The Six Challenges of Leadership — From An ADHD Leaders Perspective

Reflection questions for ADHD Leaders.

By Virginia Bauman and Casey Gipson

The Six Challenges of Leadership (6 Challenges of Leadership for CXOs) are foundational to my coaching and have been foundational to my growth as a leader. I can return to them at different stages of company growth for my clients and each time there is something new to focus on. These challenges are not specific to ADHD leaders. They are challenges that all leaders encounter; that said, they serve as an excellent diagnostic tool for ADHD leaders as well. ADHD can serve to exacerbate these challenges if not faced head-on and with an awareness of how ADHD shows up for the individual leader.

So we have created a series of inquiry questions that can serve to help you explore each challenge from an ADHD lens. Some of the terms we use below are explained more in our workshop, Connecting ADHD Science to Resilience. If you want to dive deep into ADHD with us, we are running this workshop on October 25th, 2023.

Overcoming Delusion: Are we willing to face the hard questions and face reality? Where are we pretending that everything is okay? Are we deluding ourselves because we are unaware? If so, how do we uncover our lack of awareness?

Reflection Questions for the ADHD leader:

  • In what ways is your self-assessment self-awareness deceiving you?
  • Where are you not owning your ADHD?
  • How might you rely on your team to see more clearly?
  • What part does inhibition play in creating delusion?

Disappearing into the Fire: Are you merging yourself with your business or your product? Are you working in your business or on your business? The frenzied and frenetic life of startups can destroy you, your family, and your company as you Disappear into the Fire (as you lose yourself in the work, in your company). How can you lead yourself and your startup to success without a meltdown? The magic happens in the crucible that forms a leader.

Reflection Questions for the ADHD leader:

  • Where does leadership need to slow down?
  • Where does leadership over or under-react? Take too much ownership, or too little?
  • How could a leader externalize inhibition to avoid getting absorbed in less valuable fires?
  • How could leadership model sustainable familial balance/integration?

Misunderstanding Your Role: How well do you understand the role of the CEO? If not a CEO, how well do you understand your role? As CXOs, team leads, and co-founders, clarity around what is our work to do and what isn’t helps us and our teams function smoothly. When everyone on the team understands their role and other’s roles, the clarity creates boundaries and better cross-collaboration. As a CEO, it’s uber critical that you understand what your job description is. In working with CEOs, common questions pop up. Among them are what seems like a basic one: What is my job as CEO? Sometimes the question is: What is my job as CEO, now, at this stage of the organization? It’s a role that, when played well, shifts and scales as the company grows and develops.

Reflection Questions for the ADHD leader:

  • How is lack of self-control contributing to taking tasks outside your role?
  • What boring but important parts of your role are you consistently trading for more exciting, less important tasks?
  • How do we need to update our internalized definition of our leadership roles to reflect the stage the company is at today?
  • What new definitions and rules are needed to support leadership focusing on the highest value they can create for the company?

Being Unclear: Lack of clarity is the single biggest problem in management and among teams. As Brené Brown says: “Clear is kind. Unclear is unkind.” What are the job descriptions on your team? Do folks know what it means to succeed? Do they know what failing would look like in their role? You don’t want people to learn these things when they are getting fired. Do what it takes to be clear in your communications. Repeat what you heard and ask clarifying questions. As the CEO, you have to be able to find new ways to say the same thing, especially as it relates to promulgating the vision and making sure it’s understood. (As one client said, “I feel like my role is Chief Repetition Officer!”).

Reflection Questions for the ADHD leader:

  • How is your strength or weakness in verbal working memory impacting your clarity of communication?
  • What executive functions could be reinforced to improve clarity in the company? How would you externalize these functions?
  • How might impulsive action be muddying the waters?

Relating Poorly to Uncertainty: How do you handle the unknown? How does market volatility affect you? How does market volatility affect your leadership? What aspects does it bring out in your personality? Relating poorly to uncertainty often brings out the sub-optimal parts of us. Our go-to reactions and behaviors when we are afraid can give us a glimpse into the shadowed parts of our personality. Times like these give us opportunities to learn more about ourselves so we can act from a place of groundedness. “Between stimulus and response there is a space,” wrote Victor Frankl. “In that space is our power to choose our response. In our response lies our growth and our freedom.” The more we can learn to pause and find that space, the greater our capacity to handle the complexity of what’s in front of us.

Reflection Questions for the ADHD leader:

  • Where does leadership have impatience and a low tolerance for delayed rewards?
  • How does uncertainty affect your emotional state?
  • What impulsive actions do you take during times of uncertainty?
  • In what ways does your ability/inability to recall past events affect your relationship with uncertainty?

Being Fierce: Work is a very people-y place. Managers need training. People need performance feedback. Some folks need to be fired. Perhaps your co-founder relationship is tense. And, maybe you have a board member overstepping bounds. How do you handle conflict? What are you not saying that needs to be said? Do you avoid difficult, fearful, or challenging situations, people, or conversations? How do you resolve what is really going on? How do you deal with trust issues? Being fierce doesn’t mean being ferocious. But it does mean leaning into the hard conversation, being clear, and sometimes making a hard decision.

Reflection Questions for the ADHD leader:

  • What conflicts caused by misunderstanding ADHD could be resolved? How?
  • What does fiercely owning your ADHD look like?
  • Where have you been avoiding the truth about how your ADHD has affected those around you?
  • Knowing more about ADHD, what hard conversations do you need to have with yourself?

Every leader needs support. If you are a leader in need of support managing your ADHD, don’t hesitate to reach out and start the conversation.

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