify” the prospects. Had they stayed in the game and been patient with their prospects they would have considerably increased their sales success rate.

    • Somen Mondal

      Hey Brian – Disqualifying a lead might mean after 3 times or 25 times. It depends on the nature of the sale. My point is you want a process to disqualify leads that makes sense for your company and products.