I have enormous respect for the generations that came before me in the workforce.
Boomers built many of the companies and institutions that still define our economy, and Gen X—my generation, though I’m among the youngest of it—came of age during one of the most dramatic technological transitions in history.
It's usually me who seeks the advice of older professionals and there is rarely a week that goes by where I don't call my Dad, a Harvard MBA, for business advice. But this column seeks to give advice to older professionals in the workplace.
A lot of very smart, experienced professionals—people with decades of knowledge and judgment—are quietly terrified of their computers.
If you’re someone who still cares about having a career, that’s a problem worth fixing.
Part of this isn’t anyone’s fault. In fact, it’s a structural artifact of how companies used to operate.
Twenty-five years ago, large organizations were filled with assistants and secretaries. If you were a mid-level executive or salesperson, you often didn’t type your own documents, schedule your own meetings, or process your own paperwork. Someone else did.
In a sales department back then, placing an order meant filling out physical forms. It made perfect sense to have administrative staff handle the busywork.
But that world no longer exists.
Today, the secretary has been replaced by software. CRMs (customer relationship managers) handle orders and customer data. Online calendars schedule meetings. And in most cases, it actually takes more time to explain a task to someone else than it does to simply type it yourself.
I consider myself lucky because I came of age when keyboarding was no longer a class just for females. It sounds trivial, but it isn’t. In seventh grade, I learned to type without looking at the keyboard, a skill I still use every day. I’d happily hold my own in a speed-typing contest. That one class removed a barrier that stops many people from interacting comfortably with computers.
In my own company, I’ve been encouraging everyone to experiment with artificial intelligence tools. Recently a colleague told me they just need to “find the time to learn AI.” But here’s the reality: Time is being wasted by not learning it. This is because AI is the secretary. AI is the assistant. AI is the researcher. AI is often the fastest way to draft an email, summarize a document or answer a question.
You don’t need to become a programmer or a technologist. You just need to start using it for everyday tasks. And it's not perfect. This week, I got really annoyed with ChatGPT because it was failing at a task where it performed successfully in the past. So I tried Claude instead—something a keynote speaker at a recent conference recommended—and it handled the task immediately.
That’s another lesson: this space is evolving fast, and there are multiple tools. If one doesn’t work, try another.
I've recently used AI to help create ads for a couple of clients. Now, here's another important point. The ads it designed were far from complete. I then sent it to our Creative Director and she fixed it up. She took what was perhaps a C+ or B-, and she turned it into an A.
AI didn't remove my work or her work. But the point is that it made both of us more efficient.
Another huge time-waster in modern workplaces is password management. I’ve watched people really struggle with this, and lose 10 or 15 minutes because they can’t remember a password or because they’re juggling dozens of different login systems.
There’s a simple solution: use a password manager. The password manager doesn't simply remember your passwords. It actually fills in the blank for you so you don't even need to type it. I personally use Google Password Manager. That means I only really need to remember one password. Everything else is securely stored and automatically filled in. And the funny thing is that I don't even need to remember my Google password. On my phone, I can unlock it with my fingerprint. On my computer, Windows remembers the password for me.
For anyone who is concerned about security, you just need to add two-factor authentication. This is where you receive a quick text message code after entering your password, and you’ve dramatically increased your security while making your life easier. In this scenario, if a hacker stole your password, they still wouldn't be able to log into important sites without receiving the code that was texted to you.
Ultimately, the goal isn’t to memorize more passwords. The goal is to stop thinking about them entirely.
One final concept I encourage people to understand is something called “the cloud.”
At our company, every employee has a Microsoft 365 subscription. That means all documents can be saved in OneDrive. Think of OneDrive as a filing cabinet that lives on the internet instead of inside your computer. Your laptop isn’t the office. It’s just the doorway to the office.
If my computer burned in a fire tomorrow, I wouldn’t panic. I would walk into Staples or Best Buy, buy a new laptop, log in, and be back running the business within an hour.
In fact, I’ve lived through the evolution of this firsthand.
For years we ran our own physical server. At one point during COVID—when my staff started working remotely—I even kept a far-too expensive server in the basement of my house because cloud storage for large newspaper files was too costly only a few years ago.
But technology evolves quickly. Cloud storage has become far more affordable, and we’ve since moved our systems online.
Boomers and older Gen X professionals bring something incredibly valuable to the workplace: experience, judgment and perspective.
But those strengths become even more powerful when paired with a little technological curiosity. You don’t need to love computers. You just need to stop being afraid of them.
And ironically, the people who should be most concerned aren’t senior professionals—it’s entry-level workers. For decades, entry-level roles existed to handle the exact kinds of tasks that technology now performs instantly. That first rung on the ladder is getting smaller.
That’s a bigger conversation—and one worth its own column. But for those already established in their careers, the message is simpler.
At a recent conference hosted by the company behind our CRM, a keynote speaker put it plainly: the gap between organizations that embrace these efficiencies and those that don’t will determine who survives—and who doesn’t.
That’s not a future prediction. That’s already happening.
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