How to Turn Dating Agony Into Sales Success

image of guy on couch with roses

At some point in your life, you’ve had one. I’ve had one. Everyone’s had one.

I’m talking, of course, about a really awkward, torturous, embarrassing first date.

You misread a cue and leaned forward for a kiss when your date was just reaching forward to grab their laptop bag.

You find yourself with nothing to say for a full ninety minutes, and sit in agonizing silence as you get increasingly desperate looking for a way out.

The agony of a bad date for most people is matched only by the agony of a really bad sales call. Thankfully, I’ve got a few methods that will help you avoid both.

Just like customer relationships, selling and dating have some striking similarities:

  • If you really, really need a sale (or a date) the likelihood of you getting some action drops significantly
  • If you have the thought “I have to make this one work,” in the first interaction, you will crash and burn
  • Self-confident individuals who enjoy the process have the best outcomes

Early on in my consulting business, I had the good fortune to work with Skip Miller, experienced sales trainer and author of ProActive Selling.

Skip helped me to get over my own fear of selling by teaching me the natural steps in the sales process that totally match the needs of your prospective customer.

Step One: Initiate

This is the very first time that you meet a prospect. It could be an in-person meeting or an online one. Maybe you ran into this person at a networking event, maybe you’re looking at their website, but this is the first impression each of you is making on the other. During that time, there is only one important question you need to answer:

Is there a reason to keep talking?

If you and your prospect have a lot in common or complementary interests and needs, it’s likely one or both of you is interested in taking things to the next level. Calmly and confidently invite them to meet with you formally — kind of like a first date.

In a professional sales situation, this goes something like this:

It was great meeting you, Tom. From what you described about your event, I may have some more ideas for marketing and promotion. Do you want to chat more about it next week? When would be a good time?

Online, you can initiate that same meeting by inviting them to “Call me to learn more” or “Send us an email to set up a free consult.”

If there’s no chemistry, there is no need to play out an awkward sales version of a dating dance, where you politely agree to first, second and third meetings even when you both know that you don’t have much to offer one another. Tell this prospect that you don’t think you’re a good fit for the project, and wish them luck finding the right person.

And if you happen to know someone who might be a better choice, go ahead and set them up with a simple referral. “The project isn’t a good fit for me, but my friend Suzanne might be excellent for you — would you like her number/website?”

In dating and in sales, there’s no point in wasting time when you aren’t right for each other. After all, there are plenty of fish in the sea. In fact, the goal of an effective sales process is to get rid of bad fits as quickly as you can, so that you can continue to fill your sales funnel with more qualified prospects.

Step Two: Educate

While you’re actually on that first date (a phone meeting, consult over coffee, lengthy email exchange), you’re in the Educate stage. This is when you’re going to:

  • Learn as much as possible about your prospect’s situation
  • Find out if he has the money and time to work with you
  • Determine if you could deliver value to him with your solution

While you’re finding all of this out, be on the lookout for any information they’re asking for that is above and beyond “first date” material.

For example, if you were on your first date with a nice person who abruptly asked whether you’d like to have kids, that might be a bit of a red flag. After all, you haven’t even determined yet whether you’re enough of a match to consider kids.

Similarly, if someone asks you for a price quote or proposal before you’ve had the time to get a full background on their situation, it should raise some alarm bells. First you need to learn a little more about one another so you can find out if more serious planning is in the offing. That’s what the Educate stage is for.

Good questions to ask while you’re “dating” a prospect:

  1. What do they want to do?
  2. Why do they want to do it?
  3. When does it need to get done?
  4. What will change for the better in their life or business if they work with you?
  5. What does success look like in their view?

And in turn, they’ll want to find out from you:

  1. Can you really deliver on your promise?
  2. Do you have the capability and resources to solve their problem?
  3. What have you done for others before?
  4. Are you trustworthy?
  5. How do you work?
  6. What do you charge?

