How to Drive Lifelong Learning: Practical Ways for Digital Trailblazers

At a recent Coffee with Digital Trailblazers, a LinkedIn audio event I host on Fridays at 11am ET,  we discussed the topic of driving creativity and lifelong learning. I wrote in Digital Trailblazer, “How you encourage innovation, experimentation, learning, and smart risk-taking is critical in transforming organizations,” and I was eager to learn how other transformation leaders respond to this challenge. Thanks for sharing your insights, Joanne Friedman, Emily Ricketts, John Patrick Luethe, and Ashish Parulekar.

Lifelong learning for Digital Trailblazers

Lifelong learning for Digital Trailblazers

Here are some of the insights we discussed during the coffee hour. Digital Trailblazers must expand their networks, promote learning within their teams, and manage up by guiding executives on transformative learning objectives.

Here are the details.

1. Build connections and develop relationships to learn from people

Joanne opened the session by sharing her story of meeting and learning from one of her heroes. While interacting with leaders and influencers is not an everyday occurrence, building connections is something Digital Trailblazers should do proactively by setting weekly and monthly objectives.

Most leaders respond positively to your requests to connect, and many will answer questions.    

One of my favorite questions to ask leaders is, “How would you go about solving this problem?” I phrase the question this way because leaders may not have a direct solution to a problem but can express their steps and thought process about how they would solve it. It’s their how that I am most interested in.

2. Scale lifelong learning by promoting team activities

I forget who said this insightful comment during the coffee hour. “There’s a mismatch of what companies offer versus what people want to learn,” they said.

“Bingo” was ringing in my mind as I heard it. So many companies focus on skills training and deliver simplified packages of lifelong learning by subscribing to services like LinkedIn Learning, Coursera, Udemy, Pluralsight, and others.

Skill learning is very important, especially as technologies evolve so quickly. Helping employees gain certification is a key investment in building organizational best practices. But skills and certifications are just one element of lifelong learning, and I offered this breakdown during the coffee hour:

  • Training and certifications to learn specific technologies, skills, and best practices so people have the knowledge and tools to do their work.
  • Research-based learning where a person or team is learning by problem-solving, researching, discovering tradeoffs, and presenting findings.
  • Experimenting by rolling up the sleeves and trying new technologies, executing proof of concepts, market testing new ideas – then gathering data and sharing insights.
  • Experiencing by encouraging people to step out of their comfort zones, taking on responsibilities outside of their core skills, and recognizing what it feels like to work through challenges and obstacles.
  • Teaching, developing lesson plans, and facilitating workshops are incredible learning opportunities that test people’s abilities to simplify messages, adapt approaches to support different learning styles, and answer all kinds of questions.

Individual contributors and teams benefit most from training, research-based learning, and experimenting, and it’s the Digital Trailblazer’s responsibility to promote these activities. From lunch and learns to hackathons, there are many ways for Digital Trailblazers to create fun and exciting learning opportunities.

Career checklist for data leaders Digital Trailblazers should focus on experiencing and teaching for their own learning objectives. If you haven’t read Digital Trailblazer yet, you’ll love my stories of surviving a pivotal board meeting, handling objections while demoing a new product offering, and traveling to India to collaborate with my teams. Digital Trailblazers in DevOps, data science, and product management roles may also want to download my Digital Trailblazer Career Checklist.

3. Change the culture by guiding executives on their learning objectives

I ended the coffee hour with one key question:

How can Digital Trailblazers “manage up” and ensure that executives in their organizations also invest in their own learning? The world is transforming too fast for executives to rest on the knowledge and experiences that earned them seats at the table.

Without upfront learning, it’s extraordinarily difficult to bring digital transformation initiatives to executive leaders for making big innovation investments and taking on culture transformational roles. Just try asking the CEO to invest in building a private LLM when all they know about generative AI is from trying ChatGPT a few times. The teaching and learning must come before the big pitch.

Here are some panelist suggestions for guiding executives to learn more about digital transformation and the evolving technology landscape.

  • Schedule 15-minute learning sessions at every leadership meeting with different presenters and topics. Digital Trailblazers should schedule sessions with their teams, then look to drive a bottoms-up culture change and see if their leaders will adopt the approach. One way to use 15-minute learning sessions is to jargon-bust and explain how key trends, technologies, and other innovations impact the business. Thank you, Patrick, for this suggestion!
  • StarCIO Vision Statement Template Simplify pitching ideas – Ashish and I are proponents of the one-page pitch. I share my vision statement template and encourage organizations to adopt one or a handful of standards. Learning is two-way – helping people share their ideas and encouraging executives to review lots of them.
  • Involve leaders in how the industry and ecosystems transform as yesterday’s competitive threats and promising opportunities are old news today. Joanne frequently shares how manufacturing practices are evolving by developing digital twins or taking on greater sustainability challenges. Beyond industry, executives must understand how they compete and partner in digital ecosystems.
  • Digital Trailblazer by Isaac Sacolick Share books and discuss insights to break the ice with an executive leader with whom you have a weak, underdeveloped relationship, especially if you discover they are readers. Emily and I are both readers, and I regularly share my favorite reads with my clients, teams, and audiences. See my enlightening books of 2023 for examples.

Lifelong learning requires developing and executing a plan for yourself, your team, and those you influence. What’s yours?

Isaac Sacolick
Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.

Coffee with Digital Trailblazers hosted by Isaac Sacolick Digital Trailblazers!  Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!

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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,, 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.