The Secret to Selling Without Being Salesy

Was forwarded this email? Don’t worry, subscribe HERE

THIS ISSUE

1. THE QUEST: A Talk About The Reincarnation of Brand

2. FEATURE: The Secret to Selling Without Feeling Salesy (4 ways to do it)

3. #PSYCH!: The Blemishing Effect: Why Imperfection Makes You More Irresistible

CHECK OUT THE NEW FORMAT!

(Please reply to this and let me know if you have feedback because you = legend 🙏🏽)

THE QUEST

Hey legends,

I’m introducing this new section to let you in on my journey to impact 1M people (help them go from unknown to legendary using the principles of influencing human behavior).

So last week I gave a “transformation talk” at the Marketer’s Community and I felt absolutely alive! It’s been awhile since I spoke to a crowd and I loved it. So I’m going to do more of it this year. What was my presentation?

It was about the reincarnation of brand - we stripped away all the assumptions around brand and built back up a framework that is ultimately about influencing human behavior.

I received a tremendous response - it was the unlock they’ve been looking for:

And since most of you weren’t able to attend, I’ve created a free resource for you. Enjoy!

FEATURE

The Secret to Selling Without Feeling Salesy

Does selling feel weird to you?

Ever hopped on a sales call and felt awkward as hell? You don’t want to sound pushy. You try so hard not to be that sleazy salesperson. So, you tiptoe around the offer, or whatever the solution was and you secretly hope they’ll ask for a proposal or help.

Honestly I’ve felt that way for a long time, until I was working with a senior partner at my previous agency.

He would always seem so comfortable, while I squirmed in my seat and so I asked him what the secret was and this was what I learned:

If selling feels uncomfortable, it’s because you’re focused on yourself.

I would catch myself thinking these things:

🔹 What if I say the wrong thing?
🔹 What if I lost the deal?
🔹 What if I sounded desperate?

Me, me, me.

But selling isn’t about you.

It’s about them.

And when you shift the focus, everything will change. It did for me!

The Best Salespeople Don’t Sell—They Diagnose.

Most people think selling is about persuading someone to buy. But the real pros? They act like doctors, they find out what is the problem and then connect that problem to a solution.

Imagine going to a doctor for a headache, and they immediately hand you pills without asking a single question. Red flag, right?

Instead, doctors dig deeper:
✅ When did this start?
✅ What have you tried before?
✅ What else is going on?

Only after understanding the real problem do they offer a solution.

That’s exactly how selling should feel—a natural, problem-solving conversation, not a high-pressure pitch. And so whenever we start solving a problem and not use any prepared slides, that would always be the best indication of a closed deal.

The irony? When you stop trying to sell, you actually sell more.

You’re Not Here to Close—You’re Here to Serve.

Sales feels gross when you think your job is to convince. But when you realize your job is to guide—to help people make the best decision for them—it’s a game-changer. Crazy right?

And sometimes? That decision won’t include you. That’s okay. Because when you operate with honesty and integrity, trust booms. And trust? That’s what fuels long-term business growth. There are so many times now where I say the fit just isn’t there and that’s totally fine, because it would more disastrous if I forced my solution onto something that would probably fail anyway.

Here are 4 Ways to Sell Without Feeling Salesy:

🚀 Be Curious, Not Convincing
Ask powerful questions instead of pitching:

• What’s your biggest challenge right now?

• What does success look like for you?

• What have you already tried?

🚀 Detach from the Outcome
If they say yes, great. If they say no, also great. You’ve built a relationship either way.

🚀 Challenge Assumptions
Sometimes people think they need a solution—but the real issue is deeper. Example: A business owner thinks they need a logo. But after talking, you realize their real problem is weak brand positioning.

🚀 Trust the Process
Not every call leads to a sale today, but every conversation builds future opportunities—referrals, partnerships, and unexpected deals.

Final Thought: Selling Should Feel Good—For You and the Client.

The next time you get on a call, serve like a legend.

If you want to listen to the podcast episode where I break it down, listen on Apple, Spotify or on the web.

#PSYCH!

This new section will give you a psychological effect and human truth each week that I’ve come across that can help us influence human behavior. (If you reply and send me something awesome you’ve seen, I’ll post it in the next issue!)

The Blemishing Effect: Why Imperfections Make You More Irresistible

I recently read about this weird thing—being too perfect actually makes people trust you less. Wild, right? And so having a small flaw is actually better.

It’s called the Blemishing Effect, and it basically means that a tiny, harmless flaw can make something more desirable.

💡 Quick example—Ever seen a product that says, “Not the cheapest, but the best”? That little “negative” actually boosts sales because it feels real. Or think about reviews—if a product has only 5-star ratings, don’t you kinda not trust it? (View an ad using this effect).

📖 Crazy stat: A study found that when a product had a minor downside (like, “This book starts slow, but the ending is amazing”), people were 22% more likely to buy it than if the flaw wasn’t mentioned at all. (Study here).

So next time you’re selling something (or even just being you), don’t stress about being perfect. A little imperfection? That’s what makes people love you more- you might even want to reveal a small flaw or defect.

Bye for now, I’ll see you next Sunday!

In the meantime, go make your mark, live your legend 🤘🏽,

Howie Chan

Creator of Legend Letters

​Read my story​

​Follow me on LinkedIn

P.S. I hope you enjoyed the new format - email me, let me know! 🙏🏽

WHENEVER YOU ARE READY

Make your mark with a powerful brand 👇🏽

1/ Power Hour

1:1 60 min executive brand coaching to help you pivot from corporate life to business owner.

Learn more

2/ Personal Brand Strategy Program

Get clarity on your story and your brand so you can attract what and whom you want into your life. I work with you directly and craft your one page personal brand strategy.

​Learn more