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Questions to ask leaders

I always freeze when I'm in a advice/learning/mentorship situation (watching a panel, in a 1:1, having a hallway conversation) with a leader who I admire and we get to the end of the conversation and the leader I'm talking to asks me if I have any questions for them. In that moment I forget all the questions I wanted to ask, which is so unfortunate becuase I miss out on the most useful moment. So, I'm collecting questions to jog my memory:

  • What do you do to wind down from the day?
  • In 1-2 words, what is your biggest strength as a leader?
  • How do you find out what your weaknesses are?
  • Who is your confidant (someone you get advice from consistently, lean on in crisis, share frustrations...)?
  • Can you finish this sentence for me? "I am inspired by the people on my team who..."
  • How do you deal with fear, uncertainty and doubt (personally or projected onto you)?

This is a quest to make the perfect pico de gallo for @kelly

The Backstory

Over the past few months my husband, Kelly, has been asking me to get him a specific kind of pico de gallo. "It's the store's brand, they have it next to all the prepared food," he tells on my way out the door. I grab the store's brand of hand made pico, and bring it home. We've been through this routine no less than 10 times, each time with the wrong type of pico procured.

So, instead of continuing to fail at the local Whole Foods, I decided to take matters into my own hands. I've embarked on a journey to prepare the best pico de gallo I can. It's a lesson in culinary skills, attention to detail, listening to what my customer husband wants, but most importantly acceptance of feedback.

Who knew pico would be so powerful?


A product idea is something that you want to explore further --- you have some information but not all of it. This template provides questions to help get Product Managers focused and help them dive into the idea. It serves as a guide as PMs decide whether or not to pursue the opportunity and draft a Product Opportunity for their team.

Product Idea Template

The purpose of filling out this template is to set up a plan for further exploration. The questions are designed to help determine where to investigate further, and to encourage discussion with the team. This template is intentionally lightweight, can be used to quickly give ideas structure, and record ideas so they don't get lost. Product idea docs can be closed/archived and re-opened/unarchived later. They are not to be prioritized, rather product idea docs serve as a 'bulletin board' for ideas that come from other product opportunities, customer conversations, market research,


This is a template for writing product opportunities. These are documents that illuminate some level of strategic thinking related to a particular product pain point that customers have. Typically they are accompanied by research (data, customer conversations, competitive analysis, etc.). This template helps break down the work so that Product Managers can keep moving quickly.

Product Opportunity Template

The purpose of filling out this document is to provide enough information for your colleagues to understand the opportunity, research (customer conversations and data), and value of tackling this work. It is not intended to provide solutions, scope or anything necessary to start the project or determine the next steps to start the project. This document focuses squarely on the problem space.


simpsoka /
Last active Oct 8, 2019
This is a list of questions to check our decision making.

Do I want to die on this hill?

  • Pass: This is morally good and if not handled has long term consequences
  • Fail: This if self serving

Am I including everyone?

  • Pass: My ego is not driving this conversation
  • Fail: The people in this conversation will only tell me I'm right and not push back
simpsoka /
Last active Sep 11, 2019
simpsoka product philosophy

Product managers

  • There are hundreds of methods for building products and running teams. As a quality PM, it's important to have an open mind about all of it, but finding your own process and philosophy can be grounding. It helps you find your pillars so that you don't smash into things while you're building. Remember, however, that you can always find budget for remodelling. 😉
  • The beautiy of a good process is when it just becomes how you do your work. When you forget you're following a process at all is when you know the process is working for you, your team, your company and your customers.
  • The advice I give new Product Managers or PMs coming onto a team for the first time: put your ego away, don't be 'the big idea person' and help your team ship as much as possible. If you ship products you'll learn about them, and people around you will benefit from the momentum you're building.
  • The advice I've given myself throughout my career: put your ego away, you don't have to be the 'the big

Kathy Simpson

415.637.1111 |


My background is in engineering, and I’ve always been a maker. I am extremely motivated, intensely curious, and radically passionate about technology. I am interested in helping teams navigate the ever expanding world of tech, but leveraging it to solve strategic challenges is just half of the puzzle. Product innovation is a by-product of cohesive team dynamics and strong leadership. I believe that successful products are second to smart teams. I love exploring new ways to build products, and with today’s breadth of devices, the options are seemingly endless. At work, I love finding new ways to get my hands dirty; exploring new tools, prototyping potential solutions, trying different processes, and kicking-off initiatives. At heart I’m a geek who’s often found engaging with the SF tech community through meetups, Twitter, Facebook, etc. I’ve played a critical role in the cre


Hi! My name is Kathy. I’m from Alaska, and I’m a product manager in San Francisco. I believe all great products are a result of effort that starts with a conversation. I've taken products from early prototypes to launch day consistently for the past 10 years. Through my successes (and failures) I've developed a philosophy about the path we take to make products that shine. My process thrives on the delicate dance between data driven design, business goals, and user feedback. I've worked with a lot of great people through the years. Now I work at GitHub, and we build tools to help people build apps. Say hi 👍😎.

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