Where Are You in the Digital Transformation Journey?

Where Are You in the Digital
Transformation Journey?

Navigating the digital transformation journey and what that means for your organization, your initiatives, and your teams is hard stuff, right? Change is unfolding at a rapid, non-linear pace through a barrage of noise, tech, and shifting priorities. Even for seasoned tech veterans, it can be incredibly difficult to know where you are and what to do next. In this article, we’re going to wrestle with this complexity at a real level to share what it means for your transformation so that (hopefully) your work can be a little less complicated.

But first, we have a question: What are you talking about when you talk about digital transformation? We’ve asked this question before, but it’s important to stop and consider our beliefs about digital transformation as we get going on the journey—because our beliefs have powerful implications.

Let’s get nitpicky about what we’re saying.

When you see the words “digital transformation,” what do you imagine? brands like Amazon, Uber, or Airbnb come to mind?

How do you feel about applying the idea of digital transformation to your work? Fear, hesitation, relief, excitement—any and/or all of those?

Do you envision one day being able to look around and say to your colleagues, “We’ve made it. We’re digitally transformed”?

Here’s why this matters: There’s a dangerous misconception about the digital transformation journey. It’s the idea that, one day, it will be over. We will be done transforming and we can go back to “normal.” This misconception is subtle, but it inhibits our ability to think in new ways—to continuously recognize new opportunities, devise new solutions, or adapt to new roadblocks. We forget that the mindsets, behaviors, and habits that brought us forward into the new way of working are the keys to digital transformation—not just temporary measures to achieve change.

When someone believes that there is a destination or an endpoint when it comes to going digital, they will invest resources in achieving whatever feels the most like that endpoint. But transformation doesn’t happen in a series of well-planned moves. As much as we love journey maps and well-crafted “from-to” statements, the reality is that the state of transformation truly emerges from the journey itself.

This isn’t to say that choosing milestones to aim for isn’t a good idea. It’s just that milestones aren’t enough. You also have to consider the people factors at play—all the stuff that makes change messy, complex, and truly transformational.

Digital transformation requires organizations to empower people to make the necessary shifts in mindset, behaviors, skills, and habits in order to truly think and act like a digital organization. Transformation happens in pockets across an organization at different rates. People need to see meaningful examples and stories of digitally mature teams in order to believe that the journey is possible. If your people believe “we aren’t digital enough yet” to think about digital opportunities or challenges, then your organization could be holding itself back from achieving its full potential.

We hate seeing great potential go to waste.

That’s why we’re sharing a simple framework for how to approach your digital transformation journey. It won’t answer all of your questions, but it will help you gain clarity around where you are in the journey and how to take steps forward. We’ve found it’s a particularly helpful tool to use as a conversation starter with teams to see where others’ perspectives differ or align.

The basic premise: 3 meaningful moments

When assessing with our clients where they are, we keep in mind three moments that really matter for people as they experience the digital transformation journey: awakening, emergence, and breakthrough. These moments exist as part of a cycle, often feeding into one another.
Diagram of digital awareness, emergence, and breakthrough
Digital Awakening: No digital transformation journey is the same, but every journey has a beginning. The good news about being in the middle of a digital awakening is that people are opening up to possibility. Urgency and momentum flow. This urgency might come from a recent shift in the industry or something that has emerged more slowly over time. However, getting anything off the ground means pairing that urgency with an aligned and coherent sense of direction.

Digital awakening occurs when someone is wrestling with:

  • Articulating what going digital means to their team.
  • Assigning resources and ownership for what matters.
  • Picking the approach to pursue in response to a new digital threat or opportunity.
“Urgency without specificity is a recipe for disaster when it comes to digital transformation.”

Some companies have chosen to boldly announce they are “going digital” without a clear plan, and they have since stumbled from that proclamation. Urgency without specificity is a recipe for disaster when it comes to digital transformation. That’s what makes moments of digital awakening so important. At the same time, don’t confuse specificity with certainty. Being specific about the next step forward is important; being certain that it is or must be the right one will paralyze you.

Digital Emergence: Digital transformation sounds high level, but real change takes real work. Even after investing in digital with a budget and a dedicated team, focusing direction, and doing all the “right” things—despite all the gradual wins that have come along the way—after a while it may feel like your efforts stall. Maybe your digital pilots haven’t made the impact you had hoped, or your people are going back to business as usual.

You’re not alone. These are the symptoms of emergence; something has taken shape, but it’s struggling to break through.
Digital emergence is a messy, creative, ambiguous process. As you focus energy to solidify an approach to the solution, remember to also rally people and resources around the plan to make it shared, strong, and sustainable. Sometimes growth looks less like a vision and more like triage. It requires a team to ask: What are we willing to let go of in order to discover the breakthrough we’re seeking?

