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How to Build Resilient, High-Performing Teams

Building
June 18, 2025
Hilary Gridley shares a playbook for building tough, growth-focused teams using behavioral tools and mindset shifts.
Topics discussed in the episode:
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How can founders use AI to build mental models of customers or stakeholders?
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How can founders help their teams handle disagreements with leadership decisions?
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How can AI be used to develop team members' skills rapidly?
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How can founders encourage their teams to balance work and personal well-being?
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Why is it important for founders to embrace the CEO's vision?
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How can AI be used to enhance team communication and understanding?
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How can founders help their teams understand executive thinking?
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How can founders build effective habits within their teams using reward loops?
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How can AI tools accelerate team learning and development?
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How can founders help their team learn to take a punch?

How can founders use AI to build mental models of customers or stakeholders?

AI assists in developing insights into behavior.

"LLMs are really good at pattern matching... You could feed all of those in and say, come up with the top 10 ways that this person is likely to pick apart an argument."

• Utilize AI to analyze communication. • Anticipate questions by identifying patterns. • Align with customer needs using AI.

How can founders help their teams handle disagreements with leadership decisions?

Navigating disagreements requires understanding.

"I really try to get to the bottom of, let me make sure that I have done my best to understand this person's point of view."

• Encourage empathy towards leadership. • Teach effective advocacy skills. • Promote respectful dialogue culture.

How can AI be used to develop team members' skills rapidly?

AI offers innovative ways to accelerate learning.

"I made a GPT that... create LSAT-style questions to test logical reasoning, but put them in the scenarios of things that a PM would encounter."

• Leverage AI for customized training. • Increase learning speed with AI tools. • Enhance skills with AI simulations.

How can founders encourage their teams to balance work and personal well-being?

Promoting well-being enhances performance and happiness.

"I'm asking them, are you doing something every single day that's bringing you joy in your life? And if they say no, I'm like, that's a problem."

• Encourage activities that bring joy. • Model work-life balance as a leader. • Recognize well-being boosts success.

Why is it important for founders to embrace the CEO's vision?

Aligning with the CEO's vision is crucial for success.

"Your job is to understand what the CEO's vision is... and figure out how to operationalize that in a way that results in the best possible manifestation of it."

• Execute the CEO's vision effectively. • Contribute uniquely within that vision. • Recognize alignment is key to success.

How can AI be used to enhance team communication and understanding?

AI can simulate perspectives and improve team communication.

"Hypothetically, you could feed all of those in and just say, come up with the 10 criteria that this person is most likely to use to assess a possible recommendation."

• Use AI to analyze communication patterns. • Prepare for meetings by anticipating questions. • Simulate leadership interactions with AI.

How can founders help their teams understand executive thinking?

Sharing insights into leadership thought processes aligns team efforts.

"I try to make an effort every week... to send my team just a quick rundown... Here's what that person said verbatim... Here's why I think they say that."

• Communicate leadership insights. • Build mental models of executive thinking. • Align decisions with leadership priorities.

How can founders build effective habits within their teams using reward loops?

Establishing strong habits is essential for team performance.

"You are not thinking enough about the reward loop, and the reward loop needs to be powerful, it needs to be immediate, and it needs to be emotional."

• Design immediate, meaningful rewards. • Create incentives that motivate behaviors. • Recognize achievements to reinforce habits.

How can AI tools accelerate team learning and development?

AI can enhance learning and skill-building within a team.

"I have like a 30 days of GPT I call it, of like a list of 30 things to do one every single day... I don't know anyone who has gone through this and not come out the other side feeling 100 times more confident in their skills."

• Implement daily AI exercises. • Start small to form habits. • Use AI for personalized learning.

How can founders help their team learn to take a punch?

Learning to handle setbacks is crucial for team resilience and growth.

"I try to focus them less around how you litigate another person's impression of you and more on what is the action that you can take to counterprogram the narrative that you are afraid that this other person has of you."

• Encourage actionable steps over fixating on perceptions. • Build resilience by demonstrating true capabilities. • Foster growth by viewing setbacks as opportunities.