The one thing that makes or breaks all digital transformation

Over the past few years, I’ve worked with many organizations on their digital transformation work.

When they first come to me, it is common that they ask about the tech, features, how superior the performance is, and try to access the platform with a long list of requirements.

Biggest mistake: Thinking that choosing the right tech is the most important step

While it is important to pick a future-ready platform, this belief is one of the biggest mistakes that companies make.

On top of all that, there is something else that is even more important that will either bring wind to the sails or make the process like you are swimming against the tide.


What does this encompass?

  • Top management’s clear directives with bottom-up buy-in and alignment
  • Willingness to change and belief that change and the inconveniences along the way are worth it. Even if it means changing well-established processes and digging deeper to solve cross-departmental issues, which can be politically tricky at times

Expect and plan for these obstacles along the way:

  • an uncooperative colleague in the IT or neighbouring department
  • poor or no documentation of processes
  • difficulty in gathering requirements or getting sign-offs
  • long delays to getting things done or people in meetings due to conflicting schedules or lack of prioritization
  • systems are not set up to support the change and more development work is required than expected
  • expectations of stakeholders can be unrealistic where they expect a one-shot success and chastise mistakes
  • lack of commitment and time for stakeholders
  • political wrestling among stakeholders

Either one of the above is enough to set you back or undermine the entire transformation works.

Find your “Skunk Works” team to power create and model success

Skunk Works is widely used to describe a team that has a high level of autonomy and is not hampered by bureaucracy. The wider organization needs confidence and models they follow, so gather your first batch of “Avengers” to power through and show and convince people that it can be done.

Putting too many people in the team, thinking that they will be transformed through osmosis is just wishful thinking. More often than not, they will create communication and unwanted interpersonal friction.

Always start with people who can propagate change, much like intra-preneurship.( More about that in a later post)

Image credit: Nick Fewings




I run an AI tech startup and have a little toddler ‘startup’ at home. I strongly believe in how tech can uplift the lives of people and businesses.

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Peiru Teo

Peiru Teo

I run an AI tech startup and have a little toddler ‘startup’ at home. I strongly believe in how tech can uplift the lives of people and businesses.

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