In May, I reviewed "The Digital Mindset: What It Really Takes to Thrive in the Age of Data, Algorithms, and AI" by Paul Leonardi and Tsedal Neeley. The goal of their book was to enlarge the number of business leaders with the couth to add value to a digital transformation conversation. The Digital Mindset aimed to make them 30% knowledgeable of the technologies needed to turn organizations into digital winners.

Now, Isaac Sacolick provides a counterbalance with "Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership in which he shares how CIOs and their key reports can become digital change masters. The book provides CIOs a mix of principles and personal transformation stories. It puts CIOs, to quote Hamilton, “In the room where it happened.” As such, it is a must-read for any CIO wanting to be a co-creator of change — or even better, a change agent.

The Pace of Change for CIOs

In #CIOChats, we have had numerous discussions about the pace of change — and COVID has clearly increased that pace. According to Sacolick, the pace of change is making CIOs reevaluate their digital strategy and priorities. In the digital era, being a transformation leader requires “working in and out of weeds.”

Unfortunately, some CIOs did not dig into the weeds of transformation prior to COVID, which hampered an opportunity to build tangible business credibility. The reasons are clear. Technology today is less about business productivity and more about business model and growth — technology drives business impacts, culture changes, growth, efficiency and quality differentiators. I would add, as Paul Leinwand and Mahadeva Matt Mani declare in "Beyond Digital: How Great Leaders Transform Their Organizations and Shape the Future," “the future will belong to companies that are willing to shed past belief systems and define new and much bolder value propositions.”

To be effective in this environment, CIOs need to talk to business customers and end users and understand their pain points. They also need to reflect on the skills they have and whether they will get their companies to their digital future. Part of this means that CIOs have to be skilled at talking to the board and stepping out of their personal comfort zones.

Related Article: CIOs Step Up to the Role of Change Leader

Digital Transformation Is Not a Discrete Project

Without question, the digitization of business has taken place for over 50 years. This led to massive improvements in business productivity and operational cost efficiencies.

However, Sacolick points out that the move to digital transformation is driven by competitive, technological and disruptive forces. This means that technology and business leaders need to view their business strategy through the lens of technical capabilities.

In contrast to the past, this change involves a decision to shift from selling only physical products to digital offerings. As Jeanne Ross, Cynthia Beath and Martin Mocker note in "Designed for Digital: How to Architect Your Business for Sustained Success," “A successful digital offering leverages the capabilities of digital technologies to provide a solution to a problem or issues that a customer invariably has not articulated."

To succeed here, CIOs need to make sure their organizations are ready to transform to future market or customer needs. In many cases, the fix involves expanding their organizations’ technology and data competencies. And being ready involves understanding digital transformation is not a discrete project. There is no endpoint, just a continuous process.

Sacolick suggests that CIOs start by evolving their vision statements and making sure they align with customer and strategic goals. With this, CIOs need to find fellow digital trailblazers that "The Digital Mindset" authors' reference. They can accelerate what Sacolick calls bottom-up transformation. The internal startups that drive this type of transformation need to build around agile principles and practices, learn through experimentation and conduct outside activities.

Being an Effective Digital Leader

For inward-facing CIOs, this can prove a challenge. But a successful digital leader requires softer skills, empathy and the ability to develop appropriate communication strategies at the right level of the organization.

In addition, effective CIOs successfully partner with their colleagues while serving as more of an assembler of discriminating technologies than a builder. This means knowing something that is hard — the best technology does not always ensure high reliability.

Lastly, after COVID, strong CIOs protect their team and the internal and external digital trailblazers.

Related Article: How Should Organizations Consider Risk After the COVID-19 Crisis?

Transforming Culture: Diverse Recruiting

Part of being an effective digital leader involves transforming culture. This starts, says Sacolick, by cultivating diverse teams needed to boost innovation and performance.

To do this, it is essential to actively recruit people with diverse backgrounds and experiences. With a diverse team in place, you need to encourage everyone to contribute to your way of working. This means having the courage to seek opinion and engage leaders to listen and extend their EQ range.

Building Partnerships

Without question, many of the problems that digital transformation goes after cannot be solved in isolation. Partnerships are essential. For example, understanding customer experience involves reviewing customer pains and desires.

Fixing this is built on partnering with marketers on where technology, analytics and hyper automation can improve business results. For more complex organizations, it can involve promoting global team collaboration by helping colleagues learn the culture and foster personal relationships.

