Sep 19, 2023  |  By Wei Sun, CEO

Why Confidence Is the Antidote to Holiday Sales Stress

The holiday season is undoubtedly the most stressful time for sales representatives. Lines are long, customers are impatient, and there are new offers to learn and sell. 

Self-confidence is a powerful force that transforms our ability to handle any situation. A combination of resilience, optimism, and competence, self-confidence is a secret weapon that helps reps stay calm and enjoy the higher commissions that come with holiday rushes. 

In this guide, we’re diving into the impact of confidence on both stress and performance. Plus, we offer practical tips on how to instill confidence in your sales team. 

The holiday season is stressful, and workers aren’t having it

Self-care is important to Gen Z employees, who expect the companies they work for to prioritize their mental health through a positive work environment, flexible scheduling, counseling, and other programs.

82% of retail workers say their job contributes to stress and burnout. The issue compounds, as 58% say they’ve had to work more due to high levels of employee turnover. 

Especially for workers who struggle with anxiety and stress, the holiday season isn’t worth it. They’ll quit, leaving the rest of the team understaffed during the busiest time of the year. But, self-confidence can be a powerful antidote to holiday stress and turnover.

The neuroscience of confidence

Confidence is a powerful force in the fight against work-related stress. When we feel confident, our brains are locked into the chemicals and circuits that release rewards and pleasure. We actually feel good, and we spread those positive feelings to others around us. 

Sales reps who feel confident in themselves and their skills can more easily respond to high-stress situations. But confidence killers are everywhere—and what saps confidence is different for every person. So if you want to help your workers use the power of confidence, you’ll need to build it up from multiple angles. 

What workers need to see them through the holiday season

To get through the holiday season—with the maximum amount of confidence and the minimum amount of stress—here’s what frontline workers need. 

  • Good customer service habits and skills - Sales reps need to have essential customer service skills drilled into their brain, so that they become automatic. Reinforcement learning is essential. Reps need to continuously practice skills, like how to pitch a certain product or diffuse a dissatisfied customer. 
  • Expertise in holiday promotions - It’s also important for reps to practice the features and benefits of new products hitting the shelves during the holiday season. They might need expertise in special services, subscriptions, warranties, or financing options. 
  • Confidence in their ability to handle customer needs - During the holidays, reps need to go into each day feeling confident they can handle whatever will come their way. When they start their day with confidence (instead of fear, worry, or dread), they’ll be more likely to carry that feeling throughout their day. 
  • Higher commissions that make the holiday season worth it - Better training equals better commissions, which make the stress of the holiday season worthwhile for employees. This contributes to lower turnover rates.
  • Knowledge on how to handle holiday rushes - Reps need to be prepared to handle longer lines and customers who are frustrated with higher-than-normal wait times.

How to use peer-to-peer training for real-world customer service challenges

So how do you actually instill confidence and real-world sales skills into your team?  Here’s how to put strategy into action:

Make real engagement a priority

Implement a training program that drives real engagement. Active learning naturally builds self-confidence because skills are more readily retained for future use. 

Passive learning (like watching training videos) has been proven to be ineffective, so make sure that your holiday training program facilitates participation. 

Choose a platform that’s easily scalable

Scheduling participatory training sessions across your entire organization could be an operational nightmare.

Choose software that will make it easy for you to scale your learning environment. For example, a pairing algorithm can spin up peer-to-peer learning sessions instantly and automatically. Reps can hop on a session at any time during the day and be connected to another rep from another location—without you having to schedule hundreds of sessions manually.

Pass knowledge between reps

Experienced salespeople who’ve handled the holiday rush before have a lot of knowledge that could help newer reps. Their stories, ideas, strategies, and approaches are more useful than most top-down training programs. That’s why it’s so important to connect reps with different experience levels. 

Build confidence naturally through teaching

When we teach, we learn. This phenomenon is known as the protégé effect. No matter what formula you use to match up reps in one-to-one sessions, they’ll get something out of it simply by sharing their experience. 

When they explain how they approach difficult situations or sell unique products, they’ll hone in and reinforce these skills. This naturally builds confidence by increasing the retention of important skills while helping them focus on what they already know. 

Train for Holiday-specific hard and soft skills

Holiday-specific training is essential. To be confident in their abilities, reps need to practice relevant skills.

Train for hard skills like:

  • Selling the features and benefits of new products
  • Pitching holiday-specific offers or promotions
  • Upselling holiday-specific add-ons

Make sure to also incorporate soft skill training:

  • How to proactively engage customers waiting their turn
  • How to pitch holiday promotions in a way that is inclusive of customers of different cultural backgrounds
  • How to move through the sales process quicker, without missing essential steps
  • How to assist with loss prevention during busy times
  • Examples of workplace multi-tasking that are and aren’t effective

Measure reps’ confidence and performance

Goal metrics should always inform your training content. For whatever metric you want to impact, you can create conversation prompts, get all reps involved, and see how the training impacts business goals.

But it’s also important to measure employees’ confidence. How ready and prepared do they feel for the upcoming holiday season? After the holidays are over, did they feel like their training was adequate? Survey reps to find out how you can improve your holiday-specific training the next time around. 

Prep for the holidays with Upduo

Upduo’s peer-to-peer learning platform makes it easy for everyone to become a teacher. Organizations have reported double-digit performance growth on key metrics they targeted with Upduo within a 30-days.

The Upduo learning experience is engaging, participatory, highly relevant, and quick to deploy across teams. Reps share real-world experiences and the strategies they rely on to navigate common issues. With Upduo, you can create conversation prompts that get all of your reps ready for the holiday rush. 

Here’s how it works: Reps from across your organization chat with one another during short video calls using their mobile devices. They follow the prompts on the screen to have an open conversation about a certain product or skill. 

For example, they might be prompted to…

  1. Introduce themselves.
  2. Share a product that is challenging to sell and how they usually pitch it.
  3. Tell each other which part of the other person’s pitch they liked best and plan to use for themselves.
  4. Thank each other for sharing and say goodbye.

These conversations take just a few minutes and can be done several times a week to continuously improve and reinforce essential skills.

Get in touch with us for a strategic consultation on your holiday training. Schedule a demo or reach out to