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Navigate Challenges in the Workplace Like a Pro

Ask A Manager's, Alison Green offers us practical advice on how to handle 21 tough discussions we may need to have during the course of our careers.

When it comes to awkward situations or tough but necessary conversations at work, we’ve all got our war stories. Whether it’s something small and grating, like a gum-popping co-worker, or something bigger and more complicated, like a boss that monopolizes your nights and weekends, everyone with a job has, at one time or another, found themselves faced with a quandary they’re not quite sure how to resolve. It can be a challenge to confront a peer and feel downright impossible to confront a superior. We worry about the consequences of saying the wrong thing, taking the wrong tone, or speaking up when we should have kept our mouths shut. One thing is for certain: no amount of job training quite prepares us to navigate the tricky world of office politics.

And if you’re a woman, you might recognize that office politics can be even more complicated for us as assertiveness in the workplace isn’t always encouraged. After all, many of us have seen how the same qualities lauded in our male peers can penalize us. When we’re confident and vocal, we’re at risk of being labeled bitchy or bossy, too driven or determined. With that added pressure, it can be hard to find your confidence and even tougher to speak up — even when we know we need to.

More: Women and the Yes Culture

Work life advice guru Alison Green, creator of and advice columnist at New York Magazine, offers all-new advice for navigating 200 difficult professional conversations in her new book, Ask A Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work. We’ve given you a sneak peek at twenty-one answers to big questions we know you’ve had, including how to:

  • Talk to your boss when you feel you’re overloaded
  • Confront a co-worker who’s doing something loud and annoying
  • Apply for a job in a different department
  • Take control of your work-life balance
  • Ask about a promised raise that has yet to materialize

What I appreciate most about Green’s advice is that it’s straightforward and simple. Sometimes we know exactly how to approach a situation, but we feel as though we’re lacking permission to feel or say what we need to. As a result, we let things fester and the problem magnifies in our heads. In Ask a Manager, Green allows us to approach a delicate issue head-on and with tact. By providing us with a script, we can get through a challenging conversation with grace. And isn’t the worry about what you’re going to say sometimes scarier than the conversation itself?

While Green acknowledges that some conversations are awkward no matter what, she consistently provides solid, reliable advice with which to arm yourself, ensuring that every encounter goes as smoothly as it can.

Learn what to say when . . .

work advice

1. The job isn’t what you agreed to

If you find yourself in a new job that’s significantly different from the one you signed up for, you should speak up. You need to communicate that you’re not okay with doing a different job than the one you were hired for. Start by saying something like this:

Since I started a month ago, I’ve been spending most of my time on X. Could we talk about the plan for getting Y transferred over to me? I was happy to help out with X because I knew we were in a pinch, but I’d like to focus on the Y work I was hired for.” 

2. Your boss expects you to answer emails and phone calls at night and over the weekend

If your boss regularly fills your evenings and weekends with non-urgent work calls and emails, you might conclude that she expects you to be available then. Though there’s a very good chance that your boss doesn’t actually expect you to reply until the next business day, but in the rare case she does expect you to respond immediately, say the following:

“It’s really important to me to have time to disconnect and recharge outside of work. Sometimes that means turning off my phone or not checking email for the weekend. I’ll, of course, put in extra hours when something is an emergency, but my preference would be to respond to non-urgent things when I’m back at work. Could we try that for a while and see how it goes?”

3. Your workload is too heavy

Often when people are overwhelmed by their workload, they assume their managers are aware of how much is on their plate. But in reality, no one pays attention to your workload like you do. So make sure you talk to your manager. Here’s an example:

“I’m finding that I’ve taken on way too much, and the stress of trying to juggle it all is exhausting me. I’m worried it will impact my work at some point. Can we take a look at my workload and figure out how to make it more manageable?”

