Digital transformation can fall short of business objectives for a number of reasons – so many, in fact, that if you’re stumbling, it may be difficult to determine which obstacles are tripping you up. From inadvertently missed steps, to the absence of the right people on the team, to the fatigue of continuous change, to the confusion around the term itself, digital transformation pitfalls lurk seemingly around every turn.
Digital transformation strategy questions to ask
Understanding what is holding you back is the first step. To do that, you’ll have to ask yourself a few critical questions about where you are now and where you want to be. The answers to these questions should help illuminate the path forward – as well as shine a light on the roadblocks standing in your way.
Explore these six questions about your digital transformation strategy and digital platform:
1. How would we approach it if we had unlimited time?
The urgency to transform typically looms large over teams, especially if there is a competitor nipping at the heels of the organization. Consider how taking away some of the pressure – even if only as a thought experiment – can help teams think differently, suggests Martin Henley, senior vice president, technology services at Globality.
“Asking the unthinkable can often open doors,” says Henley. “For example, if you are under significant time pressure (market launch, board deadlines, etc.), think about asking the team what they would do if they had all the time in the world and this constraint was removed. Often, this approach will drive to a very different answer or solution.”
Henley notes that eliminating the time pressure is unrealistic, of course, but “the fresh thinking can then be taken, step by step, to ‘how would we apply this approach with our constraint of time?’ This approach will often help everyone see the [forest] for the trees and move the program forward,” he says.
2. Who has the authority?
Wondering if you have the right people involved? Just ask yourself who has the authority to lead, says Clive Fenton, founder of Step5. Specifically, he suggests looping in anyone who knows what’s near and dear to the end user.
“We often find that technologists are defining and driving the digital transformation. The problem with this is that they don’t know enough about what the user needs,” says Fenton. “When you change the interface, the user experience must improve; otherwise it won’t be adopted. Say the transformation is the digitization of a call or contact center. The call center agents absolutely need to play a key role because they are the only people who understand what the end customer wants and needs. If a business is introducing chatbot or voice bot technologies, the call center agents will know the most common and likely-to-be-asked questions; they can help ensure that the tools are configured in the right user-friendly way and that the interaction is authentic from the get-go. Fail to get this right from the start, and you’ll lose the caller.”
3. What would an outsider do?
Sometimes getting unstuck means challenging your own expertise. To truly think differently, you must think like someone else entirely – like an outsider, suggests Ryan Talbott, chief transformation officer, Midwest, for Altimetrik.
“Leaders need to think and act as if they were an outsider stepping into this digital transformation leadership role. They need to challenge their own perspective of where they think they are,” says Talbott. “If you were freshly taking over your role, what would you change, how would you focus your organization, and how would you make your team more effective? Take these ideas and implement them.”
Two more minds to think like: your employees and your customers. “Leaders should imagine themselves as one of their employees,” says Talbott.“What would you be frustrated by in this digital transformation journey, and what would you be worried about with this change? This can help leaders identify the types of thoughts and feelings that need to be positively addressed. Finally, focus on the customer experience. What would your expectations be as a customer when interacting with your company? Act as that customer, and see if your experience matches the expectation you’d want to see delivered.”
Getting into these different personas can offer leaders an internal impetus to change, Talbott points out. “Asking the above questions and focusing on solving customer pain points will change your frame of reference, make you re-evaluate where you are, and ideally make you realize how much removing those roadblocks is under your own control.”
4. What is the biggest blocker to releasing software today?
It may only take one question – asked and answered continuously over time – to increase the velocity of your digital transformation. Robert Reeves, CTO of Datical, zeroed in on the one question that drives his team forward: What is the biggest blocker to releasing software today?
“Digital transformation is about getting more and better software out the door. Whether you are basing your transformation on DevOps, cloud, or Platform-as-a-Service, it’s all about getting software out the door today,” says Reeves. “But there will be parts of the process that need to be improved. Simply asking everyone on your team what the biggest blocker is identifies the area to focus on. It’s that easy. Every digital transformation will be unique, so ask your team, fix it, and then ask again. Lather, rinse, repeat.”
5. Are we trying to hit a home run when we should be aiming for a single?
Clarifying what defines success is an important step for teams – and it’s up to leaders to set realistic goals. Matt Mead, CTO of SPR, doesn’t bat for the fences; rather, he keeps his team focused on showing value early and often.
“It’s essential to take a step back and identify whether your digital transformation initiative is trying to accomplish too much at once or if you’ve defined goals that are too large,” says Mead. “It is always better to define and accomplish smaller goals and show value often, as this keeps the momentum behind your initiative, rather than struggling to keep up with steep goals that result in no progress.”
While it’s easy to get hung up on the “transformation” side of things, you can’t discount the many small steps that must go right first before large digital transformation goals can be realized, says Mead.
“Home run hitters have a tendency to strike out frequently because they swing so hard and miss,” he notes. “In business, it’s more important to get on base more often than striking out. Take it slow and show value by achieving results – even if it feels like a small win.”
6. Why is our digital transformation not delivering? Think behaviors
“When a digital transformation project is failing or stalling, sometimes the key is to start by asking the most simple and obvious question of all,” Fenton advises. “Why is the project not delivering?”
Although this question seems basic, Fenton says it is effective in getting to the root of the problem. The trick to keep asking why.
“People’s first answer to this question is rarely the real problem,” says Fenton. “It’s more likely to be symptomatic, but revealing nonetheless, and what it does is enable you to open up the conversation. The key is to ask lots of different follow-on questions to find out what has gone wrong. The issue is that digital transformation projects are about engagement of different behaviors rather than simply technology, so you need to keep probing to identify the root cause and then fix this, rather than hide behind the ‘smoke and mirrors’.”
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