Hilary Gridley

Driving AI adoption requires designing immediate, emotional reward loops that minimize the friction of learning new tools.

"Designing reward loops... The reward loop needs to be powerful, it needs to be immediate, and it needs to be emotional, so that when this person does the thing that you want them to do, they feel like..."

Managers can scale their mentorship by building custom GPTs that mimic their specific feedback style and criteria.

"I build these GPTs, that kind of think like me. And the purpose of that is so that my team can get feedback that is at least 80% close to the feedback that I would be giving them. But instead of havin..."

LLMs can be used to create hyper-personalized training simulations for specific skills like logical reasoning or engineering estimation.

"I made a GPT that I basically told it, 'Create LSAT style questions to test logical reasoning, but put them in the scenarios of things that a PM would encounter.' ... It just sort of gives you these l..."

True alignment comes from understanding a leader's decision-making framework rather than just their current opinions.

"What is much more helpful than understanding what your CEO thinks is, I think understanding how your CEO thinks. And that goes for all sorts of levels of the company. I want to understand how all the..."

Use declarative statements followed by a request for agreement to quickly map a stakeholder's mental model and boundaries.

"I talk about what I like to call the magic questions, but the thing about magic questions is they're not actually questions, they're statements and they end with, 'Do you agree?' Or 'Is that right?' ...."

When disagreeing with a superior's decision, maintain team alignment by explaining the logical rationale from the leader's perspective.

"Separate out my opinion from it, from the, 'Well, what is the insight that makes it make sense to this person' and explain their rationale. Even if I'm comfortable saying, 'I don't necessarily think t..."

Meeting size inversely correlates with candor; every attendee must actively contribute to justify the 'cost' of their presence.

"Every additional person in a meeting has a cost, because every additional person in a meeting makes the people in that meeting less candid than they would have been if there were fewer people in that..."

Help team members build resilience by focusing on proactive actions that disprove negative perceptions rather than getting defensive.

"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 counter program the narrative that you are afraid that this othe..."

Transparency in leadership involves sharing the 'note behind the note' from executive meetings to help the team build their own mental models of leadership thinking.

"I try to make an effort every week. I don't always do it, but I try to send my team just a quick rundown in Slack of, 'Here are the most important conversations or the most interesting conversations I..."

Managers should intentionally reward healthy boundaries and personal interests to prevent a culture of burnout.

"I try to find ways that I really am impressed with my team, and the ways that they take care of themselves outside of work. Because I think people, bosses often inadvertently create reward loops for,..."

1:1s should be used to monitor an employee's 'recovery' and joy to ensure long-term high performance.

"In my one on ones, and I'm checking in with people, I'm asking them, 'What do you do for joy? Are you doing something every single day that's bringing you joy in your life?' And if they say no, I'm li..."