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Tame the Familiarity Beast: Become Your Own Devil's Advocate

Risk and novelty can get us into trouble, but the power of the familiar might be even more dangerous.

That's because what we are used to goes down easily. Familiarity offers security and a sense of control. There are no new steps to take, no difficult questions, few, if any, obstacles. Life is good – until it's not.

Ease, in any facet of life, can blind us to possible hazards. It also presents no challenges, no new thinking, no creativity. Clinging to familiarity, we become stuck. We lose our ability to adapt to change, to see new opportunities, to grow.

The Familiarity Beast prevents us from seeing the danger in doing things the easy way. I propose confronting the danger by developing your own Devil's Advocate.

Are You Stuck in Familiarity?

Leaders who see the danger of familiarity – and many do not – find themselves on the lookout for the staleness it produces: a marriage that's getting tired, a leadership team that's productive but not innovative, the familiar rut of providing for your kids without engaging their independent thinking.

Most importantly, staleness stops the search for meaning. The power of the familiar leads people to stay in jobs too long, become blind to silver linings, take for granted the privileges and treasured relationships that are right in front of their noses.

How can we combat this powerful drive to cling to the known? Become your own Devil's Advocate. Think, speak and do the opposite. Go the other way, and see what happens.

Activate Your Devil's Advocate

This will take effort, and plenty of courage. It won't always be comfortable to moderate an opinion, shift a habit, or embrace what you've always avoided.

But take heart. Your own Devil's Advocate can be activated in lots of ways:

You might start by intentionally inserting yourself into an uncomfortable situation and look for something intriguing there. Buddhist author and teacher Pema Chodron advises, "Go to the places that scare you."

A woman I know and respect has spent the past year attending religious services with a variety of faith traditions. She reported: "I'm puncturing my ignorance, one service at a time."

Or, you might start in the workplace. Ask your team what they're most afraid of taking on or facing – in their work and in their lives.

The "natural" instinct is to avoid fear and discomfort. It takes wisdom and guts to walk directly into a feared reality.

For example, what would it take to get more comfortable with morality, to engage with the person you want nothing to do with, to accept an offer that you know will stretch you, to usher your child into a genuinely different setting?

In the same vein, have conversations you don't want to have. Break the icy silence between you and a cut off member of the family by reaching out. Invite to lunch the biggest prima donna in your workplace, and try to discover what this person might be up against. Raise the topic of succession in your family business. While you're at it, discuss compensation.

Consider trying a different behavior in a familiar setting. My son offered a novel kind of blessing before an extended family meal. It was out-of-the-blue and not the usual rote grace. Some people liked it, others were confused. The discombobulation proved good for discussion and got us thinking.

Make Your Devil's Advocate Work for You

Once you have energized the Devil's Advocate within you, you are ready to put this powerful inner ally to work in the office and at home. Here are a few more ideas to get you started:

Manage confusion, anger, depression and mistakes by viewing feelings and miscues as information.

If you tend to say yes automatically to invitations and opportunities, try saying no, and see what happens. If you tend to say no, experiment with saying yes.

If you mostly talk, listen more, so you can learn about others. If you mostly listen, talk more, so others can get acquainted with the real you.

Consider the bias in your point of view. Wear another hat at work. Walk in someone else's shoes. Switch roles for a day.

When you want something badly, consider it's disadvantages.

When you don't like someone, question your accuracy about them.

When you think you found the person of your dreams, list the imperfections in them that you tend to overlook.

Increase objectivity about your character assets and deficits. How accurate are the stories you tell yourself, about yourself? Do you lean more toward embellishing your accomplishments, or do you tend to "sell yourself short?"

Identify the downside of widely accepted "advantages" such as attending an A-list university, winning the lottery, receiving a prestigious award, getting a promotion, quitting an addiction.

Consider the upside of widely regarded "misfortunes" such as receiving a cancer diagnosis, losing a playoff game, discovering an allergy, closing a business, becoming deaf.

There is nothing as soothing – and toxic – as a closed mind. Open your intellect by seeking out – not just tolerating – a different point of view. When you believe strongly in anything, listen intently to an opposing view "without having an accident in your pants."

Becoming your own Devil's Advocate strengthens your decision-making because it forces a different angle into your vision. It's also one of the most powerful coaching enhancements I can think of.

Too often, as leaders, we are surrounded by people who agree with us. In many instances, agreement equals avoidance. We can moderate the perils of agreement, avoidance and familiarity by becoming our own Devil's Advocate.

It's a mindset in a skill worth working at.

I would love to hear about your experiences as Devil's Advocates and invite you to include them in your comments below.

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