How to Rescue an In-flight Digital Transformation Initiative

It’s fairly common for CIOs and Digital Trailblazers to be handed an inflight program that’s stalled or completely derailed.

Is the DevOps program for modernizing apps and transitioning them to the cloud taking too long? Has a business-led SaaS integration gone awry? Has a machine learning experiment gone through several iterations without any production deployments?

Rescue a Digital Transformation Initiative by Isaac Sacolick

There are plenty of examples of digital, data, and technology programs with underwhelming progress. Chances are, executives will ask you to make lemonade out of a lemon at some point in your career.

Rescuing programs isn’t easy because it requires identifying what’s impacting the team’s performance, prioritizing what needs addressing, and communicating changes to the program. These are critical steps for any program that undergoes a leadership change, but digital transformation initiatives have additional considerations.

What is a digital transformation initiative?

A digital transformation initiative is part of a strategy to evolve the business model. In Driving Digital, I offered this definition of digital transformation:

Digital transformation is not just about technology and its implementation. It’s about looking at the business strategy through the lens of technical capabilities and how that changes how you are operating and generating revenues.

A digital transformation initiative is one of several programs that aim to deliver on the transformation’s strategy. They often include releasing new products, evolving customer experiences, instrumenting competitive ways to leverage data/analytics, and enabling a future of work that leverages hyperautomation.

A digital transformation initiative often targets revenue growth, cost reductions, and culture change, so it can significantly impact business performance and morale if it’s underdelivering or failing.

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Digital transformation initiatives require experimentation, learning, missteps, and pivots. They aren’t projects with fixed timelines and scopes; they require an agile planning approach, and the initiative’s leaders must communicate realistic expectations. Organizations excelling at delivering business outcomes from these initiatives look to drive digital transformation as a core organizational competency.

Executive leaders must show patience to see if the initiative’s leaders (hopefully Digital Trailblazers) can get a digital transformation back on track, especially when there are evolutions to the initiative’s vision or significant priority changes. But if there are too many setbacks or if the business strategy changes, then there’s a strong possibility that executives will seek a leadership change.  

Four steps to rescue and turnaround a digital transformation initiative

So, if you’re a Digital Trailblazer and executives have assigned you a derailed or failing digital transformation initiative, here are several steps to consider:

1. Review why executives assigned the program to you

Consider these possibilities of how you may end up with a failing program. You may be new to the organization, and the program is part of your responsibilities, or you may be

  • Transferred to lead an initiative after its existing leader left the organization
  • Handed a program that’s been through several leadership changes but hasn’t met objectives
  • Asked to stabilize a business-led initiative that was initiated without IT’s support
  • Required to realign a product or customer-facing initiative that lacks vision or has been through several pivots
  • Assigned new responsibilities after M&A

It is important to know why executives sought a leadership change and why they selected you. Learn the issues with the previous initiative’s leaders, and identify what you’ll need to be more successful. Ask the executives for time to assess the program, and disclose that you’re likely to come back with recommendations to help you lead a successful program.

2. Assess the business objective and rewrite the vision

When I am brought in to rescue an initiative, I almost always start by creating a vision statement. Why?

Well, in my experience, most detailed or perceived failing initiatives fail because they never had one! Or if they did, it’s a multipage PowerPoint that no one understands or is outdated. And even when there’s an understood vision that just wasn’t documented, there are often disconnects between it and what the team prioritized to work on and deliver.

Want to rescue the initiative? Start by drafting a vision statement. Here’s how to get access to my vision statement template.

3. Define leadership responsibilities

Digital transformation initiatives are rarely successful with autocratic leaders and my-way-or-highway project management approaches. If you’re coming into an in-flight initiative, it forces an automatic reset of leadership responsibilities, and this requires some learning, collaborating, and partnering by the new leaders.

Keep in mind that the existing team leaders on the initiative are less likely to drive changes and often assume that a leadership change doesn’t impact them. It does. But it will require several conversations to align on responsibilities.

Digital transformation initiatives that I lead have three primary roles: sponsor, product manager, and delivery manager. I’ll publish a new Digital Transformation Initiative Charter soon, and please sign up here for early access.

4. Act as an anthropologist to find root causes

My next step is to dive deep into the program methodology, team makeup, partners, and architecture. Where possible, I meet with customers and stakeholders. I’m not spending too much time in one area as I am only seeking blocks holding back the team, issues that impact collaboration, and questions no one has asked the team before.

More often than not, I find people, collaboration, and process issues. The in-house team blames the vendors, while the vendors are quick to advise on where they think their client is at fault. No one set reasonable expectations with stakeholders, so they continue to ask for customized solutions. The organization assigned people to the program, but they are also working on many other priorities.

I find architecture issues too. I tell stories of how I had to change platforms mid-program in Digital Trailblazer, but this doesn’t happen often. It’s more likely that no one defined capacity requirements, set security expectations, or defined other non-functional requirements, so the team is spinning its wheels chasing after ill-defined objectives.

Now here’s the hardest part. Even when you find root causes, the most difficult challenge is finding the right level of communication with the different program participants. In a previous post, I shared five tips on communicating pivots in volatile digital transformations.

Turning around a digital transformation initiative isn’t easy. Please feel free to reach out to me if you want my advice.

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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.