Back to the blog

Preparing Your Support Team for the Holidays

December 4, 2020
Best practices, strategies and tips for preparing your customer service team for Black Friday and Cyber Monday during the holiday shopping season

On October 15th, Greg Geibel from the Zendesk Team hosted a Q&A in the Startup Central Slack Community with the Chatdesk co-founders (Andrew and Aneto) about customer service tips for Preparing Your Support Team for the Holiday Rush

If you’d like to join the Startup Central Slack Community, Click Here

The discussion covered the following topics

Greg (Zendesk): We are live with Andrew + Aneto!  To start off, please tell us a bit about yourself, home-town, and position in the company!

Aneto (Chatdesk): I'm the co-founder & CEO of Chatdesk. Companies use our software to increase customer happiness, grow sales, and scale on demand. I’m based in Brooklyn, New York! 🗽🍎

I previously worked at Google for 7+ years as a Product Manager. My most recent projects at Google included Voice Search and the Google Assistant.

In my spare time I enjoying watching European Soccer, especially Arsenal FC

Andrew (Chatdesk): Happy Thursday, everyone! I'm co-founder of Chatdesk. Prior to starting Chatdesk with Aneto, I was a Manager at McKinsey & Company, where I led projects around call center operations and customer experience design across Retailers and Financial Services. I’m originally from Atlanta!

I’ve lived and worked across North America, Europe, and Sub-Saharan Africa, with 10+ years experience within Operations, Strategy, and Finance.

In my spare time I enjoy studying consumer behavior from around the world (have visited 60 countries across 6 continents). In addition, I love supporting Kentucky Basketball, UGA Football and Chelsea FC!

Greg (Zendesk): The first question to our panelists, “What was your first job? How/why did it lead to CX or your interest to dive deep into numbers?”

Aneto (Chatdesk): My first job as a teenager was as a Summer camp counselor at the Chicago Park District. My first major experience with CX was at Google when we launched a new payment system and staffed a customer service team in India 🇮🇳. We also built automated self service tools to enable customers to check their balance and block their cards via text message.

Andrew (Chatdesk): My first job was working as a server / host at the World famous Waffle House . This was my first dive into great customer service - taking orders, cleaning tables, and making sure customers were happy. I learned how to listen to people, show empathy / patience, and make some amazing hash browns (Scattered, Chunked, and Diced)!

Greg (Zendesk): Andrew, what are some of the typical pain points or gotchas that you’ve seen happen for support teams over the holidays?

Andrew (Chatdesk): Typical pains points we hear from our customers revolve around three things:

Greg (Zendesk): Aneto, what other stakeholders within the company should leaders meet with to plan (if any)?

Aneto (Chatdesk):

1) Marketing - Confirm what promotions and marketing activities will be running during the holidays. Anticipate the types of questions customers will have and align on the messaging for responses

2) Fulfillment - For e-commerce businesses, this time of year often causes a spike in order status requests right before the holidays and then a spike in returns right after. Discuss potential approaches to create self service FAQs, tools and forms to make it easy for customers to help themselves or give your team the needed information easily

3) Your team - Confirm the staffing schedules for your team so that you have enough team members to handle the increase in volume during the busy time. Ensure that everyone has sufficient training and updated information. I’ve also seen some companies plan some fun activities to celebrate the holiday spirit and reward the team after since some of them might not be able to take vacation during the actual holidays

Greg (Zendesk): what types of holiday changes in the CX process have you’ve seen brands make?

Andrew (Chatdesk): Great question, Greg! Many best in class companies we work with focus their CX changes on educating new customers and limiting contacts. Here are a few examples:

Greg (Zendesk): Aneto, any creative approaches you’ve seen to drive awareness and customer loyalty?

Aneto (Chatdesk): Loyal customers sometimes miss out on the holiday promotions because they miss the specific time period when deals are available. This causes disappointment and further increases in ticket volume with complaints or requests for price adjustments.

To address this, one of our customers designed a promotion specifically for existing customers which was sent out prior to the broader campaign. This helped to build loyalty and also reduce ticket volume.

Greg (Zendesk): Andrew, what should the staffing plan look like? Hire temps? Bring in the team members from other functions?

Andrew (Chatdesk): First off, I encourage each company to analyze last year’s holiday volume and / or Q3 2020 to understand how your volume might spike.

Once you have a sense of the additional staff you need to handle the increased volume, identify staffing options that provide the following:

To learn more about we’re helping companies launch on-demand support for the holidays with US-based Superfans, check out or feel free to reach out to me directly!

Greg (Zendesk): Aneto, given the increase in volume, how should brands handle customer "moments of truth" such as late deliveries and returns?

Aneto (Chatdesk): Look there’s no easy answer to this one Greg. The key is to prepare and align with your leadership on what types of policy exceptions and appeasements you will be able to offer for different scenarios.

Even if there’s no budget for appeasements, we have seen companies achieve high CSAT and NPS during the holidays with the following approaches

  1. Proactive updates - If there’s a delay, don’t wait for customers to reach out. This will help to manage customer expectations
  2. Apologize profusely - Use positive language, active listening and show empathy and a personal touch in your language in all your customer interactions and touchpoints
  3. Give customers alternatives - Examples we’ve seen include shipping out an alternate product, discounts on a future order, etc. Customers won’t always take the offer but they typically appreciate the gesture to solve problems and make them a happy customer

Greg (Zendesk): Andrew, how should you measure success during the holidays? What are the key team metrics (e.g., response time, conversion) that should you monitor during this time?

