Open Letter to the Gen Z CEO from Gen X Exec

Hi. We haven’t met yet, but before we do, I wanted to get this discussion out of the way. (I’m a product guy, which makes me a planner by nature.)

It’s always a bit odd to me that when I walk in the door, you look a little, let’s just say, taken aback. Despite your looking for someone with “senior-level experience,” I know you’re going to be surprised when someone with senior-level looks (or at least middle-aged ones) walks in the door with his hand extended.

Let’s establish here and now that I’m not bothered by it. I’m confident that I probably would have done the same thing “when I was your age” (and I promise I won’t repeat those words). If you’re ready to embrace workplace diversity, which should include age, then, of course, I am, too.

So, before I make a case for myself — and, yes, my age — first, let’s talk about why so many of you are so much younger than me.

Starting a Company Is a Young Person’s Sport

I founded a company when I was in my mid-30s, giving up a high-paying job to fulfill my entrepreneurial dream. During a fundraising meeting, a curious Silicon Valley VC friend asked me, “Why do you want to give up a high-flying career to become an entrepreneur with no paycheck for a few years when you have a mortgage, and a young family?” I realized that he had the best intentions for me, but what he meant was “Entrepreneurship is for the young.” In Silicon Valley terms, by the time I was ready to start a company, I was over the hill.

From a perception standpoint, I get it. Starting a company is very, very hard work. It’s physically, emotionally, and psychologically grueling. It is also a simultaneously humbling and exhilarating experience.

When you are young with fewer responsibilities, starting a company is an excellent learning opportunity with less of a financial downside. If the startup fails (and most do), 20-something founders can build on that learning experience. They still have a choice and the time to try again or move on to less-risky, high-paying career opportunities. If the startup succeeds, you can continue your entrepreneurial journey with even more financial upside.

Founders develop great relationships during this entrepreneurial journey, mostly with people who are like-minded, believe in them, and can help them navigate the tough times. These relationships can last a lifetime but tend to lack diversity.

When the startups reach the growth stage, founders need more seasoned and diversified leadership outside their limited relationship circles. This is the time for generational, gender, racial, and skillset diversification. That is the time for founders to trust people who are from a range of backgrounds, including age.

And that’s why you hired a recruiter, asked some of your VC contacts for a referral, or posted an ad that led to me sitting in front of you to talk about what I can bring to the table.

What Gen X Leadership Brings to the Table

Young founders tend to have the same set of concerns regarding more experienced leaders.

• Can we afford them?
• Are they hands-on enough?
• Is this a good culture fit?
• Will they feel comfortable reporting to a younger manager?

A younger person may initially make you (and some of the team) feel like a better cultural fit. But young founding CEOs have to be more forward-looking than that, especially when it comes to what’s best for the company itself. Discomfort is part of the job, and so is learning how to deal with people who have backgrounds different from yours.

It’s my humble opinion that founders who are overly concerned about age differences are missing a great opportunity. Age doesn’t always equal experience, but at least in my particular situation, it does. That experience equals a wealth of knowledge that you may not know you need, but trust me, you do.

During your growth runway, the benefits of having seasoned leadership will greatly outweigh hiring someone just because they happened to have been born around the same time you were.

Experienced leaders with a comprehensive job history have seen our fair share of bad decisions, and failures. We’re that much more likely to steer you toward the right ones. We have an excellent network that you can tap into as needed, and a diverse skill set that you’ll continue to pull from as the company grows and evolves.

If there’s anything all professionals get better at with time, it’s communication. Experienced leadership can get the best out of the people you have, as well as lure in more emotionally intelligent, creative, diverse talent.

Also, “experienced” doesn’t mean less entrepreneurial. Entrepreneurship is a mindset that is needed not just for younger companies but also for more established companies. With Gen Z leaders having founded companies in the recent past or worked at companies with increasingly younger leadership, you may need the exposure and stability of a, let’s just call me a more “seasoned” executive.

Growth phases are exciting, but they can also be turbulent and disorienting for any leader. The best thing for your young company maybe your vision and energy combined with my wisdom and experience.

The only thing I ask is that you consider the benefits of a diverse workplace and the merits of candidates like me and that you hire now with an eye toward the future.

I can help bring not just experience but stability, insights, and, yes, wisdom. I genuinely look forward to helping you build a sustainable, profitable, and successful business.

Yours,

Baker