If you subscribe to my newsletter, you're probably a leader or an aspiring leader. Do you ever stop to ask yourself whether getting to that VP level or joining the C-suite is what you really want?

Here's a little secret for you – lots of the women I talk to have these thoughts.

They're working hard, climbing the ladder, doing all of the things and one day they stop and think, Is this all even worth it? Do I even want that big exec job? Is it worth the pressure?

I have to admit, the first time I got this question I was surprised because it had never crossed my mind during my career. I knew I wanted to be a VP and that I was willing to work as hard as I needed to get there. I never actually gave the job itself a second thought.

But I should have.

Don't get me wrong, I enjoyed being an senior leader. There were parts of it I loved. But at the end of it, I came to the realization that executive leadership wasn't what I felt I was put on this earth to do. And so, after 18 years of grinding and climbing and finally becoming an Executive Vice President, I gave it all up.

I have no regrets, as the lessons I learned throughout my journey allow me to help other women achieve their dreams. But today, I want to dive into some of the key questions you can ask yourself if you're not sure whether senior leadership is for you, in order to gain some clarity.

There are a total of 5 questions to ask yourself and reflect on. You may want to take your time and journal these out.

Let's jump in.

1. Why do you want to be an exec?

Often when a client or potential client tells me they want to be an executive, the first thing I ask them is, “Why?” If you haven't spent some real time thinking about this, you should.

Is it for impact? Are you driven to make things better and have a greater impact on the success of the company? Are you driven to create change?

These are all great reasons and often a ‘why' like this can keep you going when things get tough.

But if you aren't sure, you may be chasing career advancement for the wrong reasons, like external validation or basing your self-worth on your professional achievements.

The challenge with this, is when you get there you may end up feeling unfulfilled in the role. The title change and salary bump will feel great for a short time, and then it will wear off and you'll be left wondering what's next. Or even worse, you'll be left feeling miserable and wondering how you could be so unhappy after finally reaching your goal.

Not a fun place to be.

2. What's behind your hesitation?

Okay, so let's say you have a strong ‘why'. My next question would be, “What's creating this doubt or hesitation?”.

You may need to really dig in to figure it out, but it can help to ask yourself whether this emotion is rooted in fear or love. I once heard that everything is rooted in one of these 2 emotions and have found it to be largely true.

Love: This may mean your gut (or soul) is pulling you in another direction. Do you have other passions you would secretly love to pursue but have been afraid to? Do you feel as though you're not fully authentic in your role?

Fear: This may be the fear of failure, or of not being able to hack it at the next level.

If your hesitation is rooted in fear, I encourage you to work through this. Imagine giving up out of fear when this is really your dream? You may regret it forever.

The truth is, most of us can do more than we think. I didn't feel 100% ready for any of the roles I took on! But I doubled down, did the work, used my network and soon realized I was much more capable than I had realized.

3. Do you know and like the actual work?

Do you have an idea of what work at the executive level looks like? Often we have our own vision of how something will be, and once we get there it's completely different. What do you picture when you finally land that role?

If you're picturing yourself with your feet up on a desk in a corner office while your executive assistant fetches your coffee, you may be in for a rude awakening.

Being an executive is hard work. You're responsible for an entire function or department and this means being accountable for results and ensuring the right decisions are being made.

It's more likely your days will be filled with meetings and thinking strategically about how to solve a big problem, as well as preparing board materials and reports, and getting people on your side in order to execute on your vision.

Sometimes it still means getting in the weeds! When I first became an EVP I only had two direct reports: a VP and an SVP, so was largely out of the day-to-day and could focus quite a bit on strategy. Six weeks later, my VP quit and suddenly I was working to find his replacement while simultaneously taking on all of his reports and doing a lot more hands on management. This, while still trying to manage the strategy. It was rough. But as the EVP, this was my job.

Remember my question about your ‘why'? This is why is matters.

4. Are you able to get out of the weeds? For real.

Wait, didn't I just say you have to sometimes get into the weeds? Well, the key with being an executive is understanding when you need to be in the weeds and when you need to take a more hands-off approach. You need to be able to make things happen, but also carve out time to think strategically and ensure you're thinking about higher level issues and longer-term results.

If you're a doer who can't seem to delegate and get out of the weeds, you may be in trouble in an executive position because there is just so much work that will be happening in your department. Trying to have your hands in everything is a recipe for burnout and unhappy staff.

I've known leaders like this and they worked around the clock and were stressed 24-7. To me, this would not be worth it. And believe me when I say, you have a choice in this.

I recently had a friend who's a Chief Growth Officer come speak to my community. When we talked about balance, she mentioned that she used to be terrible at work-life balance, however since Covid she's seen the light and was no longer willing to live this way. Since then she's become a VP and then moved to the C-suite. So even as a C-suite exec, she's able to do the things she loves and invest in relationships, because she's intentional about it.

Bottom line – you don't have to work around the clock as an executive if you don't want to. But if you can't get out of the weeds, you may end up doing just that.

5. Are you willing to engage in conflict?

Maybe you weren't expecting this one!

Here's the thing, conflict happens. It happens in business and if you're going to be an exec, there's no avoiding it. Whether that means a debate in the boardroom about the direction of the company or sharing difficult feedback with a team member, you're going to have to manage some tough conversations and do it in a way as not to damage relationships.

The sweet spot I love to talk about is kind candour. This is the balance between ensuring people know you care about them and their wellbeing, while also being willing to say the hard thing or delivering constructive feedback.

If you're someone who avoids conflict at all costs, you'll want to work on that before getting to senior leadership. And if you're not willing to work on it, you may want to rethink an exec role.

Not only does avoiding conflict make your life harder, but it will make it impossible to be the leader you want to be at this level. Hard truth.

So there you have it – 5 questions to ask yourself to gain clarity into whether senior leadership is for you:

  • Why do you want to be an exec?
  • What's at the root of your hesitation?
  • Will you enjoy the work?
  • Can you get out of the weeds?
  • Are you willing to engage in conflict?

I hope it's been helpful!

Until next time friends… ✌️💜