Dear Businesslady: Dealing With Dealbreakers

Photo credit: John Mueller, CC BY 2.0.

Hello, Businesslady!

I started a job at a startup last year that I absolutely love — it is an excellent professional and personal fit for me. My manager is great; working with him has made a huge difference in the quality of our work and my professional development.

However, I live in City A and work in City B about 40 miles away. I take a commuter train, which, counting the time it takes to walk to and from the train station on either end, takes about two hours each way. (Driving isn’t an option.) I undertook this commute because I was promised the ability to work from home as desired, so long as I was in the office about half the time on average. In practice, there are some weeks where I’m in the office four or five days in a row and some weeks where I’m holed up in my apartment or a fancy coworking space (which work pays for).

During a discussion about an entirely different issue two months ago, my boss referenced making a policy change that would require me to be in the office essentially every day. I panicked (it was already a high-stress conversation for different reasons) and said that if we made that change, I would want to renegotiate my contract, because I would need to either move to City B (and break my current lease) or spend so much money commuting that I would want my salary to be increased. My boss was surprised at how concerned and upset I was and later (when he clarified that we would not be making this policy change) told me that he was disappointed at how quickly I jumped to financial compensation during the conversation. He also told me that he doesn’t know the details of my current contract and that he realized that we haven’t talked about my expectations or understanding of my role.

So I need to have a conversation with my boss about my contract in general, but my concern is that he has indicated that he thinks we work better when we’re all in the office. To a certain degree, I agree — parts of my work benefit from the types of free-flowing brainstorming and conversation that happen when we’re all together. Other parts of my work involve staring at a computer screen and thinking really hard. I also don’t always work best in the office — it can be distracting! Plus, I’m really not a morning person and commuting four hours a day takes a toll on my energy levels and work quality. If I have a lot to work on, I end up jumpy and frustrated because I have to worry about missing the train instead of focusing on my work.  

Other relevant details: I am not directly compensated for my commute — I negotiated for a higher salary when I started, but I specifically asked for a commuting stipend or reimbursement and was told no. My boss lives about four hours away and travels to our office for a week once a month. The rest of my team (three people) live in City B.

I’m really concerned about the work-from-home allowance because it makes a huge difference in my quality of life. Do you have any suggestions about how to approach this conversation with my boss? Any scripts I should follow?

— Seeking Schedule Clarity (and Sustaining the Status Quo)

Dear Seeker,

This is both a very specific question (“how do I resolve this issue with my esoteric schedule”) and a super general one (“how do I communicate my needs without creating or exacerbating conflict?”). Working life is full of these moments where you realize you have to Ask for Something — moments that are typically infused with an entirely reasonable worry that your boss will react poorly to the request.

I rolled my eyes wearily when I read about your manager’s “disappointment.” It’s a totally common response — so many leadership types think their staff should be motivated by pure enthusiasm first, financial compensation second (if that) — and it’s also completely unfair. No matter how much you may love the doing of your job, you also need it to pay your bills. (I’m assuming, of course, that you didn’t omit a crucial detail like “I am a multibillionaire and only joined this company for the lulz.”)

But unfair or not, some bosses expect a certain, I don’t know, demure attitude from their employees when it comes to negotiating salary and related issues. Yours is one of them! Lesson learned. It doesn’t mean you’re wrong for reacting the way you did — if I were caught off-guard like that, I probably would’ve done the same thing. Anytime I’m exposed to new information that has the potential to impact my quality of life, I immediately go into concrete-planning mode and start spinning up a whole decision tree of if/then/else possibilities. This can be a self-defeating impulse sometimes. I know I’ve wasted countless cumulative hours brainstorming hypothetical scenarios that never came to pass. Then again — to put things in business jargon — I like to think that it’s a sign of a strategic, results-oriented mind. Someone who absorbs information and immediately does a flash-forward to the web of consequences spiraling out from it? That’s someone I’d like to work with (even if we’re not solving future crimes in a Philip K. Dick–style dystopia).

If there’s any legitimacy to your boss’s reaction, it stems from the worry that good employees are flight risks. Through that lens, your “oh no, I hope we can figure out the logistics so I can keep this job I love” reads as “hm, sounds like this deal isn’t sweet enough for me anymore.” It’s understandable that you didn’t spell this out while your brain was processing the impact of a possible policy change, and that’s fine, because it’s easy enough to fold into a follow-up conversation.

Conveniently, you’ve already got that follow-up conversation in queue! “Expectations and understanding of role” talks can be intimidating, but they get a lot less fraught if you just think of them as info-sharing sessions. Assuming your manager is at least moderately competent (defined as: aware of the value you bring to an organization, invested in your success, committed to retaining talented employees), he’ll appreciate the opportunity to learn more about what you do.

If he sees this discussion as his opportunity to evangelize for the “everyone in the office together” model that he prefers (a perplexing position for him to take, considering that he himself is only in the office about 25 percent of the time, but I digress…) you’ll want to prepare accordingly. Even though you were promised a certain work arrangement and are justified in balking at a potential bait-and-switch, let’s set that aside for the moment. What are the relevant facts in terms of productivity and your job as a whole?

