Reprise: What to avoid (and embrace) in your year-end client reach-outs

by | Nov 24, 2025 | Monthly-ish tips

This post is part of our Monthly-ish Tips series.

It’s late November which means I’m braced for the oncoming onslaught of holiday messaging (emails, cards, etc.). Now seems like a good time to share some suggested do’s and don’ts for your own upcoming client reach-outs. It’s such a great opportunity to make real and lasting genuine connections, provided you avoid a few basic pitfalls.

Three things I try to avoid:

  • Generic messages. Technology is an enabler here (in a bad way). Year after year, I receive a lot of well-meaning emails with cute holiday images and a nonspecific message like, “Happy holidays from the [insert location or function here] office staff!” I really do appreciate the sentiment and enthusiasm. The problem is it just feels … well, borderline SPAMmy, like those pre-loaded replies that LinkedIn offers.
  • Nondescript delivery methods. It’s way too easy to use email, social media, and even text messaging to blast generalized messages. The easy route isn’t usually the route with the best payback.
  • You-focused content. It’s not bad to share your business successes (and offers of help) with people, just beware the wrong message at the wrong time, and be mindful what you lead with.

Four tips for connecting in more meaningful and distinctive ways:

  • Personalize your messages any way you can. Yes, this takes time and effort, though probably less than you think. One colleague routinely sends me a very short email that doesn’t seem cookie cutter. Some clients send a holiday card to my home, with a hand-written message inside that is clearly just for me. Several people share their family holiday photo collages (via snail mail as well as electronically), so I can see them with their families, and learn personal tidbits about their year that wouldn’t typically come up in a business meeting—one case where making it about you works well.
    Noteworthy: I usually take the time to say thank you in all cases above, which means every single reach-out results in a conversation that actually contributes to our relationship.
  • Be distinctive with your choice of medium. Paper stuff usually stands apart these days, and texting can too, as long as the messages aren’t generic. Each year, I get a few SMS messages from clients and colleagues that don’t seem like copy/paste is in play, and I appreciate those very much. One client used to create a video every year featuring select staff sharing things like uncommon holiday traditions, or what they’re grateful for, which I always found interesting and fun.
  • Find holidays/events/milestones to celebrate that are distinctive. Pretty much everyone gets on the Christmas bandwagon, even though a lot of people don’t celebrate Christmas (which is far more important to consider than most people realize). Personally, I lean towards a New Year’s message over a December message of any kind.
    Even better, I prefer opportunities to reach out that most don’t consider—in the U.S., that could include Fourth of July and Thanksgiving (a great opportunity for notes of gratitude), birthdays, work anniversaries (like marking the first time you met or launched a project). I’ve even been known to send Valentine’s Day cards to my clients—yes, there’s a way to do it that’s fun, not weird. And why not celebrate something more global like Diwali, or something that one of your regional offices honors that others might learn from?
  • Add a touch of humor. My all-time favorite holiday message was a JibJab message from a client and his spouse, doing The Macarena. It was distinctive, funny, and personal—all in one. Bonus that it was a little unexpected from this super-savvy business executive.

Here’s my plea: If you’re going to reach out to people, then reach out to people. If you want to make a genuine connection, that means you have to make the effort to stand out … at least a little.

Make It Real

It’s not too late to plan the ways you’ll take a more distinctive approach in the coming weeks. This week, tweak the plans you have in place for your end-of-year reach-outs using the tips above, then make a plan for at least one distinctive reach-out initiative in the new year.

Learn More

Brush up on trust-based networking dos and don’ts in Chapter 12 of The Trusted Advisor Fieldbook.

 

 

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Andrea Howe

As the founder of The Get Real Project, I am the steward of our vision and our service offerings, as well as a workshop leader and keynote speaker. Above all else, I am an entrepreneur on a mission: to kick conventional business wisdom to the curb and transform how people work together as a result. I am also the co-author, with Charles H. Green, of The Trusted Advisor Fieldbook (Wiley, 2012).

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