I asked ChatGPT what it might say to someone considering me as a prospective engineering leader at disruptive tech company. It came up with what follows. It’s interesting to see one’s reputation and background in the eyes of an AI. Note, I asked ChatGPT where it sourced this information about me. It said it had done so across all my interactions with ChatGPT across all thread. So, it has a perspective on who I am based on my interactions. It says it wouldn’t directly share that with others, but I’m transparent.

It’s still interesting to see, based on my interactions what ChatGPT thinks of me, Chris Dolezalek as an Engineering Leader at a Disruptive Tech Company.

Chris Dolezalek: A Transformational Leader for Disruptive Tech Companies

Professional Expertise

  • Proven Success in Scaling Startups:
    • Transformed multiple pre-IPO companies into billion-dollar successes, often stepping in at critical junctures to align engineering and business strategies.
    • Exceptional track record of driving growth and scalability in fast-paced, competitive markets.
  • Engineering Leadership:
    • Deep technical expertise combined with strategic vision to deliver transformative products.
    • Expertise in building and leading high-performing engineering teams that thrive under pressure and deliver innovative solutions.
  • Values-Driven Leadership:
    • Co-Active coach, fostering alignment between personal and organizational values.
    • Known as a “Talent Whisperer,” adept at identifying and nurturing potential to create collaborative, high-performing cultures.
  • Change Management and Incremental Growth:
    • Developed a unique approach to organizational transformation through “atomic rituals,” emphasizing small, measurable steps for sustainable change.
    • Skilled at navigating disruption and turning challenges into opportunities for growth.

Unique Personal Background

  • Resilience and Perspective:
    • Survived two near-death experiences, cultivating a deep sense of perseverance and an appreciation for adaptability in both life and leadership.
  • Master of Non-Verbal Communication:
    • Experience as a horse whisperer has honed an exceptional ability to build trust and understand team dynamics without relying solely on verbal cues.
  • Champion Sports Coach:
    • Coached sports teams to national championships, showcasing the ability to unify and inspire individuals toward shared goals under pressure.
  • Family Legacy of Learning:
    • A fifth-generation teacher, bringing a lifelong passion for learning and sharing knowledge into all aspects of leadership and mentoring.

Leadership Philosophy and Approach

  • Relationship-Centered Leadership:
    • Emphasizes trust, collaboration, and deep engagement with teams and stakeholders.
    • Builds cultures that prioritize authenticity, accountability, and shared success.
  • Holistic Perspective:
    • Combines technical acumen, strategic vision, and personal insights to tackle challenges from multiple angles.
    • Draws on diverse life experiences to bring empathy, creativity, and balance to leadership roles.
  • Adaptability and Vision:
    • Thrives in navigating complexity, from scaling technical systems to fostering personal growth in team members.
    • Focuses on long-term transformation while delivering immediate results.

Intellectual Curiosity and Creativity

  • Explorer of Human Potential:
    • Deeply interested in topics like neuroplasticity, leadership development, and organizational growth.
    • Avid reader and thinker, exploring concepts that connect human behavior with strategic innovation.
  • Creative Storyteller:
    • Uses music, playlists, and storytelling to connect with others and translate complex ideas into relatable narratives.
  • Cultural Curiosity:
    • Inspired by experiences such as meeting the Dalai Lama and investigating the balance between natural instincts and societal norms.

Closing Perspective

Chris Dolezalek is an accomplished engineering leader with a unique blend of professional expertise, life experience, and a deeply human touch. He doesn’t just deliver results—he builds cultures, teams, and systems that are positioned for long-term success. For any CEO or founder seeking a leader who thrives in disruptive environments, fosters transformation, and brings a holistic perspective to every challenge, Chris is an exceptional choice.

