90 Day Holiday Prep Starting in September Your Store's Survival Guide

It's September. In the north, leaves are changing. In the south, you're finally getting a break from the summer heat. Everywhere, though, the countdown has begun—the holiday season, your make-or-break quarter, is right around the corner.

Maybe you planned to get ahead in July. Maybe you kept pushing it to "next week." Maybe you're already eyeing the Black Friday calendar and feeling that familiar knot in your stomach.

Here's the truth: you're not too late. I've seen stores pull off record-breaking seasons starting right now. The key? Cut the fluff, zero in on essentials, and use the tools already inside your POS to move fast.

Why You're Actually in a Good Position

Stop beating yourself up for not starting earlier. While your competitors who started planning in June are locked into old strategies, you have something powerful: urgency and flexibility to act on today's trends.

Your POS gives you real-time data, so you can base decisions on what's actually happening now—not what you guessed months ago. The retailers who win during holidays aren't the ones who plan earliest—they're the ones who execute the essentials really well.

Your 90-Day Game Plan: Let Your POS Do the Heavy Lifting

September: Get Your Foundation Solid

This month is about systems, not decorations. Your POS reports make the critical decisions simple:

✅ Run last year's holiday sales report: Identify your top 20% of products and reorder now. No guessing, just data.

✅ Check your hourly sales reports: See which days and times needed the most coverage last year, then start hiring to match those peaks.

✅ Stress-test your system: If your POS lagged or crashed during last year's rush, upgrade now before it's too late.

If your current system isn't ready for holiday volume, upgrading through our POS optimization service includes exclusive free training so your team feels confident before Black Friday hits.

October: Turn Outward with Smart Tools

October is when you shift to customer-facing strategy. Your POS becomes your marketing partner:

✅ Use your customer database to capture emails at checkout and segment for targeted promotions

✅ Launch gift card campaigns—your POS tracks everything seamlessly, giving you cash flow now and guaranteed sales later

✅ Update your POS settings so receipts and customer communications automatically show extended holiday hours

✅ Track referral codes through your system to measure which local partnerships actually drive sales

November: Execute Like a Pro

November is go-time. Your POS becomes mission control:

✅ Real-time inventory tracking prevents those heartbreaking stockouts

✅ Sales dashboards show you which products are hot this week

✅ Integrated payment processing keeps checkout lines moving

✅ Performance tracking helps maintain sharp customer service even when you're slammed

The Procrastinator's Secret Weapons

Starting "late" actually gives you three major advantages:

Real-time trend reaction: Your POS shows what's selling right now. Adjust inventory based on current data, not old assumptions.

Last-minute vendor deals: Use your reports to identify gaps, then fill them with end-of-year discounts suppliers are eager to move.

Agile marketing: Pull segmented customer lists straight from your POS for targeted, last-minute campaigns that rigid competitors can't match.

Do Less, Do It Better

Forget elaborate holiday experiences. The stores that win focus on nailing the basics—and your POS helps you do exactly that:

• Fast, reliable checkout supported by solid systems
• Always-stocked bestsellers thanks to inventory alerts
• Smart upsells guided by purchase history
• Clear gift recommendations powered by your top-seller data

If managing all these moving pieces feels overwhelming, our Done-For-You retail solutions handle the behind-the-scenes work while you focus on customers.

Your September Action Plan 

Don't try to do everything at once. One week, one focus:

Week 1: Run POS reports, assess your system, decide on upgrades 

Week 2: Use inventory data to place emergency orders 

Week 3: Review labor reports and start hiring 

Week 4: Set up email capture and basic holiday marketing

✅ Start with your biggest risk: What nearly broke you last holiday season? Fix that first—whether it's inventory, staffing, or checkout speed.

✅ Trust the 80/20 rule: Your POS reports show which 20% of products drove 80% of sales. Stock those winners heavily.

✅ Hire earlier than feels necessary: Good seasonal help gets snapped up fast, and training takes longer than you think.

✅ Make email capture automatic: Set up "Get holiday deals first" at every checkout—build your list while you're busy.

✅ Test your payment processing now: Peak volume kills unprepared systems. Confirm yours can handle the rush.

The stores that struggle during holidays aren't the ones who started planning late—they're the ones who never started planning at all. You're reading this in September, which means you still have time to pull together a successful season.

The holidays will come whether you're ready or not. The question is: will you spend the next few weeks taking smart action, or keep procrastinating until it's actually too late?

Ready to Turn Your Late Start Into Holiday Success?

You don't have to figure this out alone:

1. Book a free consultation for a personalized holiday action plan based on your POS data and specific situation
2. Take our Blueprint for Success course for step-by-step planning you can implement immediately
3. Use our Done-For-You retail solutions to handle prep tasks while you serve customers
4. Upgrade your POS through us and get free team training to maximize every feature

The best time to start was three months ago. The second-best time is today. With the right system and the right plan, your holiday season can be profitable—not stressful.