When digital transformation stalls: 8 questions to ask

Don’t be intimidated by the much-debated failure rate of digital transformation: You may just be stalled. Ask these questions to determine the fix
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5. What cultural roadblocks stand in the way of change?

“When digital transformation is unsuccessful, often it’s an issue of execution rather than strategy. The idea itself is great for the company, but the way it’s deployed runs into too many change management issues to be a success. When introducing any new tech to ‘the way things are done right now,’ leaders should look to leverage current culture in order to align the company’s mission with the tech across departments.

“If you want to unstick a digital transformation project in the works, look first to culture.”

“If you want to unstick a digital transformation project in the works, look first to culture. Embrace the one that’s currently there, then seek to explore areas where strong leadership can encourage more innovative behavior. This is similar in some ways to driving culture with top-down support, but different in that it fits naturally within existing organizational norms rather than having to go through the much more difficult process of creating new ones.” – Douglas Graham, chief security officer for Lionbridge

6. Do key stakeholders agree on goals?

“We’ve seen digital transformation projects stall very early on in the process because there’s no internal agreement within organizations about exactly how to go about change. It happens sometimes when senior leadership has a perspective that’s very different from middle-level managers and the employees who will actually be using potential digital solutions. For example, senior leaders may like an off-the-shelf solution because it has a lower price tag and seems easy to implement, whereas front-line employees may spot a lack of certain capabilities that make the solution seem like a non-starter to them.

“Use design thinking-style workshops to pull in representatives from every level of an organization.”

“One way we’ve solved the problem is to use design thinking-style workshops to pull in representatives from every level of an organization who then identify workflows, talk through problems, and ideate solutions. Doing it that way, you get a broader understanding of the challenges from every perspective and a better chance of general consensus on a path forward.” – Steve Pike, VP of professional services at CompuCom

7. Do we have the right skills on the team?

“Most teams today haven’t had the budget aligned with continuous improvement and upskilling, and therefore are woefully underprepared for the massive amount of learning that new skills and processes require to support change. This results in teams working on less important tasks that are not critical to the end goal. To mitigate this, find subject matter experts to help upskill teams with a methodology that can help them adopt new tools and processes until the core team is capable of taking over and providing this function.” – Chris Ciborowski, CEO of Nebulaworks

8. What are we holding onto that we can evolve?

“I’ve worked with many companies where the initiative was there, but the results were lackluster. Whether it was called a digital transformation or a DevOps transformation or cloud migration or something else, the failure and stall patterns can be extracted. The thing is, they’re not normally total failures. Pockets of success exist within teams or departments.

“For example, standardization is one reason digital transformation stalls. To move quickly, you must reduce variation. For large enterprises, this is a monumental effort that can take years. This can mean process simplification and unification, not just technology standardization.

“In the end, somebody is going to have to give up their sacred cow, and it’s going to hurt. It’s also going to mean you have fewer things to evolve and move forward. Hard choices have to be made here, and if they’re not, you keep that variability drag with you in perpetuity.” – Michael Stahnke, VP platform engineering at CircleCI.

[ Get answers to common digital transformation questions and lessons from top CIOs: What is digital transformation? A cheat sheet. ]

Carla Rudder is a community manager and program manager for The Enterprisers Project. She enjoys bringing new authors into the community and helping them craft articles that showcase their voice and deliver novel, actionable insights for readers.  

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