Stop Leading Like You’re in a Situationship: Leadership Skills That Actually Work
By Nina — I'm the friend who tells you what you need to hear about your situationship. ·
I was at a happy hour in Williamsburg last week—the kind where the DJ plays just a little too loud and everyone is pretending they aren't checking their DMs—when a friend of mine, let’s call him ‘Mark,’ started venting about his team.
Mark is a mid-level manager. He told me, ‘Nina, I just don’t get it. I give them freedom, I don’t micromanage, and I’m super chill. Why are they blowing deadlines?’
I looked at him, sipped my overpriced mezcal, and said what I always say when someone tries to make a mess sound like a ‘vibe’: ‘Mark, you aren’t being a leader. You’re being a partner in a situationship.’
He blinked. And then, because he knows I’m usually right, he started listening. Because here’s the truth: most of the bad habits you pick up in your dating life—the ambiguity, the fear of conflict, the ‘go with the flow’ attitude that’s actually just emotional laziness—are infecting your professional life. If you can’t lead yourself with clarity, you have no business trying to lead a team.
Stop 'Ghosting' Your Direct Reports
In dating, ghosting is the ultimate coward’s move. It’s what you do when you don’t want to deal with the discomfort of saying, ‘Hey, this isn’t working.’ In the office, it looks different. It looks like skipping 1-on-1s because you’re ‘too busy.’ It looks like giving vague, non-committal feedback because you’re afraid of hurting someone’s feelings.
If you aren’t providing consistent, actionable feedback, you are ghosting your team’s growth. Leadership isn’t about being the ‘cool boss’ who lets everyone slide. It’s about being the person who gives them the roadmap. If your employee doesn’t know where they stand or what they need to fix, that’s on you. Stop hiding behind your calendar and start having the hard conversations. If you can’t look someone in the eye and tell them their presentation was lackluster, you need to work on your backbone before you accept that promotion.
Ditch the 'I’m Just Chill' Defense
We all know that person. They claim they’re ‘chill,’ but really, they’re just terrified of setting a boundary. In a relationship, this leads to three months of being ‘exclusive’ without actually being exclusive. At work, this leads to scope creep and missed KPIs.
Being a leader doesn’t mean being a dictator, but it does mean setting expectations. When you don’t define the parameters of a project, you’re essentially saying, ‘Do whatever you want, and I’ll deal with the consequences later.’ That’s not leadership; that’s procrastination. You need to be the one to define the 'What,' the 'When,' and the 'How.' If you’re scared that setting clear expectations makes you seem ‘difficult’ or ‘bossy,’ you’re playing a losing game. People actually crave structure. They want to know exactly what winning looks like so they can go out and do it.
Stop Romanticizing the Hustle (And Start Managing Reality)
I spent three years in a relationship where I thought if I just ‘tried harder’ or ‘communicated differently,’ I could change the outcome. Spoiler alert: I couldn’t. People (and projects) are what they are.
In your career, stop falling in love with the fantasy of how you think a project should go and start managing the reality of what’s actually happening. If a team member isn’t hitting their numbers, stop romanticizing their potential. Look at the data. If a strategy is failing, pivot. Don’t hold onto a failing initiative because you’re emotionally attached to the concept. A good leader knows when to break up with an idea that isn’t serving the bottom line. It’s not personal; it’s just business.
Radical Candor is Your New Love Language
I’m a firm believer in the ‘Rebel’ approach to life. That means being honest, even when it’s uncomfortable. If you want to level up your leadership skills, you have to embrace radical candor. This isn’t an excuse to be a jerk. It’s an invitation to be transparent.
When someone on your team messes up, don’t sandwich it between two fake compliments. Tell them what happened, why it matters, and how to fix it. When they do a great job, tell them exactly why it was great. Precision is a superpower. When you stop beating around the bush, you build trust. And trust is the only thing that actually keeps a team together when the pressure is on.
Take Ownership of Your Baggage
Finally, look in the mirror. Are you micromanaging because you’re a perfectionist who doesn’t trust others? Are you avoiding conflict because you’re a people-pleaser who needs to be liked? We all bring our ‘dating baggage’ to the office. The difference between a leader and a liability is that the leader is self-aware enough to work on that baggage instead of letting it dictate their management style.
If you don’t know why you react the way you do, you’re always going to be a victim of your own triggers. Get a coach, read a book, talk to your therapist—whatever you need to do to stop projecting your insecurities onto your staff.
Leadership is hard. It’s messy, it’s vulnerable, and it requires you to be the adult in the room even when you want to throw a tantrum. But if you can master these skills, you’ll stop managing ‘situationships’ at work and start building a team that actually respects you.
What’s the biggest leadership block you’re currently dealing with? Are you hiding behind ‘chill’ energy or are you ready to actually step up? Drop a comment below or shoot me a DM—let’s talk through it. I’m here, and I promise to keep it real.