Courtney Abbott's Key Ideas from Red Teaming
by Bryce G. Hoffman

Good leaders know that there is nothing intrinsically wrong with conflict. 

Dealing with conflict lies at the heart of managing any business. As a result, confrontation—facing issues about which there is disagreement—can be avoided only at the manager’s peril. The issue can be put off, it can be allowed to fester for a long time, it can be smoothed over or swept under some rug. But it is not going to disappear.

Conflicts must be resolved if the organization is to go forward. Constructive confrontation accelerates problem-solving.

In a business setting, a red team will be most effective when it reports directly to the CEO and enjoys his or her full support. In practice, that will not always be possible. Red teams can still be effective when they report to the head of a department or division, as long as their scope is limited to those areas. If the red team tries to tackle problems outside of those areas, it is bound to find itself in conflict with other senior executives.

Even when red team members conduct themselves blamelessly, it can still be a challenge to get the entire organization to embrace red teaming and take the red team’s recommendations to heart. In the military, resistance to red teaming has come largely from officers who do not fully understand what red teaming is or why it is necessary. Once they are briefed on red teaming, that resistance usually dissipates.

Successful units also tend to resist red teaming. They think that because they have been successful in the past, they know what it takes to be successful in the future.

It is counterproductive for a red team to analyze every decision an organization makes. Constant red teaming can be stressful and demoralizing for employees who have their every move questioned and challenged. That is not the point of red teaming, nor is it an effective use of red teams.

A red team should be used strategically and selectively. It should be brought in to analyze important decisions, major deals, and overarching strategies. It should be called on when problems cannot be satisfactorily solved through regular means.

A Red team cannot become a routine and should always challenge itself. It should always encourage its members to voice different perspectives and conflicting views.

Mixing up the way the team uses those tools and techniques is also a good idea. If you approach every problem the same way, you run the risk of making red teaming a bureaucratic exercise rather than the game-changing tool it should be. In addition, using the same methods over and over again can yield red teaming reports that read remarkably similar to one another, making them easier to ignore.

A Red Team that is always wrong will never be taken seriously. Its warnings will be ignored. Its reports will go unread. Its members will lose their credibility. For that reason, red teams do need to pay attention to their track record and make sure that they hit the ball out of the park, at least occasionally.

If the Red Team misunderstands the problem it was asked to solve, recommends actions that have already proven unsuccessful, or suggests alternatives that are ethically, legally, or financially impossible, it will lose its credibility.

Many companies like simple solutions that do not require too much effort to implement. They prefer short-term fixes that offer immediate results, even if they do little to address the underlying problem. They are less interested in long-term solutions that require a coordinated effort to implement and that often take time to move the needle in a big way.

The Red team is not to be given up, as the easy way out usually leads back in.

Red teaming is all about rigorous questioning and thinking unconventionally. Red teams consist of people who’ve proven to be contrarian thinkers. 

These are the three phases of a typical red teaming exercise:

• Using analytical tools to question the arguments and assumptions that too often go unquestioned.
• Using imaginative techniques to figure out what could go wrong – and what could go right – with the plan, in order to expose hidden threats and missed opportunities.
• Applying contrarian thinking to challenge the plan and force the organisation to consider alternative perspectives.

• Restating a problem and re-examining the same.
• Encouraging writing the problem and the solution(s).
• Dissecting an argument, which involves asking a number of questions of any argument that is used to justify a particular course of action, or that is offered as an explanation for a problem.
• Checking key assumptions and re-examining the obvious.