Planning Digital Transformation Initiatives When There are Too Many Priorities

Let's recap 2020 without losing our minds.

We went into the year with high aspirations around our digital transformation programs and all the places we wanted our organizations to succeed with experiences, analytics, and technology.

Driving Digital Transformation - Isaac Sacolick

Then COVID hit, and we switched gears to support business continuity, employee safety, and remote working. Along the journey, I recommended that organizational leaders consider offensive and defensive priorities to respond to changing events, but that digital transformation remains vitally important. In some cases, I recommended hard strategic pivots when required and shared seven steps to communicating major changes in digital transformation programs.

Focus Digital Transformation on Big Initiatives that Matter 

But in this post, I'd like to go back to basics. At the end of last year, I wrote the one transformational priority CIO must prioritize in 2020. Here was the primary recommendation I shared:

"The answer to the most important thing to prioritize is to help the organization understand how to prioritize one goal. That’s right – one goal." - Isaac Sacolick

So how did your organization fair? Sign up for too many?

Most organizations fail miserably at it. They can't prioritize, sequence, or say no when it makes business sense. They bastardize the meaning of agile by believing they can plan, prioritize, and assign teams along the way. That does work to some extent, but when an organization of four hundred is asked to commit to forty initiatives, I know they have a lot of work ahead of them. Instead of going full steam ahead on the few things that truly matter, they'll be revisiting this discussion on priorities every month as the PMO scorecard shows a sea of red.

Charter One Big Initiative Before Planning the Next Ones

That's why I advise organizations to start with one. Define the objectives well, get alignment across the organization around responsibilities, and kick off an agile process. Ensure that top priority has the leadership, teams, people, and resources it needs to succeed. THEN go on to discuss the next one.

More on this in the video below on Episode 13 of 5 Minutes with @NYIke

I know it's August and your mind is at the beach. But let's reflect on what needs to happen heading into the 2021 planning season.

Updated: Check out this more recent post on The Elephant in the Room.

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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.