Coaching and Talent Development

"Every company has AI power users who are just itching to share what they’ve learned. Set up the right channels and resources for them to train everyone else."

"True, there is more power. True, you have more say over what happens. But, what people don’t realize until they get into a management role is that you actually spend *more* time convincing people of your ideas."

"There’s a reason that there’s a *boss* on a team: to make decisions. It’s your responsibility (and, by definition, your job) to help the team achieve the best possible outcomes. Making the right decisions is a big part of the job. Don’t be afraid to use this power when you feel strongly about a direction."

"Subordinate-imposed time begins the moment a monkey successfully leaps from the back of a subordinate to the back of his or her superior and does not end until the monkey is returned to its proper owner for care and feeding."

"But the best way to manage scaling (and one of the secrets to succeeding in a rapidly growing company) is to ignore those instincts, and go find a bigger and better Lego tower to build. Chances are if you pick your head up and look around, there’s a brand-new exciting pile of Legos sitting right next to you."

"Most people intuitively understand that the transition from IC to line manager is a role change with a steep learning curve. But the notion that the learning curve from line manager to manager of managers is just as steep—if not steeper—is highly counterintuitive."

"But in general, off-the-cuff solutions and strong opinions actually undermine your direct-report managers in the management chain and disempower them in front of their own team. You rob your direct-report managers of the opportunity to get your coaching on how to handle specific situations, learn your line of reasoning, understand your context—and then apply all of this themselveswith their team in an ongoing and scalable way."

"The analogy can be applied to managing managers by engaging with the following thought experiment: “If I had zero access to any IC in my organization and could only push or pull information from my managers to make decisions, how would I go about being effective?”"

"People with great managers also feel 63% (!) more belonging, 31% less burnout, and 62% (!!!) more job enjoyment compared to those with ineffective managers. Leadership quality may be the single most important lever for retention."

"To scale myself, I distilled my most common writing feedback into a GPT called “The Executive Editor” (try it [here](https://chatgpt.com/g/g-67328e9be4988190baa9b07a00b2628c-hilary-s-executive-editor)). This tool allows my team to paste in their emails, decks, or Slack messages and receive a letter grade on structure, clarity, level of detail, and tone, along with actionable recommendations for improvement."

"I created a GPT specifically designed to help product managers strengthen these skills through scenario-based simulations that mirror real-world situations, such as feature prioritization or balancing competing metrics. I love scenario-based learning because it helps people apply theoretical concepts to real life, with immediate feedback that creates a fast, repeatable learning loop."

"Before looking at AI-generated notes, I ask team members to write down the top three takeaways they personally find essential from a meeting. This approach encourages them to prioritize, reflect on what truly matters, and sharpen their instincts before comparing their takeaways with the AI’s draft."

"The skills that make for great managers—providing clear, consistent feedback and articulating the difference between good and excellent—translate remarkably well to creating GPTs that can give your team nearly unlimited access to your insights."

"A supermanager harnesses AI to amplify their impact while fully embracing the human side of management. By scaling their efforts, supermanagers can effectively oversee larger, flatter teams and extend their coaching beyond just direct reports, fostering a culture of continuous learning throughout the organization."

"Previously, in order to avoid becoming a bottleneck, I could review only high-stakes communications, like emails to the CEO or all-hands presentations. Now my team can receive ongoing feedback from “me” on any message they want to send at any time."

"The default path is to make everyone feel good by letting OK work slide. The more courageous path is to push everyone around you to keep that bar as high as possible. Rage against the dying of the light."

"Create a self-reliant team by empowering your teammates as experts in their disciplines, encouraging them to think like PMs and keep initiatives moving when you’re not in the room. As PM, you might be the orchestra conductor, but your teammates are the star musicians."

"I really like Ravi Mehta's product competency approach. He introduces his framework here but the full guide has a rubric for the skill level at each seniority: What’s Your Shape? A Product Manager’s Guide to Growing Yourself and Your Team"

"Created a deck on business terms used at our company that many may not be familiar with. Things like MRR, ACV, CAC, CTR, ASO, etc. The idea was to enable everyone to be more proactively involved in discussions whenever these terms are thrown around."

"Start by gathering data on how your direct report did, both by seeking input from your report’s peers and a self-assessment from the individual directly. You want to get as much signal as possible at this stage, ideally as early on in the process as you can (I typically start at least a month before a scheduled performance chat, since it often takes a while to get everyone’s responses)."

"Ahead of our upcoming performance conversation, I would love to get your perspective on how things went. Could you please answer these three questions, along with anything else you’d like to share, and get back to me by X/X? 1. What were your top five accomplishments in this cycle? 2. What 2-3 areas do you want to focus on developmenting over the next cycle?"

"The reality is that an individual will have just as much impact (if not more) on an organization if they flex what they are really good at, instead of just trying to improve on the areas they’re struggling with. Here, you have a chance to highlight that. Describe their biggest superpower, and how they can flex it further. There’s a lot of research that shows focusing on strengths is much more effective than obsessing over weaknesses."

"Ask yourself if you’re ready to trust someone else with your beloved product. Many founders desperately want help but also aren’t willing to trust an outsider. To set them up for success, choose to trust them and give them plenty of feedback to build alignment over time."