What are some common pitfalls of transformation initiatives?

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Board Member in Healthcare and Biotech, 1,001 - 5,000 employees
You have to choose your battles carefully. You have to make sure the technology meshes with what you have, and is able to work within the cultural boundaries of your organization. That is one point that some CIOs don't get right: They push a solution because it sounds great. It looks lovely on the resume and you get published in CIO magazines but then it doesn't necessarily deliver.
CEO in Services (non-Government), Self-employed
There is a massive disconnect between the vision of the C-suite and the shop floor worker who has to execute. The software vendors that think, “I'll hit the global supply chain because that's where the money is for IT,” fail repeatedly. And I've watched it happen. I've also helped it fail by not warning the business, “You're in over your head. You're getting sold a bill of goods. This will never work the way you think it will and it's going to cost you 40% upcharge and implementation after the fact so be prepared.”

I've seen a lot of epic fails in my career, the most notorious of which is still when we were deploying SAP in 25 organizations around the world. It was a new upgrade. We had SWAT teams and carefully architected models that were literally copy and paste from instance to instance, bringing a lot of business systems together—enterprise resource planning (ERP), manufacturing execution systems (MES), product lifecycle management (PLM), etc. It got so bad that I had one of the team members on one of the SWAT teams jump off a building because the pressure was so great. As an enterprise CIO, that is a situation that you never forget; you carry that with you as a vendor as well to make sure that something like that will never happen because of the pressure.
CIO and Startup Advisor in Software, 10,001+ employees
When the business wants a piece of software or technology to do something like online banking, they don't realize that you can't have online banking as a technology thing and that transformation takes a long time because it's a cultural change as well - both internally and to your customers. And that's a constant. 
Our roles haven't changed; transformation is what we've been doing forever. What we are actually responsible for may have changed, but ultimately the big pitfall is when we don’t do enough as technology leaders to explain that a big bang change is not going to happen effectively until we are doing things holistically. We need to spend time educating, level setting and raising awareness about critical success factors, and focus less on the tangible tech product. 

The business wants velocity changes and agility, but you can't change what you can't even measure today. They want to get this piece of software implemented in order to move fast but Agile is not a tool, just like DevOps is not a tool. It's a culture. How do we transition into servant leadership?
2 2 Replies
Director of IT in Software, 1,001 - 5,000 employees

The CEO and the tone of the culture they set really determines how you can operate and influence inside of the organization.

Board Member in Healthcare and Biotech, 1,001 - 5,000 employees

Culture eats strategy. I’ve seen vested interests within business and IT that were equally responsible for being bottlenecks.

CEO in Software, 11 - 50 employees
Digital transformation is as much about culture as it is technology. It's as much about vision as it is efficiency, etc.. 

You can apply all the technology you want, but if you don't have a culture to match, it will fail. Culture is driven by the CEO first. Nothing written in policy or on brochures will create culture. The games you put in the break room or the free lunch won't do it, the CEO has to walk the walk and talk the talk, as they say. This is the single biggest failure area in my opinion.

Vision for what the company is trying to become (as an on-going entity, not a point in time destination) is critical to applying focus and alignment. That vision needs to be driven by the CEO as well.  This is a very common failure area. The CEO might create the right culture, but it doesn't mean s/he can articulate an appropriate vision. 

Can you imagine telling a small group of engineers, let's build a car and having each engineer work on their discrete portion of this car. Then not telling them what you expected from the car when it was ready. Every engineer might create the best solution for the car they think is being built, but in the end the car will perform poorly and inefficiently, not to mention be ugly as sin if it runs at all.

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