Learning While Leading: The Digital Leadership Challenge

The digital revolution requires leaders to think differently about strategy, investment, culture — and themselves.

digital tools, models and platforms have SEEMINGLY OVERNIGHT, emerged from their traditional back-office function to become an unstoppable strategic force, revolutionizing every industry. The global pandemic has only accelerated this transformation, with new virtual models embraced widely in healthcare, education and other industries within weeks, rather than the years it would normally have taken for widespread adoption.

As a result, today’s executives are faced with many more technology-driven conversations, ranging from new value propositions to start-up investments to disruptive competitors. Digital no longer sits comfortably within the execution purview of IT and marketing teams. But for leaders with little background in technology, this new fact of organizational life often comes with a little-discussed side effect: It can threaten their sense of identity. And when that happens, innovation can get stopped in its tracks.

In this article we will look at why this happens and provide some guidance for navigating the challenges that arise when a leader’s identity is threatened by our increasingly digital universe.

Resistance Is Futile

“None of this will work. It’s not how we do things around here.”

This sort of response is common from leaders encountering change. The declaration above, however, was not any ordinary resistance to change. It came from a senior executive at a large global manufacturer (which we will call Bigco) renowned for its innovation. The executive in question served as the sponsor of the development program for the company’s highest performing leaders, and his reaction was in response to a set of recommendations around digital transformation topics (which he himself had selected).

The company believed that these digital transformation initiatives were critical to its future success. What’s more, the express purpose of engaging this group of leaders on these initiatives was to generate new ways of thinking. And yet, just as soon as the recommendations were presented, they were met with the receptivity of a brick wall.

Change amidst a digital revolution can be so profound that previous experience simply doesn’t translate. This level of change demands a foundational shift in what it means to be a

leader today: It is no longer the leader’s job to have all the answers; instead, it is the leader’s job to ask the right questions and be open to new possibilities. But as our example illustrates, leaders who feel threatened can crush new opportunities as soon as the possibilities are conceived.

For years, leaders have been warned about the disruptive threat that digital presents to their business. They’ve been implored with the tedious (and quite unhelpful) siren call to ‘be the disruptor or be disrupted’. Yet a large majority of companies continue to struggle with their digital strategies and investments.

In order to succeed in the digital revolution, companies need to have difficult conversations more regularly, addressing questions like:

• What opportunities and threats does digital pose to our organization?

• How should we evolve our strategy and business model?

• Are we investing correctly?

• Does our team understand how to think differently?

• What do our customers really want and expect right now?

By their very nature, the conversations sparked by these questions challenge existing beliefs, practices, structures and plans. They challenge people to think differently and require them to question assumptions and adjust their ways of working — many of which have been honed over decades of success. But make no mistake: For organizations and individuals to remain competitive, these conversations are essential.

For leaders without a strong technology background (like the Bigco executive quoted earlier), being in the thick of these conversations can feel disorienting and threatening. Anxiety results not only from the sheer magnitude of change that digital represents, but also from the uncertainty of their role in that future. Overwhelmed by these threats, leaders can undermine — often, subconsciously — their company’s digital transformation efforts. The result? A failure to evolve.

Does any of this sound familiar? Have you found yourself uttering (or thinking) some version of, ‘That will never work here’? Maybe you’ve been on the receiving end of such skepticism — or, like us, you’ve witnessed the conversation unfold. To successfully engage in these difficult conversations, leaders need to recalibrate their own thinking and approach. And doing so requires first having a difficult conversation with themselves.

Recognizing the Digital Identity Threat

“I’ve been in this industry for 25 years. I know it inside and out — better than anyone else.”

For leaders who are not digital natives, these conversations can be unnerving and triggering. Our identity is the story we tell ourselves about ourselves. Seasoned executives often identify as smart, capable, successful, confident, and expert. Lacking mastery in digital when digital has emerged as a primary strategic requirement calls these well-worn senses of self into question. Often, an internal downward spiral unfolds:

• ‘I can see how important digital is, but I don’t understand all these new terms and concepts’.

• ‘I know how to run this business, but my lack of familiarity with new technologies leaves me feeling off balance and incompetent’.

