Is the Grass Really Greener? 8 Essential Questions to Ask Before Making Your Next Career Move

So, you’re thinking of jumping.

We’ve all been there—looking at a new job or career opportunity and feeling that spark of excitement. Maybe the title’s shinier, or the pay is a little higher. You start thinking, “This is it. This is my shot. Time to jump.”

But before you take the leap, let me hit you with a reality check: jumping without thinking can be like jumping off a cliff because someone said there’s a trampoline at the bottom—but you didn’t check first. Maybe you’re thinking, “Well, I’m just ready for change so I’ll take my chances!” or “This job looks amazing!” But the grass is always greener… until you land in a thicket of weeds.

So, let’s slow down a bit. Ask yourself these questions first—these are the ones you need to consider if you’re thinking of jumping, especially if you want to level up in your career (like making that move from Financial Controller to CFO). Trust me, these are not just cordial conversation-starter questions; they’re game-changers.

1. Why Leave When You Can Grow Right Where You Are?
   Before you start hunting for “new opportunities,” take a moment to ask yourself: Could I make the same move internally without uprooting my whole life? I know, it sounds boring—who wants to stay in the same place, right? But here’s the thing: internal moves are less risky. You’re already familiar with the culture, the people, the processes; you’ve already done the time… So, if you’re angling for a promotion or a role change, it’s worth considering whether that same growth is possible without the dramatic leap.Through years of executive coaching, I’ve worked with many professionals who’ve thought they had to leave to climb the ladder and get ahead. But when we took a step back and assessed their options, they realised there was potential for growth right in front of them.
2. The Inside Scoop: Talking to People Who’ve Been There
   It’s tempting to get excited about the new title, the perks, the office, the money… But let’s be honest, you can’t make an informed decision by looking at a job description or hearing someone’s glowing review from the outside (especially recruiters!). I’m talking about real, in-the-trenches insight from the people who are already on the ground, in the role.For example, if you’re in finance and eyeing the CFO position, it may look amazing on paper, and certainly from afar, but what’s it like behind the scenes? Is it the type of pressure you can handle, and can you handle it at this point in your life? It’s a conversation that most people avoid having, because it’s the one that will give you the real answers. The uncomfortable truth. When I was growing my own business, I got advice from multiple sources, always speaking to those who had been there before me.If you don’t know anyone in the position you’re aspiring to, it’s time to reach out. This is where networking and executive coaching can help. Sometimes you need a sounding board, someone who can help you ask the right questions—and guide you through the decision-making process without rushing in.
3. Are You Prepared for the Challenge or Just the Title?
   I get it—you’re a high achiever. You think, “Hey, I can learn anything if I put my mind to it.” And that may be true, but let me throw some honesty your way: the learning curve can be brutal. So the question is: Are you prepared for that?If you’re jumping to a CFO role, for example, are you ready to deal with a whole new level of pressure, responsibility, and leadership? If you’re lacking a few key skills, now’s the time to address it. Don’t wait until you’re in the role and suddenly realise you don’t know what the hell’s going on, and you’re not equipped to fill the shoes that come with it!This is another place where executive coaching comes into play. As a coach, I help my clients identify the skills they need, where they’re lacking, and how they can quickly and effectively build those skills—before they jump.
4. Does This Role Align with What You Stand For?
   Core values are non-negotiable. You can’t go chasing a job that doesn’t line up with what you stand for, even if it promises to solve all your problems. Too many people jump ship to new opportunities only to realise, months later, that they’re still unhappy because it’s a toxic culture or doesn’t align with their personal beliefs.When I talk to my clients, one of the first things I help them do is to evaluate their values. You see, If these are not in aligned with your new role, your work will feel like a grind. For example, if one of your core values is rooted in solid work-life balance, but the new job demands constant 80-hour weeks, that’s a recipe for disaster. Starting to see the value in knowing your values? Sorry, couldn’t help myself.
5. Is the Grass Really Greener or Just Well-Manicured?
   It’s easy to get blinded by flashy perks—higher salary, bigger team, the corner glass office… But what are the trade-offs? Are you ignoring the fact that the role could come with extreme stress, less family time, and sleepless nights pondering a make or break strategic decision?I’ve seen this too many times in my executive coaching career. My clients get so caught up in the excitement of the opportunity that they ignore the red flags, almost in an intentional way, consciously opting to be “blissfully unaware”. They need someone (me, preferably) to help them see the full picture and assess whether the pros really outweigh the cons.
6. Are You Thinking Clearly or Reacting to Emotions?
   Let’s be real—this one’s a big one. If you’re feeling frustrated, angry, or burnt out in your current role, your judgment might be clouded. You’re not thinking clearly about what’s best for your career—you’re thinking about running away from problems.This is again where executive coaching can really help you level up. I’ve helped clients who were on the verge of making emotional decisions that they would have regretted. Together, we talked through their frustrations, re-evaluated their motivations, and they walked away with a clearer, more rational understanding of what they wanted.
7. Comparison is the Thief of Joy—Focus on Your Own Path?
   We all do it. We look at our peers and think, “They’ve got it all figured out. They’re on a better path than I am.” But that comparison game will get you nowhere fast. Everyone’s journey is different. What worked for someone else may not be what’s best for you.I can’t tell you how many times I’ve seen professionals make decisions based on envy or comparison, only to end up in a situation that’s worse than what they had. The key is focusing on your career path, not someone else’s.
8. The Shiny Title Trap—Is It Really Worth the Jump?
   Here’s the kicker. Maybe you’re thinking, “It’s worth it to get a bigger title, even if the pay’s a bit lower.” Maybe, but maybe not. Are you willing to take a hit financially to pursue a dream job in senior management? And if so, have you fully evaluated if the long-term rewards are worth it?If you’re unsure, it’s time to pause. I’ve had many conversations with clients who felt compelled to take a pay cut to follow their passion or ambition. We talked through it, and they realised that while the opportunity was great, they had more to lose than they’d originally thought. It’s all about being strategic, not impulsive.

Final Thoughts

So, before you jump, take a step back. Ask yourself these tough questions. Get some outside perspective, and be honest about what you truly want. If you can’t answer these questions with clarity and confidence, maybe it’s time to hold off on that leap for now.

If you need help thinking through your next career move, don’t hesitate to reach out. Together, we’ll make sure you’re jumping smartly and not just running away from problems.