What Makes Leadership Human in an Age of AI?

Nov 12, 2025

Valerie Jackson, a former securities lawyer turned C-suite leader, discusses the essence of human-centered leadership in tech. She emphasizes the importance of self-awareness and building powerful partnerships for sustainable success. Valerie tackles burnout, outlining its main components and sharing recovery strategies. She advocates for AI that enhances human capabilities, stressing that leaders' unique energy cannot be replaced. The conversation also delves into IPO dynamics and the need for intentional design in tech that preserves human dignity.

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INSIGHT

Human Leadership Over Tech

Leading humans requires understanding how we think and operate.
AI must elevate people, not erase the human energetic signature leaders create.

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ANECDOTE

From Securities Law To HR

Valerie pivoted from securities law to build one of the first law-firm diversity departments.
That leap launched her long career in HR and people leadership across startups and public companies.

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ADVICE

Use Humility To Find Blind Spots

Use curiosity, humility, and a growth mindset to surface when you need to change.
Run 360s and accept anonymized feedback to reveal blind spots and improve.

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From Securities Lawyer to People Leader

01:55 • 3min

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What Real Leadership Looks Like

04:34 • 2min

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Balancing Visionary and Linear Thinking

06:18 • 3min

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What Human Optimization Means for Leaders

09:10 • 3min

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How Leaders Recognize They Need Growth

11:50 • 13min

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Understanding and Recovering from Burnout

24:52 • 8min

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Time Audits and Brain Chemistry Tools

32:34 • 4min

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Delegation, Energy Units, and Avoiding Overreach

36:05 • 3min

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How to Keep Humans Central When Building AI

39:35 • 7min

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AI's Impact on Work, Purpose, and Jobs

46:43 • 1min

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Designing for Obsolescence Without Losing Human Purpose

48:10 • 3min

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Hidden Costs of Going Public

51:36 • 5min

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Deciding Between IPO, PE, VC or Staying Private

56:40 • 3min

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PE vs. VC: Time Horizons, Risk and Control

59:37 • 4min

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Books That Shaped Leadership and Self-Work

01:03:17 • 4min

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Biggest Aha Moments and Privilege Recognition

01:07:19 • 1min

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Leader's Billboard: Know Your Ripple

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The No Asshole Rule

Building a Civilized Workplace and Surviving One That Isn't

Robert Sutton

In this book, Robert I. Sutton discusses the destructive impact of 'assholes' in the workplace, providing strategies for identifying and eliminating negative influences. He introduces the concept of the 'Total Cost of Assholes' (TCA) and offers practical advice on how to build a more civilized and productive work environment. The book includes case studies from various organizations and provides a self-diagnostic test to help readers identify and manage their own behavior. Sutton also explores the difference between 'temporary' and 'certified' assholes and how to deal with each type effectively.

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What Got You Here Won't Get You There

Marshall Goldsmith

This book by Marshall Goldsmith focuses on helping successful individuals recognize and change the behavioral habits that are holding them back from achieving even greater success. Goldsmith identifies 20 common bad habits, such as speaking when angry or adding too much value, and provides a systematic approach to changing these behaviors. He emphasizes that it is not technical skills but behavioral changes that separate the great from the rest. The book offers practical advice on how to eliminate these dysfunctions and improve interpersonal relationships, which is crucial for advancing in one's career and personal life.

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The Mountain Is You

Transforming Self-Sabotage into Self-Mastery

Brianna Wiest

The Mountain Is You delves into the reasons behind self-sabotaging behaviors and offers a comprehensive guide on how to transform these patterns into self-mastery. The book uses the metaphor of a mountain to represent the internal challenges we face and emphasizes the importance of deep internal work, such as excavating trauma, building emotional intelligence, and releasing past experiences. It encourages readers to take responsibility for their actions and to cultivate a resilient mindset to overcome their own barriers to success.

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The 5 Languages of Appreciation in the Workplace

Dr. Paul White

Gary Chapman

This book, based on the concept of 'The 5 Love Languages,' teaches how to improve workplace relationships by understanding and using the five languages of appreciation: acts of service, quality time, words of affirmation, tangible gifts, and appropriate physical touch. It includes new chapters on appreciating remote and hybrid employees, generational differences, and updated research on the positive impact of appreciation on business productivity and profitability. Each book comes with an access code for the online Motivating by Appreciation (MBA) Inventory.

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Atomic Habits

James Clear

Atomic Habits by James Clear provides a practical and scientifically-backed guide to forming good habits and breaking bad ones. The book introduces the Four Laws of Behavior Change: make it obvious, make it attractive, make it easy, and make it satisfying. It also emphasizes the importance of small, incremental changes (atomic habits) that compound over time to produce significant results. Clear discusses techniques such as habit stacking, optimizing the environment to support desired habits, and focusing on continuous improvement rather than goal fixation. The book is filled with actionable strategies, real-life examples, and stories from various fields, making it a valuable resource for anyone seeking to improve their habits and achieve personal growth.

In this episode of The Tech Leader's Playbook, Avetis Antaplyan sits down with Valerie Jackson — Harvard College and Georgetown Law alum, former securities lawyer turned C-suite people leader — to explore what it really takes to scale companies without breaking leaders or culture. Valerie traces her journey from advising public companies and serving at the U.S. Public Company Accounting Oversight Board to building one of the first law-firm diversity departments and leading people operations across VC-backed rockets, public SaaS, and PE-owned businesses. Together they unpack human-centered leadership, the mechanics of burnout (as recognized by the WHO), and why self-work is often the hardest part of scaling. Valerie shares practical tools — from 360s, “powerful partnerships,” and time audits to managing brain chemistry — and makes a compelling case that AI should elevate people, not erase them, because nothing can replace a leader’s “energetic signature.” The conversation closes with hard-won lessons on IPO vs. going private, PE vs. VC risk appetites, and Valerie’s mantra: “Know your ripple.”

Takeaways

Great leadership starts with self-awareness. Learn yourself to lead others.
Build “powerful partnerships”: pair visionary thinkers with linear operators.
Align culture: what we say (cognitive) with how we behave (emotional).
Use 360 feedback to surface blind spots with curiosity and humility.
Burnout = exhaustion + inefficacy + cynicism. Address all three to recover.
Run time audits to find your “golden ratio” of energizing vs draining work.
Support brain chemistry intentionally: dopamine, serotonin, oxytocin, endorphins.
Keep AI human-centric. Technology should amplify people, not replace them.
Design for tool obsolescence and misuse while protecting the humans.
IPOs bring capital and scrutiny; going private can restore flexibility.
PE and VC differ on time horizons, risk, and control expectations.
Leader’s billboard: “Know your ripple.” Be intentional about your impact.