3 Ways Helpful CIOs and CHROs Can Drive Experimental Cultures

Ten years ago, it was less likely for CIOs and Digitial Trailblazers to form a partnership with their CHRO and human resources departments. At that time, IT was largely focused on run and grow initiatives with little focus on transformation – and the term digital transformation was in its infancy. Meanwhile, many employees perceived HR as untrustworthy and only sought their services to complete performance reviews, gain support for promotions, request approvals for new hires, and handle difficult employee situations.

3 Ways Helpful CIOs and CHROs Can Drive Experimental Cultures
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Should product managers and innovative agile teams measure business value?

How to measure business value is a question many agile teams ask me, given how much rigor I ask them to put into estimating and capturing story points. Should product managers and product owners have an equivalent responsibility to define a business value metric, use the metric for prioritization, and be held accountable for actual business value delivered versus estimated?

Should product managers and innovative agile teams measure business value?

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10 Easy Ways for Introverted Digital Trailblazers to Manage Up

“Managing up is a career development method that involves working with your boss to create value for both of you.” This is how Google’s AI explains managing up, a set of career management practices for developing relationships with your manager and other higher-level executives.

I confess – I sucked at managing up during my days as CTO and CIO. From my naïve lens, I equated managing up to ass kissing, allowing my introversion to mask and underinvest in this critical career management practice. I believed that demonstrating strong communication, delivering continuous results, and fostering a culture of innovation and transformation were all I needed to promote my career aspirations.

Digital Trailblazers Manage Up to Advance Their Careers

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GenAI Will Drive These 3 Emerging Leadership Trends

“The pace of technology change is increasing, and you must reevaluate your digital strategy and priorities. Frequently. You will always be transforming, and your organization must establish transformational practices as essential core competencies.”

It’s been just over two years since I finalized the Digital Trailblazer manuscript, my book of stories and 50 lessons for people leading digital transformation initiatives. These were my remarks in the book’s preface, and I wrote it well before genAI took the world by storm.

GenAI Leadership Trends

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5 Practical Technologies Every Ambitious SMB in Industrials Should POC

Manufacturing, construction, and other industrial businesses can leapfrog from technology-lagging organizations to ones driving competitive advantages. A chief challenge is escaping legacy mindsets, especially in small and medium businesses where technology is a commodity component that’s bought once and used well past its depreciation date.  

Manufacturing and Construction Technologies to POC

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How Experts in Change Management Lead a Successful Digital Transformation

A couple of years ago, I led an agile transformation program for a major hospital system. Their vision statement was to pilot process changes and new technologies to improve patient experiences while simplifying work for doctors, nurses, and administrators. They asked me to train their project managers on agile methodologies and apply agile/scrum to several project types, including electronic health record system deployments and M&A integrations.

Change Management in Digital Transformation

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How Leading Digital Trailblazers are Pragmatic Vision Painters

Digital transformation leaders – people I call Digital Trailblazers – wear many hats, and one that’s come up several times during our Coffee with Digital Trailblazers is the role of vision painter. As a vision painter, we must understand business strategies, learn market needs, capture customer feedback, and identify technology opportunities. Our objectives include painting a future vision, and sometimes tailored ones for different stakeholders, to guide our organization on opportunities worth pursuing and learn their customer impacts.

Digital Trailblazers as Vision Painters

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3 Ways Construction Businesses Can Modernize With No-Code Dynamic Work Management

Ten years ago, I wrote an article for Engineering News Record on how construction businesses underspend in technology. I referenced Gartner’s survey of technology spending by industry, showing construction dead last, which was the same ranking it held the previous year.

Construction No-Code Dynamic Work

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Change Management: 10+ Ways to Ease Adoption in Digital Transformation

I invited several experts to my weekly Coffee with Digital Trailblazers to discuss change management, easing adoptions, and minimizing the productivity dip. Participants heard a change management playbook.

We used the productivity dip (illustrated below) as a reference model as it’s a useful tool to illustrate desirable versus problematic change management programs.

Change Management Productivity Dip

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3 Important Takeaways for Pioneering CIOs on the State of Agile

CIOs, CTOs, and Digital Trailblazers – we have a problem.

While many organizations have adopted agile methodologies, there’s a gap between what leaders expect from these practices and what they deliver. This year’s State of Agile report (the 17th of their annual reports) shows the gap is widening and points to some of the underlying issues for technology leaders and Digital Trailblazers to address.

Agile CIO

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24 Ways to Avoid Painful Failures and 3 Success Drivers in Digital Transformation

Every year, a new round of surveys shows that 40-60% of organizations are struggling with digital transformation. One recent survey shows that 51% of respondents have not seen an increase in performance or profitability from digital transformation investments. Other early surveys quote that 70-90% of digital transformation initiatives have underperforming results.

Avoid Failures, Success Drives in Digital Transformation

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How to Drive Digital Transformation and Survive as Your Company’s First CIO

I’ve spoken with several CIOs who were the first to hold the role and title at their organizations. It’s a unique experience, so I thought I’d share some thoughts.

When a new CIO comes on board, there’s often a mix of excitement and angst among the leadership and staff. Leadership wants to believe that what drove the need to hire a CIO materializes without too much time,  cost, and disruptive changes. The staff wonders who this new leader is and what they will ask of them.

CIO - Drive, Survive, Thrive

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7+ Must Reads for Digital Trailblazers on Leadership, Innovation, and AI

This is my fifth year of sharing my top book reads of the previous year, and you can review my previous lists here: 2022, 2021, 2020, and 2019.

This year’s list includes my usual mix of leadership, emerging technology, and books about growing small businesses. I was in a cerebral mood compared to previous years and missed reading any fiction books, but I did read Patrick Stewart’s autobiography, Making it So that trekies will love, and Hertog’s On the Origin of Time, which Stephen Hawking fans should read.

Isaac Sacolick's Book Recommendations from 2023

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How Innovative SaaS CTOs use Gen AI: What Digital Trailblazers Can Learn

I just read about how CIOs are taking it slow regarding generative AI in the enterprise. “The hard thing about this is you don’t have data on people’s level of productivity,” said Sharon Mandell, CIO at Juniper Networks, while  Kathy Kay, executive VP and CIO at Principal Financial Group, created a study group of “a combination of engineers and business people and are curating probably 25 use cases.” The article quotes a Morgan Stanley study finding that only 4% of large company CIOs launched significant generative AI projects.

How SaaS and Tech Company CTOs use Gen AI

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How to Energize Your IT Career as an Innovative Digital Trailblazer

You should evaluate your career progression and goals regularly, especially in this super-charged world where generative AI impacts many job functions and more businesses are accelerating digital transformation initiatives.

If you aspire to grow professionally, take on more challenging roles, and help your organization build competitive advantages with technology, data, and AI, then becoming a Digital Trailblazer should be one of your career goals.

Energize Your Career Digital Trailblazer

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5 Digital Trailblazer Competencies: An Entrepreneur Architect’s Perspective on Leadership

2023 is coming to a close. I’ve had a difficult year and won’t be able to share details for a while, but I’ve had several close friends and colleagues to support me. Many of them join my weekly Coffee with Digital Trailblazers and contribute on stage to our discussion on digital transformation leadership.

This week, I’d like to introduce you to my good friend, Tyler Johnson, a co-founder and CTO of PrivOps. Tyler is a true Digital Trailblazer, showing both breadth and depth of technology architecture, infrastructure, data, and security skills. Tyler is an expert on data fabrics and security, and his patents underpin the platform he developed at PrivOps.

Tyler Johnson Digital Trailblazer Attributes

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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.