#cloudchat Recap: IT Transformation Pitfalls


#cloudchat Recap: IT Transformation Pitfalls

IT transformation is no easy task – there will be landmines and pitfalls along the journey. Our group of outstanding #cloudchat experts tackled this topic last Thursday and provided some invaluable information to help call attention to some of the things to avoid.

Curious about what a #cloudchat is? Read our intro post.

Our team of expert Rackers in the chat included Rackspace CTO John Engates, Senior Director of Professional Services Jaret Chiles and our cloud evangelists Kent Kingery and Eric Johnson. They were joined by long-time “cloud chatters” including Cybric’s mike d. kail, Bluelock’s Diana Nolting, Arbela Tech’s Tim Harris and Microsoft evangelist Aaron Wislang, who provided a ton of insight into some of the gotchas of IT transformation. The group discussed the following questions:

  • What’s the #1 most overlooked challenge when it comes to transforming IT?
  • What’s a red flag that your entire IT transformation project is going off the rails?
  • What are the biggest dangers around workload migrations while implementing a large IT transformation project?
  • What are the biggest dangers around security while implementing a large IT transformation project?
  • How can IT leaders handle setbacks during an IT transformation project?
  • How do you make sure you don’t regret your technology or service provider selections?

Early on, the team identified the human element as one of the most overlooked challenges when it comes to IT transformation. CIO strategic adviser Tim Crawford noted that it “requires intimate knowledge of your business first. Not technology.”


Racker Kent Kingery pointed out the importance of executive sponsorship and that it can’t just be passé acceptance but “actual energized engagement with the process.”


When it comes to red flags for your transformation project, both Rackspace CTO John Engates and Arbela Tech’s Tim Harris pointed out that you’re in particular trouble when the executive sponsorship starts to wane:



But the biggest takeaway from the chat is that there will often be bumps in the road when it comes to large scale improvements. The group felt that it was imperative for the leadership team to own the problems. mike d. kail said that leaders should, “Own the setback, communicate the failure and the plan forward, be resilient.”


While cloud developer advocate Aaron of Microsoft said that it was key to have “blameless postmortems” as a way to really understand what went awry.


We know that IT transformation can be difficult, but we have the experts at Rackspace who know the gotchas and pitfalls to avoid. We’d love to be your partner as you embark on your own transformation journey.

If you’re curious about some of the other answers that appeared in the #cloudchat, explore our Twitter Moment below. And be sure to join the next #cloudchat on Sept. 7 at 11 a.m. CST, where we’ll be looking at some of the IT transformation war stories — hope to see you there!