Seasonal Follow-Up Strategies: Leveraging Holidays and Events

🎯 Monday Morning Follow Up Focus Huddle

As February is here, love’s in the air,
Sales pros no fear, hearts full of flair.

Ping for progress, honk for the win,
Let’s make this month magical—chocolate boxes begin!

Bumpity-bump, with ideas so sweet,
Building connections, making hearts meet.

Honk, ping, bump—let's keep the beat,
With That Follow Up Fix, success is the feat!

First week’s past, but the goals are still near,
Stay focused, stay driven, let love steer.

Let’s increase wages, with Valentine’s Day in sight,
We’re turning the pages—let the love shine bright! 💝

"Your goal as a salesperson is to help your customers solve their problems." - Brian Tracy

🎯 The Problem:

Most salespeople use the same follow-up approach all year, missing opportunities that seasonal options offer. 

😫 The Reality:

Without a seasonal strategy, you're competing with everyone else's generic follow-up mess, minimizing your chances of standing out.

💡 The Solution:

A strategic, season-aware follow-up system that aligns with natural business cycles and yearly patterns.

The #1 Reason most sales professionals fail at seasonal follow-up:

Treating every month the same instead of mixing up their efforts.

Other key obstacles:

· Missing key planning cycles

· Poor timing with fiscal calendars

· Generic holiday approaches

· Lack of seasonal relevance

Let’s explore lots of language and timing connections to make progress.

Follow Up Love Language.

Seasonal spins.

Similar in nature.

Powerful in understanding.

Make them your own.

And as always, test. Please test.

These are roadways, not permanent parkings.

Step 1: Master the Seasonal Success Formula 📊

Holidays and seasonal shifts create natural conversation starters, tap into urgency, and align with fiscal and emotional decision-making periods.

Mastering the creative CYCLE Method ensures your timing and messaging land with a unique twist.

The creative CYCLE Method Below:

📅 Calendar → Think Beyond the Obvious

Instead of major holidays (New Year’s, Thanksgiving) how about outside the box?

National “Fun” Days:

National Coffee Day (Sept 29)

→ “Coffee fix + [Company Name] fix? Caffeine cheers this Wednesday?”

Industry-Specific Dates:

Cybersecurity Awareness Month (Oct)

→ “This is meant to scare the s**t out of you-Holy cow it stinks(see what I did there) to have scary things lurking online.”

“Anti-Holidays”(Days After Big Events)

Instead of Christmas Eve, try, “Made the ham, ate the ham here, ready to go ham on this new year together?”

Creative Example:

Subject: National Donut Day + [Their Industry]? Don’t glaze over this...

Body:

National Donut Day is about indulging. You know what else is sweet? Fixing [problem]. Let’s go for it?

Why it’s good?

Unexpected humor = pattern interrupt.

📆 Yearly Planning → Seasonal Teaser & Themed Offers

Themed incentives based on the season:

• January → “New Year, New You” Audit

• Spring → “Spring Clean Sales Pipeline”

• Summer → “Summertime Heat Check”

• Fall → “Q4 Reap Resurgence”

• Winter → “Finish Strong, Start Stronger”

Creative Example:

Email Subject: Follow up, glow-up in 2025 

Email Hook:

2024 wrapped up faster than your favorite holiday gift.

Let’s make sure your pipeline makes Christmas unforgettable this year!

Why it’s good?

It taps into fresh-start energy.

🎨 Customize → Inject Seasonal Personality

Use playful, seasonal phrasing:

• Halloween → Let’s ghost-proof your follow-up strategy.

• Thanksgiving → Grateful for our connection—here’s a gift for you.

• Valentine’s Day → We’d be a great match. Let’s chat?

• April Fool’s → This is NOT a joke…knock knock

Multimedia Twist:

• Send a short video wearing a Santa hat or an apron for Thanksgiving.

• Use GIFs, memes, or holiday-themed images in your emails.

Creative Example:

Valentine’s Day Follow-Up:

Subject: Are we meant to be? ❤️

Body:

I won’t send chocolates, but I do have some sweet ideas on how we can work together.

Why?

It’s fun, unexpected, and keeps the conversation light.

🔗 Link → Make Holidays Work for You

Connect the holiday theme to business pain points:

• Spring cleaning—let’s freshen up inefficiencies in your [process].

• The holidays are about giving… let’s talk about gifting better experiences to your customers.

Creative Example:

Black Friday - Cyber Monday Outreach:

Subject: Not another Black Friday deal…but definitely a steal.

Body:

While everyone’s fighting over discounts, let’s talk about real value—how to [solve X for them].

Why?

Takes a counterintuitive approach to stand out.

🚀 Execute → Nail the Timing with a Twist

Avoid the flood:

Send before or after major holiday madness (Dec 27th instead of Christmas Eve).

Build anticipation:

Use countdown emails leading up to an event or special offer.

Use “Anti-Timing” Moves:

• Instead of December holiday emails, try a January “Holiday Recovery” Follow-Up.

• Instead of Valentine’s Day on Feb 14th, do a “Relationship Check-In” email on Feb 15th (after inboxes clear).

Creative Example:

New Year Follow-Up Hack:

Subject: New Year’s Resolutions Are Overrated—Here’s Why.

Body:

Most resolutions fail by February. Time for a super sticky strategy.

Why?

Unexpected timing = higher engagement.