Best of 1,000 StarCIO Articles: The Informative Digital Transformation Must-Reads

A couple of weeks ago, I celebrated my 1,000th blog post, an achievement I am just as proud of as publishing my two books, Driving Digital and Digital Trailblazer.

In the post, I shared three time-tested lessons for digital trailblazers and thanked many contributors to my weekly Coffee with Digital Trailblazers.

Best of Isaac Sacolick's Articles on Digital Transformation

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IT Turnaround: Know these 15 Signs + 15 Tactics to Transform From Floundering to Winning Departments

“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?”

That’s my opening statement to Chapter 1 of Driving Digital, which is just as relevant to CIOs and IT leaders when considering a technology department’s performance. I read this statement to kick off a recent Coffee with Digital Trailblazers, where we discussed IT turnarounds, telltale signs of underperforming departments, and the tactics Digital Trailblazers take to turn them around.

IT Turnaround: 15 Signs, 15 Tactics to Transform

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Grateful Digital Trailblazers Reflect on Innovation and Lifelong Learning

I love this time of year in the United States when we have a brief pause from our complex lives and get the chance to break bread with family and friends. Thanksgiving means a lot more for me this year, but I will have to leave the story on why for another time.

Long-time fans of my blog will remember some of my other Thanksgiving posts – two of the 1,000 articles I just celebrated. (See the 1000’th post here).

Happy Thanksgiving from Isaac Sacolick

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Celebrating My 1,000th Article: 3 Time Tested Lessons for Digital Transformation Leaders

Today’s post, my 1,000th published article, marks an achievement I am tremendously proud of and excited to share.

Here’s the funny story of how I started writing. My journey into blogging and speaking began 18 years ago when someone told me, “Isaac, great social networking site, but it needs to plug into the blogosphere.” All I heard was “blog,” so I wrote my first post on application logging.

1,000 articles by Isaac Sacolick

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Joe Puglisi on Digital Transformation Leaders: Calm Teachers and Helpful Simplifiers

 When you meet Joe Puglisi, see him moderating a panel on stage, or participate in his SIM members in transition calls, you instantly know he’s someone you can learn a lot from.

Joe was one of several key contributors to a recent Coffee with Digital Trailblazers, where we discussed who the right people are to lead digital transformation initiatives. Several of us collaborated after the episode and identified 50 attributes of Digital Trailblazers (publishing soon) that we organized into five competency areas. You can read more about the Digital Trailblazer Competency Areas and watch the video where I share my top five Digital Trailblazer Attributes.

Joe Puglisi, Isaac Sacolick - Digital Transformation Leaders

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Gen AI Innovation: How CIOs Deliver Short-Term Wins and Plan Visionary Impacts

How should CIOs and IT leaders prepare their organizations to pursue generative AI opportunities while mitigating risks and navigating cultural and workforce impacts?

It’s a top-of-mind question for every CIO, especially as Boards ask about company AI strategy, while 51% of CEOs expect their CIOs to lead the company’s AI efforts.

Generative AI Vision for CIO
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Emerging Digital Trailblazers: 15 Ways to Hire and Train for Entry Level High Potentials

When interviewing for an entry-level role, would you know if you had a future Digital Trailblazer sitting before you? That was the topic at a recent Coffee with Digital Trailblazers, where we discussed how to evaluate, hire, and train entry-level employees in product management, DevOps, data science, marketing, information security, and other roles with high potential to become Digital Trailblazers.

Hire and Train Emerging Digital Trailblazers

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AI’s Power Paradox: Balance Innovation and Sustainability for a Promising Future

When I was CIO at a construction industry data, analytics, and media company, I was deeply interested in how technology and sustainability would drive the industry’s future. Could a new smart building technology or a green innovation lead to funding new construction that improves people’s experiences and enables a more sustainable future?  

AI's Power Paradox by Isaac Sacolick

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Empower Agile Teams: Leadership Strategies That Inspire People, Not Micromanage

Many agile and scrum teams want to be left alone so that they can do their work. The last thing they want is leaders looking over their shoulders and overseeing their to-do lists, even when they struggle to complete their sprint commitments. Whatever the blocks impeding their progress are, they’ll work through them, though maybe not at the pace, schedule, or quality leadership expects.

Inspire Agile Teams by Isaac Sacolick

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Digital Transformation Leadership: 5 Essential Competency Areas for Success

Digital transformation is hard work, from developing a strategy to leading a culture change. CIOs, CMOs, and CDOs quickly realize that executing digital transformations requires prioritizing strategic initiatives, assigning team leaders, and establishing the right balance between self-organization and developing standards.

Digital Trailblazer Competency Areas

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The Architect has a Significant Role in Uplifting Digital Transformation

I can’t imagine guiding large-scale digital transformations without knowledgeable and influential architects. Architects guide solutions, seek standard practices, and target building extendable and reusable platforms and services. Without architects, organizations add risk to their implementations that can delay releasing capabilities, create integration gaps, increase costs, and generate operational complexities.

