Red Teaming – Defining Objection Handling Strategies & More

Strategy concept, red teaming

What’s a “red team”?

On August 2nd, 1990, Saddam Hussein invaded Kuwait, and so started the “Gulf War.”

The United States and Western allies formed a “coalition of the willing” to remove the Iraqi Army from Kuwait.

A group of military planners, known as the “blue team,” set up shop in a hanger in an air base in Saudi Arabia, and created the basic plan for Operation Desert Storm in 24 hours.

This plan was passed on to another team, known as the “red team.” They were given the following instructions: “You are the Iraqi high command. You have all the known resources, materials, and manpower available to the Iraqi military. A spy has given you the alliance battle plans. You have 24 hours to prepare your response.”

The “red team” prepared their response, which was then passed back to the “blue team.” They spent another 24 hours building countermeasures and contingency plans to foil the “red team’s” responses.

The rest is history...

What’s This Got To Do With Me? I’m A Sales Guy!

Business people work on a sales strategy together


When you face your customers, there are questions you would prefer they didn’t ask.

They may relate to your product’s weaknesses. They may relate to a change in the market which affects your product’s pricing or availability. They may relate to reputational damage caused by an embarrassing lawsuit or complaints on social media.

You have two choices. You can sit and sweat and hope they don’t ask you these questions, or you can “red team” it by asking yourself what nightmare questions they can ask you.

Write these down. Go back to “blue team” mode and prepare your answers.

Your answers may not be that convincing, but at least you have something to say if they ask.

What’s This Got To Do With Me? I’m Looking For A Job!

job search, looking for a job concept


Job seekers attend interviews. Interviewers ask questions that you don’t want to answer, such as:

  • “Why did you leave your previous job?”
  • "Where do you see yourself in 5 years’ time?”
  • “Tell me about your greatest weakness/strength/mistake?”

There are others which are related to your personal situation, or to the job you are applying for.

“Red team” it by imagining you are a hostile interviewer. Think of the worst questions they can ask you.

Write them down. Go back to “blue team” mode to prepare your answers.

You may want to try these out on a friend (who can “red team” for you) and see how she reacts. If she’s not convinced, you may need to improve your answers. Better to do that before the interview.

What’s This Got To Do With Me? I’m A Student!

Students work together on a project



I was a student too, and, to be honest, not a very good one! I was interested in military history, however.

When it came to exams, I adopted the mindset of a general preparing for battle. I reviewed each subject and “red teamed” it. What was my nightmare question? Where was I weakest?

That was where I made extra effort when revising and doing practice questions.

I really am not the smartest guy in the room. I did manage to get myself a bachelor’s degree, a teaching qualification, and an MBA, so I must have done something right.

Game On!

Bullseye concept, business


Got a big sales meeting coming up? Looking forward to a challenging job interview? Studying for a professional qualification and preparing for exams?

Get into “red team” mode and anticipate your “enemy’s” worst moves.

Prepare for them.

Be ready to use them.

Let me know how you get on!

Further reading...

Before you start “red teaming,” you need a position to defend!

Here is an article I wrote on building a business case: “What’s In It For Me?” The 3-Stage Guide To Answering This Question

Here’s one on preparing a sales presentation: Sell The Hole, Not The Drill! How To Make A Successful Sales Presentation