How Digital Trailblazer CIOs Avoid the Devastating ERP Upgrade

“CIOs loathe ERP upgrades” is how I opened my question at SAP Sapphire’s press conference after the day two keynote. It’s a sentiment I hear from CIOs and IT leaders, regardless of their organization’s ERP platform.

At the press conference, I asked SAP CRO Scott Russell and head of customer services & delivery  Thomas Saueressig to address the challenges CIOs face when upgrading last-gen ERP implementations.

How Digital Trailblazer CIOs Avoid the Devastating ERP Upgrade

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Pioneering Digital Transformation: Simplify from Industry 4.0 to Government

Manufacturing, construction, and government have a few things in common. These companies and institutions lag other industries in deploying technologies while having a key opportunity to connect the physical world with digital back-office workflows and develop actionable intelligence.

Pioneering Digital Transformation: Simplify from Industry 4.0 to Government

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12 Helpful Gen AI Strategies for Winning with Data Science

Every year, research reports cover the level of investment companies make in data science, the relatively small percentage of ML models that make it into production in front of customers, and the challenges in delivering ongoing business value. Even once data scientists successfully deploy models and deliver benefits, the complications of maintaining the models become an ongoing challenge.

12 Helpful Gen AI Strategies for Winning with Data Science

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10 Interview Questions for Digital Trailblazers: Find Amazing Candidates and Land Exciting Jobs

At a recent Coffee with Digital Trailblazers, several of us shared our favorite questions to ask Digital Trailblazers on interviews and how to prepare for them. I captured 20 key questions that job seekers should rehearse before their next interview and that leaders should use to separate the good from amazing candidates.

10 Interview Questions for Digital Trailblazers: Find Amazing Candidates and Land Exciting Jobs

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5 Decisive Questions to Ask Your Managed Security Services Provider (MSSP)

I’m a digital transformation, product, technology, and data/AI leader, but I don’t count information security as a top area of expertise. Over the years, I’ve learned a lot about putting the sec into DevSecOps, how security platforms use AI to improve incident management, and why educating employees is the frontline of defending the business. But when it comes to prioritizing security risks, developing a roadmap, and overseeing security operations, I call in experts who can advise on strategy and lead implementations.

5 Decisive Questions to Ask Your Managed Security Services Provider (MSSP)

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Why Digital Trailblazers Must Be Paranoid In These Four Important Areas

My friends and colleagues know I can be paranoid sometimes, but it’s part of my survival instincts. When you’re driving transformation and responsible for operations, as I was for most of my career, you develop anxieties over what can go wrong, how it will impact your objectives, and whether you’re missing opportunities to address a material risk.

Why Digital Trailblazers Must Be Paranoid In These Four Important Areas

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Top Leadership Attributes of Really Successful Digital Trailblazers

At a recent Coffee with Digital Trailblazers, we discussed who are the right people to lead digital transformation initiatives in their organizations – leaders that I call Digital Trailblazers. I chose this topic as an extension to Chapter 8 of Digital Trailblazer, where I ponder the advice from boards of directors and CEOs on finding the right leaders to oversee the organization’s digital transformation initiatives.

From the discussion, we captured fifty attributes of Digital Trailblazers that I grouped into five competencies:

Digital Trailblazers Top Competencies and Attributes

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5 Keys to Develop Meaningful Relationships with Board Directors

Even if you’re not a C-level company executive, you might find opportunities to speak with board directors and develop a meaningful and valuable relationship with them. You may get lucky and have an opportunistic encounter, like running into a board director in your building’s elevator, at a charity event, or during a conference.

Are you prepared and confident to turn a chance encounter into a career-changing opportunity?

5 Keys to Develop Meaningful Relationships with Board Directors

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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 na├»ve 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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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.