The 5 Do's & Don'ts for Sales and Dating

The 5 Do's & Don'ts for Sales and Dating

Everyone knows that February 14th is Valentine's Day but did you know that February 15th is Singles Awareness Day? If not, you're welcome!

You won't be surprised to learn these mid-February holidays got me thinking about #sales and how selling is not all that different from dating. In both cases two people are assessing each other and what they bring to the relationship and whether or not it's worth pursuing long-term. Both involve people and the complex emotions that go along with them and if you aren't careful, things can get ugly fast.?

If salespeople aren’t careful, they can find themselves going from celebrating Valentine's Day to Singles Awareness Day very quickly. ?I pulled together some thoughts that might help your team avoid this in life and in business!? And for some added fun, this self-proclaimed Boomer in a Millennial’s body is going to throw in some #genz approved slang so you Gen Zers out there will have to let me know if I passed the vibe check…


If you fall into one of these 3 buckets, you'll want to keep reading:

A. You’re a #salesleader of a team who is courting prospects every day.

B. You're single, ready to mingle, and in need of some blunt advice.

C. Neither A or B are true but you enjoy cheesy analogies and are open to a good laugh.


So let's get on with it! Here are 5 Do's and Don'ts for executing an effective #salesprocess that holds true for successful dating as well. The Gen Z's in my life tell me the key is to not being "cringe" and to maximize your "rizz", but I don’t know what either of those things mean so instead just follow these 5 rules:


1.??? DON'T ghost people.? This is no way to build a relationship in business or in life!

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DO build trust.? “How?” you might ask. Take a real interest in the other party, do what you say you’re going to do, and communicate openly and honestly.? Avoid being “sus” as they say.? Speaking of communication…

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2.??? ?DON’T play games.? Don’t conceal your intentions, expectations, or needs in the hopes of being more desirable to a potential client or dating prospect.

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DO communicate your needs, intentions, and concerns as they arise and be as candid as possible. ?I believe that more damage is done in any relationship by what is unsaid rather than by what is said.? We suggest salespeople navigate this by utilizing covenants.

A covenant is an upfront agreement between two people that ensures both are on the same page with expectations and permits one to hold the other accountable to the agreement.

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The reason so many people don’t do this is because of their underlying fear of rejection and the need for people to like them.? At Braveheart Sales Performance we call this Need for Approval and thanks to the data from our friends at Objective Management Group we know that 63% of salespeople suffer from this.?

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If any salespeople on your team fall into that category, I suggest you help them to practice what they will say before they find themselves in the common scenarios they might face and help them come up with some precursors they might use to make the covenant easier to set.? A great example of using a precursor and a covenant together might sound like this:

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“Please excuse me if this comes across as salesy, but I can’t send you the proposal until we agree on a time to meet to go over it.? It’s in both of our best interests as I’ve found that when this doesn’t happen, it often leads to opportunities for confusion and the potential to miss your deadline for this project.? Can we agree that we will meet on X date if I can get this to you by Y?”

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3.??? ?DON’T build relationships on surface-level elements.? Don’t swipe right just for the looks or attempt to build business relationships based on the concept of being likable or friendly.? And certainly don’t pursue a one-sided relationship where either party is significantly more interested or invested than the other.

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DO seek to establish relationships in business and in life that are based on shared values.? Sure, there might be an initial, albeit superficial spark that you discover, but that’s not enough for a lasting relationship that can weather the tests that both life and business will inevitably present.? Date for shared values and interests will follow.

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In sales, your team needs to work to uncover whatever the Fundamental Buying Motive is and establish peer-level relationships with their buyers.? Knowing why your prospect is even considering doing this project, understanding the personal impact of its success (or failure), and demonstrating and understanding and commitment to solving whatever their challenge is sets you and your client up for better success.? Just knowing that they like what you offer and that you both cheer for the same football team isn’t going to cut it.

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Pro Tip for Sales Leaders:? Your team might shy away from these conversations because they’re harder to have and might lead them to discover that there actually isn’t a compelling reason for the prospect to do anything. ?Sometimes they don’t want to believe that because they worked hard for that opportunity and the thought of starting over is painful.? See what I mean about the similarities to dating? Anyway, help them to see that the quicker they can learn this, the better.? They will be more respected by their prospect for being honest and not wasting their time, and your salesperson will be more freed up to pursue other prospects who actually do have a compelling reason to talk to them.

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4.??? DON’T assume anything and don’t shy away from having “the talk”.? This comes back to communication but so often people are afraid to ask either because they’re afraid of the real answer or they’re afraid of what asking the question might make the other person think of them.? Too often this leads to doomscrolling and unnecessary worry over things you don’t even know are fact!

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DO seek the whole truth about the other party's needs, where they are in their process, and be willing to share your needs to make this a mutually beneficial and enjoyable relationship.? If your salespeople are ready to provide a quote or a proposal but they don’t know who the actual decision maker is, how the decision will be made, when it will be made, what the actual deciding criteria are and why they even need to make a decision (Fundamental Buying Motive).? That’s akin to hearing wedding bells when the other person hasn’t even saved your name in their phone!

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And finally,

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5.??? ?DON’T put off the money conversation.? How people spend or save their money is none of your business. Until it is.? Too often couples gloss over talking about money until it’s too late and they didn’t realize that when they exchanged vows they exchanged their spouse’s crippling debt too.? Don’t assume they have a fully-funded 401k just because their bougie spending habits lead you to believe they’re financially set.

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DO bring up the money conversation in a constructive manner as early as possible.? While this might sound strange, the example shared above is far too common and far more detrimental to the trust in the relationship than if it had been brought up early and proactively, before anyone is in too deep.

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It’s no different in sales either.? If your salespeople are holding their breath and saving the money talk until the end of the process, odds are they’re signaling to the prospect that it’s going to cost a lot of money and eroding trust along the way.? If there is an imbalance in the prospect’s mind with the value your company provides and the money they must part with, your salespeople need to know that as early as possible.

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This allows them to rectify the misalignment before the deal is blown or walk before they waste too much time. Maybe the proposal is overkill for the true needs of the prospect or maybe they simply aren’t a great fit.? Either way, your salespeople need to know this before spending an inordinate amount of time proving how amazing your company is to someone who is never going to be your customer.

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So if you’re a #salesleader and you’re reading this, I implore you to consider whether or not your team is giving Valentine energy or Singles Awareness energy to their clients and prospects.?

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Hopefully, it’s the former not the latter, but if you find yourself figuratively side-eyeing your team as you’re reading this, shoot me a message or give me a call. (Yes, I actually will answer if you call me unlike my Millennial and Gen Z counterparts).

You can reach me at [email protected] or 614-641-0600.

Gretchen Gordon

Author of the best-selling book The Happy Sales Manager ??, Speaker, Entrepreneur, Sales Nerd

1 年

Who knew that you could get sales advice AND dating help all in one stop? Love these cheesy analogies sooo much Kendall Horner . So good.

Tracy Larson

I help sales teams automate their sales process from 'contact to contract' to sell more RMR and win more deals.

1 年

Kendall Horner excellent article.

Anthony Pappis, CFSP

Executive Sales Leader | Vice President, Sales | General Manager | Sales & Marketing Strategist | Sandler | Coach | Team Builder | Key Account Management | Customer Service

1 年

You're an old soul Kendall Horner. My now two adult children have been hearing these analogies for years????

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