Questions Managers Need to Ask During Their First Two Weeks

Managers should be asking as many questions as possible when they start at a new company. Different valuable insights can be easily gained from asking intentional, specific questions to the right people— right at the beginning of your tenure.

Last updated on: 
August 11, 2023
The Pathlight Team
The Pathlight Team
August 6, 2018
8 min read
Questions Managers Need to Ask During Their First Two Weeks

Naturally, when you begin your role as a new manager, you’re eager to hit the ground running. However, it’s crucial that you take the time to listen and learn during your first two weeks. Chances are you are going to have a LOT of questions. While asking questions is absolutely an important aspect of any new role, you need to be sure you are asking the right questions to the right people at the right time.

In order to ease some of the nerves you might be feeling when you start as a new manager, we have compiled this list of questions that are essential to ask during your first two weeks: Questions to ask your direct reports, questions to ask your supervisor, and questions to ask yourself.

Questions to ask your direct reports

One of the most important things a new manager should do during their first two weeks is get to know their direct reports. Two leading people scientists from Gallup wrote in this Harvard Business Review article that “the best managers make a concerted effort to get to know their employees and help them feel comfortable talking about any subject.”

When you first engage with your direct reports, you should also let them know how to work best with you. Tell them how you want to receive feedback, what your management style will be, and how you plan to operate. Claire Hughes Johnson, Stripe COO, did exactly this by circulating a document throughout the organization when she joined.

1. “What are your goals for personal and professional success?”

When getting to know your employees it’s really important to familiarize yourself with their goals for personal and professional success. A recent Gallup survey about employee engagement reported that only “30% of employees strongly agree that their manager involves them in goal setting. Employees whose managers involve them in goal setting are 3.6x more likely than other employees to be engaged.

Be sure to write down your employees’ goals. This ensures that you are actively listening to your reports. Additionally, when you need to revisit the goals of your employees for one-on-ones, they will be readily available.

2. “What communication style works best for you?”

One of the most important aspects of becoming a manager is ensuring you are communicating effectively. A recent Gallup report showed that employees who thought their managers were invested in them were more likely to be engaged. One of the easiest ways to prove your investment in your employees is to communicate with them.

In general, you should know the basic preferred communication style of your reports. Do they mind receiving direction over a messaging platform or do they need face-to-face interaction? A critical aspect of being a manager is giving constructive feedback. It’s important that you know exactly how your employees wish to receive this feedback. Are weekly 1:1s the best way to communicate feedback or would they prefer to know about it as soon as possible?

3. “What do you need from me to be successful?”

Now that you are familiar with where your employees want to go, you need to know what you can do to help facilitate or what has been blocking your report from achieving those goals.

Similar to their goals, you should record what your reports say is needed from you for their success and revisit it frequently. If your employees do not give you any concrete action items for you to help contribute to their success, try to give suggestions based on the goals that they presented to you.

4. “What worked well with your previous manager?”

This question is a great way to understand how your direct reports work most effectively (also a good interview question!). Knowing what your direct reports responded to well from their previous managers gives you some good ideas for what to implement.

Of course, the answers you get to this question might not be things you should recreate (“he let us leave every Friday at noon!”). By asking this question, you’re doing some important and potentially helpful reconnaissance — you’re not making a commitment.

5. “What could your previous manager have done differently to better set you up for success?”

This question should not turn into a previous manager-bashing session. Instead, think of it like this: every team has a history, and it’s important for you a manager to know what kind of history you’re walking into. You should encourage the employee to be truthful — explain how important it is for you to know what managerial styles are helpful and effective and which ones you should try to avoid.

Once your reports explain to you what did not work well with their previous manager, take note of what they say. If they give criticism of their previous manager, chances are it was an issue that significantly affected their performance or morale.

As a manager taking over a team, it’s important to remember that you inherit all of the good of the team as well as the bad.

Questions to ask your supervisor

Meeting with your new supervisor for the first time may be daunting. However, if you leverage your relationship correctly, your supervisor could — and should! — be a huge help towards your success as a manager.

Here are four questions that you should ask your supervisor to best set you and your team up for success.

1. “What are your expectations of me?”

If you want to be successful in your position, you need to know what your supervisor expects of you. Getting a good answer from your supervisor might also require some work on your part. Try to facilitate the discussion in a way where your supervisor is giving you explicit criteria that you can meet to be successful. The best success criteria are specific and measurable.

Once you are aware of your supervisor’s expectations, you should align your expectations for your team towards those in order to create an alignment throughout the department.

