When your best friend becomes your boss

Anonymous

February 20,2023 at 6:59PM UTC

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When your best friend becomes your boss

I'm making a career change from nonprofit MarComm to tech sales. My best friend has a Product Advocate position open on her team and she thinks it's a good jumping off point for me to break into tech sales, I initially was trying to apply for an Enterprise Account Manager role but was declined due to experience.

My best friend has a tendency to be hard on her employees and has high expectations on performance from her team. She mentioned she's also worried but doesn't want to be the reason I don't get into tech. She's a great person and I look up to her because she has navigated the tech world for the past 8 years and is now managing a team of her own.

Should I take the role with her team and hope her managing style doesn't hurt our friendship outside of work, just so I can get my foot in the door or do I stay in nonprofit until I see something else open up in tech? Is this career shift worth the risk of our friendship? How can we minimize any awkwardness or set up boundaries to help keep the relationships separate?

Any advice is appreciated. Thank you!

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AnonymousFebruary 20,2023 at 7:02PM UTC
I would not work for her unless you are comfortable with friction in either the friendship or the business relationships to ruin the other one.
Cindy GrossFebruary 20,2023 at 7:07PM UTC
Listen to your instincts.
Close your eyes and envision where you are a year from now if you do take the job. Settle in and really ponder it all. Then get up and walk around for a few minutes. Sit down and close your eyes again and envision where you are a year from now if you do NOT take the job. Look at it from multiple angles. Ask yourself - what do I want to do? #BefriendingDragons
AnonymousFebruary 20,2023 at 7:11PM UTC
It's a very personal decision. I was recruited to the tech industry by a good friend who I was also a co-worker at one time (neither reported to the other). She recruited me because she knew my skillset - capable of working in a team or individually, tackling challenging projects, and "figuring" out the answers to problems. I'm not one to sit and wait for things to happen. After three years, I had recruiters contacting me all the time. I talked with a few and realized I was very underpaid. I worked for an international company and had a great experience and exposure to so much in HR. I spoke with my friend/manager, shared six job postings comparable to what I was doing (I actually did everything in those postings plus more), and asked to reassess my position and pay. I was underpaid by $20,000. She wouldn't budge, so I left. I got a great job that paid $30,000 more; I have received increases and bonuses over the last four years. I feel valued. My friend took advantage of our friendship. I will never work for a friend again. It's difficult to keep work/friendship separate; they will always fall into the "gray area."
Susanne DowFebruary 20,2023 at 10:14PM UTC
I have often imagined hiring friends of mine, I have a position which would warrant me recommending people for employment and potentially them working under me depending on the department, and it would be a disaster for many reasons if I was their manager. One of those reasons being how much stuff we know about each other, so if they say began to consistently come in late either my bias would lead to preferential treatment because I know what’s going on, or I’d be angry with them because again I know what’s going on. Which would put a strain on our friendship and work relationship. It’s easier to not take something personally when you’re not personal with someone but once you are… yikes ?. I don’t doubt some people can make it work, however I would imagine your friendship would have to from the beginning have been a more mutually transactional and pragmatic friendship than one where you are mutually compassionate and vulnerable. Otherwise I foresee lots of hurt feelings.
AnonymousFebruary 21,2023 at 12:40PM UTC
As you weigh this decision, consider your "why." Why are you making this career change, and then, will this position help you achieve your goal? If the answer is yes to this second question, then this is a good opportunity. You will then need to be emotionally prepared to have potential rough spots in your friendship relationship. You will now have a direct impact your friend's success at work, while also developing new skills. Just keep that in mind as you take on this new journey. Don't be overly harsh of your friend, but rather listen and search for the guidance in any discussion that initially feels harsh and act on the help. If you really want to make the career change, this is a great opportunity to do it given you do not have prior Sales experience.
AnonymousFebruary 21,2023 at 1:36PM UTC
Short answer, no. I don’t think friends should work for other friends. If you were coworkers at the same level that’s different. But if you are her subordinate, I can’t think of any scenario where there would not be friction here. Sorry ?
AnonymousFebruary 21,2023 at 2:33PM UTC
If you want to get into tech sales, I suggest you steer clear of working for your best friend. There is very little that could go right and many things that can go wrong. Being her friend will cause gossip at the water cooler about nepotism, and strain your relationship, even if it is solid now. I suggest you continue searching for other companies, knowing that you have a glowing reference in your friend, which is the best way to frame it when you decline to work for her.
AnonymousFebruary 21,2023 at 8:07PM UTC
Do you want to ruin your friendship and perhaps your future in sales? Because it sounds like this is what you are setting yourself up for.
AnonymousFebruary 22,2023 at 2:17PM UTC
If she was going to be a co-worker/peer yes, boss no. The fact that you are in a subordinate role not peer to peer as friends is a tricky dynamic to navigate at the same time you are trying to learn a new job in a new industry.
AnonymousFebruary 23,2023 at 2:10PM UTC
Please don’t. I’m in a position where twice mgmt has promoted from within…co-workers/friends become bosses. Twice it’s failed. The problems surprisingly to me were the ones promoted. They were very strict to prove they were fair yet at same time expected “friends” to do more and help them when things were wrong or in crunch time.
AnonymousFebruary 23,2023 at 4:23PM UTC
Don't do it. No matter how many boundaries you try to set up, the work relationship will bleed into the friend relationship.
Francoise ThimonFebruary 23,2023 at 5:16PM UTC
Only in very few cases this is a good scenario...No matter what is said or done, the friend relationship will suffer from the work relations.
AnonymousFebruary 23,2023 at 6:21PM UTC
2 schools of thought. Yes, it may affect your friendship. Before you do this sit her down tell her how you take feedback and how you learn. Be honest, be clear. Let her know you know how tough she is and that learning from her is something you are looking forward to especially because her success is going to be your success as well. Make sure you have a clear path for what success looks like and how she will measure you and a clear path for failure and how it would end if it just doesn't work. Weigh it out and then you can make the best decision for you. If you don't address the elephant in the room it won't be the right move no matter what happens. Good luck, and treat this as a mentorship from the bottom side of it, soak it in make her proud. It's good for you both.
AnonymousFebruary 23,2023 at 6:49PM UTC
I manage my best friend - in short, keep the worlds separated the best you can.
Make sure to tell her on the front end what leadership styles you respond to and which you don't.
Barbara WhiteFebruary 23,2023 at 9:26PM UTC
I personally would not do it. Think about it, you can never really confide in her again while she's your supervisor, as it's best to keep personal "stuff" out of the workplace. Jobs come and go. A best friend is (hopefully) for life!
Liz MilneFebruary 26,2023 at 11:40PM UTC
I would be inclined to miss the job and keep the friendship.
UNLESS
you and your friend have a candid talk before you interview for the position and both of you agree that you use the job under her as a starting off point in your chosen field, with you taking on as much training/ learning as you need to then apply for another position not under her as soon as you are confident that you can cope with it.
You must both promise full honesty with each other: if you're rubbish, she'll tell you; if she's inappropriate, you'll tell her (obviously in private, away from work - at work 100% professionalism on both sides!) and rethink if it's not going to work out...
Tricky one, don't rush into a decision... Good luck!