Digital transformation: 4 strategy questions to ask

Are you putting user experience first in your digital transformation efforts? Let's examine questions to ask around change management,  internal champions, training, and metrics.
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Efforts to modernize and digitize processes have advanced considerably over the past year. A recent survey by Capgemini of over 1,000 large enterprises found that 67 percent are actively exploring and experimenting with new ideas regarding digital tools, compared to only 35 percent in 2018. However, while many companies are progressing with their digital transformation plans, not all are necessarily implementing a new suite of digital tools.

Even the best enterprise tool is only as effective as how it’s used, so any digital transformation strategy must prioritize the user experience first, followed by an assessment of the relevant tools and capabilities. If you want to make sure your digital transformation efforts are setting you up for long-term success, here are four questions to examine.

[ Read also: Digital transformation: 3 driving trends for 2021. ] 

1. Are our change management communications effective?

When change initiatives fail, a major cause is unclear or ineffective communication. Employees are now required to juggle dozens of communications tools, including email, Slack, Zoom, and a slew of other SaaS applications, to collaborate with their coworkers and access the information they need to do their jobs.

The introduction of new digital tools can easily feel like yet another application to manage and keep updated. Employees are often forced to spend time looking for answers or information critical to their jobs, so it’s important to emphasize why certain tools will improve workflows and tie into the company’s digital transformation plans.

Change management communication should be concise, goal-oriented, and user-focused. Every impacted employee should understand how digital transformation efforts will affect them and make their lives easier. If you can help your employees understand the “why” behind digital transformation by prioritizing frequent, clear communication, adoption becomes that much easier.

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

2. Who will be our internal champions?

Internal buy-in is the most important aspect of any digital transformation and adoption strategy, and the easiest way to help promote that is to identify internal champions. Clearly defining the team responsible for the implementation of a new tool or process will help give an incentive for that team to ensure adoption is prioritized throughout the organization. It will also help clarify where employees can direct questions.

Don't underestimate the importance of clear communication from your C-suite to champion digitization and build buy-in for change.

More broadly, your executive team should be leveraged as champions for digital transformation. Don’t underestimate the importance of clear communication from your C-suite to champion digitization and build buy-in for change. Ensure that the C-Suite is communicating frequently to help foster participation and enthusiasm for the transformation process.

[ Get exercises and approaches that make disparate teams stronger. Read the digital transformation ebook: Transformation Takes Practice. ]

3. How will we train our internal teams effectively?

Training teams on new processes and tools is easier said than done. It’s important to find a better way to train, not just to ensure that digital transformation is successful and to make sure training really sinks in, but also to make sure your employees feel supported. Building effective training programs is a great way to show your employees that you’re invested in their success and their careers more broadly – helping to increase retention.

Whether you approach training with hands-on practice, use virtual reality technology to replicate real-world scenarios, or leverage digital enablement tools designed to reinforce training within an employee’s workflow, it’s critical that employees retain what they’re taught and feel like obtaining information is intuitive and seamless. In addition to building an implementation plan, make sure that you’re designing an ongoing learning roadmap that includes helpful, comprehensive onboarding for new employees as well as ongoing learning and training for existing employees.

4. How will we measure success?

Finally, be sure to set measurable, attainable goals around your digital transformation strategy. These may look vastly different from tool to tool or organization to organization, but adoption will increase if every user understands how transformation efforts will be evaluated. Another advantage: Making adaptations and adjustments later will be quicker and easier.

Every new digital process should have some associated metric attached to its use, whether that’s through the use of built-in analytics native to the application or by leveraging third-party tools. Consider developing, implementing, and analyzing quantitative metrics that enable you to gauge in real-time how effectively tools are being used and to continually assess your transformation efforts.

Thinking through adoption processes and pain points is an often-overlooked component of any digital transformation strategy. If you prioritize your employees’ experience throughout the digital transformation process and ask these four crucial questions about your change management plans, internal champions, training, and measurement, your strategies are much more likely to achieve long-term adoption and meet your business needs.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

Melanie Fellay is the CEO and co-founder of Spekit, an in-app learning and digital enablement companion that helps employees learn their tools and navigate process changes by accessing training resources in real-time, everywhere they work.


Setting out for digital transformation without a definite strategy is like a bird without wings. Not many companies have even the slightest idea of developing a robust roadmap for their digital transformation initiative. Hakuna Matata, as a leading digital transformation service, we look at digital transformation holistically to help companies like yours leverage the potential of digital technologies to the fullest.