Between shopping, gift wrapping and attending holiday parties, it’s very easy to get overwhelmed during this time of the year. As an entrepreneur, your holiday preparation gets even more hectic — end of year wrap-up, send greetings to your clients, celebrate with your team, the list goes on.

Whether it’s your busy season, business as usual or a holiday shutdown, here are 5 tips for preparing your business for the holidays.

1. Set clear expectations with your customers and team

Your customers and team might need to reach you during the holiday season. Tell them exactly what to expect from you.

For your customers:

If you operate a retail location, list your holiday hours on your website and Google listing. Post them on your Facebook page, Instagram and Twitter as well. Your customers will be looking for your holiday hours — make them easy to find.

If you have an online store, make sure to communicate your shipping times for the holidays. There will always be hopeful last-minute shoppers (I’m usually one of them 😁), so being upfront about shipping estimates will result in less surprises and refunds.

For your team:

If any of your team members is working over the holidays, tell them how they can reach you if needed. Should they call, text or email you with “URGENT” in the subject line?

2. Direct your business calls straight to voicemail

Let’s face it, you don’t want to interrupt your family’s holiday dinner with a phone call. But you also want to have an option to reply to people in between festive meals.

With OpenPhone you get the best of both worlds.

  1. Turn on Do Not Disturb mode in the app. 🌙
  2. Set a holiday voicemail greeting letting your callers know about your unavailability and when they can expect you back.
  3. You will now direct your business calls to voicemail, but continue to receive text messages and transcribed voicemails so you can reply to them at your own leisure.

Here’s an example of a holiday voicemail greeting you can use:

Hi and thanks for calling OpenPhone, we are closed during the holidays and will reopen on January 2nd. Please leave a message and we will get back to you when we are back. Happy holidays!

3. Set an out of office email message

Whether you prefer using something simple or have a festive Out of Office message, make sure you include the most important information — when your business reopens and a contact method for urgent matters.

Here is an example you can copy and paste:

Hello, thank you for reaching out. We are closed for the holidays until [Date].We will respond to your message as soon we are back. If you have an urgent request, please text or call [Phone Number]. Have a safe and happy holiday season, [Your Name]

4. Thank your team and customers

For your team:

Saying thanks to your team doesn’t require a fancy party. You can invite your team out for a happy hour or order food for the office. And it doesn’t need to be a dinner either. Celebrating over lunch is much easier to organize and cheaper. Plus, your team members will appreciate more family time during the holidays.

Don’t forget about your extended team — investors, advisors and mentors. They have been very generous with their time and resources throughout the year. Send them a handwritten card, a great book or bring baked goods (if that’s your forte)

For your customers:

Our recommendations for sending holiday greetings to your customers will depend greatly on the number of customers you have. You likely won’t fancy the idea of sending more than a hundred handwritten cards.

Paperless Post has a lot of beautiful cards to choose from that look almost as special as handwritten (we really like these from The New Yorker)

Your ability to build personal relationships as a small business is a huge advantage. Don’t miss the opportunity to use it.

If you have local customers and partners, deliver baked goods to them. They don’t need to be homemade and don’t need to cost a fortune.

Two years ago my team and I thanked partners who helped us put together Product Hunt Toronto events with delicious cookies from Le Gourmand (known to be the #1 cookie in Toronto) and Drake greeting cards. This was in 2015 and Hotline Bling was the hit of the year, FYI. Feel free to steal this idea and send me happy tweets you’ve received.

Below is one of the many we got:

For your best customers and partners around the world, send a personal video. It doesn’t have to be long (under 1 minute is perfectly ok) and there’s no need for fancy editing. Use a tool like Vidyard GoVideo to record one. It’s easy and free.

Invite your team to join in to make it more fun. It’s guaranteed to make your customers smile. Just think about how many holiday videos they receive compared to plain text emails.

Here’s a simple video script you can use:

Hey! Wanted to wish you and your family a safe and happy holiday season! Thanks for your business, we really appreciate the opportunity to work with you. Happy holidays and see you in 2018!

Of course, it’s going to be better received if you customize it and add your own flavor to it.

And that’s it.

Have a relaxing holiday. You deserve it! 🙌

Do you have any holiday prep tips to share with fellow entrepreneurs? Let me know in the comments!


Co-Founder at OpenPhone. Ukrainian-Canadian in SF. Love exploring new hiking trails.

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