4. Your manager yells or talks down to you

Hopefully, you’ll go your whole career without getting yelled at or talked down to by a manager. It’s unprofessional and abusive, and good managers don’t do it. It is entirely reasonable to ask your boss not to speak to you that way. You’ve signed on to do a job, not be verbally abused. It’s totally okay to say something like this:

“I really like my job and I generally like working for you. But I have a lot of trouble hearing your feedback when you yell at me. It’s not that I don’t want feedback on my work — I do, and I value it. But I don’t want to be yelled at.”

5. Your boss contradicts herself on priorities or work instructions

Worse than a boss with fuzzy expectations is one with very clear expectations one day and a completely different set the next day and who expects you to read her mind. If your boss tends to change her mind about a project without telling you, make a point of checking in more often:

“Things are moving along with the X project. I’m still working under the assumption that we should be doing Y and Z with it. Does that still sound right, or should I make adjustments?”

6. Your boss wants to be your friend, but you want to preserve professional boundaries

If your boss is acting more like a close friend than a boss you’re probably spending much of your work life feeling really uncomfortable. Maintain boundaries by just being kind and straightforward. Frame it as your own weirdness rather than a rejection of your boss:

“You’re so easy to talk to, and I’ve realized we keep getting drawn into personal conversations. I have a terrible pattern of becoming friends with my managers, and I’ve vowed to be better about professional boundaries — so I’m going to try heading those situations off and just wanted to explain, so that you didn’t wonder why.”

work advice

7. You want to apply for a position in a different department

In a lot of ways, applying for a job within our current organization is easier than applying for jobs externally; you know the culture and the key players and you probably have a good sense of what they’re looking for. What makes it trickier is that companies often require you to tell your current manager that you’re interviewing for another role internally. That can lead to an awkward conversation with the boss. Try saying something like:

“I’m really happy with my job here, but X is a passion of mine. I’ve decided to apply for the X role in the Y department, and I wanted to be up-front about it with you.”

8. Your boss makes you feel guilty for using your vacation time

Your vacation time is part of your compensation package, and you shouldn’t feel guilty about using it. If you have a manager who makes you feel like a slacker or frowns every time you mention time off, address the situation head-on!

“I haven’t been able to have a vacation in almost X (months or years) because it’s been so hard to find a time when I could go. That’s not sustainable in the long term, and it’s important to me to have time away to recharge. I’d like to use the benefits the company is providing as a part of our compensation. Can we talk about how to arrange things so that I can get some real time off soon.”

9. You want to get out of an after-hours social event

Many offices assume that everyone will be enthusiastic about the prospect of hanging out with co-workers after hours. These events are intended to boost team morale and cohesion, but plenty of people aren’t all that enthusiastic about spending additional time with colleagues they see every day (can I get a witness, introverts?). Here’s an easy way to get out of after-hours office social events:

“I have an appointment after work that day that I can’t move.”  (And hey, maybe your appointment is with yourself on a couch; they don’t need to know that.)

10. You are going through a hard time in your personal life

If you’re going through a rough time personally, sometimes it can be useful to tip your boss off, so that she has context if she notices it impacting your work or your demeanor. For example:

“I want to let you know that I’m dealing with some difficult things in my personal life right now. I’m doing my best to keep it from affecting my work, but I wanted you to know what’s going on, just in case you notice that I seem a little off.” 

11. Your boss is considering hiring someone you used to work with and can’t stand

Hiring is far from a perfect science which makes getting candid input from people who know candidates firsthand can be hugely valuable. The key to sharing information with your boss as to why a candidate would be a bad hire is to be specific. “I don’t really like him” isn’t helpful. Try something like this:

“X and I actually worked together in the past, and I have some concerns as to whether he is fit for this job. Can I tell you a little about my experience with him?” 

12. Your co-worker is doing something loud and annoying

One of the more frequent complaints workers make relates to their co-workers doing something loud and annoying — from playing loud music (with or without headphones), to taking too many calls on speakerphone, to humming incessantly, to popping gum. Here’s how to address those issues politely:

“You probably don’t realize this, but you have a habit of drumming your fingers on our desk for much of the day. I’ve tried to block it out, but it’s pretty distracting. Would you mind putting down something soft to reduce the noise it makes?” 

