Swipe my growth resume template: https://docs.google.com/document/d/1FR6Bbdwg80Hu-6TSz-8aGe4GgIBDukUzYXTdbr4pd0I/edit?tab=t.0

New role? Get my 90-day Growth Leader onboarding plan here: https://deliveringvalue.co/90

In this solo Field Notes episode, I break down a practical framework for getting more out of your team in an era where AI and modern tools are rapidly increasing individual output. We’ll explore how managers can adapt their leadership style based on the specific task at hand, rather than the person, and how combining structured management principles with coaching techniques can unlock better performance without requiring more time.

In this episode, you’ll hear:

- Why “task-relevant maturity” helps you adjust your management style based on the task, not the person

- When to coach with questions vs. give direct guidance to keep work moving efficiently

- How to get more output from your team without increasing your own workload

Things to listen for:

(00:00) AI boosts output, adds complexity

(01:05) Two frameworks to improve teams

(02:16) What is task-relevant maturity?

(03:34) Match your style to the task

(05:03) Coaching vs. directing

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system

A huge thanks to this episode’s sponsors:

Hire Overseas: Exceptional Talent for Less - https://www.hireoverseas.com

Navattic: Interactive Product Demo Software - https://navattic.com/value

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Leaders don’t stall because of a lack of talent, but because the habits that helped them get promoted, such as saying yes, working longer hours, and proving value through output, stop scaling. In this episode, Arielle Johncox, CEO of Balsamiq, shares her journey stepping into the company’s first marketing role with minimal infrastructure. She had to quickly learn how to prioritize, embrace imperfection, and lean into her strengths. This shift in mindset ultimately led her to take on the role of CEO, where she reflects on the value of being a generalist and leading through uncertainty.

In this conversation, you’ll learn:

• Why the instinct to say yes can become a ceiling at higher levels of leadership
• How to separate old self-doubt from legitimate growth edges
• What it actually takes to move from functional leader to CEO without becoming someone else in the process

Things to listen for:

(00:00) Intro

(01:00) The early days at Balsamiq

(02:40) Arielle’s transition to the CEO role

(05:42) Challenges and learnings as a marketing leader

(08:13) Thanks to our sponsor, Hire Overseas

(09:30) Thanks to our sponsor, Navattic

(26:13) Burnout, self-doubt, and recovery

(29:29) Letting go of “doer” identity

(31:49) How the CEO offer happened

(38:47) Why being a generalist wins

(44:08) The advice Arielle would give herself

A huge thanks to this episode’s sponsors:

Hire Overseas: Exceptional Talent for Less - https://www.hireoverseas.com

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Arielle:

LinkedIn: https://www.linkedin.com/in/ariellejohncox/

Threads: https://www.threads.com/@ariellejohncox

Learn more about Balsamiq: https://balsamiq.com/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system

A huge thanks to this episode’s sponsor: Hire Overseas:

Exceptional Talent for Less - https://www.hireoverseas.com

In this episode, Jacob Woodward, a longtime product and tech leader, shares what happens when a strong resume runs into a brutal job market. He reflects on the year and a half after leaving a struggling company, attempting to go independent, applying nonstop, and still feeling invisible.

Jacob talks about how AI has changed hiring on both sides. Candidates can apply at scale with polished, tailored resumes, while hiring teams are overwhelmed by stacks of applications that start to blur together. He opens up about how repeated ghosting shook his confidence and identity, especially under the pressure of providing for his family.

After hitting a breaking point, Jacob shares how a raw LinkedIn plea went viral worldwide, and how support from strangers, including a Business Insider feature, helped restore his self belief. Now, he’s rebuilding through therapy, meditation, and yoga, and betting on himself as he builds what’s next, including a project to teach kids critical thinking in an AI driven world.

In this conversation, you’ll learn:

• How AI and mass applying have changed the job search, and why great candidates can still feel invisible
• What repeated rejection does to confidence, and how to rebuild without waiting for external validation
• Why therapy, meditation, and yoga became key tools in Jacob’s comeback

Things to listen for:

(00:00) Intro

(01:38) Early entrepreneurship and first exit

(07:20) Facing today’s job market realities

(08:50) Thank you to our sponsor, Hire Overseas

(18:27) Moving beyond a professional facade

(20:11) Sharing a raw LinkedIn plea

(22:09) How AI is reshaping hiring

(28:29) Rebuilding confidence after repeated ghosting

(31:47) Therapy, meditation, and yoga practices

(38:42) Betting on one’s self and building next

Resources:

Connect with Jake:

LinkedIn: https://www.linkedin.com/in/jacobwoodward/

Website: https://www.jacobwoodward.dev/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system