How to Survive a Software Selection Project When Your Boss Is a Sociopath

  • Written By: David Clark
  • Published: August 31 2011

Is your boss the main reason you call in sick on Monday mornings? Do you need to “manage” your boss in order to get any work done? Do you find yourself in the position of having to defend your boss when talking to colleagues?

Hello, your boss might be a sociopath. This may or may not be news to you.

Time for a quick quiz. I am going to refer to your boss as “he,” but sociopathic tendencies are an equal-opportunity affliction, as you may know.

Your Sociopathic Boss and You: The Red Flags

  • Does your boss complain about not getting the credit/salary/corner office he deserves?

  • Does your boss respond badly to change?

  • Does your boss behave sadistically toward you or others?

  • Does your boss appear to be paranoid?

  • Does your boss appear to be under the impression that everything revolves around him?

  • Does your boss often give you contradictory instructions/mixed signals that make it impossible for you to execute your tasks?

If you answered “yes” to one or more of these questions, your boss is possibly whacked. I feel for you. I have been there, done that, bought the straitjacket.

In the context of a normal working environment, working for a sociopath is painful, but not necessarily out of the ordinary. Corporations in particular are notorious for rewarding sociopathic behavior (see also: Financial Crisis of 2007-2010).

But in the context of a software selection project, which is the kind of beast that strains your sanity to the breaking point at the best of times, you’re going to need to visit your happy place early and often.

So here are 5 tips on how to survive your sociopath boss when you’re managing a software selection project.

Tip #1: Surviving the Paranoia
Is your boss convinced that your software selection project is going to make him look bad? Retain a fair, accurate, and auditable trail of all work up to and including to your software selection. TEC’s best-practice selection methodology recommends developing a report (including graphs, data, and charts) that demonstrates full proof of due diligence, as well as an audit trail.

This serves not only to justify the decision to your sociopath boss, but also as a reference in the event that disqualified (and also possibly equally sociopathic) vendors lodge protests concerning the selection process.

Tip #2: Surviving the Narcissism
Is your boss making himself and/or his department the focus of your selection project? A successful project will inevitably hang on how successfully you gather requirements company-wide, building consensus among all stakeholders by conducting some form of business process modeling (BPM).

BPM is a model or description of how a company conducts its business—the key word being company. BPM is a prerequisite for any internal process improvement, and can help businesses develop a list of requirements in order to select the software solution that is right for them.

Tip #3: Surviving the Mixed Signals
If you’re managing a software selection project, you can minimize your boss’s disruptive mixed signals by sticking closely to six important principles:

  • Designate a project champion or subject-matter expert (SME) to collect process data and fill out your BPM template (see sample model below).

  • Keep your mind focused on the processes being addressed by the software you’re evaluating.

  • Do not report unrelated processes.

  • Do not report complaints.

  • Do not try to fix a process that is not broken.

  • Do not express your “to be” processes without first assessing your “as is” processes.

Tip #4: Surviving the Sadism
Any sadist worth his salt will suggest that you use Excel to compare software. That’s just sicko behavior at its worst, man.

Realistically, you can’t use Excel to accurately compare how multiple solutions stack up side-by-side to handle multiple thousands of your organization’s required software features and functions. Use a decision support system (DSS) instead.

Tip #5: Surviving the Control Issues
Nobody likes change, especially change that makes them feel that they are losing control of their environment. This is especially true for your sociopathic boss. That’s why you need to ensure that control of your project is firmly wrested from your boss’s hands.

The truth is, the type of organizational change brought about by a new enterprise software system is going to turn most of your colleagues into sociopaths for a little while.

Your strategy should be to secure executive sponsorship of the project. Executives can eliminate many problems simply by involving themselves at the appropriate points in the process. Executive sponsorship also provides the selection and implementation process with the necessary leadership to successfully drive the implementation, weed out resistance, and place control of the project in your hands, which is where it belongs.


With all these sociopaths around, you may want to try sanity instead. TEC Advisor is calm, rational, and informative. It’s a software selection DSS that gives you free, detailed software comparisons based on your company’s profile.

Look, we all know that working with people can sometimes be a little, uh, challenging. So I give you my most valuable tip for dealing with annoyances in your workplace:

Denial. It works for me. How about you?

This blog post was conceived, written, and edited in an atmosphere of serene tranquility*, with input from a group of unflappable* writers, consultants, and editors, all of whom are in the habit of liberally sprinkling their e-mails with happy faces, LOLs, and I-wuv-yous*.

*not necessarily true all of the time

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