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

In this third wave of AI-driven digital transformation, CIOs, CHROs, and Digital Trailblazers in IT and HR must partner on evolutionary organizational changes. I believe that partnership starts by driving experimental cultures, rewarding innovation, and fostering intelligent risk-taking.  

Driving experimental cultures 

“Move fast and break things has been a tech startup mantra we’ve heard over the last decade,” says John Milburn, CEO of Clear Skye. “While the notion of an experimental culture is not dissimilar, it’s a more mature, intentional approach that involves an entire organization—not just the tech team.”

Milburn is spot-on – that leaders must involve the entire organization when driving an experimental culture. As much as CIOs believe they can influence departmental leaders to participate in agile programs or become data-driven, the Digital Trailblazers leading digital transformation initiatives cite stakeholder resistance as a common and significant drag on change management programs.  

In previous posts, I made several recommendations about how CIOs and CHROs can partner in digital transformation, accelerate innovation, empower agile teams, and drive experimentation. Here’s some reading to get started:

I suggest reviewing these posts and their recommendations before reading my next three ways CiO and CHROs must partner on driving experimental cultures.

CIOs and CHROs Empower Self-Organizing Teams

StarCIO Vision Statement Template The key to driving experimentation is empowering self-organizing teams, requiring them to draft their vision statements, review the business value of initiatives, and provide agile program management tools for tracking progress. As I’ve written about these before, below are some more specific areas for CIOs and CHROs to focus on:

1. Promote asking questions and challenging the status quo

In my post on how genAI is driving three emerging leadership trends, I say, “I am optimistic about the possibilities of using genAI; however, I am pessimistic about whether many organizations will make the necessary adaptations fast enough to compete in the AI era.”

GenAI is driving a seismic change in skillsets because of technologies like copilots and text summarization tools. Solving problems effectively and efficiently will become a more democratized skill set as copilots improve their accuracy. GenAI is already helping employees answer questions, data scientists identify outliers, software developers write code, and marketers create website content.

But what genAI can’t do (yet) is ask the right questions that can drive business value, identify operational changes, evolve experiences, or create new revenue streams. Organizations will need more people asking these questions and having the skills to evaluate a genAI’s answers.

2. Define roles and responsibilities in change management

I wrote this well before genAI:

Digital Trailblazer by Isaac Sacolick

“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.” – Isaac Sacolick, in the preface to Digital Trailblazer.

Driving change management is a top bottleneck in driving transformation. Change management is not a sole IT responsibility, a training issue, or a gap in how stakeholders participate in digital transformation initiatives. It’s all of the above and more – which is why I wrote a white paper on change management in digital transformation that includes 13 ways to ease adoption and improve experiences.  

White Paper on 13 Ways to Ease Adoption and Improve Experiences

CIOs and CHROs looking to drive experimentation and accelerate transformation initiatives can’t just leave change management responsibilities to Digital Trailblazers and change management experts. Change management must be a top-down digital transformation core competency with defined responsibilities and accountabilities. (Note: StarCIO has coaching and learning programs in these areas – contact us for more information.)

3. Promote security, safety, and quality

Milburn recommends, “To breed a culture of innovation and experimentation, CIOs and CHROs must work together to create security guardrails and effectively communicate change to the organization so everyone can participate without compromising safety or performance.”

Driving experimentation and empowering self-organizing teams can’t become an open season of doing what you want, with whichever tools you need, and by incorporating whatever datasets are available. CIOs and CHROs should look to create guardrails on experimentation:

  • Increase training and learning programs around security risks
  • Identify safety risks and ensure experimentation complies with regulation
  • Establish data governance principles on using intellectual property and third-party data
  • Define quality non-negotiables and standards

The bottom line is that CIOs and CHROs who don’t partner and seize the moment to drive safe experimentation will find struggling Digital Trailblazers.


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, 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.