In the online businessworld, you’ll be communicating this information to each other in all kinds of ways, including:

  • A phone call/email
  • A detailed “intake” form on your website where you ask specific questions to potential clients
  • Research on websites, Twitter, LinkedIn profiles, and/or Facebook pages to see what they are about and who they connect with (note that this works for both sides)
  • Well-organized case studies, samples, or testimonials on your website
  • Google searches
  • Talking with your past clients or customers (and remember, for better or worse, Twitter makes it easy to find past clients who’ve worked with you)

At the end of the Educate stage, you should have a pretty clear idea whether the two of you are a good fit for one another. If you sense they feel the same way, you can confidently invite them to the next step of the sales process, Validate.

Otherwise, you can make the same graceful retreat we talked about in the Initiate section — say you don’t think you’re a good fit, and possibly recommend them to someone who might be a better match.

Step 3: Validate

At this point, the relationship is beginning to take shape. Now it’s time to make sure you’re both on the same page.

Though you’ve gathered lots of information during the Educate stage, you’ll to clearly lay out exactly what you expect from the relationship and what they’re expecting from you.

It’s time to decide if you can make a commitment. So lay out in an easy-to-understand format like a project proposal:

  • The scope of the work
  • The specific value and benefit of the work (return on investment, saved time, reduced risk, better brand, etc)
  • Roles and responsibilities (what they’ll give you, what you’ll give them)
  • A specific time frame for the project

In dating, this step often shows up some holes in the relationship — you want to see him twice a week, he wants to see you every day. Arguments ensue.

To avoid arguments in your professional relationships at the Validate stage, put everything in writing and make sure you’re clear before moving forward.

If some disagreement comes up during this point in the proceedings, don’t make the mistake of compromising too much. If the price is not working for your client but you are not willing to lower it, that’s a dealbreaker. Time to nicely end the relationship and point the prospect toward another potential match who might be willing to meet their terms.

Step 4: Justify

Now that you both know you’re serious about this business relationship, it’s time to make a proposal.

There are a number of ways to ask for the sale, but you need to be the one to ask. If you’re waiting around for the prospect to ask you if they can give you money, you’ll be waiting a long time.

Here are a few ways to ask for that sale:

  • Send a formal proposal
  • Include a payment link in an email
  • Send them to a page on your website where they can purchase what you are offering
  • Describe the offer with the full benefits and value proposition in a sales letter
  • Direct them to a very clear “Purchase” button

Step 5: Decide

The purpose of the last step in the sales process is to ask for a decision, Yes or No.

Although it seems like a small detail, it actually causes a lot of stress for people new to sales. (And maybe for you.)

The problem is, if you don’t ask for a decision, your prospect floats out to what Skip Miller calls “Maybe Land” — they have your proposal, you think they want to work with you, they know exactly what they need to do to make a purchasing decision … but they’re not getting back to you.

In relationships, this is a little bit like someone saying they need “space.”

You sit and stare at your phone, refresh your email twenty-two times a minute, and slowly go from strong, confident ninja to insecure, miserable failure.

Take control. If you didn’t get a firm yes or no, nicely let them know that you’ll need to move on if they can’t make up their mind.

Tom, I sent you a proposal for our project. In order to meet your deadline for April 15, we need to make a decision if this is a go by February 21. If we decide later than that, I am not sure I can fit you into my production schedule.

So what happens if February 21 comes and goes and you don’t have a decision?

Move on. Consider that this project is in Maybe Land, and it may never get out.

You may want to chill out and wait to see if they get back to you in a day or two. Or you could go back to the Educate stage and make sure that you have clearly communicated the scope and value of your offer.

Whatever you do, do not call or email them every day. You are worth more than that! Get out there and meet someone new — someone who can hold up their half of the relationship.

Desperation was never good for dating, and it is worse for selling.

Happy Valentine’s week!

About the Author: Pamela Slim is the author of Escape from Cubicle Nation: From Corporate Prisoner to Thriving Entrepreneur. She has blogged at Escape From Cubicle Nation for the past six years. You can find more practical sales tidbits in her new program, Ethical Selling that Works.

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Reader Comments (46)

  1. says


    We had a good Valentine Day day presentation on how dating is like a business relationship. This presentation continued with that theme and did a great job.

    You know what would be a good future topic (now that you mentioned it)? How to write a good proposal. While I believe I perfected it in my business, I like to gather more great ideas and presentations.

