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Journey to the C-Suite, are you ready?
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Journey to the C-Suite, are you ready?

MW
Matthew Weir
··11 min read
Talk the author, Matthew Weir

How do you know when you're ready for an executive role? Are you the right person for an executive position? Is your owner/CEO dragging their feet giving you the title you've earned and deserved, or are you further off than you feel you may be? Is it the right time?

Read along with me and I'm going to do my best to answer all of those questions, but first...

Please, don't get your feelings hurt

I'm going to say some very honest, very true things about leadership. If you're executive material, your first test is going to see if you can cut through your emotions to see the truth. As much as it hurts, "being there since the beginning" doesn't make you a better, more valuable leader to a growing business... it especially doesn't make you a better leader than someone from the outside who has done this successfully for years and maybe several other companies.

The game, like it or not, is won by results, not emotions... and if you're having a difficult time pulling those two things apart, it's a good time to get very comfortable in the leadership level that you're at. Most leaders don't make it to the executive level, so don't expect an easy trip! It's time to stretch yourself not only in general business and role competency, but also in emotional intelligence.

C-Suite generally doesn't even exist until ~$10mil+ revenue

A lot of leaders I talk to in "director" or similar roles are chomping at the bit for their C-level title, yet the entire business they work for is just a few million in revenue. Plain and simple, a C-Suite (typically) doesn't exist at that size. The complexity of staff size and responsibilities just isn't in a place where that makes sense.

The company becomes too "top heavy"– meaning, too high of cost in leadership when the majority of that money needs to go to staff to execute the functions of the business to get to that higher revenue. Additionally, that level of managerial complexity is just unneeded at that scale. The owner/CEO can generally scale with themselves, a hand full of middle managers, and a fractional executive (or two).

So, what do managers/directors do until then? Be a great leader that grows the business and develops themselves, then come back for that new title.

Statistically, the leadership team is long since replaced by $10mil

I think it's important to know that the odds are against you in getting that C title at the business you've been dedicating your life to. Not because they don't appreciate you, but because you're likely incompetent to do it (try to push down the offense, I am going to get to how to make you be the right choice).

By the time the business you've put your blood, sweat, and tears into crosses that $10mil threshold, you've likely been replaced. It's nothing personal, but a leader who got a company to $5mil for the first time doesn't have any idea how to run a company that is now $10mil+... and the owner/CEO owes it to everyone who works there, and the customers paying them, to have the right people steering the ship. Often, it's not you, and yes, I know, that hurts.

This means it's critical to focus on developing yourself. Hoping that the business you work for will invest time/money into training you for the role that you want so you may or may not be successful in it is basically the worst sales pitch of all time. Maybe that plan works out in other positions, but not the executive suite. You need to change you to be who you need to be. No one owes you anything... make yourself the best choice.

Larry Griener has a great paper from 1972 that I think is a killer read that covers this topic better than I probably ever could. Here's an expert:

... All the foregoing individualistic and creative activities are essential for a company to get off the ground. But as the company grows, those very activities become the problem...
... In each revolutionary stage, it becomes evident that the stage can come to a close only by means of certain specific solutions; moreover, these solutions are different from those that were applied to the problems of the preceding revolution. Too often, it is tempting to choose solutions that were tried before but that actually make it impossible for the new phase of growth to evolve...
... Management must be prepared to dismantle current structures before the revolutionary stage becomes too turbulent. Top-level managers, realizing that their own managerial styles are no longer appropriate, may even have to take themselves out of leadership positions. A good Phase 2 manager facing Phase 3 might be wise to find a position at another Phase 2 organization that better fits his or her talents, either outside the company or with one of its newer subsidiaries.- Evolution and Revolution as Organizations Grow - Larry E Greiner (source)

Ouch. That kicks you in the gut if you're waiting to claim your executive suite title, but I stand by it that knowing the brutally honest truth of what you're against is the only way to defeat it... so hang in there.

It's your job to become the person that you need to be, no one else's

Leadership is a funny move to make. The general path is you work harder and better than everyone around you, get to be an expert at the thing that you do, then move into a role to manage everyone doing that thing. The funny part is that managing everyone doing that thing is maybe 10-20% of the thing you've just become an expert on, and the rest is doing what you have no idea how to do yet... manage people.

Great companies will provide training to help you take on that new role, but the truth is that most of them won't provide that training. While it's nice if a company does do it, if you're determined to become a strong leader and especially if you're determined to get into the executive suite, the first thing you need to start doing is stop waiting for anyone else to give you what you need. Just go get it. Go do it.

I've always said to aspiring leaders that if they truly are the executive type of person, they will get it... regardless of the owner/CEO of wherever they are now. The people that get that role are motivated, determined, go-getter types that aren't depending on anyone else to give them what they need.

How do I make myself the person I need to be to take that executive role?

I'm going to leave a list of book suggestions at the bottom of this article that I think you should read. Changing your fundamental perspective on money, business, people, and growth are core components to become the person you need to be.

