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The 13 best questions to ask during the remote onboarding process

Want to get the remote onboarding process right? Be sure to incorporate these 13 questions.

Remote onboarding process day 1

I won’t bury the lede: The one thing you’re likely missing from your remote onboarding process is what I call a “work preferences survey.”

The concept is by no means novel. You want to better understand the working style of a new employee. What do they tend to get annoyed by in a work environment? What communication style do they default to? How might they prefer to receive feedback.

When you’re co-located, it’s easier to answer these questions. You can read body language to surmise that a co-worker is annoyed with you. You can sense that the atmosphere is tense during a group meeting. And then, after registering these cues, you can act on them: You circle back to console a hurt teammate, or clarify confusion for a group that was causing a stalemate.

But when you’re remote, the fog thickens. Slack messages are incessantly pinging and Zoom meetings are streaming back-to-back… but you’re not sure what’s landing well.

Was that last direct message too harsh? Did they misinterpret the sarcasm of your joke toward the tail-end of the video meeting?

In a remote work environment, working preferences are learned through trial-and-error, rather than the usual observation that happens in-person and preempts misunderstandings and work conflicts. As a result, we’re more likely to accidentally step on someone’s toes, rub our team the wrong way with our management style, and cause our team members ire than ever before.

Thus, the remote onboarding process is a singular and significant time to learn people’s work preferences before we start working with them.

To minimize reckless and unintentional harm, I devised a Work Preferences Survey that is a part of our brand new Icebreakers feature in Know Your Team to be used during the remote onboarding process.

For years I’ve been asked many times by folks to share this full Work Preferences Survey. Now, I’m very excited to now have these questions baked into our Icebreakers tool in KYT – and to share some of the key questions with you here.

Below, I share the 13 most essential questions on work preferences to ask – and what asking them will reveal to you during the remote onboarding process.

#1: Where on the spectrum of introvert to extrovert would you place yourself?

The extraversion-introversion dimension is often too eagerly applied – or completely misapplied β€“ when we try to understand our fellow colleagues. (For instance, in a Wall Street Journal interview, psychologist Adam Grant estimates that one half to two-thirds of the population are a blend of introversion and extroversion.) However, it can be particularly useful to consider when thinking about the level of social interaction that your team desires: Will your new hire be hankering for a two-hour Zoom happy hour every week? Or would that be their idea of a worst nightmare? This question helps you gauge how much social interaction, especially in a remote team, that someone might desire – or detest.

#2: What’s your preferred way to receive feedback, in terms of speed? (E.g., right away). What’s your preferred format? (E.g., written via Slack).

Okay, so this is really two questions rolled into one πŸ™‚ But they’re equally important if you’re trying to hone in on how a team member might best receive tough feedback in the future. For example, you might discover some team members would prefer feedback given to them when things in the week have calmed down, which might not have been immediately intuitive to you.

#3: What’s your orientation toward conflict?

Conflict is the stickiest matter in the workplace, and we all have different reactions to it. Some of us relish it, viewing it as a creative exercise for promoting the best ideas. Others find it dehabiliting to collaboration, and will do anything they can to avoid it. Understanding a coworker’s propensity or aversion to conflict before a conflict occurs during the remote onboarding process will help you better anticipate how they might handle it.

#4: How would you describe your communication style?

Is a team member direct and data-driven in how they communicate? Or more passionate and idea-driven in their communication? How about in how you communicate? Sharing communication styles – both yours and your co-workers’ – can help bridge gaps when ideas or tricky conversations are having a hard time converging.

#5: What motivates you the most, in your work life?

As managers, we constantly are searching for the answer to the question, “How do I motivate my team?” What we fail to ask is what sources of intrinsic motivation a team member already possesses that they can tap into. In short, as managers we must figure out, “How can I create an environment that helps my team members tap into their own sense of intrinsic motivation?” This question tackles it head on.

#6: What’s your favorite way to decompress after work?

We all need refractory time to “cool off” after the workday. Learning how your team members prefer to do so, during the remote onboarding process, can help you support them to take that time to decompress so they don’t burn out in the long run.

#7: Who’s been the best coworker or team you’ve worked with? Why?

This question is deceptively insightful. One of the best ways to discern how to work well with your coworkers is to get a sense for the kinds of people they’ve loved working with. Do they seem to praise past folks they’ve worked with for their consistency and humility? Then its likely those are behaviors they will try to exhibit – and will seek out – when working with your team.

#8: Who’s the best boss or mentor you’ve ever had? Why?

Mimicry is the most powerful learning tool. As a consequence, possibly the most influential figures on our own work style are the bosses we’ve looked up and mentors we’ve sought out for guidance. These are people we try to emulate. Their preferences influence our own preferences. You’ll want to understand who these mentors have been for each of your team members – and be forthcoming about your own.

#9: When have you worked with someone and noticed it not going well? What happened, and what was that person doing?

The scars and baggage of negative work experiences are burdens we all bear. And it’s likely you heard about them during the interviewing process, prior to the remote onboarding process. Listening to these moments and unpacking the patterns behind them can help you avoid missteps with your team.

#10: What do you tend to have a longer learning curve around, compared to others?

A natural question to ask around work preferences is, of course, weaknesses. But it can be easy for someone to sugarcoat their weaknesses (For example, ever have someone tell you “My biggest weakness is that I work too hard.” Queue the eye roll…) Instead, ask about what tends to take longer for this person to pick up, compared to most. During the remote onboarding process, this will help people on your team to feel comfortable admitting what they feel like they’re slower at and what they might have to learn to get better.

#11: What do you tend to pick up very quickly, compared to others?

On the flip side, you’ll want to get a sense of strengths β€“ but areas that feel especially fluid for the person that might not immediately be disclosed when you first hire someone. You want to discern hidden talents and advantages in working with folks when the thing they’re working on doesn’t feel like work to them.

#12: What’s your biggest work-related pet peeves (i.e., that thing that other people do that totally annoys you when you work with them)?

What drives you crazy at work? You know what I mean… Someone doesn’t mute themselves on Zoom. An executive checks in on you too frequently via email. Your organization has way too many meetings. Whatever the pet peeves are, best to air them out in the open so an honest discussion can be had during the remote onboarding process and preventative action can be taken.

#13: What does “work-life balance” mean to you?

As leaders, we want to be conscious of not wearing our team too thin. But where that line is drawn is different to each person. As a result, you’ll want to ask about how each team member defines work-life balance for themselves, so you can have a frank dialogue about expectations with the consideration of what each person’s preferences are.


Trouble brews the more often the phrase “I had no idea” is uttered in your team.

“I had no idea that bothered you.” “I had no idea you preferred it a different format.” “I had no idea that wasn’t a good way to communicate my ideas“.

Get ahead of the “I had no ideas” and ask a Work Preferences Survey during your remote onboarding process.

The fog in your remote work environment will be lifted.


Want to ask these 13 automatically, every time you hire someone new during your remote onboarding process? Try our Work Preferences Survey today in Know Your Team.

Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.

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