4 Planning Mistakes Retailers Must Avoid This Holiday Season

  1. Home
  2.  » 
  3. Customer Experience
  4.  » 4 Planning Mistakes Retailers Must Avoid This Holiday Season

Just as Important as Taking the Right Steps This Holiday Season is Avoiding the Wrong Ones.

In such a unique year, the risk of errors in judgment or poor strategic choices are amplified. An already thin margin for error for most retailers has become vanishingly small.

In this article we will be covering the four planning mistakes that smart retailers must avoid this season in order to ensure they’re still around in 2021.

  1. Failing to Respond to Shifts in Consumer Behavior
  2. Not Pivoting to Ecommerce First
  3. Thinking Short Term vs. Extending the Season
  4. Not Understanding Who You’re Competing With


1. Failing to Respond to Shifts in Consumer Behavior

The pandemic has caused us to profoundly change our daily habits and the ways in which we tackle ordinary activities, including how we shop. In fact, McKinsey found that 75% of Americans have changed at least one aspect of their shopping behavior during the pandemic and the majority of them plan to keep at least some of those changes in place post-pandemic.

Retailers that have been able to quickly respond and adapt to changes in customer behavior and preferences are weathering the storm well, while watching their counterparts struggle and in some cases collapse.

This is the season to be aggressively disruptive in your planning based on signals from your customers (increased pre-purchase research, heavier reliance on digital, strong preference for multiple delivery options and flexible returns) vs. trying to run last year’s playbook updated with disposable masks at the door and social distancing markers on the floor.

2. Not Shifting to E-commerce First

In 2020 more than ever, your ecommerce infrastructure needs to be bullet-proof and online orders need to be the centerpiece of your 2020 holiday sales strategy, not simply viewed as an auxiliary or augmentation to your bricks-and-mortar effort.

From product discovery through to order tracking and returns management, you need to be thinking digital-first and creating a clear, navigable purchase path that leverages customer care automation to allow huge numbers of shoppers to buy with ease this holiday season.

Every year features stories of hapless retailers whose ecommerce websites crashed in the face of Black Friday traffic.

While always a major (and very costly) headache, to be unable to scale to meet online demand this year could mean that you won’t be around for next year.

3. Thinking Short Term vs. Extending the Season

Black Friday has traditionally been the kick-off to the holiday shopping season. With an in-person Black Friday on pause, retailers need to give themselves the best shot at capturing shopper attention, which means starting their holiday campaigns early and running them longer than in previous years.

Macy’s and Target, for example, are planning to kick off their holiday campaigns around Halloween, with Amazon rumored to be rolling out their 2020 Prime Day in October, too.

Limited-time deals won’t go away entirely, but will be rotated throughout the season and used to stoke a sense of urgency and Fear Of Missing Out (FOMO) in shoppers.

4. Not Understanding Who You’re Competing With

Household-name retailers are declaring bankruptcy at an alarming rate in 2020. And even if your competition is hanging tough, you aren’t just competing with other retailers in your category.

If you haven’t already identified Amazon as the 1000-lb gorilla in your space (and everyone else’s) and started working on how you’ll keep your customers from defecting to it, the pandemic should have made the ecommerce behemoth’s growing dominance readily apparent.

To date in 2020, Amazon’s stock price has risen over 60% and the company doubled its net profit over 2019 numbers.

Plan To Be Flexible

As boxer Mike Tyson famously said, “Everyone has a plan until they get punched in the mouth.”

This year, retailers have certainly taken some major hits.

Retailers and brands that want to survive what some are calling the “death of the American shopping mall” need to be entering this unprecedented holiday season not with a fool-proof plan, but with a flexible strategic approach that reflects the reality of how their customers want and need to be served in 2020.

The ones that will successfully navigate this turbulent time are those that have prioritized Customer Experience Automation and have made it their goal to deeply understand their customers and craft customer journeys, seamlessly blending the digital and physical, that reflect this understanding.

In our Holiday Planning Guide for 2020 we cover more in depth the mindset of your customers going into the shopping season and how you can prepare your brand to deliver a seamless omni-channel shopping experience for your customers.

Download our eBook- The retailer’s guide to 2020 Holiday Planning

if you want to know more about how to automate your customer experience utlizing powerful and robust conversational ai and more specifically, how you can quickly implement an easy to use conversational AI experience as part of your CX strategy, tailored to your brand, schedule a call today.

CX Resources

CX Automation Use Cases

See the Incredible CX Automation Results Linc’d Retailers Achieve


Guides, Studies and Videos on Customer Experience Automation.

Latest CX Insights

Powerful Insights and Strategies to Enhance the Customer Experience

Subscribe to CX Insights