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Closing Executive Leadership Skill Gaps: A Portfolio Approach to Career Growth

with Kathleen Vignos

November 21, 2023


Kathleen Vignos is a VP of software engineering at Capital One. Her organization, Customer Resiliency, builds web, mobile, and backend applications to meet customer needs in times of financial hardship so they can resolve their debt and get back on track. These applications run on a modern stack with ML decisioning and serverless components hosted on AWS. Previously in her 6 years at Twitter, Kathleen worked on promoted tweet review, tweet translation, abuse tooling, and infrastructure automation across on-prem, Google Cloud, and AWS environments. She also ran Twitter’s development programs for engineering managers, personally training 300+ managers across the topics of people management, hiring, technical skills development, and project execution/delivery. Outside of strategic technology work, Kathleen is a distance runner and loves travel. She lives with her husband in San Francisco. They have 2 adult children and are working on plans to visit their sixth continent.

"I was hearing this message, 'You need to be more strategic.' I realized my definition of strategy in my head was not actually strategy and I needed to reframe strategy as being willing to completely blow everything up because there's a bigger, better thing you need to do and I think that if you are very organized and very goal oriented, you don't want to blow up your plan. You want to execute your plan. You're a great executor and that will get you to a certain level. So I think that's inflection point number one, at least it was for me and I think that's true for a lot of people. I see it over and over again.”

- Kathleen Vignos   


  • How the career portfolio concept strategically drives career growth (2:33)
  • Surprising discoveries in Kathleen’s transition to tech (5:07)
  • Parallels between Kathleen’s early work & current eng leadership (7:12)
  • The impact of a career portfolio on acquiring skills in a nonlinear way (10:47)
  • Kathleen’s tips for someone reorienting their approach to career growth (15:18)
  • Common gaps / blocks people encounter on their career growth journey (17:08)
  • Understanding your audience & the reach of your influence (20:13)
  • Navigating the shift between being a great executor to a great strategist (22:23)
  • Key principles of influencing & facilitation (24:49)
  • Strategies for option limiting as a facilitator (27:01)
  • How to facilitate to achieve time efficiency & positive option exploration (30:01)
  • Applying facilitation strategies during the candidate hiring process (32:39)
  • Examples of “polite interruption” phrases to use (35:31)
  • Approaches for dealing with conflict & reframing (36:49)
  • Recommendations for negotiating & decision making (39:47)
  • Rapid fire questions (44:13)


  • Getting More: How to Negotiate to Achieve Your Goals in the Real World - Based on Professor Stuart Diamond’s award-winning course at the Wharton Business School, Getting More concludes that finding and valuing the other party’s emotions and perceptions creates far more value than the conventional wisdom of power and logic. It is intended to provide better agreements for everyone no matter what they negotiate – from jobs to kids to billion-dollar deals to shopping.
  • Playing to Win: How Strategy Really Works - A.G. Lafley, former CEO of Procter & Gamble, in close partnership with strategic adviser Roger Martin, doubled P&G’s sales, quadrupled its profits, and increased its market value by more than $100 billion in just ten years. Now, drawn from their years of experience at P&G and the Rotman School of Management, where Martin is dean, this book shows how leaders in organizations of all sizes can guide everyday actions with larger strategic goals built around the clear, essential elements that determine business success— where to play and how to win.
  • The Storyteller: Tales of Life and Music - Dave Grohl’s memoir chronicling his early days growing up in the suburbs of Washington, DC, to hitting the road at the age of 18, and all the music that followed.
  • Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts - Annie Duke, a former World Series of Poker champion turned business consultant, draws on examples from business, sports, politics, and (of course) poker to share tools anyone can use to embrace uncertainty and make better decisions.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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