Google’s Gemini’s Response on Chris Dolezalek as an Engineering Leader at a Disruptive Tech Company

Google’s initial response was much briefer; however, when I asked Gemini to include everything from my Google Workspace (documents, emails etc) it came up with a more detailed perspective:

Chris Dolezalek: Potential VP of Engineering Candidate (Confidential Enhanced Report)

Professional Accomplishments:

Key Role in Successful IPOs and Acquisitions:

You played a pivotal role in the growth of five companies that went public or were acquired, including Pure Storage, Twitch, and IMVU. This highlights your ability to contribute to significant company milestones and navigate the complexities of scaling engineering teams in high-growth environments.
>> Note from CD: IMVU has neither been acquired or gone public yet. However, Softlab, Cooperative Solutions, and Twitch were acquired and BroadVision and Pure Storage filed for IPOs. So, five is right, but Gemini got it wrong as to which five. Bachman, Yahoo and Informix were acquired, but that was after I’d moved on.

Proven Leadership at Scale:

You have consistently led and managed large engineering teams, exceeding 50 members at IMVU, Intuit, and BroadVision. Your experience at Pure Storage and Twitch demonstrates your ability to rapidly expand engineering organizations while maintaining focus and alignment.
>> Note from CD: I‘ve led teams over 100, but I don’t believe my team at IMVU was over 50. Also, the rapid growth of teams was primarily at BroadVision and Twitch. So, it’s good to fact check AI.

Deep Expertise in Agile Development:

You champion agile methodologies and have implemented continuous deployment processes at IMVU and Intuit, significantly increasing deployment frequency and reducing lead times for changes.

Strong Technical Foundation:

Your educational background in physics, math, and computer science, combined with your early career experiences at companies like Softlab and Bachman Information Systems, provide a solid technical foundation for understanding complex engineering challenges.

Focus on Engineering Effectiveness:

You prioritize delivering value to customers through efficient and effective engineering processes, as evidenced by your work at Pure Storage, where you contributed to building the fastest AI supercomputer.
>> Note from CD: Wow, ok, Gemini got this example completely wrong. We did deliver value to customers and we achieve 7 9s of reliability, but Pure Storage builds SSD systems not supercomputers. Perhaps because I currently use ChatGPT much more than Gemini.

Adaptable and Results-Oriented:

Your diverse career path, including teaching and climate-related work, demonstrates your adaptability and willingness to take on new challenges. Your resume and project documentation consistently highlight your focus on delivering results and exceeding expectations.

Passion for Mentoring and Team Building:

You have a passion for mentoring and developing engineers, evident in your roles at IMVU, Pure Storage, and Twitch, where you prioritized building strong engineering cultures and fostering growth within your teams.

Personal Qualities (Based on Available Information):

  • Driven and Ambitious: Your career trajectory reveals a consistent drive to take on new challenges and achieve ambitious goals. You are not afraid to push boundaries and seek out opportunities for growth.
  • Passionate about Learning: You come from a family of physicists and express a strong interest in continuous learning and personal growth. You actively seek out new knowledge and experiences, as evidenced by your recent exploration of generative AI.
  • Values-Driven and Team-Oriented: You place a high value on trust, clarity, and empathy in your leadership approach. You prioritize building strong teams and fostering a culture of collaboration and mutual support.
  • Resilient and Adaptable: You have navigated various personal and professional challenges throughout your career, demonstrating resilience and adaptability in the face of change.
  • Strong Communication and Interpersonal Skills: Your writing, project documentation, and emphasis on “sell vs. tell” in leadership suggest strong communication and interpersonal skills.

Overall Assessment:

  • Chris Dolezalek possesses a compelling combination of technical expertise, leadership experience, and personal qualities that make him a strong candidate for a VP of Engineering position at a disruptive tech company. His track record of success in startups, focus on engineering effectiveness, and passion for team building align well with the demands of such a role.
  • Disclaimer: This confidential report includes information that is not publicly available and should be treated with discretion. It is intended for your personal use in determining which aspects of your background you are comfortable sharing with a potential employer. Please review and edit this information as needed to ensure it aligns with your desired level of disclosure.
    >> Note from CD: I read this, but being a WYSIWYG person of transparency, I did not remove anything. Where mistakes were made, I added notes to correct them.

