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

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 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.

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 one thing should I stop?
• 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.

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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 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?

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.