Overcoming the Top 3 Challenges in Digital Transformation

    In our current markets, successful digital transformation is often what separates the winners from the rest. Read on to discover the top three challenges in digital transformation, and some practical strategies for eliminating these barriers.

    On Digital Experiences and Creating Your Own Luck

    "Luck is a dividend of sweat. The more you sweat, the luckier you get."
    Ray Kroc

    There are a lot of great quotes about luck, but this is one of my favorites, and its highly applicable to my latest purchase: A Peloton stationary bike.

    When you think about Peloton, you may consider all the advertising they’ve been doing in recent years, especially if you happen to watch cycling on TV. Or, you may think of them from an investment standpoint; they’re a clear success story of our pandemic times: After hitting a low in March, the stock price had more than tripled by the beginning of July, and the company reached a market cap of nearly $20 billion. Not bad for a firm that got its start through crowdfunding just seven years ago.

    For me, I also think of Peloton as my new exercise apparatus/torture device, as I’ve recently joined the ranks of the approximately one million subscribers that the interactive cycling service now boasts.

    As opposed to the basic digital readouts that characterized the treadmills and stationary bicycles of the past, Peloton delivered a compelling digital experience. Peloton introduced interactivity, competition, and camaraderie, transforming what was a mind numbingly dull way to get exercise. In this time of shelter in place and social distancing, Peloton was clearly the beneficiary of the shift away from public gyms. However, it is also clear that the company’s hard work on developing a compelling digital experience positioned them to capitalize in this new environment.

    In recent months, amidst all the unprecedented change we’ve seen, I’d argue that the enterprises that sweat the most in pursuing their digital transformations are now the most fortunate. However, many teams are encountering a significant number of challenges in digital transformation. While the scale and urgency of digital transformation demands are unprecedented, too many teams are still contending with the same old obstacles. The following section examines the top three challenges in digital transformation, and offers some ideas for overcoming them.

    Top 3 Challenges in Digital Transformation

    #1. Lack of Transparency

    The Problem

    Across an organization, core strategic concepts around direction, purpose, and values aren’t clearly understood. Too often, asking 10 people on a team about core strategies will yield 10 different answers.

    This disconnect becomes a chasm when you look at the strategies of technology teams and business teams. For example, in many organizations there’s a complete gulf between technology outputs and business outcomes. Without correlation to business KPIs, development and operations teams may be investing in the wrong thing.

    What to do About It

    It’s vital to establish maximum transparency around a couple key aspects:

    • Endgame. What will the ultimate destination of transformation look like? How will teammates describe that new reality when it emerges? This is different than some lofty, vague mission statement. Instead it should be a tangible, compelling, and understandable articulation of where the company needs to get to.
    • Accountability. This is another key aspect of transparency. Along the way, how will team members know they’re making progress. How will they know their team progress is ultimately translating to business results? For CIOs, this will take close collaboration with business stakeholders in order to define strategies, objectives, and KPIs. Start with top-level business objectives and where digital services can make the biggest contribution.

    #2. Lack of Trust

    The Problem

    Over the years, team building exercises have often included an activity in which different team members stand and intentionally fall backward, trusting their teammates to catch them. This trust exercise has been used a lot, and it represents an apt model for the trust that digital transformation requires.

    Make no mistake, the changes associated with digital transformation can be fundamental and scary. Ultimately, staff members need to put their own team goals and approaches to the side. They may need to take on new roles and learn new approaches or technologies. Not only does this mean leaving behind some of the expertise and skills they’ve amassed, but also giving up the familiarity and comfort associated with their prior way of working. Ultimately, this change and disruption takes a leap of faith on the part of staff. Without trust, they will not fully commit to this leap.

    What to do About It

    Across organizations, transformation efforts are stifled by a lack of trust. Built around legacy silos, teams lack effective coordination and collaboration across distinct teams. This is a problem between various organizations, particularly between business and IT teams. One symptom of this lack of trust is the fact that 25% of spending happens outside of IT.1 To build the trust required, leaders from the business and IT need to establish enhanced communications, shared reporting, and consistent KPIs. (See an earlier blog post for more information on the CIO/business leader communications gap.)

