Digital transformation: 3 mistakes that hurt agility

Digital transformations don't fail because of the technology. They fail when organizations neglect to develop better ways of problem-solving, testing ideas, and managing work - what we call agility
268 readers like this.
digital transformation reality check

Digital transformation is difficult enough to get right: Making a mistake that inhibits your agility can set you off on the wrong foot and prevent your transformation from succeeding.

Transformations don’t fail because of the technology. They fail when organizations neglect to develop better ways of problem-solving, testing ideas, and managing work (what we call agility). If you’re unsuccessful in these areas, your transformation may be sluggish and at risk of missing out on delivering the true value you set out to achieve. 

Before we get started – a quick note about the difference between “Agile” and “agility.” In this article, we’ll treat Agile as the set of processes and artifacts teams follow to manage complex work. Separately, we’ll use the word “agility” to refer to the thinking and ways of working that often come after a team has implemented Agile.

[ Read more from Rich Theil: Digital transformation: 5 types of leaders who can get in the way. ]

3 digital transformation mistakes to avoid

Let’s get started with three easy-to-make mistakes that inhibit your agility and prevent your transformation from becoming a revolution.

Mistake 1: Your strategy was born (and still lives) in technology leadership

Almost every org we talk to starts their digital transformation at leadership levels in the technology organization. The mistake we see companies making is keeping it there. Instead of developing agility through deeper relationships with cross-functional teams, the initiative ends up internally focused on operational efficiency. This misses the opportunity to start a revolution. 

The result is a transformation that produces a bigger impact to top-line growth.

Successful transformations often start with technology leaders. Then, one of the first things these leaders do is form cross-functional leadership teams and soon thereafter, they enroll entire organizations to find the best new business opportunities. This approach opens doors to ideas well-beyond the typical scope visible to the technology organization. The initiatives will be more externally facing and focused deeper on consumer needs. Meanwhile, initiatives that are internal and operationally focused get deprioritized. The result is a transformation that produces a bigger impact to top-line growth.

The challenge most leaders face here is that they’ve not previously had the responsibility to drive this type of change across so many other parts of the company. Being successful requires focus on these two things: 

  1. Building deep, trusting relationships with your peers and members of their orgs so that you can get the buy-in you need
  2. Maintaining a disciplined approach to implementing technology with excellence so that the changes you make can be sustained for the long term.

Mistake 2: Only tech teams use Agile

Agile started with software development teams 20 years ago and, unfortunately for many companies, it often remains in the ranks of the tech org. But its ability to streamline operations and boost results also offers plenty of benefits across the organization. There’s a reason why some folks are die-hard Agile zealots. They’re not crazy. They see the benefits that Agile brings to team agility, and it’s an easy jump to think about what business results could come if the rest of the company developed these same capabilities.

Take for example, the leadership team. By implementing Agile ways of working, which increase visibility and transparency, they can develop the ability to spot projects they didn’t know were happening in the org. Eliminating these projects and realigning the people working on them can create capacity to work on more important initiatives.

If you worry that your colleagues will be reluctant to adopt new processes, consider working with an agile coach who can walk your team through the process of developing agility and adjusting as you learn. You can start with lighter-weight versions of Agile and adjust as needed for the team.

[ Want Agile and DevOps best practices? Watch the on-demand webinar: Lessons from The Phoenix project you can use today. ]

Mistake 3: The culture roadmap isn't written down

We believe management guru Peter Drucker was right when he famously said, "culture eats strategy for breakfast," – so it’s ironic that we spend so little time talking about culture in our digital transformations. We avoid the conversation because culture is amorphous, difficult to tie to value, and can be difficult to quantify.

The reality though is that the statistics are overwhelmingly in favor of more intentional culture development. Countless studies find that 70 percent of transformation efforts fail and the cause is almost always attributed to a people and culture challenge. We also know that companies who focus on culture are five times more likely to achieve breakthrough performance.

In other words, it really is eating your strategy for breakfast, so perhaps some tools that let you make intentional choices to shape the culture would help. Our favorite is the Organizational Cultural Assessment Instrument (OCAI). It’s easy to understand and provides rails for the cultural conversation that will serve you for years.


To get started, get an assessment and some help writing down the backlog of changes you need to succeed in your transformation. With the right help, that backlog will change your structure, policies, metrics, and behaviors to adjust your culture and significantly increase your likelihood of success. 

These three mistakes are common but they can be overcome. So if you’re making them now, today’s a good day to start course correcting. Getting these three things right will fuel the people, culture, and ways of working that set your transformation up for success. 

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

Rich Theil
Rich helps IT Leaders fix Agile teams burdened by inadequate Product Management and broken business partner relationships. Prior to starting The Noble Foundry, Rich spent 12 years as CIO for a large, scrappy, and aggressive non-profit in Cincinnati. Additionally, Rich spent seven years at P&G in Information Technology.