5 Questions For Leaders to Ask Themselves



At Crafted Leadership we make the case for the art of skillful questioning. By asking themselves good questions, leaders can discover what's true for themselves and increase their self-confidence and vitality — a state we refer to as Above the Line.

Not all questions are equal in purposeful self-inquiry. Within Crafted Leadership's toolbox are a set of questions that lead people to disrupt patterns, develop new neural pathways or consider new options.


Here are five questions from our toolbox that we invite leaders to ask themselves:


1 .What’s the one leadership skill I’d like everyone in my workplace to master? This question helps you refine your leadership vision by inviting you to drill down to what’s most important to you. This is a personal reflection. Once you discover and name your priority skill for your team, you can observe how well that skill is being implemented across the organization, and decide if you want a plan for teaching that skill. For example, one of our clients realized that conflict resolution skills within his teams would be a core driver of success in his growing company. At the time, many people in his organization lacked training in how to effectively resolve conflict. Because his time was better spent on other priorities than on conflict facilitation, he hired us to teach conflict resolution to team members. As a result, his team is, in his words, “developing the skills to handle issues directly and developing themselves into better leaders.”

2. What is familiar about my actions, feelings and responses in this situation? In Groundhog Day, Bill Murray’s character is hopelessly doomed to repeat the same day, over and over, with similar results — until he faces his central repeating patterns. Once he learns what he’s meant to learn and makes some specific changes, his life progresses. We’ve noticed some central issues repeat in most organizations and with most people. Popular workplace issues include taking more or less than healthy responsibility, withholding feedback, suppressing key feelings, operating from the drama triangle, murky agreements, listening filters and lack of candor. By getting familiar with your own or your organization’s central repeating patterns, and learning a few specific practices, you can stop recycling those patterns. Insight follows experience. Crafted Leadership guides participants to hone their experience so that they 1) become aware of and recognize default patterns as they’re occuring and 2) learn skills to disrupt those patterns. Last year at one of our Lead by Design trainings, Julianna observed that a participant had a pattern of speaking over his wife. From that moment of awareness, the participant actively worked on changing his behavior for the remainder of the training. A skill we taught that assisted with this particular behavior change was the Art of the Toss, which promotes a balance of speaking and listening.

3 .What if nothing is wrong with me?

In the 2006 comedy Penelope, the main character is an heiress born with a pig’s face as a result of a curse. The movie cleverly explores Penelope’s certainty that there is something wrong with herself, and for a while she’s a victim in search of a hero like many fairy tales. But eventually, Penelope breaks the curse by learning to like herself the way she is. As she tells a group of children at the movie’s conclusion, “It’s not the power of the curse, it’s the power you give the curse.” As I was writing this blog, one of our clients let me know she’d been promoted to a major role overseeing multiple departments in multiple offices. What came up for her immediately, she emailed, were her stories about her flaws and a fear she wasn’t up to the role. “What if nothing is wrong with you and you’re actually in the exact right position?” was my reply. “How is the perspective that you’re perfect for the role true or truer than the ‘I’m flawed’ story you’re making up? Look for the evidence to support your story with the tiger in it.” “What if nothing is wrong with me?” is such a simple question, but actually quite profound in face of the crippling self-doubt many leaders feel at times. One of our mentors, psychologist Julie Colwell, asks this of people all the time in supporting them to do a turnaround and see things from a different perspective and in a more expanded state of mind she calls Creative Brain. We’ve found that this question, if honestly considered, can release people from all kinds of unhelpful stories that distort their leadership abilities.

4 .What am I wholehearted about? In his wonderful essay, 10 Questions That Have No Right to Go Away, poet and philosopher David Whyte tells the story of a time he was working at a nonprofit and felt exhausted, stressed, and at the end of his tether. He asked his friend, Brother David Steindl-Rast, a Benedictine monk, to talk about exhaustion. Steindl-Rast replied: You know," he said, "the antidote to exhaustion is not necessarily rest." "What is it then?" "The antidote to exhaustion is wholeheartedness. You're so exhausted because you can't be wholehearted at what you're doing … because your real conversation with life is through poetry." This story resonates with us because we see leaders who are exhausted, but not necessarily because they’re physically tired. Rather, they’re exhausted because they are not wholehearted about their primary work responsibilities. In our language, these leaders are operating outside their Zone of Brilliance; most of their time is spent in energy-depleting, rather than energy-generating activities. A significant portion of our work is helping leaders discern their Zone of Brilliance and supporting them to spend their majority of their time in their strengths, where they can make the greatest contribution, wholeheartedly. As one CEO shared, moving into her Zone of Brilliance was freeing, and helped her become the most effective she could be for the organization.

5. How can I drink from the deep well of things as they are? Jack Welch, the past chairman and CEO of G.E. was quoted as saying, “Face reality as it is, not as it was, or as you wish it to be.” If you can learn to see reality neutrally from a place of acceptance and simply as “what is,” rather than resisting it, you have capacity to respond to circumstances from Above the Line. In her poem Diving into the Wreck, poet Adrienne Rich offers a beautiful metaphor for facing reality, in the form of a deep sea diver exploring a shipwreck:


I came to explore the wreck … the wreck and not the story of the wreck the thing itself and not the myth


Sometimes leaders have trouble seeing reality. We support leaders to face the reality of those emotionally-charged situations they want to avoid, especially when they’re stuck. The capacity to see"the thing itself and not the myth" from an inquisitive, self-confident position is a vital life-force that leaders can draw on time and again. We approach the facing in a friendly way, first inviting clients to “drink from the well of things as they are,” as David Whyte says in his beautiful poem. One of the processes we use in support of facing reality and moving forward is F.A.C.T., a powerful tool we learned from our mentor, Katie Hendricks. Through this and other processes we teach, leaders become empowered to discover what is true, what they want and how to move forward in easy steps.




If you want to know more about our questions or processes, contact us at hello@craftedleadership.com, join a Lead by Design course, read more at craftedleadership.com or follow us on Facebook, Twitter, and LinkedIn. We’d love you to join our community of conscious leaders!

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