21 Questions to ask before you begin your digital transformation.


Avoid the traps that cause many efforts to fail.

We know what you’re thinking – 21 questions sounds like a lot, doesn’t it? But, do you know what else sounds like a lot? Seventy-three percent, which is how many companies report that their digital transformations failed to provide real business value. So, what gives? Is implementing new technology to solve business challenges a hoax? A miserable waste of time and money? Of course not! And we’re not just saying that because we’re a software provider. We’re saying digital transformation is worth it because we are really freaking passionate about the potential of new technology – both the stuff we can help with and the stuff that’s not in our wheelhouse – and we’ve seen firsthand how it can help businesses create efficiencies and knock the socks off of their customers.

OK… so why are nearly three-quarters of digital transformations failing?

There’s no one right answer to this. Digitalization efforts fall short for a wide range of reasons, including underwhelming project management, lack of scalability, inadequate staff training, poor communication and budgetary limitations. However, one factor that can really sink a project – and one that you can definitely fix – is the failure to define your purpose and goals from the get-go. You shouldn’t start adding tech solutions just your competitors have shiny ones or because your boss has been on your case to be more innovative. You should implement technology that solves a specific problem and makes sense for your business.

Well, duh. Setting goals is a pretty obvious first step. However, how you determine what those goals are is not always as clear. Here are some questions that can get you thinking in the right direction – 21 of them to be exact.

Brand questions

A digital transformation isn’t just an upgrade to your product line or customer interface. Rather, it’s an opportunity to enhance your brand perception and solidify your business as a must in your customers’ lives. Consider: 1. Why are customers choosing us instead of our competitors? 2. What is our brand the very best at? 3. What is the emotional value of using our product/service? 4. How specifically do we make life better for our customers?

Customer experience questions

Speaking of customers, to go about this whole digital transformation thing the right way, your customer should be at the center of your effort. After all, 74 percent of B2B buyers say they will pay a premium for a better experience. That sure makes it feel worth it to ask: 5. How easy it is it to find and purchase my product? 6. If a potential customer Googles us, what do they learn? 7. When and how can a customer ask us questions? Is 24-hour service an option? 8. How much of the buying journey and after-sale experience can be done online? 9. How could our customers benefit from a password-protected portal?

Efficiency questions

Whatever business you’re in, you’d probably be happy to find a way to complete tasks faster and more cost-effectively. Efficiency is a key area where digital transformation has massive potential. In fact, 40 percent of executives say that efficiency was the top benefit of their effort. Here are some questions to get you thinking: 10. What are our most time-consuming tasks? 11. What tasks do we complete over and over again in a single day? 12. What simple questions do most customers ask? 13. What area of the business seems to bleed money?

Forward-thinking questions

Don’t you hate it when you get your hair cut and a week later it already looks like it needs it again? That’s the worst. (Just take more off the first time, man). Kinda like how if you’re going to invest in a big undertaking like digital transformation, you want to make sure you’re thinking long-term and not putting the kibosh on future growth. Think about ways your business could radically change: 14. Is it feasible to become a full-time remote office? 15. Can I monetize my data in an ethical way? 16. What self-serve options could I empower my customers with? 17. What’s my 10-year plan look like? How about my 20-year plan?

Process questions

You can have the noblest, most well-thought-out goals and still end up with an underwhelming execution when it comes to your digital transformation. If that’s the case, you’ve most likely had some internal process issues. Before you begin, consider: 18. Who belongs on my dedicated digital transformation team? 19. What three words describe my ideal technology partner? 20. Do we have any inflexible deadlines? 21. How will I communicate changes internally and externally? Hopefully, we got you thinking! If all these questions are stressing you out, take a moment to pause and breathe. The good news is that you don’t have to answer any of these questions yet. It’s just important that you keep them on your radar as you start exploring tech solutions for your business. Of course, we’re always happy to kick ideas around with you, too. Get in touch any time!

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