Top 5 Holiday Presents for CEOs

Shopping for gifts is difficult no matter who you’re shopping for, but things get a bit trickier when you’re trying to find something for a CEO you’ve been courting. You have to keep it professional, but a good gift should also be thoughtful and a little bit personal, just enough to remind the business owner of you when he uses it — and, better yet, keep you in mind when the time comes to pursue a transaction. Life during the holiday season can be stressful, with work, friends, family, and travel coming together in a crazy way, so here’s our little contribution to make things easier during this time of year: our top five holiday gift picks for the CEO you’re working with or wooing.

1. Monthly Subscription Boxes

Monthly subscriptions are a perfect gift for CEOs, mostly because there’s such an enormous range of what’s available. Whatever hobbies the CEO in question might enjoy, there’s a very good chance that there’s a monthly subscription service catering to her interests. Is she a wine aficionado? Gift her a Club W subscription or work with the company to develop a custom package. A travel junkie? Consider an Escape Monthly subscription package, which gives subscribers food, bath products, jewelry, and other fun products from a new destination each month. Coffee addict? Craft Coffee is the luxury coffee of the month club every CEO never knew she needed. Hello Subscription’s comprehensive listing of subscription boxes is the best tool to help you pick the perfect service for a CEO whose business you’re courting.

2. A Good Book

Even with their busy schedules, many CEOs of top companies carve time out of their days to read, often citing how important it is to stay informed and creative when heading a company. If you have a good idea of a particular business owner’s interests, feel free to take the opportunity to gift her a fiction work by an author she loves, or a non-fiction text on a subject in which she’s especially interested. If you’d rather not take the gamble, there are some failsafe choices (that aren’t The Art of War) that are sure to go over well. Consider Misbehaving by Richard Thaler, Thinking, Fast and Slow by Daniel Kahneman, and The Future of Work by Jacob Morgan — all recent business bestsellers, that, as an added bonus, weren’t written by Warren Buffet.

3. Family Fun

CEOs spend so much of their time working — time that could be spent with their families instead. What better way to encourage a healthy work-life balance and get on a CEO’s good side than getting her a gift that can be enjoyed by the whole family? This movie night set, complete with two Redbox gift cards, is perfect for family nights in, and this family game night care package is a great way for families to spend together, no screens necessary.

4. Desk Accessories

An old standby, desk accessories are great gifts for a CEO because they’re immediately practical, but also allow you an opportunity to get a little interesting. We’re big fans of this retro and functional Steampunk Clock by Dot & Bo, these gorgeous leather desk accessories, and our personal favorite, the FUUT under-desk hammock.

5. Chocolate

When all else fails, go back to basics and get the CEO some chocolate — but not your basic drugstore Mars bar. Step things up to corporate-level classy by picking up some elegant Mast Brothers artisanal chocolate, made with single-origin cacao beans from sustainable independent farms, François Payard brand truffles, named after the famed French pastry chef and chocolatier, or some quirky and fun ChocStars bars for the animal- and chocolate-loving CEO in your life.