Should You Party With Direct Reports?

Posted by:

|

On:

|

The other day I was chatting with a friend who recently took a new job. It’s a super exciting move for her, one that will have her managing a big team at a new company after having worked at her previous one for nearly a decade. The first week of her new job ended up coinciding with a conference in the south of France (casual, not jealous at all…) where she got the opportunity to meet and mingle with members of her new team both during the day during lectures, but also at night. One morning we were texting and she posed a question that I’ve gotten — and asked myself — numerous times over the years…

If my team goes out partying, should I join them? 

Lucky for my friend (and all of you), I’d actually already written a draft of this article before she asked me this. So now I have the opportunity to refine it even further. The question really isn’t about partying per se, it’s about familiarity. About boundaries. So instead I’ll frame it this way: as a people manager, should you be friends with your direct reports? 

I’m going to approach this as I would with a woman who I was mentoring as she grew in her own career. The people I’m advising are often ones who are just now making their first transition from being an individual contributor (IC) to someone who manages a team (or even just one person). There are so many exciting career milestones to look forward to — that first promotion, a big raise, an important new title — but I’ve found throughout my career that the transition from IC to people manager often isn’t treated with the pomp and circumstance that it deserves. For me, this was the first time that I felt a seismic shift in the expectations surrounding my job, and thus in my own expectations for how I would show up in the office. 

(Pro tip: probably not like this…)

Did I need to come in earlier, to set an example? How was I going to handle prioritization and delegating responsibilities? But honestly, one of the biggest things I struggled with — and am still working to master today — is how to handle my interpersonal relationships with people who report to me. 

Now there are two primary ways that this can manifest itself. First, you’re brought on to lead a team or individual who you don’t have a prior relationship to (like my friend above); or second, you’re promoted within or moved to manage a team that you are familiar with. Each of these situations has its own unique intricacies that cause them to differ, but I’ll do my best to paint with a broad brush…at least for now. 

What are some key considerations when trying to think about how to build and manage your work relationships now that you’re a people manager? 

Question #1: How much of your personal life should you share? 

It’s a pretty established fact that sharing parts of who we are creates a shared understanding, shared experience, and ultimately bonds two individuals. But how much is too much to share? 

My philosophy has shifted on this one over the years, perhaps this as a product of my experience or perhaps a shift in the age and inclinations of those I’m managing (see: the generational office divide). But where earlier in my career I would actively try to share details of my life to create a feeling of camaraderie amongst my team, in recent years I’ve found value in creating some distance — in certain circumstances. 

For example, when I was younger I would share details like weekend plans (what if one of my reports enjoyed similar music and I was going to a concert on Saturday?) or even anonymous friend drama (who doesn’t bond over the ridiculous price tag of bachelorette trips nowadays?). Now, I reserve those types of anecdotes for when the situation truly, specifically calls for them — or I’m explicitly asked. 

Instead, I focus my in-office sharing on my own mindset, and who I am as an individual and a manager. What I’ve found is that the people who work for you absolutely do want to feel as though you’re friends and have a positive interpersonal relationship, but that commiserating over their latest boyfriend drama simply isn’t the best way to achieve that. First, it opens the door to sharing about situations that might make someone uncomfortable, which is why I’m selective in sharing only when appropriate, and hopefully when welcomed into the conversation or asked. Second, it can at times create such a strong feeling of friendship that the people who work for you feel betrayed when you need to switch into manager gear and maybe make some hard decisions about how to prioritize everyone’s time. So it’s not that I don’t ever share anything ever. It’s that I try to be mindful so that when I need to switch gears into management mode, I’m not giving people whiplash. Because at the end of the day, once you become a manager, it’s far more important that you’re able to compassionately explain why someone’s project is being deprioritized than relate to their current dating drama.  

Reading that, you might think that I’m actually a drone of a boss who never shares anything about her life and you could never feel close to. On the contrary, I actually share more now as a manager than I ever have previously. I just focus my sharing elsewhere. For fear of sounding arrogant — I focus on sharing myself. 

