There are few things that redeem the soul-crushing effort of a long, tedious job search. But, they do exist: Getting a job offer (finally)? Awesome. Getting a job offer at a promising young startup? Really awesome. Getting a job offer at a promising young startup headed by one of your closest friends? Um, could it get more awesome than that?
I've done it – and I can tell you that, in many ways, it is the best. But, I'll also caution you that working for your friend isn't going to be all fun and games. Even if your friendship has endured since your frizzy-haired middle school days, the dynamic will change when you merge that into a manager-employee relationship. And before you commit to an extra 40+ hours a week with your pal, there's a lot to consider.
To help you fully think it through, here are some of the most important pros and cons of working for a friend.
1. She'll already know your strengths and abilities. When a friend offers you a job, you can be relatively certain that she's well aware of your career aspirations, your professional goals, the things you do well, and the tasks you dread. And if she doesn't know those things, having that pre-employment conversation as friends will be a lot easier than having it in an interviewer-interviewee situation. ("Um, you how know I'm not so great with cold calls?").
So, as long as you have that discussion (and you're confident that your friend is looking out for your best interests), you can accept the job with the knowledge that you're entering into an enjoyable and rewarding career; one that will provide the challenges to help you grow professionally and put you on a path to your dream position.
But: You can't expect to be treated differently because you're friends with the boss. While the majority of your job should be spent doing the things you anticipated, you'll probably still be asked to assume some duties outside of your area of expertise – especially if the company is a startup with a small pool of employees. Don't be surprised (or resistant) if you're the lucky one chosen to wheel the monstrous cart around Sam's Club, stocking up on 180-packs of toilet paper for the office restroom (not that I know from experience).
Yes, your friend wants you to grow professionally and achieve your career goals–but she also has a business to run, and as an employee, you have to help make that happen, just like everyone else on the team.
2. Communication will be a lot easier. With a solid friendship as the base for your professional relationship, you'll find it's a lot easier to communicate with your boss during the workday. When things are going well, you'll be comfortable enough to stop by your friend's office to say, "I totally just nailed that presentation!" And when it comes to brainstorming, you'll love how easy it is to let the ideas fly–no matter how silly, strange, or completely impractical they are.
This kind of open communication can set the standard for a very productive and comfortable work environment–one that would take a lot longer to develop if you worked for a more unfamiliar boss.
But: Talking about the tough stuff can be a lot harder when you're discussing it with a friend. In my situation, I quickly learned that if you're not satisfied with a portion of your job, your friend's management style, or your salary, there will likely be an element of awkwardness when it comes time to have a serious conversation about it. And take the reverse into consideration as well: When you have a rough week, miss an important deadline, or show up late a few too many mornings in a row, your friend is probably going to call you into her office for a stern sit-down. Are you prepared to view her as your superior and swallow her disciplinary words without harboring resentment?
And further down the line, if things don't go exactly as you imagined, will you be able to approach your friend to maturely discuss your resignation? Or will your friendship bind you to the job because you'd feel too guilty if you left? This isn't a fun situation to think about–but for the sake of your friendship, it's important to consider.
3. She'll appreciate your input. Most likely, your friend offered you a job because she knows you're trustworthy, hard-working, and altogether deserving of the salary she's paying you out of her pocket. And because of that trust, you'll be an active part of discussions about business decisions, marketing options, and the next steps for the company. Unlike a corporate environment, where your ideas rarely make it to the top of the ladder, you'll have immediate access to the boss to collaborate on big projects and provide important input.
But: Since she's the boss, she'll always–yes, always–have the final say. I came into my position with the skewed idea that, for the most part, my friend and I would be working as equals–but it didn't work out that way. You can voice your opinion about how strongly you disagree with her choice of advertising strategies, but when it comes down to it, it's her business–and ultimately, she calls the shots. In many cases, you'll have to be prepared to take a step back and regard her as the boss. Sure, she was your friend first, but when you're in the office, she's your authority figure and deserves as much respect as you'd give a traditional manager in any other situation.
4. You'll get to spend a lot of time together. Remember why this job offer is so exciting? Because you get the perk of working with your friend–and everything else that comes along with that, including mid-morning coffee runs, Taco Tuesday lunches, networking happy hours in the evening, and everything in between. And truthfully, that can make work really fun (it definitely did in my case). You'll play a lot of pranks, tell and re-tell embarrassing stories, and laugh uncontrollably. You'll get work done, of course–but you'll have a friend by your side to make it a lot less work-like.
But: You'll spend a lot of time together. And when you hit a rough day at the office (e.g., you spend an hour arguing over the way she wants to handle the new hire training), it's going to be hard to separate your professional life from your personal feelings. All of a sudden, when she makes a few too many edits to your monthly report, you might not feel like going out to dinner with her that night. I didn't expect to feel so defensive when my friend critiqued my ideas or work, but those feelings quickly seeped into our friendship. And that can take a major toll on your relationship – if you don't learn how to separate your work life from your friendship (and you start developing negative feelings instead), you could easily find yourself friendless and jobless.
All in all, there are a lot of good things about working for a friend–but there are also some serious concerns that you'll need to consider before jumping in headfirst. To preserve your career, your future professional references, and, most importantly, your friendship–you owe it to yourself (and your friend) to completely think this decision through.
Special to The Globe and Mail
This article was originally published on The Daily Muse.