    I wonder if dating and business sometimes has the element of spontaneity? In other words, the two dating or business partners just hit the “right chemistry”?


  2. says

    The post’s introduction gave me flashbacks of awkward first dates! (thankfully behind me, with a wedding in the offing)

    I think this is a great analogy; there are so many parallels between romantic relationships and customer relationships – in how they are developed, how they are cultivated, and where they can ultimately go.

    I agree with Randy that “chemistry” is important in business, too – but I don’t know how spontaneous that has to be; a lot of it is about reading the customer and being attentive to their needs (easily ported to a different context, I know!).

    • says

      Tell me about memories of awkward dates Danny!

      I am with you on “assisted chemistry” – being clear on who you are looking for, and looking in the right places.

      • says

        Oh, I don’t want to go into too much detail… 😉

        Seriously, though – actually, I’ve found that most times that a first date sucks, it’s because one of the parties isn’t trying to do their share of assisting the chemistry (if both sides aren’t, then everyone’s on the same page and the date ends early).

        Much like a customer relationship scenario, when the customer expects you to do all the work (which is possible, and sometimes necessary, but won’t result in great chemistry).

  3. says

    Another great example of how human interaction on a micro level translates perfectly to business on a macro level. It also occurred to me as I was reading that these 5 steps are very close to the lay out a long form sales letter: 1. State the problem. 2. Educate on problem 3. Present solution 4. Establish your expertise / present your deal 5. Call to action.

    This post is thought provoking on a lot of levels, Pamela, thanks.


    • says

      So true Daniel! I am the newcomer to the world of sales letters, learning from my master teachers Sonia and Brian. I am so familiar with selling services since I have done it for 15 years. But it really does translate when selling online — and if you match the needs of the sales cycle with your sales letter, you will be more effective!

  4. says

    Awesome article Pam. This one line (“the goal of an effective sales process is to get rid of bad fits as quickly as you can”) is the answer to most people’s fear of asking for the sale, and getting a ton of unsubscribes from their email newsletter.

    Not everyone will be a right fit. We have to accept the fact that your prospects might not be looking for what you have to offer, or that their circumstances might have changed. The only thing that is unacceptable is losing the sale to your competitors – that really sucks. :0)

    appreciate the info Pam, thanks

    • says

      Sometimes it sucks to lose a sale to a competitor, and sometimes the competitor is just a better fit and you need to find *your* right customers.

      If the positioning is right, I find that true “competitors” sort of disappear. If you’re an iPhone person, the droid isn’t really a competitor … they’re for Droid people. And if I “lose” a customer to Dan Kennedy, for example, it’s because it’s a Dan Kennedy customer, not a Copyblogger Media customer. (There’s a bit of overlap, but just a bit.)

      I’d rather stress over creating a better experience for the people who are a perfect fit for us.

    • says

      So true Hector, getting rid of bad fits up front is a HUGE part of being an effective salesperson. I have really changed my thinking on this one in recent years — I used to get kind of bummed when I saw people unsubscribe after I sent my newsletter out. Now, I see unsubscribes and think “rock on! they were obviously not a good fit for me, and I was not providing value to them, so now I can focus on those who really want what I have to offer.”

      And I am with Sonia — If someone goes with a “competitor,” I have the same feeling as with the unsubscribes — not my person. Or at least right now — I have had many cases where someone chose to hire someone else, but then came back later to get some coaching or training.

      • says

        That’s the attitude we need to have, or we could end up driving ourselves crazy; wondering what the hell am I doing wrong!!?

        Same here. Clients have told me that they’ve bought this and that product, or have gotten coaching from this and that person – The best thing we can do is believe that the timing was right for them and they saw the value in what we had to offer.

        appreciate your response

  5. says

    I had many a terrible date before I was married, thank god my wife came along!

    A very unique twist and tie into dating and selling, and it’s actually very clever and works well.

    I have actually noted down your points, ok I did the layz way and pasted it into a notepad file, but the questions are ones I want to remind myself of when email marketing and selling.

    Thanks for a unique and refreshing post that was actually helpful too.


