10 CXOs Share Their Powerful Leadership Lessons for Digital Trailblazers

I leave fifty transformation leadership lessons for Digital Trailblazers, my name of aspiring transformation leaders, in my new book with that title. It has ten chapters of in-the-moment stories to see how I handled blow-up moments, responded to innovation detractors, and formed diverse leadership teams. Each chapter ends with five summarized lessons, such as, “Ask for more than executive support; seek their endorsements and commitments.”

In one chapter, I asked several leaders to contribute their leadership lessons. I won’t spill the beans and tell you what chapter they’re in, but it’s one of the most important chapters in the book.

So in this post, I went back to two of these leaders and captured their insights from their recent real stories from Digital Trailblazer episodes on the Driving Digital Standup. I also have eight more from CXOs and industry leaders for you to digest.

1. Ask smarter thought-provoking questions by slowing down

“Slow down, and I mean, slow down in your head because I think we are used to running really fast, especially in technology. Fast is good. Fast can be really good. Fast is not so good when you’re using a sharp knife, and bad things can happen. So, I think we need to learn how to slow down mentally as well as in other things. And when you slow down mentally, and you have some reflection, and you don’t feel like you have to hear yourself talk, you get think time, and you’re able to ask better questions.” – Jonathan Feldman, CIO City of Asheville

2. Drive customer-driven transformations by making their lives easier

“Always focus on the customer first. How can you add value? How can you make the customer’s life easier? And that then translates into how you do things differently in your business. Our customer wants your high-quality products. They want them in a timely manner.” – Martin Davis, CIO at Mevotech

Watch Martin’s episode on the Driving Digital Standup

3. Transition to spiritual problem solving and mature past technology religion

“I think people in tech are very religious about their stacks; Zachman or they do ITIL to the nth degree. In the real world, people who are more educated, they’re less religious, and they’re more spiritual. I think the best technologists are not religious, but they’re spiritual in a tech sense. It’s more like an awakening, and you are not tied to a vendor or a stack.” – Sarbjeet Johal, Cloud Advisor to CIO and Industry Analyst/Influencer.

4. Extend your leadership skills by volunteering at nonprofit organizations

"If you’re an IT leader, a CIO, or CSO, you can get involved at the board level or as an advisory. But if you’re not, you can bring your expertise to help how they actually execute. Roll up the sleeves and show them how to use a particular technology or get involved in solutioning around technologies. There are just so many different opportunities and also an incredible opportunity to learn.” – Helen Wetherley Knight, Nonprofit CIO and Strategic Advisor.

Watch Helen’s episode on the Driving Digital Standup.

5. Encourage creativity dialogs to foster innovation

“Create an environment that fosters creativity by encouraging everyone, at any level of your organization, to bring forward new ideas. Identifying innovative ways to use technologies both internally and externally can take companies to new heights, and it’s important that employees know their value and the role they play in making that possible.” – Ciro Donalek, CTO and cofounder at Virtualitics

6. Reimagine business processes, then implement with low-code

“Market Leaders deliver superior customer experience by thinking end-to-end, reimagining their business processes, and making it simple for customers to do business with them across products, channels, journeys, systems, and brands. Market leaders are winning by investing in low-code platforms that enable them to roll out new products and services faster, adapt to the changing market needs quickly, and innovate faster.” – Anand Raman, EVP and COO at Newgen Software.

7. Build a culture of experimentation, learning, and engagement

“Digital trailblazers know that technology is rarely the barrier and that the ability to build a culture of experimentation and be curious about problems, solutions and the user experience is instrumental in bringing new products to market. These trailblazers seek to understand perspectives versus waiting to respond. Finally, they know how to involve and engage others in the ideation and decision-making process without losing control of the business decision.” – Chris Williams, Chief Operating Officer, Interaction Associates

8.Change and transformation management is a day one priority

“Start thinking about change management on day one – even before you build your data or digital products. It’s a crucial step for adoption.” – Nir Kaldero, Chief Data, Analytics, & AI Officer at Neoris

9. Align infrastructure objectives with business goals

"While executives know that digitizing their IT infrastructure can improve scalability and profitability, their attempts sometimes fall short. Why? Leadership teams often overlook crucial steps needed to ensure their digital transformation efforts add value to their business goals." – Arthur Lozinski, Co-Founder and CEO of Oomnitza

10. Understand who and how people are impacted when driving change and transformation 

"If you are tasked with leading a change effort, big or small, think about the potential impacts on the people that will be affected.  Machines don’t care (yet).  Humans do.  Make sure you are thinking about the people." –  Walt Carter, Chief Digital Officer at Homestar

10+ Plan, deliver, and transform as a Digital Trailblazer

And here's one more that Walt shared after reading Digital Trailblazer. 

"Isaac’s thinking on transformation, change, and leadership comes from practicing in the arena: you’ll find practical wisdom and great tools and techniques in each story he shares from the trails he blazed! He has earned my highest recommendation!" –  Walt Carter 

Thanks Walt!