Before I got into sales, I had a certain pre-conceived notion of what a successful salesperson looked like – a loud, extroverted (and often annoying ) individual who is very pushy and in a rush to get their clients to sign off on documents they don’t fully understand.  I think of the famous “Always Be Closing” speech seen here:



But times have definitely changed,  especially when it comes to sales in the startup space.  Funny enough, when I reflect on my experiences on the sales side, I’ve noticed  a number of similarities with dating.


  • Don’t rush the discovery phase.

Would you try to get someone to marry you on the first date?  I think the most common answer would be “no”.  But this was a mistake that I made when I first got into sales.  I didn’t realize the importance of the discovery phase and learning more about a customer and what their pain points were, before talking about what I could offer them.  It makes sense, as when you go on a first date, you are trying to see if the other person (at a high-level) may be a good fit for you.  The first date gives you enough information to go on subsequent dates.  Maybe marriage is in the cards, but you won’t know right away.


  • If someone says “no” to signing off on a deal, don’t take it personally.

When you’re in sales, you definitely develop a thick skin, as the number of “no’s” vastly outnumber the “yes’s”.  But you live for the 1 “yes” in the face of hundreds of “no’s”.  I can safely say, that same ratio exists when it comes to asking someone to commit to a serious relationship in the dating world.  But just like in dating, everyone has a host of reasons for not wanting to commit to a deal.  With dating, it could be a bad break-up they had before, which still affects them or maybe they need to focus on themselves before being able to do that with someone else.  In business, it could be that what you are selling to them is not a “painkiller” but more of a “vitamin”.  But it could also be because they don’t have the budget right now or they have higher long-standing priorities above what you are selling, and the list of reasons can go on.


  • Sometimes the best way to revive a deal, is to go cold turkey.

Have you ever kept calling someone because you really liked them, but after the first couple of dates, you never hear from them?  But after a year, out of the blue,  you suddenly get a text or call from that same person who ignored you?  I wish that happened to me- it hasn’t.  But it has happened to other people…I think.  The point being, I’ve definitely had this happen to me on the sales side.  The customer reads a press release about another client we’ve launched with or there’s been some buzz about the company in the general marketplace.  Even though it wasn’t intentional – a lesson was learned.  In the face of rejection, just keep going and stay busy with other clients (or other dates), and the customers that you want, will eventually come knocking.


  • Building the relationship is the foundation.  They may not close with you now – but they could in the future or even refer you to other potential clients.

Dating is really this temporary stage (that could last years) between being single and being in a strongly committed relationship (either marriage or common-law).  What dating accomplishes is it gives both parties an opportunity to learn more about one another in a number of different circumstances and situations before committing to a long-term relationship.  In sales (especially enterprise sales), the sales cycles are long.  But this is not a bad thing.  Not all customers are the best fit.  Just because you want to get your product out to the market, doesn’t mean you should settle for just any customer.  It’s tempting – and sometimes you need to go through a few unsuitable customers to find the dream customer.  That dream customer will do the full dance with you (and it could take a while), but I guarantee that the process will be worth it.  The end relationship will be a true partner in the best sense – someone who is committed to making the relationship work, just as much as you.

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