The Diary of a CPO - Chapter 4

January 30, 2024

Growth is uncomfortable. Growth is often painful. But if you want to do something great, it will never come easy. And if it does, it probably won’t last.

Photo by Jess Zoerb on Unsplash

Working in HR, I’ve been a part of vastly different organizations from big, publicly traded companies to the earliest startups. One thing I have noticed moving from big public to smaller organizations is the rate in which people want to be promoted to take on big leadership roles. There’s nothing wrong with being ambitious - we should all dream big. But there is something that will backfire when you chase dreams that are too big before you’re ready.

The culture of now 

Back when I worked at really big publicly traded companies, you really had to hone your skills to even get to a management level position, and once you got there, you were there for many years before you were even considered ready to move to the next Sr Manager position. Oftentimes, the leaders above you were highly seasoned and had a track record of success. The executives that I looked up to in those years went on to become CEOs in their own right.

In those early years, I also got a glimpse of the work they took on and it was really, really stressful. If you made a mistake, you made a million dollar mistake and you were  ultimately in the hot seat as the person accountable for it. I remember the new CEO speaking at a Town Hall one day. He said that when he was younger, he didn’t want to become CEO of a company (his father was the Chairman and CEO at the time and he was being groomed for the top position). He really struggled with the high expectations that others had for him. But one thing that his mentor told him was that it was a privilege to be stressed. Even though he was ultimately going to take on the CEO role, he wasn’t born wanting it. But he also grew to understand that very few people would ever be in the privileged position he was in and so, he spent his whole life getting ready to be in the top spot. And it was never easy because you were always judged and everyone was looking at you all the time. You had nowhere to hide.

Photo by Israel Andrade on Unsplash

As I moved into fast-growth companies, I noticed something vastly different. Due to the fact that fast-growth companies are essentially growing so rapidly (often doubling revenue year over year), young employees were fast-tracked in their careers. I witnessed directors who were in their twenties and VPs who were barely 30 years old. Opportunities were plentiful and you no longer needed to be grey-haired to take on the top executive roles at these companies. This was a blessing and a curse at the same time. 

The blessing was that if you took on a role that was 2-3 levels above where you should normally be,  you were accelerating your career sometimes by decades. We are living in the culture of now where immediate gratification is like a drug. The curse was that you get what you ask for and the expectations of that senior level role doesn’t change just because you were offered it early in your career. Some people didn’t understand that and they paid the price for it.

Be careful what you wish for

To put things into perspective, if you are striving for title, salary and the acclaim to be “at the top,” you must also commit to the accountability, responsibility and the stress that comes with it. If you are a 30-year old VP/C level executive, you have signed up for the top job. You now have to deliver it. As a top level executive, you have no one else to go to above you who can guide you on your decisions or strategy plans. The only person above you is the CEO and that is not their job to do. Their job is to hire the best leaders around them who can guide them on the best decisions about their verticals - you are the hired expert. If you don’t know how to lead your team on the strategy and the plan, you need to figure it out. If you don’t have experience in how to achieve the plan, you need to learn (fast). There are high expectations in taking on the top spot and no one will feel sorry for you, even if you are struggling. The fact is, as the person at the very top, no one is coming to save you. You must save yourself.

Photo by Anthony Tran on Unsplash

Entitlement rarely wins the crowd

I remember interviewing a candidate for a VP level position. She had only been in a director position for a year and she felt strongly that she was ready to take on the VP level role. The CEO and I tried to convince her that she had great potential but she wasn’t ready to take on the executive role quite yet. We offered her the Sr Director position with an opportunity to be groomed to get to where she ultimately wanted to go but she wasn’t having it. When asked how she would step into this executive level position and succeed, she confidently shared her expectations of what she wanted with her VP level position. She demanded entry into a company-paid leadership development program, a company-paid mentorship program and grooming from the CEO to ensure she was supported in her new executive position (she also demanded the top VP level salary for someone who had never been a VP before). When I asked why we wouldn’t just hire a seasoned executive instead, she was perplexed and felt strongly that this is what companies should do to support their hires. Anyone who believes in this mantra is wrong. You should have no expectation from your company to support your development into a role that you are not ready to succeed in. And if they do, that’s a bonus but not a requirement. We did not hire her (and she later came back offering to take the Sr Director role but that had long expired).

There are of course, certain exceptions where people skip multiple job levels and come out highly successful, but they are the exceptions. It’s not an easy road and if you are going to succeed, you must commit to the hard things.

So what makes these folks more successful than their counterparts? 

They carefully decide that this is what they want to do and they do whatever it takes to succeed. That doesn’t mean that they didn’t get there without some plain old luck (being at the right place, talking to the right person, at the right time), but what you do with that luck is up to you. It’s all about commitment to the task at hand. And that commitment doesn’t expire once you take on the role. In fact, you are now wholly committed to the accountability, the responsibility, the stress, the achievements, the failures and everything in between that comes with this top job. Not only that, you are now on the fast track to develop your leadership skills. You need to fill your personal gaps to ensure you fill this role as much as you possibly can, and that means you need to put in the effort every single day.

You must be a clear presenter and communicator because you’re going to do a lot of presentations in front of the company and the board. You must be a strong people leader because you will lead bigger teams and you must ensure they are engaged. You will need to recruit and hire the best, as well as performance manage your team. You must learn new ways of doing your job because it continues to evolve. You must deliver on bigger expectations because that’s what you got hired for and it doesn’t end, year over year. The ones who are successful doing the above are the ones that never stop working on themselves (a good dose of self awareness and high EQ helps you along your leadership journey). You must be successful in a challenging job that has high expectations while striving to be GREAT at what you do. You can’t be just good enough. You must be great because there are other people who can replace you at being great if you’re just good.

Not everyone wants to be in this highly competitive and often stressful role. But there are a lot of people that think they can do it and they underestimate how difficult it really is. Once the pressure starts, you can’t complain that it’s not fair or you aren’t prepared. That’s why it’s important that you really think about what you want and ensure you are ready to take on the challenge which includes the good, the bad and the ugly (because truthfully, there are more ugly days than good). It’s not as glamorous as people like to imagine.

For those of you who take big titles too early but you realize that you can’t take the pressure, you now have a big decision to make. Will you move on to another company and take on that big title again, even if you know you aren’t fully ready yet? Or will you take a step back and move into a role where you can learn more, develop your blind spots and work with a leader that can provide mentorship and guidance? The ego in you might tell you that you should keep moving up but only you will truly know if you’re ready to take that on again. Sometimes, it’s better to take a step back so that we can take that leap forward when the time is right.

Photo by Ferdinand Stöhr on Unsplash

The world is a big, scary place and there are so many directions we can go. My advice to anyone who is at a crossroads is to stop and think about what they truly want to do. What motivates you? What matters to you the most? What does success look like for you? What are you willing to sacrifice to get what you want?

There’s a reason why the most coveted jobs are so hard to get. You will earn a high compensation, lead a large team and showcase a big title, but if you can’t deliver, you will likely be replaced very quickly. There’s nothing unfair about that, it’s just reality, so just be careful what you wish for. Being great at what you do is hard, but if you’re willing to put in the work everyday and sacrifice to succeed, you will probably be highly successful.