1 - If we learned the cautionary tale that you kill yourself when you stop offering discounts and promotions (i.e. JCP), then why was JCP struggling so badly leading up to 2011 when it still generously offered discounts and promotions?
2 - If omnichannel and bricks 'n clicks are the future, then how do you explain why Borders went out of business? Bonus questions ... how do you explain that Barnes and Noble didn't gain market share when Borders went out of business ... and how do you explain that Amazon, without a retail presence, sells books and eats into retail book store market share?
3 - If omnichannel and bricks 'n clicks are the future, then why did Blockbuster Video die while Netflix thrived? Wouldn't the retail presence have been enough to crush Netflix? And if your answer is that Blockbuster made key strategic errors, then shouldn't we be worrying about merchandising/service strategy first while giving omnichannel very little attention?
4 - Assume that omnichannel and bricks 'n clicks are the future and Macy's is the omnichannel poster child for omnichannel success. Why, then, is Macy's consistently posting negative comp store sales results? And if your answer is "it's merchandise, stupid", then why are we choosing to not focus all our efforts on merchandise?
5 - If catalogs are a vital part of an omnichannel future, then why have total catalogs mailed declined by a whopping 40% in the past six years (click here)?
6 - If mobile is the future, and it most assuredly is the short-term future, and if most folks will access your brand via mobile within three years, then why are mobile conversion rates so horrifically awful, even among rabid early adopters, and what does that mean to the future of e-commerce?
7 - What does it mean for the future of catalog marketing when the average catalog customer is sixty years old?
8 - Explain why Safeway requires a club card for cheap prices and loves couponing, but Trader Joes can sell at full price and thrive?
9 - Why do you happily pay Amazon $79 a year ahead of time to get products shipped to you, but you won't buy from your favorite e-commerce brand unless they offer you free shipping?
10 - What did Amazon do different than everybody else to achieve an approximate 25% e-commerce market share? And why do we think that the solution to this battle is to simply become more "omnichannel", a solution that seems to have only helped Amazon get bigger?
11 - How do you plan on keeping your business on level ground under the assumption that Amazon could represent 40% of e-commerce in five years?
12 - Why does Forrester Research promote a digital / social / mobile / big data / omnichannel future, but use Direct Mail to generate business? Furthermore, why does Forrester Research describe their own social media practices in their 2012 annual statement as not materially moving the sales line? In other words, why is the research brand responsible for promoting a digital future not capable of fully leveraging digital for it's own future?
13 - Of what value is it to generate $2,000,000 of Cyber Monday demand at 30% off plus free shipping at a 40% gross margin when you could generate $1,000,000 of Cyber Monday demand at full price and a 60% gross margin?
14 - If "All Magic Comes With A Price", why are so many of us willing to pay that price?
15 - Why would the USPS consider cutting Saturday service for catalogers while jacking up the price of a catalog mailed to a customer, but happily accept money from Amazon to deliver Amazon's packages to your home on Sunday in major markets, helping put you out of business in the process? Discuss.
16 - How, in a mobile environment, do you plan on sharing your full assortment with your customer, when you are so limited by what you can share with your customer in a mobile environment?
17 - If you promote an omnichannel future of sameness across all channels, then why do you allow your email marketing team to offer discounts and promotions that are not available to best customers who fully use all other channels but do not subscribe to your email channel?
18 - If you built a business on search engine optimization - in essence - if you built a business on free traffic and free information from Google, then aren't you, and not Google, accountable for the problems you face now that Google has essentially repealed organic search keyword information? Remember, all magic comes with a price.
19 - How many new products did your company launch in 2013? What percentage of these products became best sellers? How did this rate change vs. 2012? If you don't know the answer to these questions, describe the ways you are at a competitive disadvantage to those who know the answer to these questions.
20 - Why do you match back orders to your catalog that would happen anyway, even when you have the mail/holdout test results to prove that you should not practice this "best practice"? Are you worried about what will happen to the future of your catalog if you do what is truly most accurate and most profitable for your business?
21 - If you ask 100 attribution vendors to allocate orders to marketing activities, and you get 100 different answers, how exactly do you know which answer is the right answer?
22 - If all channels are supposed to be representative of our brand, and by aligning all channels perfectly we achieve omnichannel excellence, then please describe why Microsoft, first with the Zune music player, and today with the Surface tablet (which integrates with your desktop so well that you can use Outlook or Excel or Word - killer apps, right), is unable to make a dent on what Apple accomplished? And if your answer is that Apple has all the apps, well, then didn't you just prove the point of how meaningless omnichannel really is, because you've just demonstrated the importance of product (apps)? And if you've just demonstrated that product/apps/merchandise are so important, then why are your practices and analytics not aligned around merchandise in the first place? Discuss.
23 - If social media engagement is the difference between success and failure, then wouldn't Best Buy, with their Twelpforce, be crushing the competition?
24 - If social media should not be measured via sales and profit, but instead, via engagement and metrics aligned with anything that is non-revenue producing, then describe why your company should continue to invest $80,000 in salary plus benefits for your position, when your company could invest your $80,000 salary in paid search and generate $250,000 of sales and $20,000 profit?
25 - Is it possible that you and your co-workers, and not vendors / trade journalists / bloggers / social experts / mobile experts / management consultants / researchers, are most knowledgeable about the dynamics surrounding customer behavior at your business?