11 questions to ask your boss the first day of a remote-only job


Starting a remote job is hard. With everyone hiding behind their computer screens, it’s not obvious who’s who, who’s working on what, where important files are kept, how things get done, and, most importantly, what’s expected of new employees. Ambiguity can be a challenge, yes, but, as I learned from interviewing over 500 professionals, ambiguity can also be an opportunity.

Uncharted territory or undefined expectations provides new employees a chance to step up and show how hungry they are to succeed. To help you guide you to success in a new job, I’ve outlined a handful of questions new employees can ask a manager. After clarifying each, you’ll feel you have a greater understanding of your new workplace.

1. “What does success look like in my role? What am I responsible and accountable for?”

Asking this question can ensure that you are managing what others expect you to manage—and doing what others expect you to be doing.

2. “What should I be able to do by the end of the first month, three months, and six months?”

Even if your manager doesn’t mention it, they have a mental picture of how quickly they expect you to get up to speed. Clarifying can ensure that you remain above expectations.

3. “Who do I report to on a day-to-day basis?”

If you have multiple managers, ask, “How should I allocate my time between you and ____ person?” to prevent others from assuming that you are working with them exclusively—and overworking you.

4. “What should day-to-day and week- to-week collaboration look like between us?”

Different managers have different expectations. When in doubt, try asking, “Would it be helpful for us to have some sort of regular check-in?” followed by “What’s most convenient: Weekly? Biweekly?”

5. “What have your highest performers done that you’d suggest I do as well to make your life easier?”

Such a question can help you not only understand your manager’s working style, but also show that you are eager to learn—and eager to perform.

6. “Who worked on this project before me? Can you please introduce me to them?”

It’s stressful inheriting someone’s work and not knowing their methods and practices. A 30-minute chat with your predecessor (if they are still around) can save you 30 hours of digging and guessing later.

7. “Which folders should I have access to—and which files/templates should I review and use?”

Knowing the three folders you should pay attention to and the five templates you should use for your work can, once again, save you hours of digging (and reworking).

8. “Would it be possible to share calendar invitations to upcoming meetings you think I should attend?”

It’s important to be seen and heard when you’re new—and you can only be seen and heard if you’re in the room. If you don’t ask, you might get overlooked and miss meetings people expect you to be at.

9. “Are there any upcoming deadlines or milestones I should be aware of or can help with?”

You may have deadlines before you even start working, especially if you are taking over for someone else. Knowing what they are can help you avoid scrambling last minute or missing a deadline altogether.

10. “Is there an updated organization chart or team list I can reference?”

Knowing who reports to whom—and who does what—can help you better navigate the politics of your new environment, as well as more effectively figure out who to go to for what.

11. “What’s the usual process for this?”

Every team has its own way of doing things. Showing deference to how things have always been done early on can earn you the political capital you need to change things up later.

Good managers, despite their best intentions to set you up for success, can look forgetful and uncaring when their own boss summons them for that surprise meeting minutes before you arrive. What’s the result—a workplace that favors the proactive. Therefore, if you can’t find anyone to show initiative and help you, take charge of the situation and help yourself.

Gorick Ng is the Wall Street Journal Bestselling Author of The Unspoken Rules: Secrets to Starting Your Career Off Right. He is a career adviser at Harvard College, specializing in coaching first-generation, low-income students and professionals. He is a former management consultant at Boston Consulting Group and researcher with the Managing the Future of Work project at Harvard Business School.

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