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A trusted friend and mentor recently told me a story about a highly successful, aging executive who had the wisdom (and humility) to set up a small group of people to advise him. He assembled this team to help him with big decisions—in and out of the office. Their mission was to tell him the absolute truth—even when it wasn’t necessarily what he wanted to hear.

He set it all up while he was 100% capable and completely competent to make his own decisions. He knew he would not always have the desire or the perspective to make the right calls—especially if the decisions were highly personal like when to turn over the leadership of his family business to the next generation or even when to stop driving.

This “brutal-truth team” helped him make these kinds of hard calls—especially when it was time to give up something that was extremely important to him.

A trusted team of truthtellers is a good idea for all of us—no matter our age or position or status.

Years ago, I worked with a young CEO of a start-up technology company. He was a typical entrepreneur: self-motivated with lots of grit, willing to work long hours and humble enough to do whatever it took to get a job done. But over time, I watched him change; he developed a large and unhealthy ego, and he was always bragging about his abilities and success. It didn’t take long for this hubris to cause a falling out between him and his investor, and eventually, the investor replaced him. The company has been wildly successful, but the former CEO never achieved the level of success he once enjoyed. It’s a classic example of pride before a fall. A brutal-truth team might have prevented his self-destruction.

Here are some tips for picking your own team of truthtellers:

  1. Select wisely. Who you select is vitally important. I suggest not choosing anyone on your leadership team or your friends. Co-workers might not be able to offer authentic feedback for fear of being marginalized or fired. Advice from friends can often come across as criticism. Do select a small group of people you respect and absolutely trust.
  2. Meet before you need to make tough decisions. Start meeting when there are no big, life-changing decisions to be made. Get comfortable with your team and their feedback. (I refer to this as “getting comfortable with being uncomfortable.”) Don’t wait until it is time to make a big life or work decision to begin meeting. That looks more like an intervention instead of an opportunity for valuable feedback and growth.  
  3. Empathy has a place on this team. By setting up a “brutal-truth team,” you clearly understand that uncomfortable or unwelcome change is coming. There should be a sense of empathy in your group. Your team should understand just how difficult some of these decisions might be for you. Most people who set up these kinds of teams are used to being in control and possessing power. Relinquishing that is sometimes like letting go of who you are as a person.
  4. Incorporate accountability. When you first meet, establish a model of accountability for implementing decisions. Include markers and deadlines. Consider whatever will be coming next and have a roadmap to guide your decision making—”if this, then that.” As difficult or painful as it is to hear that you need to make a tough decision, implementing that decision is likely even harder. Your team should not resort to stalling techniques. If change is needed (and clearly indicated by the roadmap you have in place), then that change needs to happen.
  5. Have a process for working through vulnerability. However much thought you put into choosing your team of truthtellers, there might come a time when you don’t (really don’t) want to follow their advice. You might not think it’s time to give up the keys to your car or transition your leadership role to the next generation or hear that your pride might lead to a tragic fall. Make sure you surround yourself with people who understand you, who truly have your best interests at heart and who will take the time to work through these changes alongside you. Have a process for addressing any vulnerability. At some difficult point, you might even want to dissolve the group, but before you do, remember exactly why you chose them to be your truthful advisors in the first place.

These are just a few things to consider when establishing a team of truthtellers to save you from yourself no matter your situation in life. Do this correctly and thoughtfully, and you will continue to do what you do better.