I want the people who work for me to know when I’m having a bad day. Rather than leaving them guessing whether my mood has something to do with their own performance, I think it’s important for people to know that bosses have off days too. Sometimes it might be because of something happening in my personal life (which I often may then choose to share, see above), and other times it might turn out that I’m just as frustrated about a recent reprioritization as everyone else is. 

If I’m struggling to figure out the best way to achieve our next milestone, I tell my team. Not because I want them to think me weak or indecisive, but because they may have insights I’m not seeing from their own perspectives on the business. If they know it’s something I’m working on, they may be able to help. But furthermore, if they know I value their opinions when I’m working things out, they’ll feel both closer to me and that I value their expertise on the team. Because no matter the level, IC, manager, or executive, everyone has insight that could help move the company forward. 

Question #2: Do you go out for drinks with everyone the same way you might have before? 

Back when you were all peers, maybe you went out to grab drinks at happy hour every once in a while. But now you’re the big boss…do you still go? 

My personal answer: yes. Of course you go! You may be their manager, but you’re still a human being who wants a positive relationship with not just your direct reports but everyone else in the company. So of course you still want to bond a little over beers and perhaps some benign gossip about how the company stationary closet seems to be stocking cheaper paper these days. 

The biggest difference I started to make once I became a manager? I stopped staying until the end of the night. As the drinks flow deeper, the conversation gets looser, and sometimes the presence of a manager makes people feel that they can’t be open around their peers — or worse, they overshare in front of you by accident. Let’s all disabuse ourselves of the notion that colleagues don’t gossip, or that sometimes venting about your manager isn’t a necessary stress release that people just need. Instead, I say you give them the space to get that out and find deep connections with their peer groups as well, without the boss’s shadow looming over things. 

My favorite move? After whatever my personal work drink limit is hit (mine is generally 2, but I’m not here to define your own limit or tell you what’s right, you do you boo), I buy a round of shots for whoever remains and leave them to it. Obviously, this signature move may not be appropriate in certain offices, but in my experience it’s been quite a crowd pleaser, and everyone has still made it back to the office just fine (but perhaps a bit more slowly) the next morning. 

Question #3: How do you assert authority when prioritization or delegation conflicts arise? 

While this is certainly a problem for all managers, the distinct awkwardness of this situation is most acute in a scenario where you’ve been promoted into a position where you now manage a group of people who were once your peers. It’s now your job to tell the very people you used to b*tch with over happy hour drinks about how management was constantly messing up priorities what projects they need to be focusing on and which they need to leave behind. 

This one can lead to a lot of unspoken tension, so my personal advice? Tell them the truth. Tell them you’re in a difficult position now that you’re straddling the requirements of being a manager with your understanding of what it was like to be an individual contributor. Even better? Explain to them the things about being a manager that perhaps you didn’t realize when you were in their shoes that might have given you a little more grace with your last manager had you known about all the balls they were trying to juggle at the same time. 

We all hate to think about the budget, but money is not infinite. We all want to believe that our project is the most important one happening at any given time, but different projects push different levers on the company’s balance sheet. The best way to get buy-in from the people below you on what needs to be done and what sacrifices might need to be made is to be honest with them. Because sometimes it hurts you just as much as it hurts them to axe that exceptional new product idea. But if there genuinely isn’t enough marketing budget to give it a fighting chance once it’s developed, that will hurt even worse when you launch the project but can’t support it long term. 

At the end of the day, the thread that weaves its way through all of my management philosophies is honesty — because both ICs and managers are just people, too. Sometimes that honesty needs to be strategic or selective to avoid making people feel uncomfortable (see item #1) or to make sure everyone’s roles are fairly established (see item #2), and sometimes it needs to be you, the manager, who is a little uncomfortable to do your part to bring your team on board (see item #3). 

What other struggles have you all experienced when transitioning from IC to people manager? We know there are many, and we want to hear about it! Let us know in the comments. 

Posted by

in