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Magic Questions
Anish → How are you feeling? 😃
Anish
Take a breather and tell me a little about how you’re feeling about your work, your career path at hike and especially your personal life.
Date →
2025-11-04
Magic Questions
Score
Jot down your thoughts
How are you feeling about your life at work?
The work itself is engaging, but I'm feeling stretched thin across too many projects. I love the problem-solving aspects, but the constant context-switching is draining. Need better boundaries around my time.
What is your 5 year career vision? Is what you are doing now at work leading you toward your 5 year career vision
I want to be leading a product team at a mission-driven company. Currently, I'm getting good operational experience but not enough strategic product work. Need to push for more ownership of the product roadmap.
How are you feeling about your personal life?
Finally found a good rhythm with my morning workouts and weekend hiking. Relationship is solid. Main challenge is maintaining friendships - everyone's so busy. Started a monthly game night to fix that.
How are you feeling about our remote first setup?
Honestly struggling with this. I miss the energy of being in-person. Zoom fatigue is real, and I find myself working longer hours because there's no clear "leave the office" moment. The async communication often leads to delays.
How are we performing as a company?
We're hitting our numbers and the product-market fit feels stronger each quarter. Worried about our competitor's recent funding round though. Feel like we need to move faster on mobile.
What is it like to work with the rest of leaders?
Mixed bag. Some leaders are incredible - transparent, supportive, strategic. Others feel disconnected from day-to-day realities. Wish there was more cross-functional collaboration at the leadership level.
What is it like to work with me?
You give clear direction and I always know where I stand. Sometimes wish you'd share more of the "why" behind decisions. Your 1:1s are super valuable when they happen, but they get cancelled too often.
Is work fun? How can we make work more fun?
It's intellectually stimulating but not always "fun." Would love more celebrations of small wins, not just big launches. Maybe monthly demo days? Or bring back those random coffee chats we used to do.
How many 'Oh Shit' moments have you had in the last 3 months? What are they?
Score: 3 Had three big ones: When our main competitor launched that feature we'd been building for 6 months; when we lost our biggest enterprise client; when I realized our new feature adoption was 40% below projections. Each taught me something though.
Are you investing in yourself to grow to match the expectations of your role in the next 12 months? Give examples
Enrolled in a data analytics course, started attending product management meetups, and got a mentor from outside the company. Also reading one industry-relevant book per month. Could probably be more systematic about it.
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