The questions I ask new hires in their first week, the 1:1 shape they're walking into, and how I set up a pairing with a lead who isn't their manager.
Week 1 with a new designer is mostly logistics, and I’ve learned to steal an hour of it back for a different purpose: figuring out how the person ticks before the work starts telling us. I did that recently with a designer who just joined the team, and writing it down afterward made me realize it’s the same 4 conversations every time. Here they are, in the order I run them.
The 1:1 shape. Before anything else, I describe what our weekly time will look like, because the structure carries a value I care about. We start human: what’s going on in your life, what’s going on in mine. Then feedback, in both directions, every single time, even when it’s minor. “I noticed you talked over someone in that review, and that’s a trigger for them” counts. “Great job on that presentation, and here’s how I’d tighten the narrative next time” counts. Only after that do we get to the work: what you want to cover, where you’re blocked, what I need from you. The reason for the order is simple. The worst relationship you can have with a colleague is being surprised at a mid-year check-in by something you could have avoided in week 1, and the only defense against that is a habit of small feedback that never gets skipped. It’s cheesy, but I do believe feedback is a gift, and I’ve never regretted hearing it, even the poorly delivered kind.
The worst relationship you can have with a colleague is being surprised at a mid-year check-in by something you could have avoided in week 1.
The recognition question. I ask it plainly: how do you like to be recognized, and how do you want to be rewarded? Some senior people want the raise and none of the spotlight. Some are fueled by being front and center. Most are somewhere in between and have never been asked, which is why the question is worth the slightly awkward 30 seconds. The answer changes what I do with their wins for the next year.
The venue map. Every company has a ladder of rooms, and I walk the new person up it: the company all-hands, the product-org all-hands, the PM and designer channel, our design org, and the weekly design crits. I tell them which rungs are optional and which aren’t (nobody gets a pass on crit; showing up and participating is the job). Then I ask which rooms they’d dread. For some designers, presenting to a few hundred people is mortifying, and that’s fine, because there are ways to frame someone as a leader without ever putting them on that stage. I’d rather know in week 1 than find out by watching them suffer.
The story. Every new hire gives a PechaKucha at a Monday warm-up in their third week: 20 slides, 20 seconds each, on an automatic timer, about anything they want. Kids, travel, the art they collect, whatever they’re comfortable talking through. It’s the fastest way I’ve found for a team to get to know someone in their own words, and the timer keeps it honest.
There’s a fifth conversation when the new person will pair closely with a lead who isn’t their manager, which is how this hire is set up. That’s a tricky shape, because the lead oversees the work without owning the person. So I do reconnaissance first. I meet the new hire and ask how they want to collaborate. Do they want to own something end to end, or start with snack-sized work handed over directly? Separate 1:1s, or the 3 of us in one room once a week? Then I go back to the lead and hand over what I heard, along with an honest download in the other direction: what the lead is great at, what they’re slow with, how they communicate. The lead knows that download is happening. From there we write a V1 of ways of working, and I judge the pairing on the 2 measures our leadership will recognize, velocity and quality. My line to the lead was that it’s okay for the new person to splash in their swim lane, but it’s still their swim lane.
None of this is complicated. It just has to happen in week 1, while everything is still negotiable, instead of in month 6, when it isn’t.