Architect's role in uplifting digital transformation by Isaac Sacolick

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How DevOps and Agile Team Leaders Can Organize a Successful Workshop

I’m a strong proponent of hybrid working.

Requiring a strict in-office presence can be hard on many employees with long commutes, family caretakers, or people with physical disabilities. The collaboration needed by Digital Trailblazers, especially ones leading DevOps and agile teams, is rarely achieved by jumping from meeting room to meeting room or expecting people to develop meaningful relationships at the water cooler.

Sacolick, StarCIO Agile DevOps Workshops

During the pandemic years, DevOps and agile team leaders had to adjust their collaboration practices to support remote work. I’ve previously written about how to conduct remote sprint reviews and retrospectives and other tips for hybrid work for agile and DevOps teams.

Today, Digital Trailblazers must be more strategic about collaboration and decide why, when, and how to organize in-person and hybrid meetings. Executives and leadership groups often do this through workshops and offsite meetings to bring people outside their day-to-day responsibilities and focus on collaboration, problem-solving, and decision-making. Digital Trailblazers, especially DevOps and agile team leaders, should consider workshops as a critical tool to enable hybrid work while empowering team and cross-team collaboration. 

Why DevOps and agile team leaders schedule workshops 

Am I alone in this belief that in-person meetings and workshops can help Digital Trailblazers accelerate transformation and improve collaboration with DevOps and agile teams? I’m not!

“As with many engineering teams, in particular, many of our engineers are hybrid or fully remote and, with that, comes a separate set of demands, so it’s important to get the balance right on in-person meetings,” says Naggi Asmar, chief engineering officer at Matillion. “Ultimately, hybrid and remote team leaders must be agile and willing to adjust their leadership style to best fit their employees’ needs. Whether developing better communication, improving collaboration, or being more intentional with face-to-face time, businesses must be open to adjusting their approach to accommodate today’s global workforce.”

Here are several reasons to schedule workshops:

1. Channel emotions toward creative collaborations

“In the realm of hybrid work, mere office presence is not the same as meaningful collaboration,” says Marko Anastasov, co-founder of Semaphore CI/CD. “Do gatherings reignite passion, synergy, and innovation?”

In other words, workshops can help teams raise their emotional intelligence (EQ) and drive creativity – two key elements needed to drive innovation, and that’s often less effective when done on Zoom, Microsoft Teams, or through the drudgery of in-office meetings.

2. Realign organizations on mission and goals

There are good reasons why sales organizations schedule at least a once-a-year gathering. Digital Trailblazers should also consider yearly offsites, full-team get-togethers, and workshops aiming to align on yearly objectives.

 “To build a great engineering culture, the entire team should get together once a year for at least three days,” says Jim Gochee, CEO at Blameless. Use this time to align on shared goals, to educate and train, and to build connections. I’ve successfully used this approach for over a decade.”

StarCIO Vision Statement Template

For medium and large enterprises, CIOs, CTOs, and CDOs should consider gathering the entire DevOps and agile team organization to create meaningful self-organizing standards, discuss learning objectives, and review vision statements of digital transformation objectives.

3. Solve problems and improve communications

Grant Fritchey, product advocate at Redgate Software, shared several reasons you might want to schedule workshops and offsites to address common challenges facing DevOps organizations and agile teams.   

  • When making the initial social shift necessary to DevOps, an offsite helps the team establish a newer, better means of communication. 
  • If you attempt to move your established processes into new technologies, an offsite where people can focus and brainstorm may also be useful. 
  • If you suffer a major outage or problem with your process, an offsite as a way to understand what went wrong and how to fix it can benefit from the focused, face-to-face communication that being away from the office can provide.

Plan the workshop: Agenda, attendees, and homework

At a recent Coffee with Digital Trailblazers, a LinkedIn audio event I host on Fridays at 11am ET, we discussed several best practices for organizing offsites and workshops. Executing a meaningful workshop where people walk away with deeper relationships and the group solves key problems requires planning.

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!

