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Winning at WFH: What to ask a manager when you’re working from home

Some of us rejoice at being able to work from home. Others dread virtual meetings, unclear expectations, and intranet messages interrupting our days. For most people, going remote makes communicating with your manager that much more important.

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Why it’s important to be able to talk your manager

How to build good relationships with questions

Do managers benefit from conversations with employees?

10 questions everyone should ask a manager when starting out

25 questions to ask a manager during WFH arrangements

Put it into practice

Coping with remote work conditions while making meaningful progress on your tasks can be a hard ask if you’re unfamiliar with relationship-building in the workplace. 

Employees are experiencing everything from family distractions to unresponsive colleagues and micromanaging bosses struggling to find their feet.

However, the key to making the most of your virtual work screen time is knowing how to ask the right questions. 

The fact is that asking for thoughtful, timely advice from a good manager can build the foundation for a successful work-from-home experience. 

In this article, you’ll learn how to use the right questions to create a relationship with your boss or manager. You can return to this connection as a way to avoid workplace dilemmas and even further your career goals.

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Why it’s important to be able to talk your manager

Communication — it’s the key to trust and, with new work-from-home arrangements, trust may be in short supply. In the WFH world, err on the side of over-communication.

Even though we have more technology than ever before to help with communicating, time-tracking, scheduling, project management, and online learning, the trust between managers and employees is decreasing. 

In a recent column about work from home, Alison Green, the creator and moderator of the popular website, “Ask a Manager,” says that work-from-home arrangements seem to make managers managers uncomfortable. 

Some managers worry that, out of sight, workers are more likely to skip productive hours and binge-watch Netflix instead. 

But the facts about remote work say something different: 

  • 75% of employees say their job performance has either increased (45%) or remained consistent (30%).
  • 76% use video conferencing to check-in with teammates.
  • 46% of employees are actually working more hours each week. 

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Even though these numbers are the result of a pandemic, the fact is that remote work has been a viable employment arrangement for over two decades now.

So why are managers failing to trust their teams?

Navigating the modern workplace has always been an evolving conversation. But putting a screen between managers, employees, and coworkers seems to be adding to the strain. 

Communication that forms trust is the key to sealing those cracks. 

That’s precisely why it’s so important to be able to use the right questions when communicating with your manager. 

Strategic communication isn’t just about eliciting information — it’s also about subtly letting your managers know they can trust you. 

The right questions will instantly put your manager at ease about your intentions and help create transparency, even when they can’t necessarily see you. 

In other words, you’re setting the stage for trust in a manager-employee relationship through strategic questions.

You can use one-on-one conversations inspired by these questions to...

  • Showcase what your priorities are (contributing to the bigger picture)
  • Gain valuable insight into your manager’s unique management style
  • Avoid pitfalls or tricky situations that might occur because of “fuzzy” expectations

As workplaces continue to offer a greater level of flexible working arrangements, the questions you ask to build relationships can transform a good manager into a great one for your career advancement.

How to build good relationships with questions

Building relationships in the digital workplace comes down to forethought and preparation. The questions we’ll discuss in a minute will give you all the tools you need to achieve your desired outcomes, even if you’re remote. 

However, before you jump to adding these questions to your arsenal of communication tools, you should create a structure for building trust through conversations. 

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Harness these seven steps to take your strategic communication to the next level:

  1. Understand yourself and your goals before starting a conversation.
  2. Learn to articulate this information when it’s relevant to the situation (you can use questions to do this).
  3. Listen in on the goals of others to discover their priorities and focus. Are there resources you can send their way to help?
  4. Seek feedback, opinions, consultation, and collaboration (As UC Berkeley’s Career Advancement activity for connecting with key leaders points out, “it’s your responsibility to build and sustain your networks over time”).
  5. Generously reciprocate and respond to others who want feedback from you.
  6. Create a mini CRM (customer relationship manager) for your work relationships — a simple way to tangibly track who they are, how to reach them, how you may be able to help them, and who you’d like to connect with further.
  7. Try and identify the type of relationship you want with both colleagues and managers in your organization or network — mentoring, informational, interviewing, support/encouragement, and feedback.

