Career & Finance

How to Talk to Your Boss If You’re Struggling Right Now


You’ve got a lot on your plate right now. And while some have characterized this time as the world’s greatest work-from-home experiment, the reality actually couldn’t be further from the truth. Granted, if we’re in the position to have a boss to talk to, then we’re certainly fortunate to have work in these difficult times. However, many of us are just trying to make it through the days running any combination of an office, daycare, school, health clinic, and counseling center right from our living rooms.

We may all be living through this crisis together, but we are all experiencing it very, very differently depending on where we are living, our family, health and financial needs. If you are struggling right now, you are not alone. And, talking through the challenges you are facing with your boss can help give you some breathing room.


1. Schedule a separate chat

Book some time one-on-one with your manager that’s dedicated to catching up as a check-in outside of your routine work discussions. This way, you can be sure that you aren’t overrun by work tasks, or feel rushed through a difficult conversation. But keep it to 20-30 minutes tops. As with all of these challenges, your goal should be to come out of your conversation with your manager with solutions to help you improve your work-life balance.

If what would really assist you is some greater emotional support during this time, then use your chat with your manager to ask about resources for employees that could more directly support you in that way. Some companies now are thoughtfully extending free mental health services or discounts to therapy or meditation apps.


2. Get specific with your struggle

Hone in on the exact ways that you’re having a hard time. Walk yourself through the different questions that might be affecting how you’re feeling right now. Is it that you’re managing too much at home? Are you navigating a family member’s health challenges? Do you need to unplug after a period of all hands on deck at work? Feeling disconnected from your friends and colleagues? Having financial challenges from reduced hours or loss of a family member’s job?

These are all really difficult life issues we are managing. We may even be working through a number of them simultaneously. A successful conversation with your boss will start with being clear about exactly what these issues are, so that we can craft some talking points that could help get us to a better place.


3. Come ready with an ask or suggested solution

What would “better” look like? After we’ve identified which areas of our life are trigging the biggest challenges right now, we can fill in the blanks to think about exactly how management could be in a position to help us make things a little easier. For example, ask yourself, “If my manager or workplace knew X, it would make Y much better right now”, or, “If my boss supported me doing X, my life would improve by Y.”

And remember, if you don’t ask, you don’t know. These are unprecedented times. Want to flip your schedule to nights and weekends? Ask! Could you really use a week or so off right now, even if it’s unpaid? Ask! Would some additions to your at-home office make your client meetings run more effectively? You get the picture: now is the time. Don’t struggle in silence.


Conversation starters

It’s also OK if you’re not all the way through to a solution space. Being crystal clear on an outcome shouldn’t prevent you from raising how you’re feeling to your manager. You can also approach this conversation with a spirit of collaboration. Share what you’re feeling and ask some open-ended questions. That’s what management support is there for!

There are different ways to approach talking with your boss about what you’re going through, depending on what type of crisis challenge you’re struggling with. Here are a few conversation starters to help you think through how you might begin to frame a conversation with your manager.


If you’re struggling financially


  • My reduced hours are really affecting our family’s income. What kind of financial support programs might our company be offering? 
  • This crisis is affecting me financially. I’d like to look for additional work outside of this company—are our outside activities restrictions being relaxed at all during this time?
  • My partner has recently lost their job because of this crisis. What opportunities might there be for additional work or overtime right now?


If you’re managing health issues


  • I’m supporting a family member through a health issue related to this crisis. Could we talk about how I might adjust my schedule and workload while we get through this?
  • I have some health considerations that are making this current crisis a little more challenging for me personally. I need to revisit how much I am out of the house or where I am working. Could we talk about alternate work arrangements during this time?


If you’re having a hard time balancing your schedule


  • I am needed a lot more at home right now and I’m feeling stretched really thin. Which projects can we rethink so that I can give some additional time to my family right now?
  • I am running a daycare/school/co-working space from my home right now. Could we review team workflows and see where others might have bandwidth?


If you’re in an emotional funk


  • This is a really emotionally challenging time and I’m anxious. I know I’m not entirely feeling like myself at work. How are you managing? What are some ways that others on the team are navigating this time?
  • Working in this city/office/division feels like I’m experiencing this crisis differently than some of my colleagues because of X, Y, and Z. How are people you know in this city/office/division handling these specific challenges?


Know that it’s possible that your manager doesn’t have a great answer for you in terms of how to solve what you’re going through. But sometimes, just feeling heard, acknowledged, and being transparent with what you’re dealing with can be enough to help us hit the reset button and move back to a little more grounded space.


How is your management supporting you through this difficult time?


DISCLAIMER: This is for informational, educational, and marketing purposes only. It does not constitute medical advice, and is not a substitute for professional therapy, diagnosis, or treatment. Always seek the advice of your physician, mental-health professional, or other qualified health provider with any questions you may have regarding a medical/mental health condition.