Should Force Multipliers Be Friends with Their Bosses?

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Friendships and business partnerships. It can be a tricky situation to navigate. Should Force Multipliers be friends with their bosses? With the amount of time you spend together, how do you NOT cross over into a friendship with your Executive?

A couple of weeks ago this topic came up during one of my webinars. I had to pause and give this question some thought. Personally, I’ve never had to battle with trying NOT to be friends with a boss. In fact, for me, the opposite is probably true – I need to make an effort to be social in general! And I’ve never considered my bosses to be my “friends.”

As I began to think more about how to answer these questions, I do what I always do first, go to the dictionary. I’d like for us to all start out with the same understanding of what we’re going to talk about. So, let’s level the playing field. As with most words, the definitions vary. However, for the purposes of today’s discussion, we’re going to define friend as follows:

  • a person you know well and regard with affection and trust
  • your buddy, your pal
  • someone you like enough to hang out with on a regular basis by choice and not circumstantial obligation (i.e. work)

A case study: Is my boss my friend?

Let’s break this down using my Principal, Adam, as an example. Do I know Adam well? Yes. Do I trust him? Definitely. Do I regard him with affection (fondness or liking)? Sure! Is he my buddy or pal? No.

In the eleven years that I have known Adam, have we ever hung out outside of work or a work function? Nope! Would I? Sure, but we spend enough time together as it is! He has priorities and boundaries for his work and life and I do too. It’s been a non-issue since day one.

Does that mean we don’t have a close working relationship? Quite the opposite. I think we have a very direct, transparent, fun, challenging, engaging, honest, friendly, and mutually beneficial relationship where neither one of us takes ourselves or each other too seriously. We have friendly banter and seriously tough conversations. But friends, we are not. At the end of the day, Adam is my boss and I’m his employee, and those are clearly defined roles that we both respect.

That is just my experience.

But, should assistants be friends with their leaders?

The question is should Force Multipliers be friends with their bosses, and how do you avoid it if you don’t want that type of relationship? I think it entirely depends on the individuals, their preferences, and their work styles. Here are some things to consider:

Are you willing to set clear boundaries?

Setting clear boundaries is going to be the most important part of building or maintaining a friendship between leaders and Force Multipliers (or NOT building a friendship). Boundaries are a healthy part of any relationship and will become even more imperative when you are navigating the relationship between a business partnership and a friendship.

Knowing when to put on your “work” hat and when to wear your “friend” hat will be a delicate dance.

For example, how do you know when you’re heading into the office early and grabbing coffee and bagels as a friend, or as an employee? I know, seems harmless, right? But what happens when an early-morning coffee run turns into weekend errands or staying late to cover a project for your boss? Is that part of your scope of work? Or are you on friend-time? Are you and your Executive able to tell the difference?

Are you beginning to feel resentment?

This is a sure-fire sign that something might be amiss. Those early morning coffee runs don’t feel friendly anymore, but rather like your boss is taking advantage of you. This works the other way too. Are you leaving early every day because you know your friend, I mean boss, won’t mind? Maybe they are starting to feel resentment and that you are taking advantage of their good nature. After all, they have a business to run.

And consider this, which comes first, the business or the friendship?

Have you discussed this with your boss? Real friendships can weather the ups and downs of a lot of challenges, but they don’t usually have the complication of an employment contract to contend with. What happens when the friendship starts to adversely affect the working relationship or vice versa? Have you talked about how you will handle these situations? Do you know where your Executive stands on the matter? What about you? Would you walk away from your job to preserve the friendship? Would your boss?

How are you and your Executive treating each other in public and behind closed doors?

Is there a level of professionalism and respect? Or are you both allowing the friendship to shine through in front of others? How does this affect the morale (positivity or negatively) of the rest of the team? Conversely, do you and your boss put on a professional face in front of the company and then verbally berate or dismiss each other when one-on-one? Granted, I don’t really consider those behaviors being characteristic of a good friend relationship, but having a friendship with a colleague can quickly slip into plain bad behavior.

One final thing to think about.

Does your Executive like to be friends with their employees? Have they successfully navigated this in the past? Do you prefer to be friends with your Exec (or not)? Have you successfully navigated that in the past? Whether either of you has been able to be friends with a boss or employee and still have productive and professional working relationships will speak volumes as to whether or not it will work again. I do think that a desire to build a friendship is always a good place to start, as long as both parties are on the same page.

And that’s the thing, isn’t it? If either you or your Executive does not want to move into friendship territory, then that conversation needs to happen early. Whether you should become friends or not is a non-issue if it is not something that either of you wants. However, boundaries will need to be clearly defined and reinforced (usually more than once).

What do you do if you were friends with your boss before you were hired?

Start at the top of this list and go through all of these considerations on your own. Determine how you want to approach the business partnership and your friendship. Then sit down with your boss and discuss.

While it’s not for everyone, there is nothing wrong with being friends with your boss. It’s not a requirement for having an incredibly effective strategic business partnership. Nor will it necessarily adversely affect your career if you are friends with your boss. The key is to enter the friendship without any illusions that it won’t change the dynamics. Because it will. Be aware of them, set clear boundaries, and do not hesitate to speak up and adjust those boundaries if they are no longer serving you or your boss.

What do you think? Are you friends with your boss? Why or why not? Do you think Force Multipliers should be friends with their bosses?

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