Breakthrough Agile Transformation: The Important Leadership Roles

I've written several posts on the CIO and leadership roles in agile transformation, agile adoption, and agile practices.

StarCIO Agile Transformation

For example, in the CIO's role in agile transformation, I stress the following four leadership roles:

  • Asking questions to drive collaboration on business, tech, and data
  • Taking one for the team and challenging the status quo
  • Driving iterative thinking and minimally viable products
  • Leading, exploring, and reviewing partnerships

I also have another article on what is an enterprise-wide agile transformation. Hint: it's not about scaling! It's about changing the culture with agile mindsets and establishing agile planning practices.

Let's get a little bit more tactical this week. We know CIO and IT leaders must establish the environment, governance, and collaboration to enable large scale agile transformations to succeed. Now once they are created, how should IT leaders work with teams, domains, squads, tribes, chapters, or whatever your organization's terminology is around agile teams.

1. Define Boundaries of Self-Organizing Teams Versus Operational, Architecture, and Practice Standards

StarCIO Agile Planning

One of the agile manifesto's twelve principles states, "The best architectures, requirements, and designs emerge from self-organizing teams."

That's very true, but only to a point. Self-organizing teams that can do whatever they want is chaos. In The Scrum Fieldbook, J.J. Sutherland writes about how leaders have to provide just enough structure to operate between the worlds of chaos and rigidity. Defining the boundaries is a crucial role for CIO and IT leaders.

Some examples of where standards are needed:
  • I don't believe teams should be picking their own tools as some profess unless the organization wants to accelerate to a mountain of technical debt.
  • Self-organizing teams need architecture standards and a very lightweight process to review when exceptions are warranted. 
  • Aspects of agile practices such as roles and responsibilities, KPIs and their dashboards/reports, and agile planning practices require standards.
  • If your organization is also maturing devops and SRE, then setting guidelines on roles, practice intersections, goals, and cultural values across agile, devops, and SRE is essential.
  • Whether you're practicing continuous deployment or other release management practices, teams need some standards on testing, documentation, terminology, communication, and other release protocols. 
Most importantly: CIO and IT leaders must recognize is that where there are no standards, then agile teams should self-organize and solution for what works for their teams. When leaders find something that works, then help other teams succeed with them by drafting standards. It's these principles and behaviors that enable the agile enterprise. 

2. Balance work on innovation, technical debt, and business drivers

Balancing technical debt, innovation, and business drivers
Almost five years ago, I wrote on how to get an agile product to pay off technical debt. Here's a spoiler; most product owners don't invest enough priority to address technical debt. They won't make it a priority without guidelines, governance, incentive, or whatever CIO and IT leaders put in place to make sure it happens.

The work on innovation can suffer a similar fate, especially when product owners feel overwhelmed with requirements and deadlines from internal stakeholders. 

CIO and IT leaders have to counterbalance these tendencies and ensure teams capture and manage technical debt. If there isn't sufficient innovation work being prioritized, then they should sponsor the agile spikes that deliver proof of concepts. Another leadership responsibility is to free up time and money that can be reapplied to innovation.

Without leadership driving work on innovation and technical debt, it just doesn't happen.

3. Demonstrate and Market Returns on Platform and Process Investments

When IT practices are broken, legacy systems are impacting business operations significantly, or when the organizations are void of digital capabilities, then smart CIOs and CDOs can often (but not easily) make a business case to drive transformation and change.

Whether stated directly or not, there is a  honeymoon period of instrumenting the change. Eventually, the Board and business executives expect a new digital IT operating model to demonstrate wins, success, and ideally growth and business operational efficiencies. 

But we know that digital transformation, organizational change, and platform investments are all journeys. Initial investments in money, time, talent, and technology should drive an initial step up, but it takes ongoing, agile, and iterative improvements to truly deliver value.

That's where CIO and IT leaders must step up and demonstrate, communicate, and market where the investments are making impacts. 

It may not show up in ROI, growth, or bottom-line improvement right away, but there should be improvements in areas such as team happiness, productivity, quality, reliability, data capabilities, and customer experience sooner.

Without CIO and IT leaders taking on this critical responsibility, transforming to an agile organization and maturing digital programs will fall short of the vision and promise.

What's your plan to drive agile transformation? Please reach out to me if you'd like to discuss!

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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.