Gifting Guide: What to Buy for Boss or Coworker?

Editorial Team
Gifting Boss

Here at TRULY, we receive many gift ideas requests concerning gifts for colleagues, gifts for managers, gifts for coworkers, etc. One particularly common and tricky question is:  what to buy for the boss?

Gifts for the office (especially what to buy for boss) has the added complexity of potentially being very public (i.e., oftentimes, the gifts are exchanged or opened in front of everyone). This means that anything you pick will have the added level of scrutiny, not just by the recipient but by all your colleagues.

Based on the thousands of recommendations we’ve responded to related to office gifting, we’ve summarised our learnings into 3 simple guidelines:

1. Be thoughtful, but not too personal

Being thoughtful simply means that you know what the person is likely to enjoy or will absolutely hate. For instance, someone with a dreadful fear of flights would probably not enjoy a wing-walking or skydiving experience as much as you’d like them to. Conversely, knowing the intimate preferences of a colleague (or boss) and gifting correspondingly may give off the wrong impression.

Different office dynamics may dictate differently, but when in doubt, stay on the professional rather than on the personal side of the line.

2. Gift as a Group

The notion here is quality over quantity. Based on feedback we received from our customers, often times a bigger gift where everyone chips in is more meaningful (and substantial) than smaller individual gifts. Additionally, the element of social pressure to spend more (or less) goes away because the cost of the gift is evenly split.

For instance, we recently had a group of colleagues pitch in to buy a luxury weekend break to Rome for their boss (and his wife). The gift included 5-star hotel stay for 2 nights, Michelin-starred tasting menu for 2 people and a Vatican night tour.  By pooling resources together, the group was able to make a much more meaningful purchase while keeping costs equitable for everyone.

3. Stretch the imagination

The best gifts aren’t always “exactly what they’re looking for”. In fact, our customers tell us that a subtle element of surprise and inspiration can go a long way. A gift that nudges someone slightly outside their normal circumstance or comfort zone can be very refreshing indeed.

For example, we had a customer who said their recipient enjoys driving sports cars but has done all of the usual “super car around the track” type of activities.  So our recommendation was to stretch the imagination further with a Germany Romantic Road package in a Porsche 911.  The price was a bit higher than the group’s original budget but gave their boss something to remember for a lifetime.

Do you need help buying gifts for your boss or colleagues?  

If so, we’d be happy to help.  Just submit a Free Gift Ideas Request and our concierge will get back to you with recommendations.


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