2. “Are there any team dynamics that I should be aware of?”

One aspect of managing a team that is hugely different than being a frontline employee is that you not only need to be aware of various dynamics at play between your employees, you have to manage them. Being aware of these dynamics from the start will help you avoid potential people issues in the future.

You may have to do some work to actively improve a toxic team dynamic. Here are a couple of ways that you can help a difficult dynamic:

  • Act quickly once you are aware of a bad dynamic — provide constructive feedback to the employee that seems to be negatively altering the dynamic by making them aware of the impact of their actions
  • Break down barriers — if you notice that there seem to be barriers that are keeping people distant, try to use team-building activities to improve employee relationships

One of the benefits of being the new manager is the opportunity to create a reset on some of the problems from the past.

3. “What have been some of the team’s issues to date?”

When starting to oversee a new team, it’s crucial to be aware of some of the biggest issues in the past that have affected them. An obvious reason you should be aware of these issues is so that you can prevent them from arising again. A less obvious reason is that it will help you understand what your supervisor defines as “issues” so you can better understand how they work and what their expectations are.

4. “Are there records of past performance?”

Records of past performance are extremely helpful for you as a new manager. Hard data helps you cut through the subjective feedback and qualitative information you’ll be getting in response to these questions to see where real issues are. You may even pick up on problems that the team isn’t even aware of yet.

Questions to ask yourself

During your first couple of weeks as manager, you will be critiquing your performance constantly. Introspection is an important part of growth, but you should ensure it’s constructive, and not just constantly criticizing or doubting yourself. Here are some important questions to help guide that productive introspection.

1. “How do I receive feedback?”

When you were a frontline employee, did you receive criticism well? As a manager, you should encourage your employees to give you feedback. Once you’ve received feedback, act on it.

If you reflect and come to the conclusion that you have not previously received constructive feedback well, Harvard Business Review has some tips:

  • Don’t rush to react — Take some time to process what is being said rather than responding irrationally. Self-affirmation is one response that can help in processing critical feedback. By affirming your contribution to your team and seeing the larger picture, you have a clearer view of the changes that need to be made.
  • Get more data — If you receive feedback that is especially startling, try gathering opinions from a few other trusted sources. This helps avoid over correcting and will also help you get more detail about what you are doing to elicit certain negative responses.
  • Remember change is just one option — If it’s not possible to change, being clear with your team and admitting your flaws is the next best option. It’s important to let go of things that you are not able to change.

2. “How will I remain organized?”

Soon after you begin your role as manager, you might find your schedule crowded with team meetings, one-on-ones, department meetings, phone calls, and lunch meetings. You’ll find your desk and inbox bombarded with memos from your direct reports, information from HR, meeting requests from your supervisor, etc.

The most precious thing a manager has is their time, and when you go from individual contributor to manager, you realize just how little time is now your own. It’s really important that you’re using your time efficiently.

A couple of under-utilized tips for time management:

  • Create labels for incoming emails (i.e., automatically put emails from your direct supervisor in a separate folder and be sure to answer those emails within 24 hours)
  • Own your calendar! Be disciplined on the meeting invitations that you accept and block off time to be on the floor, prepping for meetings/calls, or working on specific projects.
  • When onboarding new employees, be explicit on certain times you will be available to answer their questions. This will ensure they have what they need to be successful and will also help you avoid interruptions.

3. “What and how am I communicating?”

Communication is the number one soft-skill that managers need to have in their tool belt. They need to be able to communicate well with their supervisor and their direct reports. Take a look at our previous blog post on communication to see how managers can work on this super important skill.

4. “Who do I admire?”

One smart thing for new managers to do is seek out a mentor. A study by MENTOR showed that the businesses in the study showed “Mentoring helps foster employee engagement, retention, and recruiting efforts” and that “Mentoring enables companies to cultivate and develop the future workforce.”

One easy way to find a mentor is by thinking about those people in your organization that you admire. Another way is to see the people who seem the happiest in their positions. Don’t be afraid of reaching out to potential mentors — most people love being admired. Try inviting them for coffee to see if they would be willing to offer mentorship.

During your first two weeks as a manager, you may feel nervous, intimidated, or overwhelmed. This is completely natural and expected when starting any new position.

However, those first couple of weeks help set the tone for your time with the organization. With that being said, it’s crucial to focus on intention. By focusing on the intention of questions you ask, you will ease the transition in management for all parties involved.

The questions that we have compiled have specific goals to establish the framework for long term success.

Want to see a custom demo of Pathlight or get help finding the right plan? We'd love to chat.

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