IT Turnaround: Know these 15 Signs + 15 Tactics to Transform From Floundering to Winning Departments

“Look at your company as if it were your first day on the job. What would your first impressions be of how your business is operating?”

That’s my opening statement to Chapter 1 of Driving Digital, which is just as relevant to CIOs and IT leaders when considering a technology department’s performance. I read this statement to kick off a recent Coffee with Digital Trailblazers, where we discussed IT turnarounds, telltale signs of underperforming departments, and the tactics Digital Trailblazers take to turn them around.

IT Turnaround: 15 Signs, 15 Tactics to Transform

15 Signs IT Needs Improvement 

I reminded everyone that there are many shades of grey between failing and winning departments, but in IT, there are many signs that the department requires improvements. Here’s a short list of signs that we discussed:

  1. Systems are down, especially if there are repeats of the same or similar issues
  2. Manual workarounds with no firm plans to improve, automate, or upgrade workflow
  3. Buzz around the company: IT is not serving their needs, and employees work with outdated tech
  4. Complaints about IT are way more frequent than anyone praising IT for good service
  5. Viewed as a back office function, a necessary evil, or only a cost center
  6. IT leaders are repetitively resetting expectations with stakeholders and delaying timelines
  7. Working on “IT projects” or “infrastructure projects” with no clear business partnerships
  8. Poor retention, little/no training budget, or missed performance objectives
  9. Undefined roles and responsibilities, especially at the leadership level
  10. No KPIs/OKRs, or too many of them, or are misaligned with business outcomes
  11. Agile teams aren’t making regular, high-quality releases on schedule
  12. More work centers on defects and technical debt than on business priorities or innovation
  13. DevOps is still dev versus ops, and with security lagging even further behind
  14. IT reports to the CFO and fights uphill battles for innovation and longer-term investments
  15. The CEO doesn’t “get” IT, or conversely, gets it too much and tries to micromanage

15 Tactics to Drive an IT Turnaround

We could have gone on with the list, but I wanted to transition and discuss solutions. Below are some tactics recommended by the Coffee Hour’s Digital Trailblazers of experienced CIOs and transformation leaders.

  1. Ask IT employees, “Are you happy?” Find the signs of morale issues that underpin floundering departments.
  2. Apply the theory of small successes and champion quick wins.
  3. Synchronize innovation efforts with serving business needs, even for POCs and experiments.
  4. Focus on three lanes: Business of IT (day-to-day services), cyber (protecting the business), and programs targeting business outcomes.
  5. Look for overcomplications and signs of overengineering; seek simplifications, deliver faster, and apply continuous improvements.
  6. Find the big rock – the big problem that more people in IT can focus on and that business leaders recognize its importance.
  7. Build courage to stand up for the team and confront detractors who blame IT.
  8. Recognize that the highest priority may not be the biggest fire or today’s operational issue.
  9. Avoid blaming the outsourcer, vendors, and contractors – improve partnerships or exit the relationship.
  10. Empathize to learn the business and customer perspective around IT issues or missed opportunities.
  11. Identify what’s blocking agile development teams and help remove the obstacles.
  12. Convey and set high but realistic expectations with IT teams and employees.
  13. Shift from waterfall project management to product management and agile programs.
  14. Communicate the department’s vision (CIO), top programs (product and delivery managers),  and IT services. Explain the who and the why in vision statements.
  15. Use your initiative and escape “stay in lane” thinking that stymies innovation and transformation.

The key for Digital Trailblazers is recognizing that winning departments prioritize continuous improvements.

Thank you, Joanne Friedman, Joe Puglisi, and Martin Davis, for your contributions!

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,, 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.