Andrew (Chatdesk): Key success metrics should center around sales, customer happiness, and efficiency. Here are three metrics that most of our customers are tracking:

  1. 📊 Utilization Rate: Ratio of time your agents are handling tickets by total time worked. Industry Average is 60 - 70%
  2. 🌟 CSAT / NPS (Net Promoter Score): How satisfied are customers with their experience and are they willing to recommend your services to others. You can enable Zendesk Satisfaction Ratings if you don’t have this setup already
  3. ✉️ Response time: Time taken (in seconds) by the customer service rep to respond to a customer’s message
  4. 🛒 Conversion rate: Percentage of visitors (online/social) who purchase something on your site. Industry average is 1 - 2%

Greg (Zendesk): Aneto, what Machine Learning and AI tools can companies use to manage costs and increase efficiency?

Aneto (Chatdesk): There are a lot of great tools out there. Here are few that companies can roll out quickly in time for the holidays

  1. 🤖 Zendesk Answer Bot is a great option for teams to help deflect repetitive tickets from email and chat
  2. 📚 Zendesk Guide has a feature called Content Cues which will provide automated suggestions for new articles in your Helpdesk Knowledge Base and ensure that you have a complete guide for your customers
  3. The Chatdesk Teams solution that Andrew mentioned earlier is also a great add on to Zendesk to help solve repetitive tickets and increase conversion by 10%+ on Facebook and Instagram with additional personalization. It works with the Zendesk CRM and you can be up and running in a few days with a free pilot for the holidays and no dev work or pre-work is needed. This is particularly helpful for small businesses to ensure that they can compete with the service experience of companies like Amazon.

Greg (Zendesk): Andrew, what are some risks of rolling out new tools or processes so close to the holidays?

Andrew (Chatdesk):

😞 Key risks we see include potential errors and decreased customer satisfaction scores and sales. Unfortunately, some companies are not able to fully test the new tool or process in time to ensure the entire team (especially temporary workers) can comfortably utilize them

📅 We recommend that companies launch new tools and processes at least 3 weeks before the holiday period begins

Greg (Zendesk): What do you expect to be different this holiday season because of COVID?

Aneto (Chatdesk): To be honest Greg, like everything else in 2020 it’s a bit difficult to predict! Here are some things we know for sure

Greg (Zendesk): Andrew, what best practices have you seen for “post-mortems” and reporting on the results from the holidays?

Andrew (Chatdesk): This is a great point! Since purchase intent for most customers remains high directly post-Holiday into January, companies should brainstorm how to capitalize. Here are two areas:

1. People/Process: Identify leaders within your company to summarize key metrics for their team during the holidays and action items

2. Tools: Leverage tools to quickly understand customers' needs as well as patterns / insights in the customer journey. Chatdesk’s free customer insights dashboard is an easy way for companies to automatically tag conversations from customer feedback on every channel you interact with your customer on. To launch in minutes set up a free account at

Here is the potential impact of this work

Greg (Zendesk): We have a few minutes left, but wanted to ask, do you have a mentor, or mentor others shaping your success?  What is your personal leadership style or approach to coaching?

Aneto (Chatdesk): For me, being a leader is about being a servant to your team members to help them achieve their goals and full potential. My personal leadership style comes from some books that are Required reading for new managers on our team including High Output Management and The First 90 Days

Greg (Zendesk): Looking forward to a little vacation, got any book or podcast suggestions for me?

Andrew (Chatdesk): Two of my favorite podcasts include Timesuck and Jalen & Jacoby. Check them out!  

Fernando (OpenGov): I like your recommendation to launch new tools and processes at least 3 weeks before the holiday period begins.What is your onboarding and acceptance methodology to ensure 100% adoption by the teams?

Andrew (Chatdesk): Hi Fernando! Regarding an onboarding / acceptance methodology, I recommend the following best practices:

  1. All key stakeholders (e.g., IT, Support, Operations, Marketing) should align on the “value-add” of the technology and how it will impact their teams (e.g., increase sales, reduce service costs)
  2. Before launching, decide on 2-3 metrics to measure the success of the tool (e.g., sales, efficiency, error rate)
  3. Create and stress test scenarios that will evaluate (1) how robust the tool is and (2) how comfortable the team is using the new tool
  4. Always create a contingency plan in case the new tool fails and you need to revert to the old process/tool. Make sure all key stakeholders play a part in this contingency plan

James (Zendesk): Great stuff thoroughly enjoyed the insights around providing great customer experiences during the busy retail season.  Given that it feels like holiday shopping season has kicked off a lot earlier because of the pandemic are you ramping your staff earlier than you normally would compared to when you prepare for the traditional “Black Friday/Cyber Monday” kickoffs? Thanks again for sharing!

Andrew (Chatdesk): You're spot on regarding online sales starting early. We've heard from several customers and agency partners who will launch their online sales as early as late October.  As a result, many of our customers have already started to ramp up their customer support.  For companies who haven't launched their prep yet, start asap!

If you’d like to join the Startup Central Slack Community, Click Here

Subscribe to our newsletter

Keep reading

Get a free quote.

Schedule a quick demo with our sales team.
Five out of five starsHello!

Download Content

Oops! Something went wrong while submitting the form.