  1. Define an agenda – Speakers at the Coffee Hour recommended identifying the desired outcomes and then working backward to define the approach. What decisions are needed? What problems do you want attendees to focus on and aim to solve? What types of relationship-building are useful, especially if people can’t meet frequently?
  2. Identify the attendees – Do you want a wider audience so that more people are part of the process or fewer to drive more efficient decision-making and problem-solving? There are a couple of schools of thought, whereas some agendas require a more inclusive group, and others benefit from collaboration by a specially selected team. The workshop organizers should discuss and agree on an approach.
  3. Assign responsibilities – Organizing a workshop requires one or several people with the following responsibilities:
  • Sponsor - to finalize the objectives and target outcomes
  • Agile project manager – to oversee the timeline and deliverables by the meeting organizers
  • Logistics organizer - to select the location, invite attendees, handle travel, plan for meals, and manage other event logistics
  • Content coordinator – to create a program that aligns with the objectives and outcomes
  • Facilitator – to run the workshop and lead collaborative discussions
  • Supporters – to “read the room” and recommend any changes to the agenda and to take on smaller table/team-level facilitation roles
  • Scribe – to capture parking lot items, decisions, and follow-ups 
      Digital Trailblazer by Isaac Sacolick
    1. Create attendee materials -  This should include work attendees must do before the workshop, such as required reading, data analysis to ground the discussion, and presentations you expect people to make. A best practice is creating a post-workshop checklist for attendees and teams to follow up after the event. 
    2. Review the plan – Even though responsibilities are assigned, the planning team needs to coordinate on meeting location, agenda, communications, and who’s doing what at the event. Consider what materials you need at the meeting, including screens, mikes, and whiteboards, and whether you want attendees to use their laptops or phones. Another question to resolve is whether you are hosting an all-in-person or hybrid event where some people can attend remotely.

    During the workshop: What to look for and when to pivot

    The best well-laid plans should be open to real-time adjustments and pivots. Below are twelve considerations:

    1. Are there unforeseen logistic issues that require some adjustment to the agenda?
    2. How will you adjust the agenda when bad weather impacts your plan or when really nice weather distracts attendees? 
    3. Was the agenda too ambitious, and do people need more time to work through the program?
    4. Were enough networking breaks scheduled, or do you want to extend the networking time?
    5. Does it look like people are learning and enjoying themselves, or should you step back from the business agenda and focus more on the attendees’ needs? 
    6. How will you champion the best ideas, contributions, and behaviors to influence others?
    7. Are conflicts becoming overwhelming, and should the organizers table stressful discussions for another time, place, or smaller group?
    8. Who’s responsible for reaching out to quiet participants or silent detractors who aren’t participating? 
    9. What is your plan if an attendee becomes unruly and distracts the group from the agenda?
    10. What happens if a leader elects to “pull rank” to control the conversation? 
    11. Who takes charge to ensure a positive outcome if there’s a blow-up moment?
    12. Who decides how to handle a crisis that may require a major pivot or cancellation of the workshop?

    After the workshop: Keys to success are in the follow-ups

    Here’s where workshops miss the mark:

    • The organizing team doesn’t regroup and conduct a retrospective.
    • Communications on decisions are emailed but not recorded in platforms to share with wider audiences and institutionalize.
    • Follow-ups are emailed but never recorded in the platforms used by teams and attendees to track progress.
    • Post-event checklists are distributed to attendees, but the timeline and responsibilities for reviewing them aren’t in place. 
    • Leadership-level communication is an afterthought; they’re left wondering whether the event was valuable to attendees and delivered on promised outcomes.
    • There’s little discussion on when, why, and how to follow up on the next in-person gathering.

    Bottom line: Big offsites and workshops are expensive and are outliers to standard meetings. Significant good can come from them, but the value is in the follow-ups. The to-do lists and decisions need to be folded into the appropriate tools to ensure that short and longer-term actions aren’t lost in emails and documents.

    If you need help organizing your offsite or workshop, let me know, and please review our Driving Digital Workshops.

    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.

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    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

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    How Fearless Digital Trailblazers Prepare for Big Investment Presentations

    At some point in your career, you’ll be handed the microphone and asked to deliver a presentation for a big investment. You may be a product manager looking to develop a new product offering, a data scientist seeking additional funding to experiment with large language models (LLMs), or a DevOps engineer seeking buy-in for a new AIOps platform. Whether it’s your first big pitch or you’re a veteran presenter, you know that successful investment presentations require preparation.

    Fearless Digital Trailblazers pitching Digital Transformation Investments

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    How Data Governance Leaders Can Identify Quick Wins

    I am writing today’s blog post from Tucson, where I wrote the epilogue to Digital Trailblazer.

    “I’m taking a different type of walk today, a hike actually, on one of the trails winding through Saguaro National Park in Tucson, Arizona,” is how I opened the chapter where I reflect on my journey writing the book. I took a similar but much longer hike yesterday through Sabino Canyon.

    Data Governance Leaders find quick wins by Isaac Sacolick

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    3 Key Risks to Address to Safely Experiment with Generative AI

    We had an active conversation at last week’s Coffee with Digital Trailblazers on navigating the risks when experimenting with generative AIs and large language models (LLMS). My panel included Joanne Friedman, Joe Puglisi, Heather May, Tyler James Johnson, Ashish Parulekar, Roman Dumiak, and Gary Berman. They shared where gen AI provides value and what risks Digital Trailblazers must address when experimenting with them in their organizations.

    Risks in Generative AI and LLMs by Isaac Sacolick

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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.