Many businesses see digital transformation as a kind of technology ‘pot-luck’. However, a splash of machine learning and a dash of analytics will not ignite a digital transformation. Nor does digital transformation proceed even if the company has the right strategy. The organizations that will flourish in the digital era will combine the ingredients of a strategic mindset with a leadership skillset.

In our first blog we shared our perspective on how to build the right strategic mindset. The notion is that it’s not about technology or about a disruptive business model, but it requires thinking differently about your customers, value, strategy, data, leadership, innovation and culture.

In this blog we will share with you what you can do to develop the thinking skills of your most adaptive asset, leadership.

Leadership development has had an abysmal track record in helping businesses to transform. Never has so much been opined about change but so little delivered in getting leaders to execute on it. Part of the problem is that leadership development is focused on training leaders in behavioral recipes for change rather than developing their thinking. Training is transactional whereas development can be transformational. 

So how do you rapidly infuse leadership development to get leaders to think and act in ways they are unaccustomed to and make this tangible in your organization?

1.    Learn from other leaders

As we mentioned in our first blog, for the most part our thinking runs on factory settings. Furthermore, each of us has our own view of reality. There is much to be gained from the recognition that no one has a monopoly on reality. The most beneficial stance is to see alternative beliefs as learning opportunities to be respected, applauded and understood. We learn nothing from someone who sees the problem the same way we do. Taking leaders into the market to discover with leaders from other industries can rapidly shift thinking in your organization’s strategy. Spend time mapping out existing beliefs and business narratives and identify what needs to change.  Invigorate and inspire your leadership talent with discovery-based, market-immersion, learning to think differently about strategic challenges.

2.    Embrace fallibility in thinking

The increase in customer connectivity and platform technology promises benefits that will change the way in which many business models operate. Cultivate the mindset in your leaders that better business models exist that are not yet realized. Do this by leveraging insights, data, compelling stories and encouraging relentless questioning. Our mind has boundless capacity to reject disconfirming evidence and rationalize our decisions. We expend energy explaining our model to others or defending it from criticism.  Evidence that confirms our thinking is comfort food for the mind. Creating a mindset where leaders embrace the notion that the current model will be eclipsed and that the goal is to disprove the incumbent business model embraces a culture where refutation represents not failure but progress.

3.    Think about thinking

Get leaders to reverse-engineer their thinking from the outcomes, to the behavior that produced the outcome, to the thinking behind their behavior. In doing so leaders realize that they do not spend much time thinking about their thinking. Second, that thinking about their thinking is a form of self-reflection. Third, that reflecting on how they think is the most potent way to change how they think. Moments of insightful incredulity – What were we thinking? – come only from thinking about thinking. Many organizations are investing in ‘innovation lab’ type environments, since the incubation to realization approach is known to yield high results. Creating platforms for this type of thinking and building it into the ecosystem of you organization enables leaders to see where they may have missed significant signals in the data or overlooked crucial causal relationships.

4.    Develop new mental models

Digitalization will drive new product offerings and value chains that we have not yet conceived of. Discovering a pattern between disparate data points allows leaders to make leaps in their thinking that can open the door to new possibilities and ways to reimagine competitive advantage. Getting leaders to actively seek out the data that doesn’t fit neatly into existing models makes them less defensive when confronted with disconfirming evidence and they will have more of an appetite to seek novel solutions. One of the most effective ways we’ve seen this strategy realized is to bring diversity to the leadership table. For the first time in history we have five generations in the workplace and a unique opportunity to leverage each generation’s insights to build new mental models.

5.    Build in feedback loops

Design feedback loops that extract value from the learning.  Measuring leaders’ behavior has been standard fare in development initiatives. But to resonate, the information must be relayed to the individual, not in the data form in which it was captured, but in a context that makes it meaningful and digestible. The information must help the leader make a choice, and act. One of the most effective ways to do this is to offer executive coaching to your highest potential leaders. Fast track them using feedback loops that measure their outcomes against key business metric. This enables the leader to recalibrate their new behavior and embodies the digital culture of fail, learn and adapt in rapid cycles.

More than 50% of companies in the Fortune 500 list of 2000 did not make it to the 2015 list. This is a reminder of what happens to businesses that do not adapt fast enough. One of the most agile ways to make change happen rapidly is to change the mindset of your leaders. Digital transformation begins with changing how a leader thinks about it.

Both Marisa Paterson and Audrey McGuckin consult with top CEOs and HR Executives to solve their toughest and most complex talent and leadership challenges in a digital era.

To connect with Marisa on how she can assist you as an Executive Coach or Leadership Specialist, message her directly at

To connect with Audrey on how she can assist you as an Executive Coach or Talent Specialist, visit our contact page or message her directly at