• ‘If digital is so critical and I don’t understand it, is my role at risk? Am I no longer fit to lead? Am I being rendered irrelevant?’

Conversely, many technology leaders may feel that the expansion of digital’s application across their enterprise poses a different set of threats:

• ‘I am the expert on this. Digital is my domain. Why are you taking it away from me?’

• ‘The senior team is engaging other executives on digital developments and strategy. Those executives don’t know digital at all and will mess it up’;

• ‘If digital is so critical and I am not in charge, does it mean my role is at risk? Am I no longer fit to lead? Am I being rendered irrelevant?’

Either way, many of today’s leaders find themselves disoriented and off balance, causing them to react in ways that undercut the possibility of real transformation. The result? They may:

• ‘I’ll show everyone else they are wrong!’ ANCHOR IN CERTAINTY:

• ‘ I’ll bluff my way through this’.

MASK INSECURITY:

• ‘My experience is unparalleled FIND COMFORT IN ARROGANCE: and translates directly to this new environment’. or

• ‘This ‘digital revolution’ isn’t really any different LIVE IN DENIAL:

from other change we’ve faced. Our organization has always faced big changes, I don’t buy that this is any different’.

Each reaction serves as a blindfold for the executive, because embedded in each is a dismissiveness and desire for the change to disappear. This is wishful thinking, at best: Not only is digital not going away, its pace is accelerating. So, how can leaders navigate this aspect of ambiguity and uncertainty?

Following is our advice for getting out of your own way and moving towards a new way of engaging.

RECOMMENDATION 1: Name What Is at Stake

“When this doesn’t work, I want everyone to remember that I said it would flop — so the failure can’t be pinned on me.”

During a fireside chat, we listened to an executive at a global technology company relay a story about a recent idea from his team. He thought the idea was terrible. This company, however, was in the midst of a strategic transformation required to compete in a dynamic, mobile, cloud-based world.

To successfully make this transformation, senior leadership knew it needed to nurture a learning mindset across the enterprise. To promote such a mindset, this executive gave his team the green light to run with the idea — with one important caveat: He wanted everyone to know that the idea was not his — ensuring that any resulting failure wouldn’t stick to him.

This executive, like many out there, was used to having all the right answers and being the smartest person in the room. His response to his team allowed him to preserve the narrative that he was always right; but it also sent a message that he was only paying lip service to the value of a learning mindset. In fact, he was undermining the very effort he was supposed to be advancing.

Our beliefs around our identity drive our behaviour subconsciously, and for this reason, grappling with threats to our identity is difficult. Speaking about ‘identity challenges’ is also uncomfortable. But being able to surface and clearly acknowledge which identity beliefs are at risk in a given scenario is the first step to negotiating yourself to a place where identity threats no longer undercut your effectiveness. To get started, leaders can ask themselves the following questions:

• What is the story I tell myself about who I am?

• What parts of my identity feel at risk right now?

• What would it mean if a part of my ‘identity story’ were no longer true?

Writing out your responses to these questions allows you to sit with and engage with them more objectively. Because identity beliefs are not always easy to identify, you may need to ask yourself these questions more than once. Consider sharing your responses with a trusted colleague, mentor or coach, and ask them specifically to challenge you. Doing so can reveal new insights or crystallize your responses with greater depth and honesty.

As you reflect on your answers, step outside of yourself and put someone else in your shoes. Imagine these were their answers. What observations, questions, coaching or encouragement would you offer them?

RECOMMENDATION 2: Evolve Your Identity

One of the challenges of our identity beliefs is that they can become all-or-nothing proclamations about ourselves. ‘I am either competent OR incompetent; I have all the answers OR I know nothing at all’. Such all-or-nothing thinking leaves a leader’s sense of self in a precarious, fragile position.

An evolved identity incorporates growth and recognizes that we operate in a constellation — one in which parts of our story can develop and evolve as we move though a life and career that is itself complex, varied and unpredictable. Embracing the concept of an evolved identity makes an individual more robust and resilient, creating a foundation that enables learning and the opportunity to succeed in the new world. Because the world will continue to change, no matter how much we resist.

