Who’s Training Your Customers?

And If It’s Not You, Why Are You Still Surprised They Don’t Buy From You?

July 1, 2025 | Jonathan Lipson | Founder & President | The Cigar Profit Consulting

The Quietest Problem in Your Shop Has the Loudest Impact

It starts with a harmless comment.

Somebody walks into your shop, looks over the humidor, and says:

"I heard this one tastes like a Cuban. Reddit loves it."

Or:"

A guy on YouTube said this other brand uses 20-year-old tobacco, so I think I’m gonna grab that instead."

And suddenly, you’re not just a cigar shop. You’re trusted family.

You didn’t say it.

You didn’t co-sign it.

You didn’t sell it.

But now you’re stuck playing defense on someone else’s pitch.

Welcome to modern cigar retail.

Where you spend rent on premium inventory, payroll on half-informed staff, and your marketing budget on trying to stand out -

only to have the real education of your customer done by a Facebook group, a cigar “influencer” with a ring light, or some guy who’s smoked every “rare” cigar twice and still buys samplers online.

Here’s the hard truth:

If you’re not the one shaping the way your customer thinks about cigars,

what makes you think they’ll keep buying them from you?

You don’t have to be a blogger.

You don’t need a newsletter or a social media strategy.

You just need to be the authority in your store.

Because the moment you surrender that role,

you’re not a tobacconist anymore -

you’re a vending machine with a checkout counter.

If You’re Not the Authority, You’re Just the Checkout Counter

There’s a dangerous delusion in cigar retail today:

“If the customer walks in the door, I’ve already won.”

But if your customer walks in armed with misinformation, half-truths, or the loud opinions of people who’ve never stepped foot in your store -

you haven’t won anything.

You’ve been cast as the passive facilitator of a sale someone else already influenced.

Retailers complain that margins are thin, loyalty is fickle, and customers are buying with their phones in one hand and your cigars in the other.

But the truth is brutal: you trained them to act that way - by not training them at all.

You gave up the right to guide the experience.

You let the algorithm win.

And now, you’re standing there like a silent cashier wondering why you can’t add on to the sale.

Authority in your shop doesn’t mean ego.

It means expertise with the courage to speak it.

When a customer says, “’X Blogger’ says this tastes like a Cuban,” you don’t have to scoff or get defensive.

You calmly respond:

“Interesting take. I get how some people might say that, but the profile’s driven by Estelí Ligero - peppery, full, with an intense retrohale. Sure, it’s not like some Cuban cigars can’t do that, but it seems to me that a Corojo forward Honduran may be a better bet for what you’re referencing. Want to compare the two side by side and see what your palate tells you?”

Boom.

Now you’re the expert.

Now you’re in the conversation.

Now you’re moving the customer into your world - not chasing them through someone else’s.

That’s how you train your customers.

That’s how you earn the sale.

And that’s how you become more than just a place they shop - you become the place they trust.

Train for Trust - And Trust Converts

Trust isn’t built with a smile at the register or remembering someone’s name. That’s hospitality. Necessary, yes - but not enough.

Trust is built when your customer realizes:

“This place knows what I like, and they don’t just want my money - they want me to enjoy what I buy.”

And here’s where most retailers blow it:

They think education is a luxury - something for the membership lounge, or “when I have more time.”

Meanwhile, customers are getting trained daily - just not by you.

You want to win? Start making training your customer part of the sale.

They like full-bodied cigars but want to branch out? You guide the move.

They’re obsessed with one brand but you’re overstocked on a competitor’s slow mover? Find the overlap in profile and reframe the conversation.

They’re price-sensitive but want a celebratory stick? You bring out the underdog blend that punches above its MSRP.

This isn’t manipulation. It’s professionalism.

The best cigar reps do it to you every day - why shouldn’t you do it for your customers?

Because when you train a customer well,

they stop asking Reddit.

They stop defaulting to “what got 94 points.”

They stop driving across town to save fifty cents.

Why?

Because you’ve become their algorithm.

They don’t have to search - you already know.

And that trust?

It doesn’t just keep them coming back.

It makes them buy more when they do.

Next time a new box hits your shelf, you’re not making a blind recommendation -

you’re handpicking who to call.

Because you trained them.

And now, you can activate them.

You Know Their Name. But Do You Know Their Buying Pattern?

You know John.

He comes in on Thursdays, grabs a coffee, smokes one in the lounge, and walks out with a five pack.

You know Maria.

She buys for her husband. Medium-bodied, open draw, bands he can show off to his golf buddies.

You know the names - but do you really know the patterns?

Because the real edge in retail isn’t just about being friendly. It’s about being informed.

If you don’t have a system - digital or analog - that tracks what your customers buy, how often, and when, you’re missing the easiest upsell of your life.

John didn’t just come in today - he skipped last Thursday.

Maria’s husband hasn’t had a different cigar from you in three months.

There’s a medium-bodied Connecticut with better margin collecting dust on your shelf with sharp branding that’s perfect for that crowd - but no one’s pulled the trigger because no one’s made the call.

That’s where customer intel becomes retail leverage.

