Sales Tax Institute Book Club: Dare to Lead by Brené Brown 

Leadership is not easy. Leadership is also not picky. We all have the ability to strengthen our leadership skills and become daring leaders. Our team chose Dare to Lead by Brené Brown as our book club book this quarter. We learned new skills paired with actionable items that we can apply to the workplace. 

To be a daring leader requires vulnerability and courage – two seemingly opposite characteristics. Brown breaks down the book into four parts: “Rumbling with Vulnerability,” “Living into Our Values,” “Braving Trust,” and “Learning to Rise.” Our team was particularly intrigued by Brown’s thoughts on living into your values and how to become a daring leader. 

Living Into Your Values 

Brown delves into the significance of values and what it means to live into them. The book demonstrates living into your values with three steps.

Step One: We Can’t Live into Values That We Can’t Name 

Brown created a list of values and suggests that everyone pick the two values they hold most important. Even though this is a challenging task, everyone needs to funnel down their list of 10+ to their two core values. Brown supports this with a statement from Jim Collins, “If you have more than three priorities, you have no priorities.” 

Try finding your two core values here! As you are reading through the list, you should feel a deep resonance of self-identification when finding your two core values. 


Step Two: Taking Values from BS to Behavior 

Values can either be verbalized or actualized. Brown accentuates the necessity of translating values from abstract concepts to tangible behaviors by delving into each of your chosen core values and addressing these three inquiries: 

        1. What are three behaviors that support your value? 
        2. What are three slippery behaviors* that are outside your value? 
        3. What’s an example of a time when you were fully living into this value? 

 * “Actions we find ourselves tempted to do even though they are counter to our values.” 


Step Three: Empathy and Self-Compassion: The Two Most Important Seats in the Arena 

Brown underscores, “Silence is not brave leadership, and silence is not a component of brave cultures.” The most important seats in the arena are empathy and self-compassion. Empathy requires relationships with one or two people who know our core values and support our efforts into them. Self-compassion empowers us to be our own cheerleaders, rather than relying solely on external validation. 


“Daring leaders who live into their values are never silent about hard things.”  


Daring Leadership

One essential element of daring leadership is cultivating commitment and shared purpose. In Brown’s work, the opposite of daring leadership is considered armored leadership. Armored leadership could look like leading for compliance and control (not legal, safety, or privacy compliance – think “fear and power”), where the leader reduces work to tasks and to-dos and is stuck in a power and resentment loop. Brown uncovers an approach that allows a task’s mission and connection to priorities to be shown, taking time to explain the “why” behind strategies: TASC approach – the Accountability and Success Checklist. 


        1. T – Who owns the task? 
        2. A – Do they have the authority to be held accountable? 
        3. S – Do we agree that they are set up for success (time, resources, clarity)? 
        4. C – Do we have a checklist of what needs to happen to accomplish the task?  


Brown goes on to elaborate on other techniques used when assigning work, such as the Scrum technique of “What does done look like?” – where she takes it even further to painting done. To ensure team members understand what “done” looks like, painting the image (verbally) cultivates commitment and contribution while reducing fear. An example would be a supervisor asking you to make a project brief by EOD and when you ask, “Paint done for me,” the supervisor says, “Pull results from the last four quarters and use a SWOT analysis to present as much information to the Board as possible.” By painting done, an employee can police themselves and deliver above and beyond expectations. 


What are your core values? How are you a daring leader? If you have thoughts on Dare to Lead by Brené Brown, email us here! 


Next, the Sales Tax Institute will take on Emotional Intelligence by Daniel Goleman. We would love to have you join us on our next journey. We encourage you to support your independent local bookstores. Our neighborhood bookstore is Sandmeyer’s Bookstore in historic Printer’s Row Chicago. Join us and support your own favorite local store! 

Posted on August 31, 2023