You asked: Power struggles and co-worker crushes

4 min read
Shayna Hodkin
  •  Oct 6, 2017
Link copied to clipboard

Editor’s note: This is the sixth post in our advice column (read the first one). Have a question? Ask it here.

How do I teach myself to play nice?

After 6 years of freelancing as a UI/UX designer, and over a year of looking for a full-time job, I’ve finally gotten an offer. Yay!

Here’s the problem: I started freelancing because, after a pretty unsuccessful stint as team leader at a big-time studio, I realized that being bossy and being a good leader aren’t the same thing. I decided to take some time off, work on myself, and figure out what my strengths *really* are.

My new position is Head of UX, and I already have some big ideas, but I don’t know how/when/if I can start bringing them up without rocking the boat. I’m worried that trying to make big changes too early will make me seem bossy, and I’ll end up repeating my old mistakes, But, then again, isn’t that what I was hired for?

How long do I have to wait until I can start pushing new ideas?

-Sitting on my Hands

Congratulations on the new job, Sitting! Good on you for being so honest with yourself. It’s not easy or pleasant to deal with these realizations, and even moreso to make such big changes.

You’ve made a really good point about fitting into the team. If you’re not totally in yet, you’ll have a hard time getting your ideas across. Here’s why.

Know, like, trust.

Marketing 101 goes like this: to get people to trust you, they have to know and like you.Twitter Logo

So, what you want to do here is come in and lead your team: get them to work better, become more effective AND creative, and ultimately become a cohesive unit that makes your product sing.

But like any transfer of power, you have to build up your trust.

The first step is getting to know your teammates. Your first few lunches, happy hours, and coffee breaks should be spent getting to know the people you’re working with. Ask a lot of questions, and don’t be afraid to share about yourself. We’re humans, and we want to work with humans.

“To get people to trust you, they have to know and like you.”

Twitter Logo

After working solo for a few years, this is going to be weird. When you’re a freelancer, while your work may be your life, your clients usually aren’t—but now, you’re going to have to start letting people in.

Hopefully, getting your teammates to like you won’t be far removed from getting them to know you. Being liked, at least in the workplace, often comes from being thoughtful. If you bring cupcakes for a teammate’s birthday, or coffee for the pal who stayed late pushing through those wireframes, you’ll be ensuring yourself a place in your team’s collective heart.

Related: Handsome’s lead designers on how to build trust with your team

It might feel fake or saccharine, but the same way you’d make a new pal, you’re going to have to get in good with your teammates. For them to trust you with their guts and Wacoms, they’re going to have to believe in your judgement—which is something that comes from knowing a person as a whole creature.

Until you’re comfortable enough with your teammates to send them funny memes on Slack, I wouldn’t start throwing around dramatic changes. If you skip these steps and go straight for the revolution, you’re setting yourself up to become the hipster boss in the second Bridget Jones’ Diary: unfamiliar, terrifying, and not to be trusted.

The art of persuasion is all about getting people to feel attached to your ideasTwitter Logo: making them feel a part of the ideation process so they’ll feel the idea is their own—and therefore won’t need to be sold on it.

“For them to trust you with their guts and Wacoms, they’re going to have to believe in your judgement.”

If you can walk your team into your ideas, having them ease into your new direction and feel a part of the change, it’s possible you won’t even have to do the presentation process that you’re dreading. The key is to act gradually so no one’s taken by surprise and no one feels overwhelmed.

Keep in mind that this isn’t just a transition for the team: it’s a transition for you. Not only are you going to have to acclimate to all of the normal parts of a new job—new office, new team, new snacks in the kitchen—but you’re also going to have to get into working from an office with a team. Give yourself time to meet everyone, get acquainted, and feel a part of the process. It’s just high tech; we’re not putting out fires.

Taking “in love with my job” too far

My job is perfect. I came into an early-stage startup as one of the first hires and got to build my own job. I work on the things I love with a team of talented, smart, funny people who I can’t imagine my life without.

And therein lies the problem.

I have a big crush on one of my teammates. A really big crush.

I can’t help it! We spend so much time together, and she’s funny and nice and everything I want. We’ve never hung out outside of the office, and I’ve never done anything to let her know I’m interested, but my stomach gets weirdly fluttery when she sends messages in our Slack channel.

I feel like a third-grader, but I need to be a professional, grown-ass man in the workforce. What do I do?

Crushed Like Paper and Scissors

Welcome to the struggle of everyone who works in an office full of young, talented people.

If anyone says they’ve never felt this, they’re lying. We all have someone on our team who makes us smile a little bit more than everyone else. It’s a natural consequence of spending a lot of time pursuing a shared goal.

Basically, Crushed, this is totally normal. Don’t freak out.

Good on you for holding this in until now. Having a crush is probably one of the least pleasant experiences you can have in the workplace, and it seems like you’re doing a great job at preventing any awkwardness or tension.

“We all have someone on our team who makes us smile a little bit more than everyone else.”

Twitter Logo

My gut inclination is to tell you to hop on Tinder, OkCupid, Bumble, or whatever else is out there and to find yourself someone nice outside of the office, but I’m going to go rogue here and ask:

What if she likes you back?

See, my parents met in business. My dad was the CEO of a company, and my mom was brought on as legal counsel. If they hadn’t taken that leap—and, full disclosure, I’m not sure that I would take that leap—my sister and I wouldn’t exist.

On one hand, no risk means no reward. But on the other hand, yes risk means potential loss of work friendship, potential ego crushing, and potential unpleasant conversations with HR.

I can’t tell you what to do, because I don’t know how you really feel. Are you the kind who falls in and out of love all the time, or is this the real deal? Is the object of your affection single and looking, taken like the last slice of veggie bacon (forgive me, I’m vegan), or a cat lady? Do you have the kind of open communication where you could bring up your feelings without being shut down?

The best thing I can tell you: feel it out.

We live in a world where meeting people is really hard! Especially organically, especially with common interests. If you’ve met the woman who makes your heart sing, then I can’t tell you wholeheartedly to pass because of your job.

But you also love your job, which isn’t a common thing. If you pursue this love interest and it doesn’t work out, you might give up on something you really enjoy.

Let’s say it works out. Get it, Crushed! You guys are on your way to adopting 2 dogs and taking sweet vacations.

How do you tell your teammates? Take it slow.

First things first, check your contracts. Is anything written in there about inter-team extracurriculars?

If you’re contractually in the clear, you should still tell HR and your superiors before you go telling your teammates. Even though you’ll know that you’re keeping it professional in the office, it’s going to be a little bit weird for your teammates at the beginning—and rightfully so. The best way to show your people how professional you can be is to come out as a couple tactfully.

A few things to avoid:

  • Don’t touch each other in the office. Duh. It will make people feel uncomfortable, and it’s not a good look.
  • Don’t be sappy on Facebook/Twitter/wherever your work friends live. It’s hard to be cool after seeing “No baby I love YOU more!!!!!” comments on a picture of you and her making out. Spare us.
  • If you fight, leave the anger at home. It might help you get over your anger quicker, which is a cool plus.

Basically, discretion. Be discrete in and out of the office. Remember that you were teammates before you were a couple, and the goal is to stay teammates no matter what.

Have a question for our advice columnist?

Ask it here.

Read previous columns in this series

Collaborate in real time on a digital whiteboard