Holiday Retail Readiness: 5 Ways to Strengthen Your Team and Drive Sales
Key Takeaways
- Holiday retail readiness goes beyond staffing. Retail leaders need to ensure both new hires and experienced employees have the skills, confidence, and preparation to deliver results during peak season.
- Prioritize hands-on training and coaching. Give new hires time to practice essential skills, receive real-time feedback, and apply what they learn on the sales floor before business peaks.
- Refresh the skills of tenured employees. Previous holiday experience is valuable, but changing products, promotions, systems, and customer expectations require ongoing preparation.
- Equip experienced employees to mentor others. Prepare store leaders, assistant managers, and designated coaches to provide consistent training, guidance, and feedback across shifts.
- Make continuous development part of daily operations. Use pre-shift huddles, on-the-floor practice, skill refreshers, and frequent check-ins to reinforce learning, strengthen team performance, and support sales goals.
The holiday season isn’t every retailer’s peak season of the year. For some (like tire and auto, fitness centers, and home design), peak season has already passed. But for those retailers in categories like apparel, cosmetics, grocery, gifts, crafts, and others, the busiest season of the year is fast approaching. Not only do the holidays mean increases in customer foot traffic, it’s also the last quarter of the year for most retailers, which puts even more pressure on profitability and sales goals.
Last month, I focused on assessing whether your retail field leaders are “fully staffed” or “fully prepared” for the holiday season and why that distinction matters. Hopefully, retail stores and field leaders spent most of October hiring to meet their 2027 staffing, floor coverage, and sales projection needs. Now, as we enter the start of the holiday season, it’s time to shift our focus to talent development and strengthening of skills.
Especially in the lead-up to peak season, this often comes in the form of structured onboarding for all new hires, with an emphasis on getting the new team members quickly up to speed on the necessary systems, skills, and processes. As for the rest of the team, a store leader may feel their existing, tenured team members are all set and don’t need much of their time and attention or further development. The problem with that assumption, however, is that familiarity can hide preparation gaps. This issue can be compounded when experienced employees are also expected to support new colleagues.
As we gear up for this holiday season, your store and field leaders need to both prepare their new hires and equip their tenured staff to mentor them. For store leaders, this means being intentional about leveling up and leveraging your experienced team members: Coach often, in real time, with frequent check-ins during every shift. For retail multiunit and field leaders, focus on strengthening and coaching the store leaders who guide them.
5 Tips for Strengthening Talent and Sales This Holiday Season
These tips will help you get the most from your peak season while creating a more engaging and productive experience for your team members as well as your customers.
- Give new hires time to practice before the pressure builds.
Where hiring is still underway, plan start dates around time to learn, not simply the first shift that needs coverage. And keep in mind, completing orientation is a starting point. Application of what they learned on the job is where the real learning and skill retention takes place. As part of that, self-directed microlearning can be used to introduce (or refresh) a skill. Leaders also need to help people apply and reinforce the learnings for sustainable results.
To streamline the process, prioritize essential skills, frequently check new hires’ ability to apply what they have learned to the job, and pair them with tenured team members who are prepared to serve as mentors. To set expectations and be able to track and monitor new team member progress, leaders need to consider: “What should this person be able to do confidently by the end of their first week, second week, third week … and who will help them and be accountable for getting them there?”
- Prepare for this season, not for a repeat of last year.
Just meeting last year is never a standard we aim for in retail. We need to exceed expectations and flex to the changing needs of customers and the business today. While a team member’s experience from last year’s holiday season is valuable, it does not automatically prepare them for everything that is different now. Instead, they need to be curious and not assumptive.
Leaders can prompt them by asking: “What has changed in our products, promotions, systems, service expectations, or team? Where did we struggle last season?”
- Recharge, equip, and empower your tenured employees.
Experience is a strong foundation for continuous learning and growing. Acknowledge the experience your tenured team members bring, and give them opportunities to refresh their skills, prepare for changes, and share what they know.
Use realistic situations to practice this year’s expectations together, providing them with the tools, clarity, and training to succeed as expectations change. Position quick, on-the-floor pop quizzes, skill blasts, and refreshers as an investment in their success to keep them sharp, not a doubting of their abilities.
Best of all, they can use many of these same drills with new hires, building a common language, capabilities, and expectations across the board.
Your tenured team members also have a wealth of valuable knowledge that should be tapped into. Ask what needs clarification, what customers are finding confusing, and what they would recommend you start, stop, or enhance based on their experience working previous holiday seasons.
- Prepare the people who will teach and coach others.
Your strongest team member or assistant store manager may need guidance before becoming someone else’s mentor or coach. Make sure designated coaches can demonstrate a task, explain the reason behind it, allow practice, and give useful and specific feedback. Align and schedule managers and assistant managers so that new hires receive consistent direction across shifts. Make sure there are leaders and mentors on the team who can train, coach, make decisions, and keep the team moving when the store leader is occupied with other strategic tasks or otherwise unavailable.
- Keep development going even when business gets busy.
Training is a process, not an event. Even in the busiest times, there is opportunity for development, and often, these are some of the most powerful learning moments — if you take advantage of them!
For example, highlight one skill in a pre-shift huddle and provide a brief practice opportunity. Then, during the workday, give feedback on who is using it and the results they are gaining. Set goals and keep score to track and reinforce success. Engage your customers in the learning and make it a fun experience for them to join in as well. After all, every day is a chance to learn MOHR!
Are you retail ready this holiday season?
As you prepare for a productive and successful holiday season, I challenge you to take these three actions this week:
- Confirm which team members will serve as coaches to each new hire.
- Identify one skill the whole team needs to refresh, and determine how you will teach, coach, and reinforce it for continuous improvement.
- Schedule the first practice session on the floor to demonstrate and empower associates to grow and share, and then allocate time to follow up.
Remember: The coaching and development habits leaders establish now can strengthen their teams well beyond the holiday season and into next year.
