3 Expert Questions to Focus on Winning Digital Transformations

About a year ago, around this time a year, I spoke to a CIO about how to best kickoff digital transformation initiatives. His question, "How do I start? How do I find opportunities that will make a business impact and have the potential to drive transformation?"

I don't recall the specifics of the call and his circumstances but can answer these questions. 

My answers do not depend on whether you are new to the role of CIO or transformation leader. It also doesn't matter whether you are just starting a transformation journey, or, if you're at an inflection point and evaluating the initiative portfolio on where to focus, and what priorities to invest in.

As I said in the opening to Chapter 1 of Driving Digital

Look at your company as if it were your first day on the job. What would your first impressions be of how your business is operating?

I look for transformation initiatives by asking three questions:

1. Where are the burning fires

Before you address the exciting opportunities that drive growth and innovation, a more critical aspect of transformation is to consider fixing, improving, and broadly addressing some of the burning fires that impact crucial elements of the business.

As I work with many organizations as part of StarCIO's transformation programs, it's not that hard to identify their list of significant issues. I ask people and confirm with others. I seek out data and analyze it independently from how the organization defines and reviews their KPIs and metrics. If StarCIO is doing an assessment, we'll dive into customer experiences, evaluate tools, and speak to customers. 

Those activities often provide a reasonably comprehensive list of the issues. But how do you evaluate their impacts and priorities? How do you know when problems are burning fires?

I go back to my dialogs with employees. Digital transformation programs are stressful journeys that you can't begin optimally if there is already built-up frustration, angst, anger, or bewilderment. Burning fires are issues that consume many people's time, energy, and coordination. Addressing the primary issues, especially any quick wins, and people will be more open to participating in initiatives that drive transformation.

2. What's fundamentally broken that requires a restart

This question can be applied to business models, products, business processes, organizational structures, practices, and technologies. When I ask CIOs this question, I often hear that their agile practices are fragile, the impact of technical debt, inefficient business processes, and opportunities where automation can drive efficiency and quality.

All important answers, but' that's not what I am seeking.

First, I'm considering the organizational culture. Where areas of the culture are fundamentally broken, they become significant barriers to driving change. Mission, goals, values, incentives need to be reevaluated. Communication practices likely need an uptick. If the way the organization is collaborating, communicating, and driving has fundamental issues, then activities and initiatives tied to improving them are also critical transformation needs.

But I also seek out a definition of the organization's DNA and fundamental "infrastructure." I'm not talking about servers, networks, etc. - I'm more speaking about fundamental practices. More specifically, I'm looking for practices tied to sales, marketing, agile collaboration, product management, DevOps, becoming data-driven, and portfolio management - practices that I review in detail in Driving Digital

And it's not any one of these practices that I focus on - it's their aggregate. To drive a transformational impact, it requires a blend of these fundamentally digital practices. The question is, what aspects of them are fundamentally broken, and that will inhibit successfully planning, delivering, and driving business impact?

3. What should be the organization's calling

In my post on CIO.com, the one transformation goal CIO must prioritize in 2020, I asked CIO to leave their project portfolios behind and to consider their one focus area in 2020.

Every organization has its long list of projects and goes through considerable effort to rationalize them into priorities. What's the business value? How expensive and complex is the initiative? What resources are required, and what's the impact on organizational capacity?

I think if it as the bullshit list.

Most organizations can't estimate any of these things well. The fear of saying "no" to key stakeholders will drive them to commit to too much, and they'll spend half the year rationalizing the list.

That's why I wrote the article

Tell me one thing that everyone agrees on is a high priority. Something that has the potential to be a game-changer. Ideally, something that has these characteristics;

  1. Has the potential to grow the business into new markets or customer segments
  2. Delivers a new product/service, or drastically improves the customer experience in an existing one
  3. Enables the organization to collect new data and leverage analytics to further competitive advantages
  4. Cleans up operational business processes - ideally making legacy practices obsolete and enabling the creation of new intelligent practices that are more automated and data-driven.

That one initiative becomes the organization's digital transformation calling. It drives culture, practice, and technology changes. It forms a new basis for how the organization uses data.

If you've gotten this far reading this article, don't feel bad if you think that I'm speaking about you or your organization. It's not you, it's everyone. I see this problem in the smallest of non-profits to the most significant CPGs and everything in between.

The question is, what are you going to do about it? Reach out to me if you want some help. 

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld, CIO.com, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.