Everyone has a boss — including managers. And managers must meet their employees halfway with thoughtful and incisive conversations, especially as we continue with work-from-home arrangements.

Do managers benefit from conversations with employees?

Without thinking about workplace conversations and communication strategically, you may not have the workplace relationships you desire. Remote work has a way of making this kind of gap glaringly obvious. 

As an employee, you have the opportunity to spark these highly effective conversations with your managers. And, believe it or not, they need you to do so. 

According to a Gallup report, the value of conversations between managers and employees can help boost the bottom line. 

“Great managers who have meaningful ongoing discussions with their employees also take ongoing action based on what they hear in those everyday conversations. They ask good questions, including disarmingly simple ones, and they pay close attention to the responses. They keep the wheels of engagement turning all the time, just by talking.”

Conversations with employees are a form of work motivation and engagement. While managers managers worry about productivity, what they should be concerned about is overall employee experience and whether that is leading to commitment or disengagement. 

Whether you're looking at employee engagement levels or a sense of meaning and purpose, improving how employees experience their work and how effective they are in it starts with clarity among leaders and managers.

Those employees who have a high-quality manager and are coached along a distinct and clear path, based on communication with an engaged manager, produce better business outcomes. 

According to findings from Betterup, for example, employees who score highly in employee experience have:

  • 37% lower turnover intention
  • 28% more productivity
  • 59% higher job satisfaction

High employee experience is strongly influenced by a good relationship with the manager, and it has a range of other postive effects for the manager, the emplyee, and the business.

effects of employee experience

What’s more, 65% of employees want more feedback, but 69% of managers feel uncomfortable communicating with employees. 

Other perceived barriers to having conversations with employees include:

  • Fearing that conversations may upset or disrupt an employee’s pace
  • Wanting to avoid potential conflict
  • Displaying a reluctance or an aversion to being known as “the mean boss”
  • Feeling inadequate when it comes to being trained to effectively coach employees
  • Being concerned that there’s no documentation to support these ongoing conversations, especially if they’re corrective

These valid concerns should tell you something significant. 

Even managers are humans. They, like you, need support to be supportive.

So the questions you ask a manager will help them breathe a sigh of relief. It’ll be clear that you’re interested in doing your best work and cultivating high-quality relationships at work.

Ready to take your managers to the next level? Try a demo of BetterUp.

10 questions everyone should ask a manager when starting out

All other things remaining equal, companies — and a hiring manager in particular — will look for candidates with emotional intelligence. 

Also known as “EQ,” emotional intelligence can help job seekers land the right position. It can help you segue to leadership roles in your own right with greater confidence from managers who put you up for promotions. 

components of emotional intelligence

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The questions you ask a manager can help you convey a high level of emotional intelligence or self-awareness. These traits account for 90% of what sets high performers apart from their peers, especially in the virtual or remote work environment. 

The questions you might want to ask include: 

  1. What are your expectations of me as an employee for this position?
  2. How can I help to meet your project goals and objectives?
  3. What kind of skills and training should I seek out?
  4. What do you feel are the most significant contributions of a manager in the workplace?
  5. What advice would you give me at this point in your career?
  6. What is your personal definition of success?
  7. How have you rewarded an employee's excellent performance and hard work?
  8. What does upper management’s care about most?
  9. Why did you choose me for this role?
  10. What performance goals should I be setting?

These questions can help establish a baseline relationship for a new employee with management. Whether you’re remaining in-office or working from home, it would help if you built a connection with your superiors. 

These highly effective communication starters will go a long way toward helping you build solid workplace relationships. 

And don’t forget to communicate even after you’re hired. You need to build ongoing relationships if you want any hope of advancing your career. 

There’s a “hidden job market” out there. Organizations fill up to 57% of their positions through networking contact referrals. If you don’t actively build relationships, you won’t reach your full potential.

