5 Lessons Sales Can Learn from Dating



If we have said it once, we have said it a thousand times…business is all about the relationships you build.

We are all familiar with the traditional ways of selling, the old-school push to sell sales tactics and of course, the ABC message—Always Be Closing. However, this outdated message fails to address how buyers buy today. Relationships between brands and customers have changed. With increased competition, the buyer’s ability to perform their own product research, and new technology, today’s buyer expects a personalized buying process.

As Marketo’s very own VP of Product Marketing, Matt Zilli explains, “Brands that win in this world build lasting customer relationships with every single customer.” This reinforces why successful sales leaders today have stepped away from the traditional ways of selling towards a new mindset—relationship selling.

Simply put, relationship selling is a sales approach focused on creating relationships. People buy from people they trust; and the best way to build trust is by first establishing a relationship that’s based on authenticity, concern, and honesty.

It may be weird, but if you feel like this is starting to sound a lot like dating, you’re right. In this blog, I will share with you a few lessons sales people can learn from dating, and how those lessons will improve your selling success.

1. Don’t Talk about Yourself

Plain and simple, talking only about yourself on the first date is not the best approach to take. It’s important to show interest in the person you are with so ask them questions. As sales people, it’s hard to not talk about your product but keep in mind, the final sale comes down to one thing: how can your product solve the needs of your customer?

People buy because of pain, and to identify what that pain is you need to get your prospect talking about themselves to uncover frustrations. The more information you gather, the better position you’re in to create value and identify your advantage over competitors.

And keep in mind, not everyone knows what their pain is. In this case, I’ve found that using leading questions can really help. For example, “How have you been able to track the ROI of your marketing programs?” (Maybe they aren’t!). Or even try walking through their process start to finish to uncover bottlenecks and gaps along the way.

2. Look for Signs

Just like in dating, it’s important to pick up on non-verbal cues from your prospect to understand what they are thinking or even discussing offline with their counterparts and key decision makers. One of the biggest deal killers (aside from timing of course) is being blindsided late in the sale cycle without a solid game plan.

Imagine this, after months and months of dating, the time has come for you to propose. All your energy, time, and effort invested into the relationship are about to pay off spectacularly. You get down on one knee and present the most stunning proposal with absolute confidence. There is no way your partner can say no…

The response, “Sorry, but the contract with my current boyfriend doesn’t expire for another 18 months!”

And just like that, everything makes sense—all the ignored late night calls, the missed text messages, the lack of future commitment. Just like a relationship, it’s critical to be upfront and talk about a timeline, deal-breakers, etc., rather than operating on assumptions, which can put you in an awkward and painful position. 

From my own experience, here are a few signs of a not-so-serious buyer:

  • They stand you up, over and over again
  • They avoid sharing necessary information (budget, timeframe, competition)
  • They don’t introduce you to the parents … I mean stakeholders
  • There is no next date—lack of interest for future commitment

3. Charm Them with a Story

You may have heard the saying “A good salesperson knows how to talk; a great salesperson knows how to tell a story.” When used the right way, storytelling is extremely powerful and can help you more effectively relate to your buyer, create urgency and build trust.

Studies show that when we listen to a story, our brains act as if we are living it. At Marketo, we use journey decks to tell our story and help prospects visualize how our solution can solve their needs, create value, and help them achieve success. 

When creating your story don’t forget to:

  • Use numbers and statistics—stories combined with statistics create “stickiness” that improve retention
  • Invite the prospect into the story—phrases like “Imagine this…” or “Let’s assume…” help your prospect envision themselves as the subject and are more impactful
  • Be relevant—your story should be relatable to your prospect and their priorities. If you can’t “click” on the first date, it might make for a rocky start.

4. Leave a Little to the Imagination

It’s important to not share everything about yourself on the first date. Why not leave a little to the imagination and keep your date intrigued? Similar to sales, you want to provide value to each encounter while giving your prospect a reason to speak with you again.

Taking it slow can not only help your dating life, but it can also help your prospect better digest and retain important information along the sales cycle. For example, instead of running a customized demo on the first call, it may be more beneficial to use the first conversations to learn about your prospect and their interests. Why not hold back a bit and give them something to chew on in the meantime (preferably something that pertains to their interest and what they have shared to keep them wanting to learn more—maybe a whitepaper, a short overview demo, or a customer story). That way when it comes time for a customized demo, you are in a better position to make “sparks fly.”

5. Know When to Move On

Just like dating, it’s important to know where you stand. The time it takes to chase down a not-so-serious buyer is time taken away from other valuable deals in your pipeline. During my first few weeks on the Marketo sales floor, I overheard someone say “‘No’ is the second best response to a ‘Yes.’” And it’s true—sometimes it’s not worth wasting your time on someone who’s just not that into you.