February 25, 2021 — 2 minute read

Questions to kickstart a design career conversation

It’s a privilege learning someone’s hopes and aspirations. It’s a special responsibility supporting someone in reaching them. Seven years into management, I haven’t found a silver bullet that replaces the time, trust, and vulnerability needed to deeply understand someone’s career.

Learning from four companies and 32 direct reports from intern to senior manager, I come back to a few same questions that pave ways for a new designer on a team to get to where they want to go in their career.

I made a template for the team I support at Instagram. If you’re a manager looking for ways to better support a designer, or a designer looking to better engage with your manager, try bringing these questions to your 1:1s!

Career Conversation: Designer & Manager

What projects in your career—Instagram or elsewhere—drained you?


What projects in your career—Instagram or elsewhere—energized you?


How would you personally rank these in order of importance in your career?

1 is most important, 7 is least

  • Challenging projects
  • Company exposure (e.g. awards, shout outs, presenting work)
  • Compensation
  • Industry recognition (e.g. awards, spotlights, speaking, writing)
  • Job title
  • Leadership I work with
  • Scope of my responsibilities and influence

Beyond the above areas of importance, what else matters to you in your career?


What’s one of your proudest career milestones, so far?


What might your next best role look like to you?


What’s a moment where you felt within yourself you leveled up?


Who is someone that has inspired your career journey? Do you model yourself after anyone?


When you felt a strong link between your career progression and someone’s support, what did that look like?


What do you hope people say about you when you’re not in the room?


Hopefully these are a fun start for us. Over time, I’d love to have our career chats feel light, casual, and regular, versus momentous meetings or occasions. Excited to support you in where you’re trying to get to next.


— Mig