5 Rules of Strategic Gifting That Changed How I Approach Client Loyalty

1. The Search for Genuine Connection

As a business owner, you know the struggle. In a crowded market, how do you genuinely stand out? We’ve all received the branded coffee mugs, pens, and generic gift baskets. While the intention might be good, the impact is often forgettable. We want to build loyalty that goes beyond a contract—we want to create true advocates for our business. But how?

I recently synthesized the key insights from a webinar by business consultant Matt Makowicz, and his perspective offered a complete reframe of this challenge. He argues that most of us are thinking about gifting all wrong. It’s not a line item in the marketing budget; it’s a powerful strategy for relationship building. I’ve distilled his philosophy into the five most impactful and counter-intuitive lessons on what he calls “strategic gifting.”

2. Focus on ROR (Return on Relationship), Not ROI

This is the fundamental mindset shift. We’re conditioned to measure the direct financial return of our business activities, but this approach misses the point entirely when it comes to gifting. The real goal is to strengthen the human connection that underpins the business relationship—to achieve a Return on Relationship (ROR).

Makowicz shared a powerful story from when he sold his own Managed Service Provider (MSP). His client contracts were intentionally easy to cancel. Potential buyers saw this as a weakness, viewing the contracts as worthless. But Makowicz knew the truth: his business wasn’t built on iron-clad legal documents, but on rock-solid relationships. When the company was sold, not a single client left. That’s the power of ROR. Shifting your focus from transactional outcomes to relational depth is how you build a business with clients who are true, long-term advocates.

“Really what we’re talking about is ROR the return on relationship and that’s really the the crux of what we’re talking about with strategic gifting.”

3. A Strategic Gift Must Meet Four Key Criteria

Once you’ve embraced the ROR mindset, the next step is understanding that not all gifts are created equal. A strategic gift must pass a rigorous checklist to ensure it honors the relationship. According to Makowicz, there are four key criteria, with the first being an absolute requirement.

• It Must Be Best-in-Class: This first rule is non-negotiable. “Best-in-class” doesn’t mean “most expensive”; it means the gift must be the best possible version of what it is. Giving a $500 “mall watch” to a Rolex enthusiast is an insult that wastes money and misses the mark. Your gift is a direct reflection of your brand, and giving a cheap version of a luxury item signals a low standard. This rule isn’t about impressing someone with money; it’s about honoring the relationship (ROR) by demonstrating that you hold both them and your own brand to the highest standard.
• It Should Be Used Often: A beautiful item that collects dust on a shelf won’t keep you top of mind. The goal is for the recipient to use the gift frequently, creating a constant, positive reminder of your appreciation and the strength of your relationship.
• It Must Have Longevity: Your business relationships aren’t fleeting, and your gifts shouldn’t be either. A gift should be a permanent fixture in the recipient’s life. This is why practical but temporary items, like toilet paper in a realtor’s closing basket, fail the test—nothing says “I’m a commodity” like filling a temporary need.
• It Should Involve the Whole Family: This is the knock-it-out-of-the-park criterion. A gift that can be used and enjoyed by the recipient’s entire family creates a far deeper and more personal connection. You’re no longer just a business partner; you’re someone who has brought value to their home life.

4. Most “Easy” Gifts Have a Negative Impact

In a surprising twist, the gifts we think are “safe”—food, wine, gift cards—are the ones most likely to backfire. These common choices almost always fail the criteria for a strategic gift and do little to build your ROR.

Consumables like food and expensive wine inherently fail the “Longevity” test. They are gone in a moment and are incredibly easy to get wrong. You might give a prized bottle to someone who recently stopped drinking, has a health issue, or is a connoisseur with standards you can’t possibly meet. It’s a gamble that rarely pays off.

Gift cards are an especially poor choice. While convenient for the giver, they signal a lack of thought and effort. A gift card effectively communicates, “I don’t care a lot about you,” even if that’s not the intent. According to Makowicz, it’s one of the only gifts that can have a truly negative impact on the very relationship you’re trying to build.

5. Stop Gifting on Anniversaries, Birthdays, and Christmas (The “ABCs”)

This feels wrong at first, but the logic is sound. When you give a gift during the “ABCs”—Anniversaries, Birthdays, and Christmas—it gets lost in the noise. Your thoughtful gesture is just one of many the person is receiving, which diminishes its impact and makes it feel obligatory.

The alternative is a powerful strategy called “planned spontaneity.” By giving a gift at a completely unexpected time, like Halloween, Labor Day, or a random Tuesday, it stands alone. It becomes a surprise and a delight. This approach proves the gesture is about the relationship itself (ROR), not a social or commercial obligation. It’s no longer a “Christmas gift”; it’s a “thinking of you gift,” which is infinitely more personal and memorable.

6. You Can’t Buy Evangelists

Many businesses offer transactional rewards for referrals: “Give me a referral and I’ll give you $100.” Makowicz argues you should stop this immediately. This approach can make people feel cheap or “bought,” potentially damaging the relationship. It also risks backfiring if the referred person finds out their friend was paid to recommend them.

It’s critical to distinguish between a happy customer and a true “evangelist.” A happy customer will say positive things about you if someone asks. An evangelist, on the other hand, proactively brings you up in conversation because they have a deep conviction in the value you provide. This profound level of advocacy isn’t for sale; it’s the ultimate outcome of a strong ROR. It is earned through strategic gifts given generously and without expectation.

7. A Final Thought on Generosity

These five rules work together as a complete system. Strategic gifting is a thoughtful, relationship-focused discipline, not a marketing expense. By prioritizing Return on Relationship over Return on Investment, selecting gifts that meet the four key criteria, avoiding common pitfalls, and delivering them with planned spontaneity, you stop trying to “buy” loyalty. Instead, you build the deep conviction required to turn happy clients into powerful, proactive evangelists. This is how you create a foundation of loyalty that contracts and service-level agreements never could.

As you move forward, ask yourself this one question: What is the one relationship that could transform your business, and what would be the perfect, unexpected gift to show your appreciation?