This is where you enter that tricky negotiation territory where things that are important to you aren’t necessarily important to your boss. Arguably your manager should care if you’re drained by two hours of travel or stressed about wrapping up your workday before the last train leaves — but there’s no guarantee his response won’t be “plenty of people have long commutes” or “half this office has to contend with train schedules.” The only way to ensure your concerns won’t get dismissed is to tie them explicitly to your manager’s top concern: is this good for the company?

So the fact that your commute is a drag? Objection: irrelevant. But the fact that your commute takes four hours out of your potential workday — that’s something worth noting. Similarly, I’m assuming that when you’re already home, you can finish up time-sensitive projects even if it means working late, because you don’t have to run and catch a train. Compile a list of instances where your ability to work remotely was an asset to your organization. As needed, you can contrast this with examples of how your productivity can suffer when you’re in the office, but be judicious about going negative. Those aren’t going to be as effective when it comes to selling the core idea here: that you’re a strong contributor who’s worth keeping — and keeping happy.

The other key point to emphasize is your overall job satisfaction (minor scheduling kerfuffle aside). So often, these kinds of self-advocacy conversations happen at workplaces that folks would be perfectly happy to leave behind. It gets a lot more delicate when you can’t sincerely say nice things about your job, when the ground to be gained isn’t “ensure I can stick around long-term” but rather “make this hellhole suck less while I look for something better.” To be clear, I think everyone should stick up for themselves whenever the opportunity arises, and if you’re in a less-desirable professional situation then you do your best to focus on whatever positives you can find (even if they’re as minimal as “I can do this work, and you pay me for it”). But it’s so much easier when you can honestly say that your job is “an excellent professional and personal fit” that you “absolutely love.” Make sure your manager knows that! Make him realize that it would be foolish to lose you over some arbitrary bias against telecommuting.

Then again, it might not necessarily be arbitrary bias. His (sliiightly hypocritical) notion that the office runs more smoothly with everyone onsite could be grounded in a few specific examples that are easily addressed. Maybe he’d rather have you sitting at the table for certain team meetings instead of calling in. Maybe your coworkers are unclear about your availability when you’re offsite. Or maybe he’s thinking about making a new hire and is worried about who’ll be around to help with training. When you’re managing a whole staff of people, you don’t always have the luxury (or — let’s be real — inclination) to think granularly about the needs of any individual. It can be tempting for supervisors to respond to problems by suggesting broad, sweeping changes, and that’s when it’s the employee’s job to speak up and explain why that’s not the best approach. Plus, it’s not like you’re looking to disappear from the physical realm forever. You both agree that your in-office presence has its benefits, and common ground is a powerful resource in difficult discussions.

Ultimately, this isn’t even an argument — you’re just giving him a fuller picture of the situation. The framing for that picture is your position within the company, and on that topic you’re just telling him what he wants to hear: that you’re a high performer with a firm grasp of your role. Put together some bullet points to back that up — things like trackable metrics that demonstrate your productivity, major successes, compliments from coworkers and clients, and anything else that your boss will find meaningful. If there are skills you’d like to develop or things you’d like to improve, organize your thoughts around those too. You want the conversation to flow organically so it’s fine if you don’t mention every single thing on your list, but being well-prepared ensures you have supporting data for any assertions you make, and it will help calm your nerves.

Let’s pull this all together into the script you asked for. Here are the beats you want to hit: “I’m grateful for the opportunity to talk with you about my role, so if nothing else I’m glad the discussion of [possible policy change] prompted this meeting. I really enjoy this job, and I have a vested interest in this organization. I’m a strategic thinker, which means I jump right to logistics whenever a change is on the horizon. Since I’ve built an effective workflow around my current schedule, I got concerned about the unintended consequences of disrupting that — for the company, not just from my own perspective.” Basically, you’re acknowledging your earlier reaction without apologizing for it and putting it in a collaborative context. Then you proceed with the specific details in whatever way feels natural to you, responding to your manager’s interjections and questions as they arise. His primary takeaway should be “this person does good work.” His secondary takeaway should be “I shouldn’t do anything to put that good work in jeopardy.”

As long as there are jobs and bosses, there will be managerial edicts that cause employees to break out in a cold sweat. It’s agonizing to hear a tossed-off comment that, if implemented or taken to its logical conclusion, would disrupt the most treasured aspects of your routine. You’ve got to tamp down that initial panic to the best of your abilities so you can begin developing your strategy for preventing the worst-case scenario from coming true. If the job’s worth keeping, you and your manager will find a way to fix it together.

Courtney C.W. Guerra is an editor and writer who started giving advice as Dear Businesslady on The Toast in 2014. She’s the author of Is This Working?, a career guide for anyone who’s interested in professional success — but not at the expense of their personal investments.Keep in touch via Twitter, Facebook, her TinyLetter, or her website.

Need advice? Email dearbusinesslady@gmail.com.

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