The best gifts come from the people who know you best. The friend who remembers your favorite coffee order. The family member who picks the perfect book, every time. The colleague who surprises you with something you didn’t even know you needed.

That’s because great gifting is about understanding the person receiving it.

In even a medium-sized company, that expectation can quickly become infeasible.

Leaders don’t always have the time—or the close personal knowledge—to find the perfect gift for every employee. And when you scale that up to dozens, hundreds, or even thousands of employees? The challenge gets exponentially harder.

So how do you make corporate gifting feel personal without the guesswork?

Two Approaches to Personalized Gifting

A good gift lands because it means something. Because the person who gave it knew something about you: what you like, what makes you pause, what you never buy for yourself but always want.

But a company is not a best friend. It is not a spouse or a sibling or the coworker who’s seen you drink the same oat milk latte every morning for three years. A company is a system. And systems don’t really know people.

So what then? One option is to push the decision down. 

Give managers a budget and let them pick. This can work if the manager has one or two direct reports. But a manager with five, ten, twenty direct reports has enough on their plate. Knowing exactly what someone wants takes time that they may not have. And, the less you know somebody, the higher the odds are of getting it wrong.

There’s another way. One that doesn’t rely on good guesses or hopeful intuition. You can take the pressure off the gift giver and put the choice where it belongs: with the person receiving the gift.

You don’t need to pretend you know everything about your employees. You don’t need to take a shot in the dark. You need to give them the ability to choose something they’ll actually use, actually like, actually want.

Instead of trying to nail the perfect, hyper-personalized gift at scale, focus on what you can control: the recipient experience. That means getting the messaging right, designing a beautiful presentation, and finding the right timing for the gift.

When a Gift Matters Most Depends on the Person

Most companies gift at obvious times like holidays and work anniversaries. That’s a great start. Some companies go a step further and celebrate their team’s success at the end of a big project or after the ink dries on a major deal.

The next level up the corporate gifting strategy playbook is to time gifts throughout a project based on the personalities of the people on the team.

Some people run on competition. They push for the finish line, eyes locked on the prize. For them, the gift at the end makes sense. It makes the moment of victory tangible.

However, other employees are connectors. They thrive in the in-between, in the shared effort, in the late nights and the problem-solving and the we’re in this together of a team in motion. For them, waiting until the end is too late. The moment to recognize them is during the project. Give them a gift that lets them take their team to lunch, so they can use that opportunity to keep the momentum up when the grind gets heavy.

Then there are the ones who set the tone. The influencers, the motivators, the ones who get everyone else excited. Their moment isn’t the end or the middle. It’s the beginning. Consider giving them a gift before the work even starts to stoke their fires. Their investment in the project from the get-go will help fuel the whole team.

Get the timing right, and a gift can both acknowledge effort and amplify it.

Smart Gifting Is About Choice, Timing, and Impact

If you know an employee well, a personal gift is always the best move.

But if you don’t, we suggest you give them the power to choose, and focus on the presentation and the timing of the gift, rather than the gift itself.

Let’s talk about how to create a gifting program for your team that is tailored to the personalities on your team, timed right, and designed to resonate.