You've found a role that's a strong fit. The posting says hybrid. You need remote. What do you say, when do you say it, and how do you not blow the opportunity?
I've coached a lot of people through this, and the biggest mistake is either (a) saying nothing and hoping it works out, or (b) leading too early with the ask before you've built any rapport.
When to bring it up: not in the first screening call unless they ask directly. Get through to the hiring manager round. At that point you've shown interest and they've invested time.
How to frame it: not as a demand, as a clarifying conversation. "I want to make sure I understand the day-to-day expectations. I've been working remotely for the past X years and have a strong track record in that setup. How does the team currently think about in-person vs. async?" That's a question, not an ultimatum. It also gives you real information.
If the manager says 3 mandatory days per week, you can follow up: "Is there flexibility in exceptional cases, or is that a firm team policy?" You'll know quickly.
If the answer is no flexibility: you have to decide whether to continue. Don't accept a role assuming the policy will bend. It usually doesn't, and you'll be miserable and job-searching again in six months.
If there's some flex: express genuine interest, then at offer stage put specifics on the table. "I'd like to propose a primarily remote arrangement with planned in-office visits for quarterly planning and key milestones. Is that something we can formalize?" Then get it confirmed in writing.
What not to say: don't tell them about your personal situation (childcare, elderly parent, long commute) in the first conversation. That's negotiation context you keep close. Lead with your professional track record.
The companies most likely to flex: remote-native teams that added an office, distributed teams with no real in-person culture, and teams where the hiring manager herself is remote. The companies least likely to flex: ones with exec mandates tied to real estate contracts. You can't negotiate against a lease.