
Rinse, Repeat, But Don’t Try – The Playbook of the Repeat Offenders
Pattern recognition is critical in software delivery. In some environments, implementation is a breeze. The culture, the executive support, the lack of politics, and the technical ability all favor a successful implementation. Those environments are incredibly rare, but when you get a chance to implement in these environments – it’s like falling in love. It’s breathtaking because the sky (aka budget and time) is the limit.
In other environments, it’s less about where you can go and more about where you can start. In other words, the end is so far away that the task is really to start. In consulting circles, challenging implementation environments are pretty easy to recognize because they have clear warning signs. These are the Just Start Organizations.

One subset of these “Just Start” environments is the Repeat Offenders group. These Repeat Offenders are large organizations where money is not the issue, but the direction, sponsorship, and risk tolerance are lacking. So instead of looking inward, they consistently lash outward – firing whomever they wish because they can. And then hopping back on the implementation hamster wheel only to fail again and fire the messenger…again.
In Daniel Kahneman’s book Thinking, Fast and Slow, he tells the story of psychopathic charm in medical clinics. One of his professors said, “You will from time to time meet a patient who shared a disturbing tale of multiple mistakes in his previous treatment. He has been seen by several clinicians, and all failed him. The patient can lucidly describe how his therapists misunderstood him, but he has quickly perceived that you are different.”
Mr. Kahneman then talks about how those patients should never be seen because of clear psychopathic tendencies. But, again, the research supports this conclusion.
As a software implementer, you walk into an organization and are welcomed as a savior after several other failed implementations – you should probably have the same concerns—especially when you look at the end-users, who look like they’ve been through the wringer. So I wouldn’t necessarily say “Run,” but you should proceed cautiously. These customers tend to eat through implementation consultants, and you should know that an escalation is likely coming. And yes, Organizations can be psychopathic, too, like the Repeat Offender group.
If you have a choice, the best way to handle this is to document everything. You know that this customer will likely take advantage of any misstep, regardless of who caused it. Documentation will save you from being toxic fodder in the unhealthy patterns of some customers. In addition to documenting, you’ll want to extend discovery to include past failed implementation attempts by talking to the end users. Once you know what they’ve been through, you will likely understand where to start.
If you are one of the organizations where you find yourself in this cycle of trying a significant change only to fire the Partner Organization attempting to help you – read these articles on Partnerships and Executive support.
I fully recognize that this may come off as a tad bit draconian. I don’t mean to imply that every Organization or every person within an Organization is psychopathic. That would be hell. No, I mean that some Organizations and some people within Organizations may have unhealthy patterns that are unbeknownst to them.