5 Questions to Ask Yourself Every Week as a Leader

Let’s get real for a second—when was the last time you actually stopped and checked in with yourself? And no, I don’t mean in the “did I remember to send that email or defrost the chicken?” kind of way. I mean really checked in, like, “Hey, how’s it going up there?” As a leader, it’s way too easy to get caught up in the daily grind and forget that your brain isn’t some endless, magical productivity machine. Spoiler: It needs maintenance too.

Self-questioning isn’t about overthinking or spiraling into existential dread—it’s more like giving your brain a quick tune-up. Think of it as your weekly “you” meeting. It’s a chance to hit pause, take stock of what’s working, what’s not, and figure out what you need to do differently to keep things running smoothly. Basically, it’s you, talking to you, to make sure you’re not accidentally sabotaging yourself.

And let’s be honest, who doesn’t need that? It’s the difference between wandering around aimlessly and having a GPS for your life—although even the best GPS reroutes occasionally, right? So before you dive headfirst into another week of chaos, take a second to check in. Trust me, it’s worth it.

Assessing Goals and Priorities

Let’s talk about goals for a second—do you even know what yours are this week?

Or are they hiding in the chaos, like your car keys when you’re running late? The truth is, without clear goals, you’re just out here winging it, hoping for the best. And let’s be honest, winging it doesn’t exactly scream “leader of the year,” right? So, take a beat and figure out what you actually want to get done. Not ten things, not twenty—focus on the handful of things that will make a real difference.

Next up: priorities. Here’s a fun fact—not everything is important. I know, shocking! But if everything is a priority, nothing is. So take a hard look at that to-do list. What really needs your attention? What can wait? And, maybe most importantly, what can you hand off to someone else? Delegation isn’t just for the lazy—it’s for the smart. You can’t do everything yourself, and if you try, you’re just setting yourself up for stress eating an entire box of cookies later.

One more thing—don’t forget to leave room for the unexpected. Because, let’s face it, something always comes up. Whether it’s an urgent request, a team issue, or your laptop deciding today is a great day to quit on life, you need wiggle room. So set those goals, nail down your priorities, and be ready to pivot when life inevitably throws you a curveball.

Team and Relationship Evaluation

Okay, let’s talk about your team for a second. Are you helping them thrive, or are you accidentally turning their workdays into an episode of a survival show?

Leadership is a significant driver of employee engagement, which predicts how well your organization performs. Engaged employees are the secret sauce to productivity, commitment, and innovation, while disengaged teams often deal with high turnover and inefficiencies. If you’re not creating an environment where they feel supported, then it’s no wonder projects are stalling or morale is low. Check in with them—not just about deadlines or deliverables, but about how they’re doing overall.

Also, let’s get real about mental health. You can’t expect people to perform at their best if they’re barely hanging on. By promoting well-being, psychological safety, and work-life balance, you can see a 21% increase in how well your team performs. If you’re not paying attention to these things, you’re leaving a huge amount of potential untapped. And nobody wants to work in a pressure cooker, right?

Lastly, are there any simmering conflicts on your team? Even tiny issues can snowball if left unchecked. Don’t let workplace tension turn into a full-blown soap opera—tackle it before it becomes “must-watch drama.”

Personal Development Check

Now, how’s the personal growth game going?

No, seriously, what’s new with you? Learned anything cool lately, or are you just running on autopilot, surviving on caffeine and crossed fingers? As a leader, you’ve got to keep leveling up. And no, I don’t mean reading a motivational quote and calling it a day. I’m talking about real, actual growth. Maybe you tried a new approach in a meeting, tackled a skill you’ve been avoiding, or even just figured out a better way to organize your calendar so it doesn’t look like a chaotic mess of overlapping colors.

Also, let’s be real—are you stepping outside your comfort zone, or are you camped out there with snacks and a blanket? Growth doesn’t happen when you’re chilling where it’s safe. It happens when you take risks, even if they make your palms a little sweaty. And, while we’re at it, are you actually taking care of yourself, or are you burning out while pretending everything’s fine? Pro tip: burnout isn’t a badge of honor—it’s just exhausting.

Lastly, think about what’s inspiring you. Have you read something, seen something, or had a conversation that made you think differently? If not, it’s time to shake things up. You’re leading others, but you’ve got to lead yourself first.

Decision-Making and Problem Solving

Let’s get into the nitty-gritty—how’s your decision-making game these days?

Be honest. Are you crushing it, or are you flipping coins and calling it strategy? Decisions come at you fast as a leader, and some days it feels like every choice you make could either save the day or send everything spiraling into chaos. No pressure, right?

First off, think about the big calls you’ve made recently. Did they pan out the way you hoped? Or did you end up learning a “valuable lesson” (a.k.a. a gentle smack from reality)? Reflecting on what went well—or didn’t—is like putting together a highlight reel of your own thought process. It’s not about beating yourself up; it’s about figuring out what worked and what definitely didn’t.

Now, what about those little fires popping up? Are you handling them while they’re manageable, or are you waiting for them to turn into full-blown infernos? Pro tip: ignoring a problem doesn’t actually make it go away—it just gives it time to invite its friends and turn into a whole situation. Identify what needs your attention now, so you’re not blindsided later.

Oh, and let’s not forget: are you overthinking every tiny detail? Sometimes good enough is, well, good enough. Not every decision needs a six-hour brainstorming session and five spreadsheets. Know when to go deep and when to trust your gut—it’s there for a reason, after all.

Future Planning and Vision

Are you just hoping the wind knows where to go?

Here’s the thing—if you don’t have a clear vision for where you’re heading, how can you expect anyone else to follow? Spoiler alert: they won’t. Take a step back and ask yourself if what you’re doing today is actually helping you move closer to your big-picture goals, or if you’re just stuck in a cycle of putting out fires and calling it progress.

And while we’re at it, when’s the last time you thought about what’s next for your team? Maybe you’ve been so focused on crossing stuff off your to-do list that you forgot to think about how to make life easier (or better) down the road. Are there tools or resources that could make everyone’s jobs less of a hassle? Maybe there’s training that could help your team crush it even more. Or maybe you just need to sit down and ask them, “Hey, what would actually help you right now?”

Planning isn’t just about filling up a calendar; it’s about setting yourself up to look back later and think, “Yeah, that was a smart move.” So, what’s the plan, captain?

Action Plan

So now that you’ve gone full introspection mode, what’s next?

Sitting with all those thoughts won’t magically fix anything—this isn’t a self-help montage from a movie. It’s time to turn those “aha” moments into actual steps. Think of it like this: you’ve just done the grocery shopping, and now it’s time to cook the meal.

What’s on the menu? Maybe it’s finally delegating that project that’s been haunting you, or setting up a one-on-one with someone on your team who’s been unusually quiet. Maybe it’s as simple as blocking off time on your calendar so you can focus on that big idea you’ve been putting off.

The key here? Keep it doable. Don’t go overboard and try to overhaul your entire life by Friday—it’s not a reality show. Pick a few things that really matter and actually commit to them. Oh, and write it down. Seriously, don’t rely on your brain to remember it all—your brain’s got enough going on. And don’t forget to circle back at the end of the week to see how you did. Think of it as a little accountability date with yourself. You’re not aiming for perfection here; you’re aiming for progress. Small wins add up, so start stacking them and see where it takes you.

Selling a property? Give us a call today and learn more about our professional photography services that can boost your property listing!

Also, explore our sister company for exclusive luxury listings you won’t want to miss. Don’t forget to tune into our new podcast for even more valuable insights!