Working with skeptics can be painful. They consume valuable time with questions that can seem pointless. Nevertheless, the right kind of skeptics can be highly valuable, especially during project planning.
Skeptics come in two flavors: negative and loyal.Negative skeptics actually hope for failure. Their dire predictions never end. They frequently slow progress by revisiting previous decisions. They can demoralize their teammates and derail projects.
Loyal skeptics, however, are invaluable. They challenge commonly held beliefs and ask questions others avoid. (Like toddlers, their favorite question is "Why?") They help teams anticipate problems and develop contingency plans. When disagreements arise, they force debate until solutions are developed. Loyal skeptics can come from any department in the enterprise and any level on the org chart, but they are all competent, respected and objective. The best skeptics have widespread organizational creditability, and their seal of approval helps convince others of project viability.
It can be difficult to distinguish between negative and loyal skeptics. The difference often lies in their objectives and motivations. Negative skeptics criticize everything; loyal skeptics scrutinize everything. Where one is mainly interested in finding fault and pointing fingers, the other seeks to clarify and improve project planning and execution. Negative skeptics are often motivated by power or politics, loyal skeptics by a desire to reduce risk and thus help ensure project success.
Once they're comfortable with the final plan, loyal skeptics sometimes function as guard dogs, protecting the project from external disruptions. They push back against the inevitable requests for additional functionality in the middle of a project, questioning the impact of proposed changes. They will fight to defer new features in order to protect schedules and resources.
Projects that produce no benefits make organizations reluctant to invest in other IT-enabled initiatives. Skeptics often question a project's business beneficiaries closely about how they will achieve planned benefits. After the project is complete, loyal skeptics help push the organization to deliver the benefits specified in the business case.
Project managers (and other team members) often dread interacting with skeptics, and many try to keep them off their teams, fearing they will slow progress and be divisive. Some misguided organizations punish (or even fire!) skeptics for questioning aspects of important projects. At one Fortune 500 company, the QA leader on a large project asked such difficult and embarrassing questions that the project leader had her transferred off the project. Six months later, when the project's schedule and viability were in jeopardy, the company hired consultants to rescue it. The consultants' approach incorporated many of the skeptic's initial suggestions. Listening to their own insightful QA leader would have been a more effective, more timely and far cheaper solution. Bad news does not improve with age.
Don't avoid skeptics -- seek them out! Teach your team to value the contributions of loyal skeptics. Their pesky questions will save you time, money and effort down the road. It's always better to know where the potholes are so you can avoid driving over them. A loyal skeptic is an invaluable resource and a critical element of long-term project success. Who is yours?