Dating is just sales.
When I was nineteen I was not having a great deal of success with the opposite sex. My older sister’s boyfriend, said something that stuck with me for the next thirty years.
“You’re good at sales. Dating is just sales. Ask ten girls to go for a coffee and one of them will say yes.”
It transformed my dating life. More importantly, it gave me a framework for thinking about sales that I have never found a better analogy for. The parallels are so exact, and so consistently instructive, that I still use this comparison when I am coaching salespeople who are struggling with the fundamentals.
Here are seventeen of them.
1. Stop looking for a perfect match
A prospect pool of one is not a prospect pool. It is a lottery ticket. Your chances of finding love, or a sale, by focusing your energy on one specific person are close to zero. You need to talk to far more people than you think is reasonable. I went on thousands of dates over the years. Not figuratively. I took the advice seriously. The numbers work if you commit to them.
2. Ask exploratory questions
Learn how to ask questions that open a conversation rather than close it, with genuine curiosity and genuine empathy. Then stop talking and actually listen. Not listening while you wait for your turn to speak. Listening with the intent of learning something you did not already know. This is the skill that separates the salespeople who build relationships from the ones who just deliver pitches.
3. Do not collect red flags
Look for a mismatch early and get out cleanly. In sales this is called qualifying out, and it is one of the most valuable disciplines in the profession. Good salespeople do not drag bad-fit prospects through a long sales process hoping something will change. Good daters do not ignore obvious incompatibilities because they are lonely. The same principle applies in both contexts. The sooner you identify a bad fit, the sooner you can find a good one.
4. Take the no and move on
There is nothing to be gained from spending significant emotional energy trying to understand why a specific person did not want what you were offering. It does not matter. It really does not. Some prospects are not the right fit, some timing is wrong, some people just said no. Take it, learn what you can from it, and move forward. Wallowing in a rejection is time you are not spending on the next conversation.
5. Win some and learn some
Every no is data. The question is whether you are collecting it or discarding it. After a rejection, in dating or in sales, try to work out what you actually did. Was the opening wrong? Did you talk too much about yourself? Did you misread the buying signal? The people who improve consistently are the ones who treat every lost deal as a debrief rather than just a disappointment.
6. There are plenty of fish
Ask for referrals. Actively. Your existing relationships, both personal and professional, are the most efficient path to the next good prospect. But also get into the wider ocean. Referrals alone will not build a pipeline. You need to be finding people who do not already know you, which means channels, activity, and a willingness to go wider than is comfortable.
7. Do not confuse attention with interest
This one costs a lot of salespeople a lot of time. Just because someone is engaged in a conversation with you does not mean they are serious about buying. Look for intent. Ask the questions that reveal whether the person is a genuine prospect or someone who enjoys being sold to without any intention of committing. Work out the time wasters and let them go. Politely, but early.
8. Improve your pitch, not your persona
If you are getting consistently shut down, the problem is rarely that you are fundamentally unlovable or that your product is fundamentally unsellable. It is almost always that the way you are presenting yourself or your offer is not landing correctly. Be honest about what you are offering. Do not undersell it out of bashfulness and do not oversell it out of desperation. Be direct and be bold. And accept that not every product is for every person, which is information, not failure.
9. If it is not a fit, say it
Stop ghosting people. In dating and in sales, the person on the other end of a conversation deserves a clear answer. It takes thirty seconds to give someone a direct, non-hurtful response that closes the loop and lets both parties move on. Without honest feedback, nobody improves. The salesperson who can deliver a clean, respectful qualifying-out conversation is doing both parties a service.
10. Timing matters more than you think
Sometimes a no is not a no forever. It is a no right now because the person is mid-implosion, mid-divorce, mid-board restructure, mid-something that has nothing to do with you or your offer. The right thing to do is note it, give it appropriate time, and follow up. Once. Maybe twice. Not seventeen times. Timing sensitivity is a real commercial skill and most salespeople either ignore it entirely or overdo the follow-up in a way that makes the eventual yes impossible.
11. Good salespeople tell stories
People do not buy products. They buy people. They buy the version of themselves that owns the product. The spec sheet is not the close. Your story, your reason for being in this business, why you believe in what you are offering, how it has changed things for people like them, that is what creates the emotional permission to say yes. Learn to articulate it.
12. Confidence beats desperation
Nobody wants to buy from someone who is desperate for the sale. Nobody wants to date someone who is desperate for a relationship. Desperation is visible before a word is spoken and it is repellent in both contexts. Confidence is not arrogance. It is the quiet certainty that what you are offering has genuine value and that the right person will recognise it. That energy is attractive in both personal and commercial contexts.
13. Understand your buyer persona
Know what a good prospect looks like. Not in a vague, intuitive way. Specifically. What are the characteristics of the people who have bought from you before and been genuinely happy with the outcome? What problem were they trying to solve and why did your offer fit it? That picture is your buyer persona and it is the filter that makes all your prospecting more efficient.
14. Do not be afraid of the big account
Someone is going to win that enterprise client. Someone is going to get the date with the person who is out of their league. It may as well be you. The willingness to go after accounts that feel larger than your current size is how you grow into your current size. Do not disqualify yourself before the conversation has happened.
15. Do not overprice what you are offering
Know your market value and be honest about it. Just because you love your Toyota does not mean you can charge Ferrari prices. Too many business owners, and too many people in general, overestimate the value of what they are offering relative to what the market will bear. Pricing yourself out of consideration is not confidence. It is a misreading of the room.
16. Some people just like being wooed
Not every conversation that goes well is going to convert. Some prospects genuinely enjoy the process of being sold to with no intention of buying. Some people like being taken to dinner with no intention of a second date. Recognise the pattern and do not let it flatter you into wasting resources on someone who is enjoying the attention rather than evaluating the offer.
17. There is no perfect customer
We are all a version of crazy. Every client, every partner, every long-term relationship comes with its own specific brand of difficult. Your job is not to find the person with no quirks. It is to work out whose particular flavour of complicated you can work with productively, and whose you cannot. That self-knowledge will save you enormous amounts of time and frustration on both sides of your life.
The older guy who gave me that advice when I was nineteen was not trying to be profound. He was just solving a practical problem. But the analogy holds across every dimension of sales because the underlying dynamic is the same. Two people, working out whether they are a good fit for each other, with one of them responsible for creating the conditions in which the answer can be yes.
That is the job. In sales and in life.
For more thinking on the fundamentals of commercial sales, there is more at www.outsold.com.au/blogs.