To put this more complex form of identity into practice, leaders can adopt the ‘AND stance’: ‘I am an expert in finance AND a novice in digital; I am inquisitive AND entirely overwhelmed by the Internet of Things; I am a capable, confident leader AND I have far less control than ever before’. And for our Techco executive: ‘My instincts are phenomenal AND my team has new insights to offer; I have a track record of executing flawlessly AND leading is about much more than perfect performance’.

In short, leaders need to think about the story of who they are, notice the aspects of their identity that are at risk in the current environment, and identify the AND statements that will help them regain their footing to lead their own digital journey.

RECOMMENDATION 3: Acknowledge and Solve for Interests

It is not only a leader’s identity that is stake due to the digital shift. Often, real, tangible costs are incurred as an organization makes this shift, including:

• Loss of resources, status or power;

• Loss of energy and time as the leader works to understand a new domain; and

• Costs of renegotiating expectations, dismantling familiar structures, and realigning incentives to support a new way forward.

Facing these threats, it is a natural, human response to try to exert more control or become more positional — to be all the more committed to what you know and resistant to the digital change. To wrestle with your reticence and negotiate yourself towards the possibility of change, consider taking these two steps:

1) ASK YOURSELF: WHAT INTERESTS UNDERPIN MY POSITION?

A position is what you say you want — for things to stay the same or to not have to engage with technology you don’t understand. Behind each position are interests — needs, goals, hopes, pressures and concerns that are the reasons why you hold that particular position. Whether your interests involve substantive, relational or process concerns, understanding the interests driving your position expands the number of ways those interests could be met. Doing so opens the possibility of change without losing what may be of greatest importance to you.

2) GENERATE AND EXPLORE DIFFERENT OPTIONS

Having identified the interests most important to you, what are some other ways to meet those interests? If the interest is in ‘maintaining status amongst peers’, what could you do to preserve that? If the interest is ‘streamlining your energy as you upskill in digital’, who could you enlist to help you? With each option, what opportunities or upsides become possible? How could each of these different options meet your key interests?

Change introduces uncertainty into our worlds, and clinging to what we know is an entirely human response. Feeling paralyzed by the sheer scope of implications is normal. Breaking down our strongly-held positions to understand the underlying interests allows us to solve for them in different ways. Exploring the range of options to meet the varied interests you have identified offers a concrete path towards addressing what matters most while continuing to evolve.

RECOMMENDATION 4: Embrace a Learner’s Stance

Adopting a growth identity in the digital revolution is something everyone needs to do — digital natives and non-natives alike. This involves embracing three truths:

1. Strategy is no longer about placing big bets. It is about emergence.

2. Lack of digital mastery is not a personal failure. It is a normal result of digital’s speed.

3. Everyone needs to learn more. Strategy itself is about continuous learning.

As a result, your responsibility as a leader is no longer to have all the answers, but to make three key shifts:

I know it all.

FROM:

Learning is a sign of strength rather than weakness. TO:

I need to have all the answers.

FROM:

My experience over the years will help me distill the right TO: questions.

Change and uncertainty make my job difficult. FROM:

Managing uncertainty and complexity is my job. TO:

These three shifts enable you to learn while leading. The key questions then become:

• What do I need to learn about strategy in the digital revolution? Who from?

• How can I apply my existing experience to this new world without anchoring myself and my conversations in old beliefs?

• How can I extend my personal conversations to create a culture of diverse insights and learning across my organization?

In closing

Digital isn’t just an evolution, it’s a revolution. New enabling technologies often scale suddenly, new ecosystems form, incumbents stumble and new business models appear overnight. Organizations have always experienced change, but this is different: This change is relentless, and it can be overwhelming.

As leaders progress through their own digital journeys, self-awareness around their identity will enable them to better support the evolution of their organizations. They will also be better equipped to skillfully handle the subsequent — and inevitably difficult — conversations with leadership teams, boards, employees and ecosystem partners that are necessary for achieving digital transformation.

It may not seem immediately obvious that the first place to initiate and embrace change is within yourself. But we hope we have convinced you that, in the midst of profound uncertainty, it is within yourself that you have the most influence and control.