What should I ask in my 1-1s

There's much more to talk about in a 1:1 beyond status updates! When you're the new engineer at the company, there is so much more to learn beyond the core workflows of your job:

• Org structure
• Historical decisions and why they were made
• Upcoming problems (not just the current problem you're solving)

I'd encourage you to share something "awkward" in the 1 on 1 as a way to get much more out of the meeting.

Go through this masterclass: How To Have Impactful 1 on 1 Meetings

If you're just going with the flow in these 1:1s, you may be wasting time.

Some possible questions:

• What's taking up the most time for you when it comes to these tickets?
• How well has your boss been keeping up with big picture goals/how could you help them achieve those goals?
• What are some things that are unproductive for you that you spend too much time on?

These are all basic discovery questions coming from the mindset of "how can I make my life/boss's life easier?"

Not all of the conversation needs to be ultra-structured. I try to get the important things out of the way first (productivity, team dynamics, workflows, etc) so that the later half of the 1:1 can happen more organically.

Using 1-1 time effectively is one of the biggest career hack most people don't use.

I will answer it two ways. First, when you are new into your role, you want to use 1-1 for

• Understanding the context of the problem you are solving. (Why of the problem.)
• Get feedback about you -- and there is always some. If the manager keeps saying: you are doing great, message here... there are ways to get the feedback. This will also help you understand the expectations of the role.
• Give some updates about what you have up to, provide where you are stuck and ways to get unstuck (technically or people-wise, depending on where the manager can help).

Second, once you are there for a few months, you want to do all of the above and also start to ask about your career path how growth (and great rating) look like. Over time, you also want to do your job better than your manager can, so at that time, communicating your work in a way that is easily digestible is also super important.

There is a lot more to optimizing 1-1 conversations with manager for growth (there is a big part of what I work with in coaching for some people) -- there are emotional aspects, there are difficulties of getting feedback, there are conflicts, there is using peer relationships well and so on.

Happy to expand more if this is something valuable for you.

Things I would focus on:

• Focusing on big picture goals
• Are there any places you're struggling or need help with
• How is your work going to evolve over time? what areas do you want to own expertise over?

If you truly don't have anything tactical to talk about (i.e. you are crushing onboarding and you 100% understand the workflow now), you can use the 1 on 1s purely to build the relationship and further understand big picture.

Being a founder is really stressful, so it's probably valuable for them to talk through the challenges with you, both to think out loud and maybe vent a little. Just ask them how things are going and what's the biggest challenge they're facing right now. A fun UXR question that could work here is: "What's the biggest thing keeping you up at night?"

This can also be an opportunity where you flip the dynamic. Instead of having this be a meeting where you extract value (i.e. ask questions on how to do stuff), make it an opportunity for you to proactively surface product/project ideas you came up with that are relatively fleshed out, derived from your solid understanding of the company's product. This is the kind of stuff that you should be doing at startups that you can't really do at FAANG (it's possible there but just so, so, so hard). If you do this, you will be providing value instead of extracting value.

A good startup will value truly independent, proactive thinkers who are taking the initiative to bolster the company. That's how the best startups thrive.