You want to turn that buying mistake into a sale without putting it in the three for $15 bin?Start with the people who’ve shown they’ll actually smoke it. If they haven’t seen it, it’s new to them.

It’s not about pulling a fast one or selling harder.

It’s about rewarding their loyalty by acting like you remember them - because you do.

Even if you don’t use a CRM, you have a POS system.

You have a lounge manager.

You have employees who see the traffic;

So why are you still running your shop like it’s 2004 and everything resets every Monday?

This is how the online guys beat you.

They don’t know the customer - but they know how they buy.

They weaponize that data into retargeting, cross-selling, timed offers, and relevance.

You have something stronger: relationships.

So combine both.

Know the name and the pattern.

Because that’s what turns casual customers into consistent ones.

Be the Guide - Not the Gatekeeper

Too many retailers mistake gatekeeping for expertise.

They turn their nose up at customers who mispronounce “seco,” scoff at bundled cigars, or laugh at anyone who doesn’t get advice from Cigar Aficionado.

That’s not authority. That’s arrogance.

And it’s killing your sales.

You don’t win loyalty by proving you’re smarter.

You win it by guiding - calmly, confidently, and without ego.

Think of it this way:

Your humidor isn’t a museum.

It’s a jungle - thick with options, noise, and risk.

To a new smoker or even a casual one, it’s intimidating. So they either ask ‘dumb’ questions… or they don’t ask at all.

And when you act like they should already know?

They’ll go somewhere they’re not made to feel dumb.

Maybe it’s online.

Maybe it’s the guy down the street with the same inventory and a better attitude.

But if instead you become the Sherpa of their cigar journey -

someone who shows them, explains without condescending, and guides without pressure - you become more than a place that sells cigars.

You become their cigar shop.

There’s a way to build trust without lowering your standards.

You can still move the slow stuff. You can still work your margins.

But do it from the posture of partnership - not superiority.

Because your best customer tomorrow might be the guy today who doesn’t know the difference between Corojo and Connecticut.

And if you treat him like a project instead of a problem?

He’ll bring all his cigar money to you.

Insights Are Currency Here’s How to Spend Them

You’ve built trust.

You’ve tracked the pattern.

You’ve guided the sale.

Now what?

Now you cash in.

Not in the sleazy used-car-dealer way. In the smart retailer way - the way that uses what you know to make better moves, faster.

Let’s say you’re considering a new brand.

Their rep’s been in twice. The samples? Decent. Packaging? Solid. Price point? Manageable.

Still, you're not sold.

So what do you do?

You don’t guess - you leverage insight.

Hand out a few unbanded samples to your most trusted regulars - those who actually smoke that blend profile.

Ask for honest feedback: burn, draw, strength, flavor, finish.

If their palates light up, that’s signal - not noise.

If some of them ask, “When are you getting this in?” - now you’ve got buy-in before making the investment.

And if it tanks? You just saved yourself shelf space and cash.

Now you’re not making a decision in isolation.

You’re using your community as a built-in tasting panel - and they love you for it.

That’s a move most retailers don’t make because they don’t think like a data-driven business.

But that’s exactly what your shop should be.

When you spend insights right, you:

• Avoid dead inventory

• Get faster staff buy-in

• Strengthen customer loyalty

• And position yourself as a shop that listens and acts

You stop being reactive.

You stop chasing “the hot thing.”

You start curating instead of guessing.

And the customer feels it.

They know they’re part of the process.

They feel seen, respected, even valued.

Which means when the new cigars hit the shelf, they move.

You want conversion rates that beat online?

Use your insights like cash.

Reward loyalty with involvement.

Reward involvement with recognition.

Reward recognition with access.

Because the truth is:

In premium cigars, insight builds trusts.

And trust is what opens wallets.

Make It Personal - So They Don’t Have To Google It

You ever get a customer’s spouse wandering into the shop before a birthday or anniversary?

They’ve got that nervous energy.

They want to get it right, but they have no clue what their partner smokes.

They’re hoping you know.

Now, if you’ve built that relationship right, you don’t just point to a shelf.

You say, “Don’t worry - I got you.”

You pull the exact cigar, maybe even package it with a lighter or pairing suggestion.

You look like a mind reader.

And suddenly, you’re not just a cigar shop.

You’re trusted family.

That only happens when you know your customer better than the internet does.

Which is why collecting, tracking, and applying customer data is more than a tech tool.

It’s the backbone of modern tobacconist loyalty.

It lets you:

• Suggest cigars that match evolving palates

• Offer alternatives during out-of-stocks

• Notify someone when their cigar lands back in

• Keep tabs on who deserves a heads-up when something special drops

That’s concierge-level service.

That’s what the internet can’t do.

That’s what makes a customer yours for life.

Retailers like to complain about margins, taxes, online competition…but most haven’t put in the work to be irreplaceable.

This is how you do it.

You give a damn.

You pay attention.

You make it personal.

Because if a customer has to Google what they bought from you last month…you didn’t sell them a cigar.

You rented a transaction.

And rented transactions don’t build thriving businesses.

