I’ve been in corporate sales since I was 21 years old, and in the dating scene since I was 16 years old. I’ve had successes and failures in both my career and my dating life and I’ve learned from both worlds how to improve my abilities, style, and approach in order to increase the chances for success. The main thing that I’ve learned over the years is that being successful in both dating and sales uses a very similar skillset.

Here’s what I’ve discovered:

Be Genuine:

The first and most important element of both sales and dating is to be genuine. People are smart and can usually see through lies and false acts. Sincerity is key when establishing a relationship with the intention of exploring a potential partnership down the road.

Emotion Always Trumps Logic:

People “buy” products or other people based on their emotions more so than on logical thoughts. The study below, performed by the Corporate Executive Board (CEB), demonstrates how the emotions impact our buying decisions twice as much as logic. If that’s the case in the business world, how could it be any different in the dating scene?

In addition to demonstrating how your product or service will help your prospect’s business, be sure to speak to their personal motivators also (that’s the emotional side of things).

Similarly with dating, make them laugh, smile, and let them see the fun person, not just your serious and intelligent side. Of course you need to show them both sides, but lead with the fun and interesting element first.

Making the First Move (Prospecting):

Introducing yourself to a stranger at the bar or online is no different then cold calling, sending an intro email to a prospect, or approaching someone new at a business function.

The first few seconds of your introduction will either set you up for success or destine you for failure. The pressure is on and you need to engage the other person by conveying your value early on in order to earn their permission to continue the conversation.

Don’t be Desperate, Sleazy, or Pushy:

No one wants to buy from a desperate, sleazy, or pushy sales person, nor do they want to go on a date with someone who comes off as dishonest, fake or who is trying too hard to “win the deal”. Don’t be over zealous and just ramble on about yourself or your product with shameless self-promotion. That’s the easiest way to scare someone off forever.

Instead, approach a new “prospect”, business or otherwise, with confidence and demonstrate your value by talking about interesting adventures, fun stories, and so on. I emphasize again the importance of showing your fun side early on, but always be yourself. Drop tidbits of info that help raise your value without coming off as bragging.

Don’t be a “Yes” Man or Woman:

Even though most people like being right, what benefit do you bring to someone in the long run if you’re always agreeing with them? None really. By always agreeing with them, you might make them feel good at first, but you’ll quickly end up boring them and falling into the same pile as all the other “yes” people.

Having your own opinion, different from theirs, adds value to yourself. By respectfully challenging some of their views and opinions, provided you can back up your own point of view, you greatly increase your chances of keeping them intrigued into hearing what you have to say and getting them thinking a bit differently and out of their comfort zone. This will help set you apart from the rest of the crowd.

Sealing the Deal (Going in for the kiss):

If you’ve conveyed enough value to your prospect and have gained enough trust and interest from their part, then by this point you should have received all the right buying signs and are in a strong position to seal the deal. In both the business world and the dating world there are several ways of approaching this depending on the circumstances.

You might feel confident in simply using an assumptive close, or in dating life going in for the kiss. Certain situations might call for you to ask for the sale, or “Would you like to kiss me now?” – bold, but highly effective in the right circumstances. Sometimes you might require a follow-up meeting, or a second date. Sometimes many meetings will be necessary, and depending on the culture of the organization, or your potential future girlfriend/boyfriend, you may need the approval of a committee, or a large family. Either way, learning how to accurately gauge the situation is of most importance.

Communication is Key:

If you’re lucky enough to have met a good match and approached them the right way, you might find yourself forming a partnership. From this point forward it’s mostly about effectively communicating with one another and setting expectations that you both are willing and able to meet. This applies to building either an ongoing business partnership or an ongoing romantic relationship.

Know When to Move On:

Finally, no matter how good of a sales person or “catch” you are, you will not be a match for everyone every time.

Unfortunately, not everyone is straight forward with their intentions, nor does everyone have the courage to face a situation directly and let you know where you stand. Sure it would be great if everyone who wasn’t interested in you or your product would kindly tell you so and let you down gently. The truth of the matter is that it’s rarely the case and your prospect, or the object of your affection, is more likely to go silent, not return your calls or emails, or simply keep telling you that now’s not a good time, call back later. If this happens over and over again, they’re probably not interested in what you have to offer.

Know when to call it quits and how to do so gracefully without burning bridges and with your dignity still intact. There are few things worse and more painful than walking away without your self-respect.

Once you’re in a healthy relationship, you’ll quickly learn a very important phrase: “I’m Sorry”. To get a head start on this one I suggest reading my article, The Power of an Apology.

What tips do you have for dating and/or selling?

Happy Selling (and Dating)!