    #3. Lack of Traction

    The Problem

    Maybe because of the failings above, or maybe due to a host of other reasons, near-term results may not be realized. This lack of traction can be disastrous, and lead to a vicious cycle. Presented with a lack of traction, those team members who were committed may waver. Those who were originally unconvinced or disengaged will view subpar results as justification for their lack of commitment. These repercussions can also hold true for executives, whose continued support, engagement, and investment is so critical.

    What to do About It

    It is important for teams leading transformation to establish a culture and focus on getting results. In this effort, teams are well served by adopting an agile mindset, breaking projects into smaller components of work, speeding delivery, and doing more frequent iteration.

    This also often requires leaders to figure out a way to make fast changes in culture. To start achieving the results needed, it is important to recognize that culture change, which is often the biggest impediment to transformation, also needs to happen fast. In a report, Gartner analysts describe pragmatic approaches for instituting the change required, referring to these tactics as “culture hacking.”2 Culture hacking is about taking fast actions to make change real and immediate. This can include a range of tactics:

    • Using a weekly meeting to collect new ideas and committing to testing one idea within a week.
    • Changing terminology, for example instead of using the term “fail,” using “experiment and learn.”
    • Selecting the team note taker at the end of the meeting.

    How BizOps Can Help

    In many ways, BizOps offers a way to build on the speed and agility benefits of DevOps, and to establish the systems and workflows needed to align technology investments and activities with business outcomes. At its core, BizOps is a framework for optimizing your software development and delivery practices so they meet or exceed business objectives. Through BizOps, your teams can realize significant advantages in eradicating the challenges in digital transformation:

    • Transparency. Traditional IT outputs are inward facing, for example, focusing on uptime, database availability, and software defect rates. Through BizOps, teams can correlate IT outputs with business outcomes, such as conversion rates, sales per hour, user retention rates, and so on. By gaining more clarity about how their efforts map to high-level business outcomes, individuals from across the organization can gain a much stronger sense of purpose. This enhanced sense of purpose boosts employee engagement, meaning staff will be more likely to make better decisions and achieve better results.
    • Trust. By adopting BizOps approaches, your organization can begin to establish unified capabilities for planning, tracking, and reporting that span releases and teams. Consequently, you can make progress in eliminating the silos that exist between different teams and organizations, which is essential in establishing trust across the organization. Further, by enabling more seamless collaboration across the software delivery cycle, teams can release new code into production with much more confidence, and more effectively mitigate any risk of potential negative impact on customers.
    • Traction. IDC analysts describe how BizOps teams’ activities can be summed up as “learn quickly, experiment, fail fast.”3 This agile mindset is core in gaining the near-term traction that is critical to long-term success. By taking an agile, fail-fast approach, BizOps teams can deliver quickly, learn quickly, iterate quickly, and therefore deliver results quickly. Further, the reality is that BizOps can boost operational intelligence and execution that foster near-term traction. For example, through BizOps, product management teams can do much more intelligent near-term planning and execution by leveraging holistic insights on customer experiences. Within IT operations, teams can more intelligently prioritize their remediation efforts based on a clear sense of business impact, which can yield immediate benefits in customer experience and business outcomes. 


    Digital transformation can’t wait, nor can the move to leverage BizOps. By successfully employing BizOps strategies and principles, your organization can overcome a lot of the challenges in digital transformation, and establish the transparency, trust, and traction that fuel success.

    1. Donna Scott, Gartner, “3 Practices to Create Business Demand for Enhanced IT Value Beyond ‘Run the Business’”

    2. “The Three Magical Ingredients of Transformation,” Analysts: Mary Mesaglio, Darren Topham, May 22, 2019, ID: G00388448

    3. Marc Strohlein, Joseph C. Pucciarelli, Mike Rosen, IDC, “BizOps: The CIO's Guide to Multiplied Business Transformation”

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