When Data Drives Delight - Creating Unexpected Moments That Convert

This is where the rubber meets the road.

Let’s say you’ve got a customer who always grabs medium-bodied Nicaraguan toros. He swings by every other Friday, hangs for an hour, and grabs a box every two months.

Most retailers stop at, “He’s a good customer.”

You?

You use your data to flip that into a moment.

The next time a new release drops that fits his profile - even if it’s limited, even if you only got five boxes - you make the call.

Not a mass text.

Not a newsletter.

A direct call:

“Hey, this just came in. It’s your kind of smoke. Want me to hold some aside?”

Now you’re not selling cigars.

You’re selling access.

You’re giving that customer the dopamine hit of being in the know, of being prioritized.

That’s not just good service.

That’s retention by design.

These unexpected, data-informed moments lead to:

• Higher purchase frequency

• Stronger word-of-mouth (they’ll brag to their buddies)

• Deeper brand attachment (to your shop, not just the cigar)

And if you’ve done this across your top 20–30 customers, you’ve basically built your own brand advocate base - quiet, loyal, and rooted in real buying behavior, not hashtags and hype.

You want to create unforgettable customer experiences?

Stop guessing.

Start watching.

Then deliver something so thoughtful it feels spontaneous.

Because when you know your customer better than they expect,you create a kind of magic that can’t be matched by price or promo codes.

Educated Customers Buy With Confidence - And That Means They Buy More

An uncertain customer hesitates.

A confident customer spends.

The beauty of education - real education, the kind you give them over time in your shop - is that it removes decision friction. A customer who knows what they like and trusts your recommendations doesn’t need to hem and haw at the register. They don’t need to  “Google it”, “shop around” or “think about it.”

They buy.

And they come back.

This isn’t about creating cigar snobs. It’s about equipping buyers.Because when you teach your customers:

• What strength means in your humidor,

• How different wrappers might shift their usual profile,

• Why X cigar pairs better with their go-to whiskey than Y…

…you’re building loyalty rooted in clarity, not just convenience.

They stop asking, “What’s good?” or even worse, “What’s new?”

They start asking, “What’s something in my lane I haven’t tried?”

And that’s when you know you’ve moved from store to staple.

It also sets you apart from the guy down the block who has a bigger humidor but no clue how to guide a customer through it. It separates you from the online cart that suggests cigars based on algorithms, not actual palate memory.

Educated customers don’t buy less - they buy better.

They buy for friends, because they trust their own recommendations.

They upgrade.

They stock up.

They become your best asset, because they’re proud of what they know - and where they learned it.

Your Staff Should Be Your Students - And Then, Your Teachers

Let’s be honest:

The biggest missed opportunity in most cigar shops is standing behind the counter, either reciting a Halfwheel review or parroting the shelf-talker.

That’s not sales.

That’s order taking.

If your staff isn’t trained, they’re winging it. And if they’re winging it, your customers are being under-served - and probably educated by YouTube, not your retail floor.

Here’s the fix:

Make every team member a student of your humidor first.

Not just what’s in it, but why it’s there.

Teach them:

• The profiles of each line you carry

• The brands you’ve decided not to carry (and why)

• The buying patterns of your top-tier customers

• How to ask the right questions, not just make recommendations

Because when they understand the why, they stop sounding like generic salespeople.

They start sounding like specialists.

And when they’ve absorbed that knowledge?

Now they become teachers.

Your staff becomes the frontline of customer education - translating cigarspeak into everyday conversation. They help the first-time buyer feel seen. They help the regular discover something new. They help the collector make sense of what’s worth chasing - and what’s just press release hype.

You don’t need to hire cigar “sommeliers”.You need engaged, informed, curious people who care about delivering better experiences.

If that’s not who’s on your floor right now?

Start training.

If they don’t want to learn?

Start hiring.

Because your humidor might be full, but if your staff’s heads are empty,

your register is going to stay light.

Don’t Just Sell Cigars - Build a Business

Let’s say it plainly:

You don’t need a bigger humidor.

You need better habits.

If the only thing you’re doing is opening boxes and hoping customers come in and spend money, you’re not running a cigar shop. You’re renting space to chance.

Retail success in this industry isn’t about buzz, backorders, or name-dropping brand owners. It’s about intentionality.

Knowing your customers.

Holding your reps accountable.

Training your staff to create experiences - not just ring up SKUs.

It’s not harder.

It’s just smarter.

And it’s the reason the retailers who do it right don’t fear the economy, the internet, or the shop down the block. They’ve built trust, they’ve built systems, and they’ve built real equity - in the form of customer loyalty that money can’t buy.

If any of this felt like a wake-up call, it probably was.

And that’s why The Cigar Profit exists.

Whether you need a full audit of your retail strategy, staff training, margin analysis, or help turning underperforming SKUs into repeat winners - I’m here for that. I’ve been where you are, I’ve worked for the brands you carry, and I know where the profit leaks hide.

Don’t just stay afloat in this business.

Run it like you mean it.

Let’s Talk.📩 Book a Consultation with The Cigar Profit