Digital Breakthrough: You’ve had a win—celebrate a job well done and rest easy! The work is over, you’re transformed…wait. We talked about this; digital transformation doesn’t really have an endpoint. We know it isn’t as simple as pointing to a map that shows a linear journey from point A to point B. Digital breakthroughs may look simple in hindsight, but a lot of trial and error led to that win. When organizations do make a point of celebrating wins, too often they focus purely on celebration. Yet, sharing the full messy journey with other teams is the very thing that feeds future momentum for digital awakenings across the organization.

Digital breakthrough implies that your team is more comfortable with going digital. Now is the time to encourage curiosity AND celebration. Ask yourselves:

  • Where have certain stakeholders been resistant to our ideas? Will this breakthrough impact those conversations?
  • Where has our team felt blocked on previous projects? What have we learned from this breakthrough that could help them envision a new possibility?
  • We’ve had a win with something specific—why not amplify what worked across the organization to encourage more digital breakthroughs?

Where this premise comes to life: 3 levels of digital transformation

During the digital transformation journey, we all experience these meaningful moments again and again—awakening to roadblocks or opportunities, emerging with prototypes and solutions, breaking through with wins and lessons learned. And these moments of digital transformation are happening at different rates within different functions of an organization.

It can be overwhelming to figure out how to foster and amplify all the meaningful moments if you don’t know where to start. To clarify the complex, we recommend viewing your digital transformation journey across three levels of your organization: your initiatives, your leadership, and your organization’s vision. Each level brings a different lens to the people opportunities and risks at play. We’re also including a “gut check” you can do by way of conversation starters with your team; these checks can help you assess where you are in the journey.
Diagram of initiative readiness, leadership adaptability, and organizational maturity

Initiatives: the readiness check

Each organizational transformation (digital or not) is often characterized by a portfolio of initiatives. Your vantage point might be across all of these initiatives, or you might be spearheading one initiative among many. Either way, transformations are measured by the total success of the initiatives that make them up.

When initiatives succeed, they make way for leadership to support the next phase of the change. Initiatives that stagnate can become distractions and political landmines. Having the discipline to choose when to resource initiatives (and when not to) is essential to building and maintaining the momentum for your transformation.

The readiness check: There are certain goals or objectives that an initiative must achieve to be ready for the journey ahead. Initiatives and their teams are either enabled or held back from achieving their objectives. Some barriers to initiative readiness are within the control of the team, and some require input from those with a different vantage point or who have additional influence. As you assess the readiness of your initiatives, compare how the most important initiatives measure up against the overall group. Are resources misaligned to the organization’s broader goals? Where might you make the smallest change for the biggest win?

Leadership: the adaptability check

Readiness among teams and initiatives doesn’t happen overnight. Neither does the growth of our leaders supporting them. Along these efforts, teams must assess the leadership skills needed to support and enable their digital transformation.
As disorienting as the complexity of digital transformation might be, many organizations are also questioning how much of their existing leadership toolkit still applies. Leaders provide the coaching, support, and direction that are necessary for teams to move forward into uncertain space as they strive to deliver on initiatives that are ever evolving.

The adaptability check: Not all of the skills required of leaders in a digital transformation are technical. In fact, more than ever, leaders in digital environments are focusing on how to help teams navigate complexity and bridge initiatives to strategy, rather than just having deep knowledge of the tech. As a leader, how prepared do you feel to adapt to shifting business priorities as well as managing the people side of change as it’s happening?

(Want to brush up on ideas for how to lead teams in a digital world? Check out our article on adaptive leadership.)

Organizational vision: the maturity check

Interestingly, often before organizations take stock of the readiness of their initiatives or the adaptability of their leadership, they first start here: an overall assessment of their ability to take on a digital transformation.

When helping clients assess where they are, we use the idea of maturity as a way of articulating an organization’s journey through transformation. While some businesses are more mature than others, digital transformation is an ongoing process. Articulating an understanding of where the organization is helps to align teams and build a shared language on where they are and where they are going.

The maturity check: A variety of factors impact an organization’s level of digital maturity, including:

  • Decision agility
  • Leadership structure
  • Culture
  • Digital integration
  • Leadership development
  • Digital skills and talent
  • Strategic priorities
  • Innovation practices

Where does your organization measure up for each factor? Where do you see strengths and where are there roadblocks?

(Just getting started in this space? Check out this list of resources for learning everything you want to know about digital transformation.)

The digital transformation journey centers on people.

Digital transformation is complicated and complex. That’s not to say there aren’t plenty of wins to celebrate, but we all know transformation is hard. It takes grit, patience, humility, and some good old-fashioned luck. Yet, don’t let that stop you. Eric Ries, author of The Lean Startup, talks about decisions to “pivot or persevere” as critical moments in a transformation journey. We hope these insights help you uncover the best next decision that will serve your digital ambitions.

No matter where you are in the digital transformation journey, what’s important is to keep in mind all the people factors that impact our collective ability to go digital. If you keep people at the center of your plans, you’ll unlock the collaboration, creativity, and empowerment your organization needs to sprint forward into its digitally transforming future.

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