Do your digital strategy meetings remind you more of an experiment in Brownian Motion rather than a managed conversation aimed at structured decision making? You’re not alone. The levels of frustration and tension across teams are on the rise.

When I talk with teams about barriers to progress, they quickly highlight the lack of cohesion, often expressed as absence of “a joined up conversation”. Much of the time, discussions about digital transformation devolve into several different conversations taking place at the same time. It is perhaps the one complaint I hear more now than ever before.

I was in this position myself recently and for a long time was scratching my head trying to figure it out. In a room full of intelligent, passionate people wanting to advance adoption of digital approaches to better meet the clients’ needs, the discussions bounced around from one topic to the next. The more I focused, the less I seemed to be able to follow what was going on. People were talking at each other rather than interacting to share ideas.

With a great deal of difficulty, I tried to pick out the key threads unifying what seemed to be randomly colliding interactions and tried to put them into some order. Leaving the room my overriding thought was not about the progress made in the last few hours. Rather it was a puzzled brow and the question “what the heck was that all about?”. No surprise that people just treated the meeting as an aberration and went back to whatever they were doing before.

Sitting quietly with a hot cup of tea, I reflected on what I’d seen. It reminded me of similar situations some years back when working with teams investigating disruptive technologies. Faced with rapid innovation in technologies and business models, innovators looking to drive meaningful change across their organizations needed to overcome similar challenges. How did the address this?

One of the first steps was to recognize the variety of people involved in the conversations. Each of them comes to the table with different experiences, roles, and motivations. This is well described in writings such as Tom Kelley’s “10 Faces of Innovation”. There, Kelley outlines 10 distinct roles in the innovation process and characterizes their actions and behaviours based on them.

Much has already been written about these different roles and their impact. However, what is important is to recognize that:

• There is wide variety in motivation and experience across the people involved in discussions about innovation. Kelley identifies 3 key types of people from learning personas such as “anthropologists” and organizing personas such as “directors” to building personas such as “architects”.
• The challenge (and opportunity) is to create an integrated team that reflects a combination of these roles. By explicitly recognizing the importance of each persona, an appropriate blend of experiences can be identified, nurtured, and aligned.

From three faces to one voice

Considering this approach makes me wonder about the key roles of those involved in digital transformation strategy and delivery. Reflecting on my recent experiences, I believe there are 3 distinct personas that I can readily identify in many of the discussion. These I refer to as Engineers, Evangelists, and Entrepreneurs. As characterized below, it is important to consider the implications for any organization involved in digital transformation to recognize where these different views exist and to spend time considering how they can be coordinated to form a single voice of change. Without that, discussions on digital strategy will likely remain confused and ineffective.

The engineer

The engineers and technologists in the room want to fix the plumbing of digital infrastructure, upgrade out of date (and out of fashion) tools, experiment with the latest digital technologies, and build their expertise in more advanced areas such as data science, AI, and cloud architectures. They look at the impact they can make in digital transformation in terms of technology improvement and the providing new capabilities that demonstrate mastery of digital techniques.

The strategic priorities from their perspective often include expanding the rollout of newer versions of hardware and software with improved performance, capability, and integration across different functions. Of critical importance for many is cloud deployment. This includes the core infrastructure necessary for delivering the cloud capabilities required and migration of services to the cloud.

A key concern is inevitably the security, resilience, and robustness of this digital backbone. Risks are evaluated and decisions made that ensure the quality of all delivered solutions. Consequently, engineers spend a lot of time debating how to speed up technology adoption while managing the risks involved.

Those with an engineering focus measure their success by looking at traditional technology factors such as availability and uptime, storage capacity, speed of moving bits and bytes, increasing adoption of technology, the use of digital channels, etc. They also benchmark their own capabilities and approach with digital technology. This allows them to ensure they are sufficiently advanced to meet the expectations of stakeholders, attract new staff, and build their own careers.

The evangelists and futurist want to look ahead to present a vision of a digital world that provokes, excites, and inspires the people around them. They spend a lot of time reading the latest books, attending conferences, and discussing the impact of emerging digital capabilities with their peers. As a result, they want to bring some of that vision to colleagues to encourage them to drive change and overcome obstacles in the way. Typically, they express an urgency to accelerate change to ensure the organization remains relevant, effective, and at the forefront.

Accelerating change on this path is a priority for evangelists. They highlight the importance of creating momentum in various forms including through education, external engagement, branding, communities of practice, and much more. A key to success for evangelists is to create a “new digital culture” in the organization, with all the issues and implications of this.

Progress for evangelists is measured in terms of engagement and coordination across the organization. By bringing forward a vision that inspires, they hope to increase the pace of change in all aspects. Participation levels are key. Individuals and teams are encouraged (or mandated) to take part in education activities, discussions, and self-formed communities to share a common view of the future and the steps required to get there.

The entrepreneurs and negotiators are those in an organization who bring all the pieces together, manage activities in flight, and coordinate the diverse communities that must work together to ensure progress is made. Their skills and interests lie in working with different groups to build bridges and align diverse priorities.

The entrepreneur’s success is based on results. While they get a lot of enjoyment from forming teams and negotiating with different parties, they recognize that the most import measure of success is to get things done. Hence, they find ways to overcome barriers. This may be by employing internal mechanisms such as updating hiring practices, coordinating budgets, and aligning strategy priorities. It may also involve more imaginative approaches to engage external parties, encourage small-scale experiments, and adopt new behaviours.

As a result, entrepreneurs manage risks and measure success based on the outcomes achieved. They are willing to make rapid judgements about how to balance priorities and move resources as appropriate to changing circumstances with the objective of speeding up time to results, or maximizing impact for stakeholders. They often push the boundaries within organizations. While some may see them as “rule breakers”, they would see their role as challenging orthodoxy to open up opportunities.

All for one and one for all

To deliver digital transformation requires a coordinated approach across many parts of an organization. This is proving to be difficult and is creating a great deal of tension, push-back, and disappointment. One reason for this is that different people have a wide variety of experiences and expectations from digital ways of working. In my discussions I often see 3 key groups with distinct behaviours and attitudes. I call these the Engineers, Evangelists, and Entrepreneurs. By identifying them it can help you to recognize their motivations and focus digital strategy discussions on overcoming the barriers to success.

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