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25 questions to ask a manager during WFH arrangements

What do you wish you could ask a manager? Is it workplace advice about a new opportunity? Is it some insight into how they might react in the situation you’re currently facing? 

These 25 questions to ask a manager or a new boss will help you create and sustain meaningful dialogue and trust, even if you’re working from home. 

Questions about expectations

Expectations set the stage for your participation. If you don’t know what’s expected of you when you work from home, it can be very easy to feel disengaged or unmotivated.

The following questions will help you set specific expectations for daily tasks as well as contributing to your organization’s larger goals.

  • What are the project’s deliverables and how do you envision my role in this project?
  • What do you feel my strongest skills are, and how could I put those to use?
  • What goals should I be setting for this project?
  • What are your priorities and what are we trying to achieve for this project/client?
  • Are there resources I can turn to for help on tasks before I ask you? 
  • What is your communication preference (timing, mode) in general, and how would you like me to keep you updated on progress?

Questions for workflow and process

Even though technology handles a lot of the “how” of workflow and process, you need to gain clarity on both “what” and “how.” 

The right questions about workflow and process include:

  • If you were me, how would you work on this particular task?
  • Is there anything you’d like me to know about streamlining the process?
  • Are there any skills I can work on that might make this workflow smoother?
  • What do you think is the biggest challenge our team is facing right now?

Questions for clarity and follow-up

Questions for clarification and follow-up can help your manager understand that you’re paying attention. They can trust you to move forward with minimal to no supervision and get the job done. 

That’s important because details on Zoom calls, Slack messages, and email can get lost in the shuffle.

The right questions include:

  • Could you take five minutes after this meeting to discuss my tasks for today?
  • What one or two outcomes would make this project/task a success from your perspective? 
  • Would you be open to an idea I have or a proposed change that could make things easier?
  • Is there anything you’d like me to know about [this team, you, the project, my performance] that might not be apparent?
  • What can I do to support you further?
  • How’s your day going?

This last question is especially important. It has no other purpose than to build rapport with your manager and acknowledge that you are both in this together.

Questions to help get feedback

To spark a conversation about feedback and receiving constructive criticism, use the following questions:

  • Is there anything you feel I can improve on that would take my contributions to the next level? Even better, help your manager by being specific: what one thing should I start doing and what 1 thing should I stop doing?
  • Do I need to communicate more or better with you about specific aspects of my job (deadlines, progress, process, client communication, etc.)?
  • Is my performance so far in alignment with why you hired me or put me on this project?
  • Is there someone on the team you feel I can learn from through observation or conversation?
  • Do you prefer ongoing chats or check-ins when it comes to feedback or would you like to have more formal feedback conversations?

Questions about new opportunities and personal growth

In 2019, the number one priority for people entering the workplace was professional growth and learning opportunities.

3 things to look for when choosing a job or an internship

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And it’s not just an employee priority. In a 2021 study by Gartner, 68% of HR leaders highlight skill-building as a priority.

Generally your manager isn’t in a position to be your full-time mentor. But a good manager can give you some coaching — set you off in the right direction. After all, your manager knows your work, your strengths and your style. Don’t miss the opportunity to benefit from their educated perspective. 

Questions you can ask to transform a managerial relationship into one of coaching and guidance include:

  • What do you love most about working here and what’s your least favorite part of the job?
  • Is there any advice you can give me about maintaining work-life balance with this new remote work environment?
  • What new skills or competencies could I add to my toolbox and would you (or the company) be willing to sponsor my training?
  • Is there anything you feel is holding me back in my current position? How can I work on it?
  • Can you recommend networking events or organizations you might think are right for me?
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Put it into practice

It’s surprising but true: a simple thing like a conversation between you and your manager can ease a lot of the common work-from-home stresses. 

The fact is that the old adage is true: “People leave managers, not companies.” 

BetterUp can help you broach these conversations with confidence and teach you how to take ownership of the responses you receive. Learn more about how we help people, teams, and companies create positive relationships through communication.