    • says

      Thanks Alex, so glad you are happily off the market. :)

      If you take the time to map out your specific sales process, and what you do at each step, it makes it so much easier! Especially if you use technology to help organize things and keep them efficient.

      I am really glad you found the post helpful. Now go sell! 😉

    • says

      That is how we know we are part of the animal world Eric — dogs can smell fear, and prospective customers can smell desperation.

      The funny thing is the more you truly own the fact that you don’t desperately NEED customers (lots of fish in the sea), the more attractive you are. :)

  6. says

    “Maybe Land” :-) I’ve sent a lot of customers backpacking in “Maybe Land” because a part of me just can’t bear to ask for the sale. I’m getting better though.
    Great post! Thank you.

    • says

      That is a great point Jax — how funny that WE can be the ones to keep things in “Maybe Land.” The best advice that I can give is that it becomes much easier to ask for a sale the more you practice.

      And it doesn’t have to be dorky like “Jax, I need to know TODAY if you are going to work with me.” it can be “Jax, I really think I could help redesign your website, and would love to do it! In order to set my production schedule, would you mind telling me by Friday if you want to go forward or not?”

  7. says

    I have always loved the dating analogy.

    Now, let’s talk about what happens after a first date. If you’re interested in a long term, wonderful relationship you’ll act in a certain way. If you’re after “one thing” you’ll act in another way.

    I’m thinking of one click upsells. The first “buy” is your first date. And what would you think if a suitor, immediately after the first date was arranged put a proposal in with obviously manufactured pseudo-scarcity?

    “Hey, Darling, I’m SO GLAD you decided to go out on a date with me. That’s what smart people do! However, you know, time’s winged chariot and all, you must ACT NOW if you want to get blissful lovin’….which includes a backrub, but ONLY if you act now. That’s right, you know, I’m going to be middle aged soon, so that backrub won’t be freely given, and you’ll be raked over the coals for it soon. But you’re smart, you’ll make a commitment right now.”

    If we think of people as a long term relationships–instead of one night stands–we’ll act differently.

    And you’re right, the stink of despair is the best repellent ever.

  8. says

    Great article!

    I have to disagree with asking about kids on the first date, however :)
    It’s good to get the deal-breakers out of the way!

    • says

      HAH Joanna — I bet you have no problem screening out “Maybes” early in the sales process by saying “So, Pam, before we get to far, to you actually have money to pay for my services?”

      (the equivalent to the “do you want to have kids” question)

      Deal-breakers are great. The more robust your qualifying questions are, the more success you will have closing the right sales.

  9. says

    Thank you, Pamela, for laying the groundwork for a business plan, or a website. I love your analogy too. I have never seen someone lay the foundation so clearly before – A leads to B leads to C. etc. This article really clicked for me and was one of those “aha!” moments. I didn’t just bookmark it – it’s printed out!

  10. Ronald Sieber says


    Cute analogy that is also very appropriate. I kind of already use it in business, so this blog is a nice affirmation that others are thinking & doing as well.

    I think I’ll apply some of it to my dating to see if I have any better luck there. Hah!

    All the best!

  11. Rob says

    Love the question- What does success look like in their view? Sales people, well all employees should ask this question!

    Loved the blog

  12. says

    I agree with the “there are plenty of fish in the sea”. People don’t realize that we do not live in the world of scarcity, but in the world of abundance. It’s important to shift this belief and once we do that, new opportunities begin to rise in front of our eyes.

  13. says

    Nice piece – and dead on about the similarity of the methodologies. For me personally, I find the process very nerve-racking – guess that’s why I was a terrible salesman (and am glad I’m married now!).

  14. says


    You make some great points. Sales and dating ARE totally tied around the concepts of confidence and an inverse of how much you seem to need it. Desperation is a stink that scares away all potential suitors. Taking the steps to at least seem as is if you are not desperate and full of confidnce can radically improve your chances of success.

  15. says

    Great analogy Pamela.

    I like you saying ‘If there’s no chemistry, there is no need to play out an awkward sales version of a dating dance, where you politely agree to first, second and third meetings even when you both know that you don’t have much to offer one another. ‘ It will save you a lot of time.

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