I have a upcoming interview with an associate at a boutique firm where I can ask them questions about the firm. What should/can I ask the associate, and are there things I should still avoid discussing? I presume the associate will report back what we discussed. Any advice is appreciated!

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Ask about whatever could be a deal breaker for you. (Diplomatically, of course) For me, that’s the option to WFH a few days a week. Fortunately, I’ve been doing all zoom interviews & a lot of the people I’m meeting are clearly at home. In my book that’s a good sign and opens the door for the question about what in-office policies are right now & what they’ll be in the future.

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I would ask what type of work will you being, who will be supervising you, who you will be working with, expected billables, will you be managing your own caseload and handling almost everything on your cases, what is the typical caseload, are you confined to one practice group/area or can you dabble

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Ask away about WFH and benefits. Need to know exactly what you're getting into

I’d echo what A1 wrote, but since this is a boutique firm, I would ask a lot about who the clients are, what the firm actually does for them, how long they’ve been clients, etc. That would serve two purposes: it shows you’re interested in what the firm actually does and will give you some idea about the firm’s overall stability.

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Then by all means ask about it! But phrase it correctly. Something not as direct to start with, then be honest about the work environment you want. Perhaps phrase it terms of “flexibility.” Ask the person who is interviewing you what his (or her) typical schedule is like, where they’ve been on vacation recently—leading questions like that will tell you a lot. Then when you get the hard sell and it seems you both want each other, be more direct. That’s what I’d do, anyway.

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As an associate at a boutique, we’re small enough that I would answer everything honestly and keep it in confidence. But others may not share this view.

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