Related Article: Why — and How — CIOs Support Customer Experience Programs

Selling the C-Suite

Sacolick shares the importance of working with the C-Suite to make progress on the digital transformation agenda. He suggests CIOs need multiple skills to succeed.

First is the ability to ask for more than support. CIOs need executive endorsements and commitment to the transformational project. As well, CIOs need to be more sophisticated about executive presentations. This means formal role plays for potential objective parties when selling an innovation.

This is especially important in a recession. It is critical that CIOs simplify and share their visions. In this process, they need to ruthlessly prioritize and define success criteria.

And one more thing, because pushing change is never easy, they should find their personal stress release valves.

Importance of Fixing Tech Debt

Tech debt has been a frequent CIO discussion for me. For those not familiar, the analogy is a pile of spaghetti with three different sauces. Tech debt happens when you try to get something done in too little time or with insufficient expertise. It is often compared to duct tape and band aides.

In reality, technical debt, legacy systems and half-developed integrations pile up over time. They create a barrier to entry for legacy firms into the digital world. Sacolick, however, stresses that it is unfair to pin the problem solely on developers.

Learning Opportunities

With this said, fixing tech debt involves focusing everyone on technological simplicity. Sometimes this involves challenging business leaders to simplify their requirements in terms of what to fix and when there is time and resources. Sacolick suggests that data be your guide when making tech debt decisions. CIOs clearly can play a role in helping their teams prioritize which issues need solving and when.

I ran an interesting discussion a few years ago with IT executives from the hottest Silicon Valley startups. They all had been at more established companies before and said that they had established a program to track tech debt and to eliminate it piece by piece in future product releases.

Related Article: Why CIOs Must Become Data Champions

Product Management: Implementing Agile, Scrum Fundamentals

Sacolick correctly perceives the move from IT project management to digital product management. Here he stresses the need to align the product visions because roadmaps rarely are a straight-line journey. I would add that product managers need to do things suggested by pragmatic and other product management training. 

Here product management should align everyone on the product vision. Sacolick suggests it is best to do this by creating single-page vision statements. These should — just like I did as a software PM — detail the user persona, journey maps, value streams and functional requirements.

Another key element is implementing agile and scrum fundamentals. The goal is to implement agile continuous planning after the vision statement. In this process, it is important that PMs when interacting with leaders answer questions top down without jumping into underlying details.

Lastly, Sacolick suggests that product teams target supportable platforms because cutting edge tech may cost more to support. And they should know the costs and risks.

Agile: Starting With Problem Statements

When I was a PM, agile became the rage, but for a long time it was a mix of waterfall and agile. The biggest thing that changed was the notion of sprints and the need to always have a functional requirement in a sprint.

Sacolcik suggests more is needed. To start, agile teams need to involve the broader team in brainstorming which means starting with problem statements. They are not just for us PMs. This means providing time for everyone’s opinion, collaborative debate and joint decisions. This is honestly transformative for PMs.

Sacolick says trust and a shared understanding are essential to agile. Sacolick believes that CIOs should drive the delivery of digital transformation by emphasizing the why and coaching the how and what. This is a substantial change.

For it to work, an agile team needs to develop a shared understanding with product owners, stakeholders and teammates. As well these digital trailblazers need to teach teammate empathy. And finally, they need to make reducing tech debt everyone’s responsibility.

Bad Data: Identify Citizen Data Scientists

Data clearly is critical to digital transformation. And fixing data involves more than IT.

Sacolick suggests that it is critical to identify citizen data scientists and deploy data visualization and data access tools. The goal should be to empower people with data. To succeed, CIOs need to understand how company culture and norms impact data quality initiatives. From the process perspective, they will want to establish a proactive data governance program that gets data owners assigned with tools, processes and data quality metrics.

Sacolick is aware of the depth of data quality issues. For this reason, he claims CIOs should focus on meaningful data problems because data journeys can be long and complicated. Sacolick seems to perceive the move to "modern data stacks" by suggesting that organizations move to picking data technologies that will support their future way of working.

Parting Words: Find Your Personal Stress Release Valve

"Digital Trailblazer" is a terrific book for CIOs who need to drive consequential digital transformations. To be fair, these are never easy, even when everyone is aligned.

However, considering digital change as a process rather than a project makes real sense. There is work to do and hopefully the principles and experiences that Sacolick shares will get you there faster.

And one last thing — remember please find your personal stress release valve. COVID-19 has made your work harder, but even more important.