Sales is just like Dating

SALES IS JUST LIKE DATING

Sounds strange? Maybe.

But after years of pitching collaborations, building partnerships, and letting go when things didn’t align, I’ve realized the same emotional intelligence that helps us in personal relationships is essential in business too.

“Doing Business Like Dating”

This could be the thread for a true sales course one day and not just another manipulative “overcome objections” training session.

Something client-centric, rooted in human connection.

1. The Moment It Hit Me

It was a Monday after a long weekend in Kuala Lumpur—one of those occasional Monday blues, where my task list stared back at me, filled with proposals to follow up on, leads to revisit, and conversations left hanging. Some follow-ups felt aligned—like the right thing to do.

But one stood out. My body recoiled (and in my experience, our bodies tell us more than our logic ever could, so we are well advised to listen and take note) as I stared at the name.

A quiet voice inside whispered:

“Why are you still following up on this?”

The truth is, the answer had layers.

2. The Trap of Generous Giving

As someone in consultative sales—with a capital C—I’m used to giving generously. I offer value, insight, and time before I’ve seen even one dollar. Not unlike a movie trailer that excites the audience without spoiling the whole plot.

Except, I tend to give away more than the trailer. Sometimes, I offer the whole middle section too—so much that people might wonder, Why pay for the movie if I’ve already seen most of it?

And that’s fine—to a point (and I am a human in progress and not flawless). I believe in offering real value upfront.
But there comes a line.

3. When Silence Speaks Louder Than Words

When you’re offering insights, answers, and attention—and receiving silence, breadcrumbs, mixed signals, disinterest, or worse, ghosting—it starts to feel imbalanced. Disrespectful, even.
And while ghosting can vary by culture and isn’t always malicious, it doesn’t make it any less frustrating.

So why was I still considering to pursue—or to phrase it more nicely, “trying to conquer”—this lead, even though it was clearly not being reciprocated?
It wasn’t a scarcity mindset, external pressure, or that my livelihood depended on onboarding this potential client.

Maybe it’s the belief that what I offer could bring genuine value to that company.
Maybe I see so much potential in people and in companies—and in how I can serve them—that I ignore reality.

But the fact is: not everybody is ready or willing to act on their potential.
And if they aren’t, you can offer the Holy Grail and they still won’t welcome it.

Then, a thought hit me:

4. It Felt Like Dating

Would we keep texting someone who clearly isn’t interested?
Would we continue investing in someone waving Ferrari-red flags or ghosting us?

Of course not ! (And if you say yes, this post may not be for you—because then we’re talking about a self-worth issue, not a sales strategy.)

In dating, we’d say:

“I’ve shown up. I’ve been real and if that’s not enough, I’ll move on. The right partner will see my value.”

And that’s when it really clicked:

A healthy sales process mirrors a healthy dating process.

Sure, dating has more emotional layers than logic-driven business ventures, and in business things can come up—unforeseen delays, approvals, etc.

But I’ll still argue this:

When a lack of communication is apparent, even in business, it shows you where a client’s priorities truly lie.
And they might not include your ideas, no matter how good you think they are.

5. The Courtship Phase– First Impression and Curiosity

Whether in business or dating, it all starts with a spark.

Reaching out. Being receptive. Being found.
Being visible, making a connection, offering a glimpse of value or personality.

No hard pitch. No urgency. You’re inviting someone gently into your orbit, not with desperation or a “fast and furious” mindset.

Great business interactions, like first dates, aren’t one-sided monologues. They require deep listening—the kind where you’re not just planning your next response while the other person is speaking.

Sounds easy?

I’m a certified life coach, and let me tell you: real listening is harder than most think.
Try it and just listen. Observe how someone speaks, what they say, how they say it.
Try not to formulate your next comment halfway through.

If you master this, you’re already rare—and far ahead of most salespeople (or people in general).

When a potential client says, “Let me think about it,” that’s not rejection, it’s reflection.
Like someone going home after a great first date to think things through.
Respect that space. Offer more clarity or communication if needed.

Only manipulative salespeople pounce on uncertainty, manufacturing scarcity or pressure.

I’ve seen it. I once sat through a presentation full of those tactics given by a salesperson, and I felt deeply uncomfortable. No—let’s call it what it was: I felt ashamed (because I indirectly worked for that company).

It went against some of my deepest core values.
Internally, I was trying to telepathically signal the prospect sitting next to me:

“Don’t fall for it. Leave.”

