Earlier is usually better than later.

The earlier you start your promotional gift-giving planning, the more options you keep open. By starting earlier and planning better, you are more likely to qualify for quantity discounts and/or reduced shipping costs. You also have more time to properly arrange for customization and personalization of your selections. Maybe even consider ordering sample items to view before making your final decisions.

I recommend: And, don't forget to round-off all that good planning with some good packaging for your promotional gift choices.  You should be able to find a variety of appropriately sized gift boxes, gift bags, gift sleeves, and gift pouches, directly from your product and service provider.  Some items include free packaging, others you will need to pay extra for (but that is money well spent to insure a good impression.)

Decide what type of gifts you want to give.

Decide how memorable and how lasting you want your gift to be.

I recommend: Some gifts, I would consider to be "at the moment" gifts, such as flowers, candy, balloons, or food items;  things that aren't meant to last indefinitely.  Other gifts, such as recognition awards, are lasting but not necessarily practical or useful on a daily basis. Another choice to consider is recognition gifts that are practical and serve as an award and more, such as an engraved paperweight , clock gift or photo frame gift.  Other gifts are primarily practical and useful in addition to serving as memorable items, such as: tool gifts, wine gifts, keychain gifts, or drinkware gifts.  Any of these gift types can consist of one main piece (such as a clocks & watches or engrave-able metal pens) or can be given as a gift basket, bundle, or gift set of complementary items.

Be clear on which occasions or expressions you want to acknowledge.

Typical gift giving occasions, in addition to the holidays, include "expression" occasions, such as: an anniversary; retirement; birthday; congratulations; funeral; get well; new baby; sympathy; thank you; or thinking of you.

I recommend: Your business gift-giving plan should cover an entire year's worth of occasions and holidays (a.k.a., relationship building and networking opportunities).  This should include not just clients and customers, but also associates, co-workers, superiors, and any and all service providers that contribute to your business' successes.  Acknowledge these personal achievements and life events while also keeping a watchful eye on keeping those  gift selections appropriate to etiquette guidelines.

Be aware of business etiquette guidelines.

For conflict of interest (and legal) reasons, some intended gift recipients aren't allowed to accept certain gifts, especially those above a certain nominal value. This should not necessarily be considered a limitation, but actually a blessing in disguise because it becomes a cost-saver for you. You might not be able to give what you would like but still give or send something small, such as a minimal value mail-able promotional product similar to that which you would give away to the general audience at a trade show.

I recommend: Use your favorite online browser to do some quick research on  business gift-giving etiquette.  BusinessWeek's Buyer Zone has a number of short articles worth reviewing for additional guideline's on:   office/employee gifts, corporate gifts, client gifts, and gifts for your boss.

Promotional product companies offer a wide variety of gift ideas and price ranges.

Choose an existing gift set or create your own custom bundle.

I recommend: The promotional product industry often surveys and lists the most  typical promotional product gifts that are bought and given each year.  Going with the norm is safe, but take the time to customize it, its presentation, or its packaging and presentation to make it more unique to your situation.