Told “No” to Technical Transformation – What’s Next

By Published On: January 3, 2023

‘No’ isn’t the end of the responsibility when a CTO sees the risk to the business.

The leadership team at Southwest Airlines will get undressed by Investors, Customers, and the Government. They deserve scrutiny. However, the leadership team will need answers to complex questions. Those answers started when the Chief Technology Officer was more than likely told no for the 100th time to upgrade the antiquated scheduling system.

Tim Crawford, CIO Advisor at Avoa, wrote a great post detailing six considerations for making difficult decisions. We’ve all been in that situation. Business leaders frequently face an uncomfortable position to extend the status quo to avoid disruption to the business. You can follow Tim’s advice to a ‘T’ and still go before Congress. In the case of SWA, I’m not exaggerating. How do you prepare for such an event? You start at the point of the business decision.

Experts in Risk Mitigation

One of the primary responsibilities of enterprise IT is to mitigate risk. Yes, technology teams suggested the best way to modernize IT systems. Sometimes, that’s not an acceptable path, given the current state. However, the CTO is on the hook for the risk. Disaster is only a nationwide snowstorm or pandemic away. What’s worse than realizing the risk is not having a detailed plan during and after the event. Here’s a list of 3 considerations to prepare for the worse case.

How did this happen?

You will get asked what seems like an obvious question. You already built the risk model when you submitted the project. You want to dedicate as many resources as possible to filling the gap in the Root Cause Analysis. The chances are things went worse than you predicted. Understand the contributing factors.

If you are in a regulated industry, you want to prioritize this activity. Regulators will feel pressured to know why this happened. Bring in external resources familiar with regulators, even if only to tell the story you uncovered. Optics matter. Take notes for the next audit; it will be intense.

How long will it take to transform?

Here’s something that needs to occur when being told ‘no.’ Great CTOs are forward thinkers. Prototyping and proof of concepts help smart CTOs get the detailed information necessary when ‘Yes’ comes in the form of an industry-defining event. Technology leaders need well-thought-out options and a solid time frame and cost estimate for the technology side of the changes.

Who are your partners?

Getting to the solution in a given industry requires partnership. We are as familiar with transportation regulations as we are with Financial and Healthcare. However, many of the same stakeholders exist internally and externally.

Successful transformation requires industry-wide participation and debate. CTO must feel enabled to engage with peers, vendors, and regulators. More importantly, CTOs need the involvement of the line of business.

Putting it all together

A simple example is remote work. A commonly held position, the technology, and culture for remote work weren’t in place for years. In 2010, I ran a pilot for virtual town hall meetings across a federal organization. While the overall government culture was a hard “no” for remote work, we piloted the idea with smaller willing groups within the agency.

We had many points of pain that included culture and technology. We had a mismatch of expectations we needed to smooth out. We held meetings of minds with the users, IT vendors, internal compliance, and IT leaders. Fast-forward to 2020, the agency possessed the people, processes, and technology to implement agency-wide remote work successfully. Ask me about the remote desktop and VDI pilots we ran.

What are some of the techniques you’ve used to mitigate similar risks?


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