What to Do When You Know More Than Your Boss

We’ve all been there. You're sitting in a meeting, watching your boss struggle to convert a Word document into a PDF, and you’re thinking, Really? ?? With the rise of technology, this scenario has become all too common - and not just for early-career professionals. As an executive search partner, I’ve seen it play out at all levels, from junior associates to seasoned executives. It’s also one of the key reasons high-performing leaders start looking for new opportunities. But what should you do when you know more than your boss?

Step 1: Don’t Be Smug - Be Strategic

Let’s get one thing straight: nobody likes a know-it-all. Your technical savvy might be miles ahead, but how you manage that dynamic can make or break your career. Being condescending or showing frustration might get a few laughs, but it won’t win you any allies, least of all your boss. Instead, focus on how you can add value without making it a competition.

Think about it this way: your boss is likely in their position because they have experience, leadership skills, and a broader strategic vision - things you could learn from. Instead of focusing on the areas where you outshine them, think about how your skills can complement theirs.

Step 2: Use Your Skills to Empower, Not Embarrass

Now, I’m not suggesting you hold back your talents, but there’s a right way to introduce new skills or ideas. Instead of jumping in with “I can do this better,” try “Would you like me to show you a quicker way to do this?” or “Here’s a tool that might make things easier.”

Believe it or not, many leaders want to learn from their teams, but they need a gentle nudge rather than a public tutorial. Frame it as collaboration, not competition. That way, your boss feels empowered, and you’re seen as someone who uplifts the team.

Step 3: Stay Humble, But Be Prepared for the Exit

In the executive world, the dynamic of knowing more than your boss can be a little trickier. I’ve had several C-level candidates who came to me because they felt they’d outgrown their current roles—not just in terms of skill but vision. They didn’t want to keep fixing tactical issues when they were ready to shape strategy.

In fact, a 2023 LinkedIn Talent Trends report found that one of the top reasons executives leave their roles is stagnation - feeling like their expertise has surpassed their leader’s, and there’s no room for growth. It’s a common issue I see in executive search, where leaders feel they’re running the company in all but title, yet there’s no opportunity for progression.

So, while it’s great to be humble and collaborative, sometimes the reality is that you have outgrown the role. If that’s the case, you may need to start looking ahead to your next move.

Step 4: The Technology Gap Is Real (and Growing)

Let’s talk about the elephant in the room - technology. We’ve all seen the memes about bosses who can’t convert a Word doc into a PDF, and while that’s funny, it highlights a deeper issue. The digital age has created a generational gap in skills, and in some cases, younger or more tech-savvy employees find themselves miles ahead of their leaders when it comes to new technologies.

This is a trend I see more now than I did ten years ago. Leaders in senior positions aren’t always up to speed with the latest tools and digital practices. And while it’s tempting to roll your eyes, this gap actually represents a huge opportunity for you. Offering to help your boss get comfortable with the tools they need can set you apart as a trusted advisor - not just within your team but within the organisation.

Step 5: Leverage It for Career Growth

Here’s where the rubber meets the road: knowing more than your boss can either be a frustration or an opportunity. The choice is yours. If you handle the dynamic well - offering support, demonstrating leadership, and building trust - you could position yourself for a promotion or bigger opportunities.

On the flip side, if you’re constantly bumping up against limits because your boss can’t keep up, it might be time to explore your next move. Many of the executives I’ve worked with came to me after realizing their full potential wasn’t being tapped. They weren’t looking to overthrow their current leadership—they were ready to lead themselves, at the next level.

Step 6: Early Career? Same Story

This isn’t just an executive issue. Even early-career professionals are finding themselves more tech-savvy than their bosses. That’s where the memes come in - endless jokes about managers who struggle with basic tech while their team members run circles around them in Slack, Excel, or project management tools.

My advice? Use this as an opportunity to demonstrate leadership, even at a junior level. Offer to streamline processes or introduce new tools that can make the whole team more efficient. If you can show that you’re not just a tech wizard but a team player with an eye for improvement, you’ll stand out—and quickly move up.

Step 7: Know When It’s Time to Move On

Ultimately, if you’ve done all of the above and still feel like you’re spinning your wheels, it may be time to consider your next career step. It’s not uncommon for leaders to feel frustrated when their skills or vision outgrow their role. And it’s totally okay to admit that the fit just isn’t there anymore.

In fact, this realisation is often the catalyst for the next phase of your career. In my experience as an executive search partner, I’ve seen many talented professionals thrive when they move on to a role that finally matches their level of expertise, often at a higher job grade.

So, what do you do when you know more than your boss? Stay strategic, stay humble, and know when to level up. Whether it’s collaborating to fill gaps or recognising it’s time to make your move, knowing more than your boss can be an advantage...if you play it right. ??