CIOs: Build an airplane while in flight

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Q&A With Mike Vitale, TalkPoint Chief Technology Officer


The Enterprisers Project (TEP): As a project management specialist, what are the most challenging projects you’ve headed?


Vitale: The hardest project you can take on is one where you have to replace a system that already has a user base. We like to joke at TalkPoint that these projects are like “building an airplane on top of another airplane while in flight.” A few years back, I recreated a web application from scratch. The existing system was seven years old and supporting thousands of people every day. The new system had to be faster, more secure and extremely fault tolerant while matching the existing features.

My team split up the projects into a series of releases. We launched a “just barely good enough” version of the platform about a year later and started migrating any user who only needed the limited software. From there, we worked into a rhythm where we rebuilt and redesigned software based on the largest number of users we could migrate after the release. This entire process took about two and a half years, but it was well worth it once completed. The platform is now future proof and ready to run for decades.


TEP: What’s the most difficult part of the project management process?


Vitale: Of the five project management processes [Initiating, Planning, Executing, Monitoring, and Closing] I value planning the most. Initiating a project is easy provided there is a real need, the right decision makers back the initiative and you have access to the right resources. The planning phase is where things are most at risk. If requirements aren’t clearly defined, it sets the stage for failure later on. I accept that the scope is going to change, but the initial plan needs to be thought out as thoroughly as possible.


It’s also essential that you know who all of your stakeholders are from day one. I’ve seen successfully running projects fail because a new, uninformed, player entered the game late and changed the goals. Ask experienced project managers about this type of scenario, and they will vent for an hour.


Another intangible principle I apply to project proposals is purpose. I won’t take on anything that looks like busy work. Projects run better when the project team is unified by the idea that what they are doing is going to help someone. A PMO that invents a project to fill downtime will have a group of uninspired team members going through the motions. This is a slow moving recipe for disaster.


TEP: Are there common mistakes you see over and over?


Vitale: Complex projects normally require third-party support. Failing to complete due diligence on the company, product, software, etc. providing that support will burn you every time. Never make an assumption about how something should work. Get the details in writing. Better yet, get the details from multiple vendors while you shop for the best value by putting out a Request For Proposal document.


TEP: Any projects where you wish you’d done things differently? What went wrong?


Vitale: My company recreated a mini-site for a financial services firm several years ago. We had a solid scope, deliverables and timeline. My project team was ahead of schedule and working well with the client’s internal technical team. One month before the launch date, our client’s boss suddenly appeared on a project update call and effectively rewrote several requirements. The new requirements were tough to swallow even while keeping an Agile mindset. We worked through the changes and completed the project to spec, but it was overdue by six weeks. Ultimately, the mini-site was never launched and ended up moth balled. We were paid in full for the extended project, but we felt like an artist who created a beautiful painting that was then put in a sack and stored in someone’s attic. While much of this was on our client, we failed to identify all of the stakeholders from the get go, and it bit us in the end.


TEP: What advice would you give to CIOs and other tech leaders?


Vitale: The best advice I can give to technology leaders is to make sure you have the right people in the right places. There are few folks more important than a competent project manager who understands the company’s goals, the project’s success criteria and has a clear plan on how to get there. Put your best people on your most important projects.


Mike Vitale is CTO of TalkPoint, which specializes in unified communications and webcasting.

Minda Zetlin is a business technology writer and columnist for Inc.com. She is co-author of "The Geek Gap: Why Business and Technology Professionals Don't Understand Each Other and Why They Need Each Other to Survive," as well as several other books. She lives in Snohomish, Washington.