Digital transformation: Learning from failure

Digital transformation: Learning from failure

Digital transformation is defined by the Gartner Research Center as the ability of an enterprise to exploit new technologies towards creating a more robust digital business model. Its design allows users to solve their traditional problems in a better way. This enables the connection between new types of innovation and creativity, that go beyond upgrading or enhancing what’s already been done.


Everyone, entrepreneur, social change agent, and corporate leader, is exposed to digital transformation. This means they need to come to grips with it, find its potential for its mission-oriented objectives, and lead the organization through deep behavioral change.


When we launched THNK, it was a highly innovative, albeit totally non-digital, concept. A part-time school focused on innovation in business and leadership through deep practice, required a strong interactive component toward of lasting transformation. The curriculum was developed in a process of continuous improvement toward what made it such a distinctive experience that transcended borders and cultures. It attracts creative leaders from around the world, and keeps them emotionally bound. Throughout the years, THNK attempted to create a digital version of itself. We committed significant leadership capacity, spent real money, and adopted a rapid prototyping process of exploration, experimentation, and improvement. None of these made a dent, nor were close to recreating the experience of the THNK program on a digital level. Something always had to give, and sometimes this happened with serious missteps.


Like any innovative, entrepreneurial endeavor, digital transformation includes learning from failure. What better than reflecting on our own efforts, especially what did not work and what we missed?

digital transformation
Everyone – entrepreneur, social change agent, corporate leader – is exposed to digital transformation. The question is: How do you realize its full potential? #digital #digitaltransformation #technology #disruption Click To Tweet

What we had in place

Some things we did well

  • Betting on the right industry and business model. Edutech is a large, fast-growing industry. We placed our bets on a collaboration platform, workflow solutions, and tools for creative processes. All of these had, and still have, large market and business potential.
  • A combination of rapid prototyping, customer centricity, and co-creation. We interviewed our target users, interpreted their needs and developed prototypes. Feedback was incorporated on a real-time basis: we pivoted to improve the product. All elements of our digital propositions went through multiple iterations.
  • Clear metrics for innovation. We took usage as our key metric. We kept tracking usage per tool, per day, on a scoreboard for all of the team to live by.
  • Eclectic experiments. While we stayed close to our bet in Edutech, we made attempts in various branches of digital and tech sphere. We tried apps, online platforms, real-time questionnaires, partnerships with coopetitors, programs, and the 360 Mirror that allowed us to stretch our understanding of digital potential.
digital transformation
#Edutech is a large, fast-growing industry. @thnkschool placed its bets on a collaboration platform and workflow solutions and tools for creative processes. In other words, we bet on the right industry. Click To Tweet

What we did not have in place

We are led to believe that with a sharp lean startup methodology in place and a focus on a large industry, we will achieve product/market fit in just a matter of time. Still, to date, our efforts have failed to ignite. So, what has been missing?

Insufficient commitment and power
It is vital for founders and creative leaders to dedicate a serious amount of expert leadership time to digital transformation. If this is not available internally, it needs to hire for this. We might have had more success had we recruited top creatives in Edutech, as well as user experience designers.

Culture eats strategy
Our culture is relentlessly customer-centric and feedback of our participants is loud and clear: it is the experience of being together in the THNK Home that is truly unforgettable and transformational. In such a culture, going digital is felt like an affront. Our digital efforts will be successful if they are developed outside the physical mothership.

Partnering with direction
External partnership can provide leverage and regenerative properties. But they need to be with best-in-class parties and need to be nurtured to build the trust base required for success. We have to spend much more time and strategy on worthy relationships.

Improving with your customer
Introducing a new product needs natural traction. When you want your customers to adopt your new software product, you better spend a lot of time onboarding them and figuring out what about the product delights and what detracts. We underestimated the amount and attention needed for this. As a result, after initial trial many customers fell back to old habits, i.e., using what they were using before.

The requirements of detail
Digital products need to work fully for them to work at all. Every additional functionality adds to the complexity, therefore one needs to be very selective in keeping the product very simple initially. We invariably launched too complex products that catered to too many customer demands.

Learning metrics
Software tools are ideal for tracking: it’s possible to track trial, usage, loyalty, which provide a wealth of insights on in particularly what doesn’t work. As a result, it is possible to quickly redesign or repair those parts that are faulty. We found it much more difficult to find metrics that helped us on a path of continuous improvement, and which functionalities would truly delight.

digital transformation
It is vital for founders and creative leaders to dedicate a serious amount of expert leadership time to digital transformation. #creativeleadership #digitaltransformation #digital #technology Click To Tweet

Conclusions and going forward

We learnt some important lessons.  Digital transformation needs full commitment of senior, experienced, innovative leaders. Otherwise, forget it.  Especially in organizations that are deeply vested in their non-digital offerings, new digital strategies are best kept within arm’s length. Digital innovation is a deep skill. Either attract in-house talent or partner closely with the best in class.

Digital transformation needs entrepreneurship as success depends on opportunity orientation, risk-taking, agility, and speed. But success is only possible when the resources are in place and the culture is supportive – otherwise the grapes turn sour. How will you get the best out of people while meanwhile creating the best technology that has a natural fit with your business?

With these insights, we have good hope for more fortune in the future. In the end, entrepreneurship is moving through a lot of failure, learning from it and improving as a result.

Have you had experience in digital transformation within your business? We would love to hear your stories of success and failure.

To discover how you can effectively seize the opportunities of digital transformation and use it to its full potential, join the THNK Executive Leadership Program.