13. Telling a co-worker that something isn’t your job

There’s an old adage that you should never say “That’s not my job.” And sure, it’s true that you shouldn’t be rigid about sticking precisely to your job description but there are times when it’s appropriate, and even necessary, to point out that you aren’t the right person to do a particular task. But you shouldn’t say, “That’s not my job.” Instead, try  this:

“My boss and I decided I needed to focus exclusively on dealing with X this month, so I’m not supposed to be taking on anything else right now.”  or “Hmm, I’m not usually the person who handles that. I think X is, and he should be able to help you.” 

work advice

14. Co-worker keeps interrupting your conversations with others

If you have a co-worker who always butts into your conversations, you probably feel awkward about asking them to stop. But when it comes to work-related conversations, you’re allowed to set some boundaries. Here’s a way to do it:

“Actually, I really want to get X’s opinion on this.” or “Thanks for the thoughts! For now, I really want to talk to X about it, since she used to work on this project.” 

15. Turning down a co-worker who asks you out

Rejecting a co-worker who asks you out can be a lot more awkward than rejecting someone outside of work because you’re going to continue to see each other every day. It’s best to be straightforward . . . and as normal as possible afterward. As for what to say, try this:

“Thank you, but I’d rather keep things between us professional.” 

16. Co-worker is a know-it-all who tries to tell you how to do your work

If you work with someone who has an opinion on everything and loves to tell you how to do your job better, your best bet is to ignore the person as much as possible. When you find that you can’t, arm yourself with the following responses:

“I’ve got it covered, but thanks.or “I feel good about how I’m handling this, but I’ll let you know if I end up needing your help.”  

17. Explaining that you don’t friend co-workers on social media

People have all sorts of preferences for whether and how they connect with co-workers on social media. Some people will connect on LinkedIn but not on Facebook because they want to preserve boundaries between work and the rest of their life. If you fall into this camp, try saying this:

“I’m hardly ever on Facebook anymore. I really just use it to see photos of my nieces and nephews. Let’s connect on LinkedIn, though!” 

18. Co-worker makes bigoted remarks

If you have a co-worker who makes racist, homophobic, or otherwise bigoted remarks, there are lots of work-appropriate ways to respond. Here’s an effective one:

“Comments like that are offensive to most people and unwelcome at work. I don’t want to hear comments like that.” 

19. Co-worker took credit for your idea

If your co-worker takes credit for your ideas, don’t stand by helplessly. Speak up and tell her that you want her to stop:

“I’ve noticed that when I mention ideas to you, you’ll often present them to our boss without noting that they came from me. I want her to know what I’m contributing, so going forward, would you let me share my ideas with her myself.” 

And if it’s happening in the moment, take the lead of the conversation with this:

“That’s actually the idea I was explaining to Jaime before this meeting. My thoughts about it are . . .” 

work advice

20. What to say to a co-worker who just got fired

People who have been fired will tell you one of the weirdest parts of the experience is how many co-workers never reach out to say goodbye in some cases, even people they’ve worked closely with for years. It happens because people feel awkward and don’t know what to say. If you’re struggling with that, approach the situation the same way you would if your co-worker left voluntarily:

“I’m sorry to no longer be working with you! I’ve really valued you as a co-worker, and I hope we can stay in touch. Please let me know if there’s anything I can do to be helpful as you look for your next role.” 

21. You’re not comfortable being a reference for a co-worker

If a co-worker asks you to be a reference and you don’t think you could give her a particularly good review, be honest:

“I don’t think I’m the right person, unfortunately, because of the struggles with X and Y when we worked together. I also know those may not be issues at other jobs, but it means I can’t be a really strong reference. I’m sorry I can’t help with this.” 



Situations and answers adapted from Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work by Alison Green. Copyright © 2018 by Alison Green. Reprinted by permission of Ballantine Books, an imprint of Random House Publishing, a division of Penguin Random House LLC, New York.



Photo Credits: Unsplash


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