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From Executive Assistant to Coach: Scaling Leadership for Growth-Stage CEOs

[HPP] Stewart ButterfieldOctober 14, 20251h 14min
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Career Evolution to Executive Coach

  • ๐Ÿš€ Kris Cordle Goodsall transitioned from an Executive Assistant role at Yahoo and Twitter to Chief of Staff at Slack, eventually becoming an executive coach.
  • ๐Ÿ’ก She supported iconic Silicon Valley leaders like Ev Williams (Twitter) and Stewart Butterfield (Slack), guiding them from product creators to company leaders.
  • ๐Ÿ“Œ Her journey included a sabbatical in Paris to learn French, which inspired the name of her company, Devenu Collaborations.

Navigating Leadership and Growth

  • ๐Ÿ“ˆ At Slack, Kris played a key role in scaling operations globally and served as Chief of Staff through its direct listing and $27.7 billion acquisition by Salesforce.
  • ๐Ÿง  She observed that effective leaders make timely decisions rather than debating endlessly, emphasizing action over prolonged analysis.
  • ๐ŸŽฏ Her coaching approach focuses on helping growth-stage CEOs build specific systems tailored to their unique teams and environments, avoiding one-size-fits-all solutions.

The Indispensable Role of Executive Assistants

  • โœ… Kris highlights EAs as the "CEO of their calendar," entrusted with managing the executive's most valuable resource: time.
  • ๐Ÿ” EAs can spot rising talent in meetings and provide valuable insights into team dynamics, offering relief to CEOs.
  • ๐Ÿ’ฌ She strongly advocates for EAs to be "in the room" and have full context, including access to communications like inboxes and Slack channels, to make informed decisions.

Combating Burnout and Fostering Balance

  • โš ๏ธ Kris critically views the "six, seven-day work week" as a "straight shot to burnout," arguing it deters quality talent and is unsustainable.
  • ๐Ÿง˜โ€โ™€๏ธ Successful leaders find balance and step back from the "rocket ship" pace to make wise decisions, which is crucial for long-term effectiveness.
  • ๐ŸŒฑ She emphasizes that quality talent brings diverse interests and needs space to do their work, contributing to a healthier company culture.

Coaching Philosophy and Future Outlook

  • ๐Ÿค Kris's coaching often involves working with the entire team, including EAs and Chiefs of Staff, to build internal capabilities rather than just advising the CEO.
  • ๐Ÿ”ฎ She believes that while AI is transformative, EAs will not be replaced in our lifetimes due to the human elements of awareness, context, and non-verbal communication.
  • ๐Ÿ’ก Her ultimate goal is to help individuals understand their own motivations and find fulfillment in their roles, whether as a long-term EA or a transitioning CEO.
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Whatโ€™s Discussed

Executive AssistantChief of StaffExecutive CoachingGrowth-Stage CEOsScaling CompaniesLeadership DevelopmentSilicon ValleySlack (company)Salesforce AcquisitionTime ManagementCompany CultureBurnout PreventionWork-Life BalanceArtificial Intelligence (AI)Founder CEOs
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