Aside from that, there's a complete emotional rework you need to go through. The books will help you do that, but you also need to take initiative in how you view things in the business. You can start acting like an exec before you have the title. Specifically:

  1. Remove your tendencies to be an individual contributor
    1. Check out my blog on this topic here
  2. Start from the result and work backwards
    1. In short, you need to find the real problems– the things holding the business back from being more profitable and ATTACK them. This is much different from the individual/manager perspective of "the biggest thing on fire in front of my face."
  3. Have ROI top of mind in every decision
    1. It's not just the cost of the thing you want to do, it's long-term costs, impact, adoption, support etc.
  4. Have a long-term mindset
    1. Think in years, not weeks/months
  5. Change your perspective to purely results
    1. Someone working 80 hours a week, not getting as much done as someone else working 20 hours a week is wasting 60hrs of yours and their own time. Working long hours does not equal a good employee. Showing up early does not equal a good employee. Education and experience does not equal a good employee. They all can mean a good employee, but that's to be seen... results over everything.

Invest in yourself

I've at all times had some form of coach, mentor, or community to help push me forward into the things that I wanted to be. The best investment you can make is in yourself. Find someone that has what you want and pay them for their time to guide you there.

Suffer for knowledge, or buy it. I prefer to buy it.

💡
I have a mentorship program for leaders in all stages. If that's something that would be helpful to you or your business, grab me on calendly.

How do you know when you're "ready"?

I don't know that you'll ever "know." At some point in what you do, if you're truly a strong leader, you start to identify things that are broken or that should at least be much better. You don't just notice them, and you don't even just fix them, but you evaluate them. You start to realize the importance of a healthy pause before implementation. So often what "felt" like the right things to change or do were just... feelings, not reality. If you read that and shrug your shoulders like "yeah easy"– there is more to it.

You start to realize the importance not just of the requirement, but of the labor to implement it, the labor to support it, the complexity to support it which then dictates the level of skill you need on your support team to keep it going. The true cost of your decisions are far reaching, and I'm not sure if there's a way to really understand or see that until you just mess it up a ton of times.

Most importantly, there's a marked difference between "being the best at what you do" and "business acumen", and the marriage between those two is what starts to form you as a true executive leader.

I always like to use the example that once people find something they love doing like being a photographer they start a photography business so now they spend the majority of their time doing sales, accounting, scheduling, customer relationships, and finally, photography. They love it so much they start a business to do it as little of what they love as possible.

Running the business of the thing you love is not the same as doing what you love and what you're good at. You'll be bad at running the business because you haven't done the reps. You won't just acquire that business acumen by doing exactly what you've been doing even harder... there's a ton of self-improvement and self-development that is not the responsibility of the company or boss you work for.

So, you need to study your ass off. Read business books, leadership books, listen to podcasts, and become obsessed with profit and growth as the #1 driver. Those are the results you're after, and all of the other stuff is just the given industry you're in, and that can be a tough realization and even feel like a cold response/perspective on the business or thing that you love... but what is the goal? To just do the things you love (that's fine), or to grow a profitable business? You don't really get to do both in equal effort.

My journey

It's hard to explain the tiny pieces of experience that slowly teach you to read a P&L like a treasure map, spot broken structures like plot holes in a shitty movie, and hear employee or delivery issues like a tornado siren (I live in Oklahoma). To be honest, I don't know which things I read or learned that did all of that, but I do know that at some point, I became obsessed with running businesses successfully, and my time spent became aligned to my obsession.

That obsession looked like reading and studying instead of TV, movies, games, or anything else. My new hobbies became getting better at what I said I wanted to do– be a strong, competent, knowledgeable, wise leader. Turns out if you learn to love what it takes to be what you want to be, you'll become it.

I started as a tier 1 service desk engineer at a company of 5 people and ended at that same company as the CTO over 75 employees, and now I'm a Fractional CTO to businesses all over the world. This is not a flex, but just a point of reference for anyone reading that this is me recounting how I did it... It works, but no one is going to do it for you. It's just hard work.

Leadership is hard.

What is one thing you could solve in your business today that you've neglected because you're "too busy" and not an exec yet?

You can put all of this to work in real life right now. Choose something in the business you work at that you know would make you more profitable, more efficient, better to customers... pick one. Find a thing if you don't know what it is. Start working from this perspective now to get your reps in. You don't need a title to change who you are.

Also, please read this blog post I wrote about understanding the importance of leverage. It's a mindset shift you'll need to make.

Disclaimer

I know there's other aspects like the political game of rising through the ranks of a business. This is a real thing, but I hate it, and I don't really want to participate in advocacy of teaching others how to do it.

The one thing in this vein that I will say is valid, is when you get wins... take them. Advertise them. Make sure boss man knows it was your initiative. Even more importantly though, highlight the people that did the work– make it more about them than you, but don't lose the credit for the role your leadership played to make it happen. Genuinely, owners/CEOs can't know (most of the time) if you don't tell them... there's a lot going on in a business.

Then, if you're going to take credit for the wins, then you need to take credit for the losses, too. Taking full ownership of your failures along with the successes starts to paint you as trustworthy executive level material.

Books I've read along the way that genuinely helped

Talk the author, Matthew Weir

Wrap up

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