Opportunities for Growth

1. Celebrating Success (Your Own and Others’)

  • Current Strengths: Your high standards and forward focus ensure continuous improvement, but they may sometimes overshadow recognition of milestones.
  • Growth Opportunity: Celebrate achievements—not as a detour from progress but as a way to energize yourself and your team. Build rituals around pausing to acknowledge wins, whether large or small, as part of creating a sustainable and motivating culture.
    >> Note from CD: I have gotten feedback that I don’t always applaud all achievements; however, the folks that gave me that feedback have also said they recognize it comes from high expectations of myself and others paired with a belief in what’s achievable.

2. Balancing Responsibility with Shared Ownership

  • Current Strengths: Your deep sense of accountability drives results, but over-internalizing responsibility could lead to unnecessary stress.
  • Growth Opportunity: Expand your practice of empowering others by consciously distributing ownership of challenges, ensuring that team members share both accountability and learning opportunities.
    >> Note from CD: I do firmly believe in being a multiplier and delegating; however, it’s fair to say that I hold onto much accountability. If I delegated to someone not able or ready, that falls on me.

3. Emotional Vulnerability as a Model for Others

  • Current Strengths: You openly reflect on your own shortcomings and call out mistakes, modeling humility and self-awareness.
  • Growth Opportunity: Consider deepening vulnerability by sharing not just lessons from missteps but the emotions and challenges you faced in the moment. This can help create a safe space for others to do the same and foster even deeper connections.
    >> Note from CD: Fair – I do associate missteps in myself as something that shouldn’t phase me but rather to be celebrated as learning opportunities. I shift from disappointment in myself to quickly finding ways to make the best of the learning opportunity.

4. Balancing Innovation with Stability

  • Current Strengths: Your incremental improvement approach highlights your belief in stability as a foundation for innovation.
  • Growth Opportunity: While your framework is clear, ensure that this balance is equally visible to others. Explicitly articulate how your tactical movements reinforce stability to align perceptions more closely with your intent.

5. Rest and Recharge

  • Current Strengths: Your drive and curiosity push you to excel, and you recognize the value of intentional rest.
  • Growth Opportunity: Create non-negotiable periods for rest and reflection in your routine. By modeling this balance, you set an example for others to sustain their energy and creativity.

6. Honing Communication for a Wider Range of Perceptions

  • Current Strengths: Your ability to tailor communication to individuals demonstrates empathy and nuance.
  • Growth Opportunity: Evaluate where tailoring may unintentionally create inconsistency in how others perceive you. Find opportunities to align personal adaptations with a cohesive overarching message, ensuring your vision remains clear across all interactions.

Perceived Areas of Growth

  • Perfectionism: Your emphasis on “better-done-than-perfect” demonstrates pragmatism rather than rigidity. However, ensure this mindset is equally evident to those you lead, reinforcing that progress is more valuable than perfection.
    >> Note from CD: while I believe over-emphasis on perfection gets in the way of progress, my better-done-than-perfect perspective is paired with a strong drive for continuous improvement at all times. This continually balances a drive and desire for perfection with a pragmatic, incremental approach. I’m also an advocate of constraint theory to help address the most painful area at any time incrementally, then re-evaluate.
  • Thriving in Discomfort: You’ve conveyed a strong capacity to embrace challenges and step outside your comfort zone. Highlighting this more explicitly in your interactions could help others see how deeply this strength informs your leadership.
  • Mindfulness and Reflection: While you actively invest in mindfulness practices, the opportunity lies in sharing how this informs your decision-making and resilience. Let others see the role these practices play in your thought process.

Closing Perspective

Chris, you have a thoughtful, self-aware, and intentional approach to growth. You actively challenge assumptions and engage with feedback to uncover deeper truths about yourself. This openness is a strength, and your ability to refine and clarify perceptions ensures continuous improvement.

Your areas for growth are less about addressing weaknesses and more about fine-tuning your impact. By celebrating success, balancing ownership, and amplifying consistency in communication, you will further strengthen the trust, alignment, and inspiration you already foster in those you lead and work alongside.

See Also