3D label Black Friday on black background

Even the toughest ecommerce veterans can agree: it seems like there's never enough time to prepare for Black Friday. The biggest retail event of the year takes a lot of proactive planning, and even with a perfect strategy, common pitfalls can still prevail.

What are the main pain points that Black Friday warriors experience, and how can you ensure this doesn't happen to your brand this November?

We asked ecommerce experts for some Black Friday tips, and they came up with some crucial insights to help you through the whole holiday season.

Fundamentals and Logistics

For most retailers, most Black Friday issues stem from basic logistics issues as systems get overwhelmed and orders pile up faster than any other time of year.

The key here is preparedness, which requires a bit of self-reflection and an analysis of past events - like a crystal ball for the future.

'Think back to last year and consider where things went wrong to inform your strategy for this year,' said Shahzil Amin, Managing Partner at WellBefore. 'For some brands, it's a matter of server capacity. For others, it's an issue with fulfillment and getting goods out to the public. Give yourself an honest audit and identify the areas in most dire need of improvement before you're in the thick of it.'

Pain points are also worsened by the long marathon that is holiday retail. Make sure that you and your employees are ready to work efficiently and have all the tools they need to get the job done under pressure.

'We put our sweat and tears into making the holidays happen for our customers, and we sometimes run ourselves into the ground as a result,' said Dylan Trussell, Co-Founder of Culprit Underwear. 'This is the time of year to stay balanced and not get overly stressed out. Treat it like a marathon instead of a sprint to the finish line, and do what you can to keep employee morale high and combat burnout.'

After all, employees are the engine of the company, and they make all the difference when keeping the gears turning through the busiest time of year.

'Your team is so vital to how Black Friday plays out, and everyone needs to be on the same page,' Trussell said. 'This is when your leadership skills will be tested, so do what you need to prepare mentally, physically, and always stay optimistic.'

While many ecommerce brands work with skeleton crews throughout the year, more staff may be required for the holiday. It's not uncommon for some brands to employ extra help or even outsource some key functions to prepare for the onslaught of Black Friday, Cyber Monday, and the first few weeks of December.

'The expression 'better safe than sorry' applies perfectly to retail strategy for Black Friday, particularly in the ecommerce arena where volume can fluctuate so unexpectedly,' said Designer and Brand Owner Daniel Patrick. 'There should be no stigma or hesitation to bring on more people for support, shipping, social media - whatever you need, get it in order ahead of time.'

As a leader in the fashion industry, Patrick has seen just how wild the end-of-year calendar can be for brands in his space.

'You just don't know what can happen with variables like social media algorithms, viral ad campaigns, and other factors that can lead to a huge spike in sales,' continued Patrick. 'If you anticipate record numbers coming up this November, it may be wise to play it safe and bring on a bit of backup, since the alternative could leave your brand high and dry.'

Sharpen Up Marketing

The victors of Black Friday don't get to the retail podium by accident, especially in a hyper-competitive e-commerce environment.

Everything happens on purpose, and it all starts with marketing.

'Your Black Friday game plan starts months in advance with your marketing efforts, and most pain points can be attributed to decisions you made in this timeframe,' said Yuvi Alpert, Founder and CEO of Noemie. 'Never be the brand that fails to keep a promise or falls short on your level of service. The way you market yourself sets the stage for all that. Messaging needs to be razor-sharp in the leadup period so you set customer expectations and are able to follow through when it's crunch time.'

Marketing also takes on a different role in this time of year, according to retail pros.

Customers are already on the prowl for gifts, so it may be beneficial to communicate with prospects on a more personal level. This means dialing back the salesmanship and reaching out in a more subtle way.

'I see so many brands that go over the top with their marketing campaigns, launching a barrage of emails and ads to capture as much attention as possible,' said Hector Gutierrez, CEO of JOI. 'They act surprised when customers are turned off by this mass-marketing approach, but the reason is simple. People don't need all the flash and flair for Black Friday, because that's the expectation across the board. Simplicity and authenticity go a long way this time of year.'

In other words, it may be wise to switch up marketing styles and let your customer relationships speak for themselves. If you've been going above and beyond all year, loyal customers will already be eager to buy from you on a Black Friday bonanza.

"During the holiday season, people are bombarded with deals on everything, from monstrous TVs to dog beds,' said Puneet Mehta, CEO of MobileROI. 'While there are some shoppers who have meticulously picked out the perfect gift for all the people on their list, many shoppers look for inspiration and ideas until Dec. 24. Marketing should go further than a mass distribution of deals."

Dealing with Customers

It's the most wonderful time of the year - until customers don't get what they want!

Every retailer can relate to the most common pain point of all, which is dealing with unhappy customers. This is bound to happen on Black Friday in some way or other, so it's important to be prepared for any possible situation.

'I suggest walking through various scenarios with customer support staff so that they're prepared on a practical and theoretical level,' said Jeremy Gardner, CEO of MadeMan. 'You'll have customers that act unreasonably, make crazy demands, or just need to be led by the hand through the most basic stuff. Give employees whatever resources they need to navigate these tough situations and remember that every interaction matters. Customers tend to leave reviews online during this time of year and you'll be under the magnifying glass, so prepare accordingly.'

As always, the best cure for cranky customers is to proactively provide great service, which starts before the sale is even considered.

Setting strong standards of service from square one is what separates winning retailers from the rest during Black Friday and beyond.

"This holiday season, retail brands have the opportunity to own the experience of every customer that engages with their brand - engaging and delighting shoppers in new ways that will earn their trust and loyalty,' said Mark Floisand, SVP of Product and Industry Marketing at Coveo. 'Shoppers want to feel that their preferences are understood. Personalization empowers brands to accomplish that and communicate with customers on a human level."

That's what really elevates certain brands during the holidays and earns them new lifelong customers. Rather than playing defense against customer complaints, they take an active approach and see opportunities to shine brighter than before.

'There is no better time than Black Friday to make an incredible connection with new customers and leave them with a great lasting impression,' said Ryan Lee, Co-Founder and CEO of Rooted. 'While other brands are struggling to stay in the fight, you're seizing the moment and providing service like no one else in your industry. That's how you level up fast and set a fantastic precedent for the remainder of the fourth quarter and the start of a new year.'

While many customers will be one-timers for Black Friday, retailers should try their best to accumulate social media follows, email addresses, and other valuable resources to fuel marketing campaigns moving forward.

Recover, Revamp, and Improve

Black Friday will be over in the blink of an eye, but that doesn't mean it's time to pack your suitcase for a beach vacation right away.

There's still much more work to be done for the holidays, and many lessons to learn from the experience, whether the outcome was good or bad.

'Never overlook Black Friday as a hugely valuable source of feedback for you as a leader and for your brand as a whole,' said Danielle Calabrese, COO of De La Calle. 'Every pain point is a small revelation that teaches you something new, and some of those lessons will be difficult to learn. However, if you ignore them, they'll persist, which is a universal truth in business and life. Be willing to invite all that feedback and quickly incorporate the changes necessary to steer the ship back on course.'

Now is the time to do away with any fear or fret when it comes to Black Friday!

It's the greatest opportunity for retailers all year, and despite some inevitable pain points, there are tactics to make this the smoothest, most successful season yet.