Get Digital Transformation Right the First Time: It’s Not About Your Tech, It’s About Your People

2020 has been a make-or-break year for many businesses looking to adapt to new customer needs, introduce new ways of working and shift to new business models. Digital transformation leaders have been at the centre of these mission-critical developments.

Unfortunately, the success stats are not favorable. Forbes reports that 70% of digital transformations fail.

Why? Because many digital transformation leaders are focused on tech, tools, and process change – and they neglect to address the people side of change.

As a top-ten rated global change consultancy, Daggerwing Group has extensive experience helping leaders get digital transformation right the first time by helping them focus on the hardest part – the people.

Here are three strategies digital transformation leaders can use to mitigate the risk of not delivering on objectives:

1. Accept that digital transformation will make some people worried and afraid 

Effective transformation leaders first articulate a compelling vision for the future and the urgent reason for the change.

However, that’s easier said than done. Even with a strong, clearly articulated vision, optimal solution, and built out implementation roadmap, employees still might not respond well to the changes. As a leader, you need to be aware of what your employees are really thinking and feeling. What your people may be saying to your face is not the same as what they may be saying to each other.

Like we mentioned, 70% of digital transformations fail. And one of the key reasons is because organizations do not address the underlying concerns and fears of the employees. They don’t go beyond the generic and organization-focused vision to be more personal and human. But this is just the first step to getting employees to feel that change is relatable and able to be owned.


2. Understand the biases that employees hold about digital transformation 

Leaders can ensure they have set a good foundation for digital transformation by trying to read the minds of their employees and then using that knowledge to influence how people think, feel, and act.

In Daggerwing’s experience, the three biases we see most often in digital transformation are:

WHAT IT IS: It is natural for people to want to stick with what they know – even when presented with something better. They prefer things to stay the same, doing nothing to change or sticking with a decision previously made.


  • Make your company’s vision tangible, meaningful, and inclusive
  • Emphasize pain points in current systems and how they will be eased
  • Make that first step easy and intuitive
  • State a clear deadline for visible impact

WHAT IT IS: Some studies show that from a psychology perspective, losses are twice as powerful as gains. With this bias, people are more focused on avoiding a loss than gaining something good – such as easier ways of working with digital transformation.


  • Make the gain clear and compelling to clarify, “What’s in it for me?”
  • Clarify your people’s notion, “What are you losing?”
  • Promote sharing of ideas and opinions that promote forward-thinking

WHAT IT IS: The Availability Bias is also known as the “Fear of Missing Out” bias – or more known to Singaporean’s as being Kiasu. This bias happens when people keep hearing about how amazing digital transformation can be and they don’t want to lose out to existing competitors if they don’t do it too. However, they don’t know exactly why digital transformation is important for your company.


  • Make your company’s vision tangible, meaningful, and inclusive
  • Clarify your company’s specific goals for your digital transformation initiative
  • Reinforce how it will benefit each and every internal/external stakeholder or group

3. Inject empathy, clarity, and safety into your leadership style 

To identify problems and barriers of change, digital transformation leaders need to build mind-reading capabilities – but that cannot happen without adopting empathy, psychological safety, and clarity into everyday leadership.

Empathy: Although ‘empathy’ has become a buzzword recently, we believe that understanding what employees think, feel, and do needs to start from an empathetic standpoint. Leaders need to look through the eyes of their employees to see how change is impacting them personally.

This is where skills of listening and observation come in – leaders need to pay attention to body language and verbal hesitation. It is good to say: “I know you have concerns…” and then address them.

Psychological safety: The fear of ‘not knowing’ and the fear of failure are common responses to change. These fears are even more difficult to address during a digital transformation when there are many waves of change in different directions. To alleviate fear, organizations and leaders need to focus on building psychological safety for their people.

To get started, leaders need to constantly reinforce that it is safe to try, to fail, to contribute, and to share – all while leading by example. Another critical component is to recognize that fear comes from how change is explained. Be clear about exactly what the final destination is – but help everyone understand the step-by-step pace of change to alleviate the fear of everything changing overnight.

Clarity: Lastly, leaders need to communicate very clearly and loudly about what the tangible benefits are for employees, not just for customers and the business. For instance, leaders can say: “You wanted a more streamlined workflow so you could focus on higher priority tasks, and our new digital tools will help you do that.” You also need to let employees know that business results, customer satisfaction, and competitive advantage can all decline if the adoption of new digital tools and technologies don’t happen as planned.

At Daggerwing Group, we’ve proudly worked with many global companies to help leaders do change right the first time, and make it stick. If you want to find out more about how to manage the people side of digital transformation, we’re happy to share more of our tips.

Ning Wong, [email protected]

Ning is a Principal at Daggerwing Group. She lives to excite change from insights to ideation and implementation across business strategy, brand culture, and organizational design to transform companies. Her work reflects her enthusiasm for leading in the new, working to identify growth with stakeholders to help them create and own their future. Spend enough time with her and you'll find yourself getting excited about the disruptive trends in Asia Pacific, human-centered systems thinking, and visual facilitation.
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