Holiday Planning Timeline
Finessing the holiday season with a minimum amount of stress is a matter of careful planning. Your small business should acknowledge customers, employees and vendors for their contribution during the year. You also need to keep your business humming and keep stress to a minimum.

Use the list of tasks and approximate completion timing in this table to keep your holiday planning on track.

Early November
Determine holiday budget. Knowing what you have to spend on gifts, cards, tips and celebrations will help in decision-making at this time of year.
Assemble card list. Ensure that you don’t leave anyone important off of your list by consulting your receivables and payables records and other business paperwork that will prompt you to remember all key parties.
Confirm contact information. One of the most time consuming elements of holiday planning is checking correct spellings of names, titles, mail stops (where appropriate) and up-to-date address information.
Research gift restrictions. Some clients, such as government agencies, may place limits on the gifts their employees can accept.
Craft company card. Some small businesses choose to design a card in-house. This process takes time and should be started early
Devise card sentiment. Most card companies now allow you to customize holiday cards with a greeting and your company name. Remember to be non-denominational in your message, e.g. "Happy Holidays" is more inclusive than "Merry Christmas".
Assemble gift list. Deciding who to buy for and how much to spend can take some time. Budget time to consult with members of your staff who may be able to contribute to your gift list because they work more closely with customer, vendors or staff than you do.
Prioritize gift lists. Placing gift recipients in priority order will enable you to determine per-gift budgets and focus on the most important gifts first.
Research gift recipients' vacation schedule.Find out when key clients, customers, vendors and other important gift recipients will leave for the holidays to ensure that your gift will get to them before they go.

Mid/Late November
Choose holiday party date and location. Restaurants and other party venues book up early so decide generally on your holiday plans and secure your location. You will need to have an approximate number of attendees to secure a location.
Notify staff of holiday celebration schedule. If you need staff to attend parties, events or other holiday celebrations, notify them early to ensure maximum participation.
Choose cards. Early ordering will enable you to get the card you want in time to get it out early before the rush of mid holiday.
Order cards. Circulate your choice of card around key people in your company to assure you are choosing the best one.
Plan for support staff time. Addressing cards, ordering gifts, planning events and handling other holiday season-related tasks may require significant time. Start budgeting time early enough that you can slate these activities for in-house staff to complete in the coming weeks or month.
Buy gifts. Consider purchasing online to save time and money. Order early to avoid out of stocks and/or rush charges, and to ensure timely delivery.

Early December
Research optimal shipping methods. If you are not having the vendor ship directly to the recipient, the type of items you are sending and their destination will shape your carrier decision.
Finalize holiday event details. Decide on details such as guest list, gift-exchange plans and other particulars. Call the event site and caterer to adjust number of attendees, if needed.
Send invitations to clients and vendors if appropriate. The earlier you send invitations, the better turnout you will have since competition for people’s time during the holiday season can be fierce. Set an early RSVP date so that you can plan accordingly.
Arrange other holiday celebrations. Plan now for small group dinners, drinks and other celebrations with key business contacts.
Invite attendees to other holiday celebrations. Calls or emails will be the likely outreach mode for these invitations. Start early to ease scheduling.
Make reservations for other holiday celebrations. Book dinner reservations, buy tickets to shows and secure other events to ensure a successful celebration.
Mail cards. If you plan to use holiday stamps, budget time for procuring them and putting them on each card.
Decide on sentiment for cards to accompany gifts. Prepare sentiments before you start the gift ordering process to avoid being rushed while you are online or on the phone ordering a gift. Consider creating several messages that can be slotted in as needed.
Ship gifts. Send gifts out as early as possible to ensure they arrive on time for the holidays. Try to get them to clients before December 15 to avoid the holiday rush.
Decide on tips. You may want to tip service people who are essential to your business, such building maintenance staff, a garage person, doorman, delivery people, etc.

Mid/Late December
Deliver tips. If you’re tipping, now is the time to deliver them. Give tips in a sealed envelope, preferably with a personalized holiday card that expresses your thanks and best wishes.
Send thank you notes. Many gifts you receive will have been sent to your business as a thank you and therefore you should not send a traditional thank you note. However, a phone call, e-mail or other acknowledgement is often appropriate.
Keep a list of gifts sent. Use this list for tracking deductions at tax time and to refer to next year when making your gift lists.
Review holiday performance. Use your experiences from this year’s gift season to help you out in the future. Record these now, while they are still fresh in your mind.

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