They didn’t buy. Whether it was my telepathy skills or their good judgment—I was relieved.

6. Mutual Effort: It Takes Two to Tango

We might have experienced lopsided dating—one person plans, initiates, keeps the spark alive.
In business, it’s no different.
When one side does all the persuing and adjusting, it’s not a tango, it’s slam dancing. As I wrote in a recent follow-up email to a client:

“It Takes Two to Tango.”

Without shared effort, there’s no real partnership—just vague interest or the attempt to extract free value.
And that rarely leads to anything meaningful or sustainable.

7. The Negotiation Phase: Are You In Sync?

We’ve identified a good match.
One or both of us may need more info, so more talks, trust-building, and meetings are required.
That’s healthy. It’s about matching pace, but with clear progress toward a decision.

The red flag?

When one crosses your boundaries.
You feel it as it’s forced, not flowing organically. You want the deal or the partner, but ignore the bright Ferarri red flags.
And even if you “win,” you know it’s a short-term win.
Deals that feel forced often backfire.

Eventually, that deal becomes more of a liability than a lasting relationship.

8. Knowing When to Let Go

One of the hardest skills in sales—and in life—is knowing when to walk away.

You can pour your heart, time, and expertise into something… but if the other party isn’t meeting you halfway, it’s time to leave.

With grace. With warmth. With self-respect.

I recently sent a goodbye email to a very warm lead I had personally talked to.
It read like a relationship closure:

“Maybe we’re just not the right match at this time. No hard feelings—you’re not wrong, and neither are we. It is what it is and I only wish you the very best for your business and should the situation ever change on your side, our door remains open in the future”

And I meant every word. No bitterness.

And it’s true. Rejection or mismatch doesn’t diminish our value as a person and also not our business services.  It simply points you toward someone—or something—more aligned (even if we can’t yet see when the next branch will appear). Of course its hard to accept when you have been striving for weeks and months and already have invested time and effort.

9. Goodbye With Grace

Just like in dating, how we say goodbye in business matters.
In both sales and love, a graceful exit honors the interaction and shows dignity, empathy for the other person and for yourself.

When you walk away, do it with confidence and knowing that you showed up fully.
It might sound a bit spiritual woohoo, but I truly believe (the trusting part is sometimes harder) knowing that what flows away wasn’t meant to stay.

And what stays?
That’s the right fit which is aligned and when the time is right.

Of course, we are human, it stings when you’ve invested time and effort. But the comfort and what gives me peace of mind, is that I did my best, and that’s enough.

There are so many external forces we cannot control. Sometimes, we have to surrender and trust that it didn’t work out for a reason, maybe even for the highest good. There are often lessons to take away (there almost always are), and sometimes, it’s even a blessing in disguise.

And yes—that includes sitting with the discomfort of not knowing when your next quality lead will arrive.

We’re human. It’s normal. I don’t have a magic formula either. I don’t sweep the disappointment under the rug, I sit with it, feel it, and eventually, it loosens its grip. It always does sooner or later.

10. Why Many Salespeople Don’t Do This

• Fear: Fear of missing quotas. Fear of losing your job. In dating, rejection stings. In sales, it can threaten your livelihood.
• Scarcity Mindset: “If not this client, then who and when?”
• Toxic Sales Culture: Think: high pressure call centers, cold calls until your fingers bleed, scripted pitches on repeat.
  (Frankly, I’d be happy for AI to replace those jobs—they must be soul-destroying)
• Lack of Trust: In themselves, their offer, or the timing of life.
• Short-term thinking: Closing fast is often valued over building trust, which takes time. It´s the difference between chasing flings and cultivating commitment.

11. Final Thoughts

Business is like dating.

Sometimes it works.
Sometimes it doesn’t.
But when it’s mutual, aligned, and real? That’s when the magic happens.

Until then:

• Keep showing up with heart, best of intentions and knowledge
• Lead with value
• Set boundaries
• Accept that sometimes its not the right time
• Walk away when it’s not right
• Stay open when it is
• If you’re chasing, it’s already a no.  Focus on those clients that see your value

What This Taught Me

In both business and love:

• Authenticity wins in the long run
• If we sold the way we date (in a healthy way), salespeople would be seen as allies—not as people to avoid
• Desperation repels
• Real connection beats polished pitches
• Detachment isn’t indifference or giving up—it’s trust and some faith.
  Trust that if you’ve done your best, whatever happens next is for your highest good
  (Even if that’s hard to believe at first)

We are not for everyone—and that’s the point.