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?

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.

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.