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21 questions to ask when taking over a new team

As a new leader, get your bearings with these critical questions to ask when taking over a new team.

questions to ask when taking over a new team

A new leader recently asked me, “What are the important questions to ask when taking over a new team?”

His voice revealed simultaneous excitement and nervousness: His direct supervisor had handed him the reigns to a role he’d been eager to fulfill – but it was a new team after all, one that he knew nothing about.

Newness and the unknown are inextricably linked. When you’re new, there are bound to be things you don’t know. As a new leader, you inherit routines and and ways of doing things you’re unfamiliar with. You’re the outsider amidst a group of people who’ve all worked together for a while.

How are you supposed to navigate and lead a new team given these challenges?

Rather than let anxiety grip you and hastily project a guise of competence – embrace the unknown for what it is, and commit to clarifying it.

Dedicate yourself to figuring out the right questions to ask when taking over a new team. Questions will be your light into dusty corners, unearth helpful insights under long-overturned stones. With the right questions, you’ll gain both the confidence and context necessary to be successful as a new leader.

Below are the 21 questions to ask when taking over a new team that we’ve found to be most effective in our research in training over 30,000+ leaders over the past decade-plus here at Canopy.

Ideally, you’ll want to ask these questions in a 1:1 setting, so you can provide a sense of safety for your team members when they answer and also so you have the opportunity to dive deeper in the follow-up questions, as it makes sense.

Additionally, you do not want to just unload all the questions at once — there’s 21 of them after all, which would be overwhelming to ask in one go (and not to mention end up being a 3 hour meeting for the both of you).

Rather, I suggest splitting up the 21 questions across 3 – 4 distinct one-on-one meetings that each focus on a particular area. Here is how it might look…

Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
Learn more

The 21 key questions to ask when taking over a new team:

The First 1:1 Meeting – Trust-building

Try these 3 questions to ask when taking over a new team in your first one-on-one meeting:

  • What do you tend to find energizing or relaxing for you, outside of work?
  • Anything fun / exciting you’ve been looking forward to?
  • Why do you choose to work at X, versus other organizations?

Then, I’d also recommend sharing your own answers to the same questions so there is a bit of reciprocity here, and it doesn’t feel like a one-sided interrogation 🙂

The Second 1:1 Meeting – Work Preferences & Team Dynamics

Try these 7 questions to ask when taking over a new team in your second one-on-one meeting:

  • How do you prefer to receive feedback? (Verbal, written, in-person)? How do you prefer to give feedback? (Verbal, written, in-person)?
  • What do you wish was communicated to you more often?
  • When have you felt micromanaged? When have you felt like you’ve needed more support?
  • Who’s the best boss you’ve ever had and why? The worst boss you’ve ever had and why?
  • What was the best team experience for you? The worst team experience?
  • How do you like to be shown gratitude?
  • How often would you like to set up a standing one-on-one or check-in meeting? Every week? Biweekly? Once a month? Once a quarter?

The Third 1:1 Meeting– Grievances + Desired Improvements

Try these 6 questions to ask when taking over a new team in your third one-on-one meeting:

  • What do you want to change in this team?
  • What do you not want to change in this team?
  • What’s typically been taboo to talk about in the past? – What have you been nervous to bring up?
  • What looming concerns or apprehension might you have?
  • What’s been the most frustrating thing to have encountered with the team lately?
  • Where do you see the biggest opportunity for improvement with the team?

The Fourth 1:1 Meeting– Motivations + Aspirations

Try these 4 questions to ask when taking over a new team in your fourth one-on-one meeting:

  • What’s been the most motivating project you’ve worked on all year? With whom? And why?
  • What excites and energizes you about the company?
  • What are you most grateful for in being a part of this company?
  • What do you think has been a big obstacle to progress?

Each of these 1:1 meetings should last 30 – 60 minutes long. While it initially feels like an inordinate about of time spend, the time invested is well worth it. From these twenty-one questions, you’ll begin to deeply understand each team member’s working styles, proclivities, and requirements for them to be set-up for success.

The time you spend also signals that you care about learning these things (e.g., their work preferences). And lastly, it sets a precedent for the kind of leader you’d like to be: One who leads with questions rather than answers, who doesn’t presume or impose their perspective on others.

Try these 21 questions to ask when taking over a new team – and with it will come your ability to lead well, for things to start off on a strong foot, and for the unknown to slowly dissipate.


Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
Learn more

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Written by Claire Lew

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