As your team’s designated gift planner, getting a head start on holiday gifts is crucial. You know you need to get your order in ASAP, ideally before the end of October, to lock in the best options for the upcoming holiday season.
However, convincing your boss to engage in holiday planning when they’re still focused on fall can be challenging! But we’ve got your back, with a 7-step proven strategy that is almost guaranteed to get your holiday gift order wrapped up quickly.
Start by scheduling a brief chat with your boss to give them a heads up and invite. Preferably, this will be in person.
“Hey Boss, do you have a minute? …I wanted to give you a quick heads up that we need to start thinking about holiday gifts for our team because the order deadline is coming up.”
Give them a minute to consider what you just said and answer any follow-up questions.
Within the same conversation, it’s time to secure critical details you will need to secure their buy-in later on:
You can approach these topics with simple questions:
These two questions help you gather insights on the types of gifts to look at, while also helping to align expectations—for both of you! Even if your boss can’t give you specific answers just yet, the wheels are now in motion.
Put together a shortlist of 3-5 thoughtful gift ideas that align with what your boss mentioned. You can check out our 2024 Holiday Gift Guide for Canadian Businesses to start generating your list.
To maximize your chance of approval, consider the following as you select gifts:
Send your boss the shortlist as soon as it’s prepared, and then immediately schedule a formal meeting to choose the gift within the next few days. This will give your boss time to review the shortlist and a deadline for making it happen.
If your boss doesn’t give you immediate approval or asks you to loop in additional people, follow their instructions and then schedule follow-up meetings at regular intervals until you get the answers you need. By keeping the gift order top of mind, you can keep the approval process moving forward.
Some gifts, like apparel, require additional coordination with employees. If a suggested gift needs sizing or personalization information, be upfront about your willingness to take this on. Bosses experienced with these types of gifts will know it’s a bit of a hassle and you don’t want a bit of extra work to result in any hesitation!
This would also be a great time to offer your help with distribution. It can be an overwhelming task for larger companies and your boss will appreciate knowing they can count on you to help out.
If your boss doesn’t give you immediate approval or asks you to loop in additional people, follow their instructions and then schedule follow-up meetings at regular intervals until you get the answers you need. By keeping the gifts top of mind, you can keep the approval process moving.
As order deadlines get closer, try to give your boss as much warning as possible and keep them informed, so they understand the risks of a delayed decision. Remember they may have other deadlines and priorities to juggle.
Once the gifts are selected and approved, thank your boss for their time and consideration! A little gratitude can go a long way in your professional career.
By approaching your boss with a casual conversation and following it up with a clear shortlist, you can make the holiday gift selection process smooth and efficient. Getting input early not only helps you secure approval quickly but also ensures your gift choices resonate with the team. Happy gifting!