When it comes to tough conversations in the workplace -- asking your manager about working remotely, a raise, parental leave or flexibility, a change to your job description or a deadline -- most people ruminate endlessly on the potential risks.

  • She could say no...

  • She could get mad that I’m asking...

  • She could FIRE me...

  • I could come across as entitled, or unprofessional, or lazy, and this could be the beginning of the slow death of my entire career…..!

The prospect of “making waves” ignites worry and even catastrophic thinking in the best of us.

But sometimes we become so blinded by the risks of having the conversation, we fail to see the risks of not having the conversation.

Risks like continuing to feel unhappy, overstressed, or undervalued; continuing to make less money than we deserve; or continuing to hold resentment towards our manager or organization (all of which lower our satisfaction and performance on the job, often resulting in many of the negative outcomes we were trying to avoid in the first place!).

Even more importantly, we fail to consider the potential benefits of initiating tough conversations:

  • She could say yes!

  • Whatever is causing you pain or frustration could disappear or get significantly better.

  • Your relationship with your boss could become clearer and closer.

  • At the very least, you’ll test your assumptions and learn the actual parameters of your work and career decisions.

Yes, your boss may not show up for you.

But you don't know whether or not she will, until you give her a chance to do so.

Here’s how I teach my clients to ask to work from home (or initiate any tough conversation) step by step:

1. Do your research.

Before you take the leap, you’ve got to build yourself a parachute.

So put on your private investigator hat. Start talking to people internally who you trust, researching online, and building your understanding of what’s appropriate to ask for -- and the best way to ask for it -- given your specific situation, your company, and your manager’s preferences.

Before bridging the conversation with your supervisor, try to learn:

  • What’s the status of remote work within your industry? We know that 46% of organizations today have virtual teams and that research shows remote work improves productivity and retention. Familiarize yourself with these statistics and any research or data relevant to your industry.

  • What about in your company? How many people work remotely, part-time or full-time? Do any of them work directly for your supervisor? Is this currently a norm, a growing norm, or an exception?

  • How have others gotten approval in the past? What worked and what didn’t? How does your tenure and performance compare to theirs? Have you built a track record and enough professional capital to make this ask?

  • Has anyone else had a tough conversation about this or other topics with your boss? How did they play out? What worked and what didn’t?

  • What do you absolutely know (not assume) about your boss’ feelings on this particular topic that will be important to keep in mind or address during your conversation?

  • When’s the right time to start the conversation? Will your manager be most receptive during a performance review, a weekly meeting, or a meeting specifically focused on this topic? (Hint: tough conversations should never be had on the fly or in passing.)

2. Lead with your feelings.

We’ll get to the part of the conversation where you share your research, any relevant data, and a proposal that makes a case for how this will benefit the business.

But the first thing you want to do in any tough conversation is establish a human connection. And human connection requires vulnerability.

This may sound controversial, but feelings aren’t inherently unprofessional; it’s how you share them that matters.

When working with my clients on how to show vulnerability in the workplace, I make sure that they understand the difference between destructive and constructive vulnerability:

Destructive vulnerability is when you share your feelings at the expense of others, prioritizing your needs above theirs. Constructive vulnerability is when you share your feelings and desires in a way that acknowledges and cares for the feelings and needs of others.

You’re not a robot, and neither is your boss. She has her own worries, stress, and personal life that she brings to work with her every day, too. The purpose of her role as your manager is to set you up to be your most successful self on the job. And if something is getting in the way of that, she should want to know.

So your goal in this situation is to help her understand how important this issue is to you and why, while also communicating that you care about what’s important to her.

It’s this delicate balance that will ensure your boss feels respected, takes your ask seriously, and responds from a place of empathy and care in return.

For instance, you might begin the conversation with:

“I wanted to talk to you about something that’s really important to me - the prospect of increasing my WFH time to 2 days per week. I’ve hesitated to bring this up because I don’t want to inconvenience you or seem less than fully committed to our team’s success. But if I’m honest, I’m feeling significantly stressed as my commute has grown from 45 to 90 minutes each way since joining the company. It’s been a big strain on my energy at work and at home.”

3. Make it an easy yes.

The one thing you always want to do when making a case to your supervisor (or colleague, or client, or anyone for that matter) is this:

Make it an easy yes.

You want to state clearly what you’re asking for, how it could work, and how the benefits outweigh the costs. Back up your ask with your research and data. Possibly bring a one-pager or bullet points detailing your proposal or a couple of potential options worth discussing.

Show your supervisor that you’ve done the heavy lifting, and that there’s no reason why she shouldn’t simply say “yes.”

You might say next:

  • “Not only would this mean a lot to me, but I’ve given a lot of thought and done a significant amount of research into how this could work while also benefiting our team.

  • From what I’ve learned, almost 10% of our company’s employee base is currently part or full-time remote and it seems like senior leadership is supportive.

  • From my experience working remotely so far, I’ve found that I’m significantly more productive when working from home, I believe due to my commute and the ability to work on strategic projects from a quiet space. I have some research with me if you’re interested on how increased productivity appears to be a common benefit.

  • I can easily arrange my schedule so that I am still in the office for all of our weekly and team meetings on Monday’s and Tuesday’s, and host my client office hours from home Thursday’s and Friday’s, in addition to leveraging my commute time saved to tackle big upcoming projects like our fundraising gala.

  • I’d of course be flexible and make sure I’m in the office whenever the team needs me. I’m more than happy to start doing this on a trial basis and only continue in this vein if you feel really positive about how it’s working.”

4. Get feedback and let the conversation unfold.

Lastly, you’ll want to briefly reiterate how much you appreciate the opportunity to present your proposal and that you’re open to your manager’s thoughts and feedback.

“Thanks for hearing me out on this. Again, the last thing I want to do is inconvenience you or the team. But it felt important to me to at least have this conversation with you and share my situation. I’m eager to hear your thoughts and feedback, either now or I’m happy to pick this up again once you’ve had some time to consider.”

As I said earlier, your boss may or may not show up for your feelings. You may learn that what you want is out of the question with this current boss or organization.

But you won’t know for sure until you give her a chance.

The truth is, you’re taking a risk whether or not you start the conversation. You get to decide which risk you’d rather stomach.

I’ve seen so many professionals -- often wondering if they should quit their jobs rather than start a conversation they were convinced would not go their way -- be surprised when their daunting ask was greeted with a simple, enthusiastic “Yes.”

If you’ve followed the process I’ve laid out above, you can rest assured that you’ve taken the appropriate steps to minimize the risk of any negative repercussions.

Beyond that, you’ve replaced inhibiting assumptions with real-world facts, and embraced the possibility of creating a more authentic career and mutually beneficial relationship with your manager. That takes guts, and if you’ve gotten this far, I already know you’re tremendously brave and deserving of what you want.

Yes, it’s certainly easier to operate in silent fear, assuming that our needs will either be fulfilled by ourselves, fulfilled voluntarily by others, or not at all. But in doing so, we set ourselves up for a deeply unsatisfying and disconnected existence.

Rather, I believe in a world where we can ask for the things that matter most to us. And that as long as we keep both sides’ needs at the forefront of the conversation, we can choose faith over fear, and build ways forward that elevate us all, together.