Six Questions Leaders Should Ask Their Teams to Start the Conversation

  1. What has been the most difficult part of this experience?

This is a tough place to start, but gives permission for a person to name the toughest aspect of their distress. The invitation alone is saturated in empathy. But the real magic is in the clarifying power of identifying the greatest source of the adversity for what it is. Converting sentiment into language begets self-awareness, which is the first step in becoming resilient.

  1. How are you taking care of yourself? Is it enough?

Solution statements work well but only some of the time. Perhaps if you are the turnaround consultant or politician running for office. But when it comes to handling adversity and the stress that comes with it everyone’s situation is incredibly unique. Your self-prescribed solutions will likely miss the mark.

Simply asking “are you taking care of yourself?” is great encouragement. Asking “how” opens the dialogue. Then tacking on “is it enough?” gives permission to make the required effort a top priority.

  1. How can we better recognize when a teammate is struggling?

Resilience is a team sport. The worst thing any of us can do is struggle alone in silence. When leaders attempt to shoulder the load as an example of strength, the team follows suit to everyone’s detriment. In fact, the best thing a leader can do is admit some of their own challenges as it normalizes the experiences of the team.

Because many of us have become so adept at hiding our inner battles under the guise of mental toughness, this question challenges our natural instinct as leaders. It encourages openness while also soliciting team support. The true mark of a resilient team is when team members proactively support one another.

  1. What personal contribution makes you the proudest?

The word “contribution” relates directly to our individual sense of purpose. Purpose may be the most powerful force for overcoming adversity, because it provides meaning and significance despite the struggle. The core of any effective purpose is the opportunity to serve others.

We all have a contribution to make. When times are tough, put purpose front and center. It can fuel each person’s recovery.

  1. Who have you been able to support through this?

Can you be a wounded healer? Perhaps the best leaders are just that.

There is a story of a hiker who became stuck in a wilderness blizzard. As he hurried to make his way back, he encountered another man who had nearly succumbed to the cold. Despite his urgency to escape the worsening conditions, the hiker stopped to rub the feeling back into the man’s legs and feet until they were both able to return to safety.

The health professionals said afterward that had the hiker pressed on without stopping, both men would have perished alone in the elements. The hiker needed a break and a chance to reset his own blood flow just as badly as the compromised man needed assistance. In reality, the two men saved each other.

Just because a person is struggling doesn’t disqualify them from helping others in fact, it may qualify them all the more. If you are leading with a limp, you may be just the leader your team needs.

  1. How can I support you?

This may be my favorite leadership question of all-time. Leaders set the example. They go first. They provide backup. Don’t make your team wonder, “Will my leader support me?” Set the tone from upfront, especially in times of adversity.

If you have picked up on the theme of “togetherness” through these questions, you have been paying attention! The only way teams make it through challenging times is together.


Sandy Chernoff
Sandy Chernoff
SANDY'S 30 years of didactic and clinical teaching in study clubs and continuing dental education, coupled with her almost 40 years of Dental Hygiene practice bring a wealth of experience to her interactive soft skills workshops. With her education background she easily customizes interactive sessions to suit the specific needs of her clients. Her energetic and humorous presentation style has entertained and informed audiences from Victoria to New York City. Sandy’s client list includes law firms, teaching institutions, volunteer and professional organizations and conferences, businesses, and individuals. Her newest project is turning her live workshops into e-learning programs using an LMS platform. Her teaching and education background have helped her to produce meaningful and somewhat interactive courses for the learners wanting the convenience of e-learning options. As the author of 5 Secrets to Effective Communication, Sandy has demonstrated her ability to demystify the complexities of communication so that the reader can learn better strategies and approaches which will greatly improve their communication skills and ultimately reduce conflict, resentment, disappointment, complaining, and confusion. As a result, the reader will be able to increase productivity, efficiency and creativity, improve all the relationships in their lives and ultimately enjoy a happier, healthier existence! Sandy blogs regularly on her two websites on the various soft skills topics that are featured in her workshops and e-learning programs.

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