Kevin was crushing it at work. Strong quarterly reviews, solid project delivery, great team feedback. But he kept getting vague comments from his 54-year-old manager Richard about "executive presence" and "professional image."
He had no idea what that meant until a colleague mentioned it over drinks: "Dude, Richard told me your LinkedIn looks too casual. He thinks you don't understand business culture."
Kevin checked his profile. His photo was a decent selfie from a coffee shop – good lighting, natural smile, hoodie. To him, it looked authentic. To Richard, it looked like someone who didn't get how the professional world works.
The Generational Divide Nobody Mentions
Here's the thing: GenX and Boomer managers still run most companies. They're the VPs, the executives, the people making decisions about who moves up. And they grew up in a completely different world.
When Richard started his career in the 1990s, professional headshots meant booking a photographer, wearing a suit, sitting for formal portraits. Your photo went in company directories and business cards. It was serious.
To that generation, your headshot isn't just a photo. It's a test of whether you understand professional norms. A casual selfie reads as "doesn't get it" – even if you're great at your job.
Research from the University of Minnesota shows that older generations place significantly more emphasis on attitudes regarding respect and authority, and have different perspectives on what constitutes professional appearance in the workplace. This isn't just preference – it's deeply ingrained in how they evaluate career readiness.
What They're Really Looking At
I've talked to hundreds of professionals navigating this exact situation. What older managers are actually evaluating when they see your LinkedIn, Slack, or company directory photo:
- Can I put this person in front of clients?
- Would they represent us well to the board?
- Do they understand senior-level expectations?
It's not about looking old or corporate. It's about looking like you take your career seriously enough to invest in how you present yourself.
Amanda, a 31-year-old consultant, got feedback that she "looked like an intern" in all her photos. She was using the same casual selfie across LinkedIn and the company website. Once she updated to more polished headshots, her manager's tone shifted over the next few months. She eventually made partner, though it took time and consistent work.
The Professional Presence Code
When older managers say "executive presence" or "professional image," they're often talking about your headshot without saying it directly. It's corporate speak for: you need to look the part.
This creates a weird dynamic. You're told to be authentic, but there's an invisible dress code that extends to your digital presence. GenX and Boomer managers grew up with explicit rules about professional presentation. Those rules still exist in their minds.
Research on generational workplace differences shows that older generations often appreciate a hierarchical structure and clear professional standards, while younger generations value a more collaborative and informal approach. Neither is wrong – they're just different frameworks for evaluating professionalism.
James, a 29-year-old financial analyst, kept hearing he needed to "look more established." He had no idea what that meant until he compared his casual LinkedIn photo to the formal headshots of senior partners. Once he updated his photo to match that standard, the vague feedback stopped.
Why This Actually Matters
You might think this is just outdated bias. And sure, there's some of that. But the practical reality is: these people are making decisions about your career.
They're not just thinking about performance metrics when considering advancement. They're imagining you in client meetings, at industry events, in strategy sessions. Your visual presentation becomes a mental shortcut for whether you can handle those responsibilities.
This plays out subtly. Not getting invited to certain projects. Hearing about "executive presence" without specifics. Watching someone else get opportunities you're equally qualified for. Often it's not about capability – it's about whether senior leadership can picture you in those roles.
What Actually Works
After working with professionals dealing with this dynamic, certain patterns emerge in what satisfies older managers' expectations:
Direct eye contact. Older professionals read this as confidence. Looking away from the camera can read as unprofessional to that generation.
Clean backgrounds. Busy or casual backgrounds signal lack of seriousness to managers from traditional corporate environments.
Professional attire matching your industry. You don't need a suit if you work in tech, but dress for the level you want, not where you are.
Consistency across LinkedIn, Slack, Zoom. Different photos on each platform reads as lack of attention to detail.
Current photos. Obviously outdated photos suggest you're not keeping up with professional standards.
If you're serious about updating your professional presence, services like ProfileMagic can help you get polished headshots without the hassle and cost of traditional photography – which matters when you need consistency across multiple platforms.
Playing the Long Game
Kevin eventually figured it out. He updated his LinkedIn, Slack, and company profiles with more professional headshots. Nothing dramatic – just more polished. Over the next several months, Richard's vague feedback stopped.
"Richard mentioned something about how I'd 'developed better professional awareness,'" Kevin said. "I realized he was literally talking about my photos."
Is this fair? Probably not. Should your work speak for itself? In an ideal world, yes. But we're operating in one where the people approving advancement grew up with completely different professional norms.
The managers making these decisions won't be around forever. But they're here now, making calls about who moves up. You can spend energy being frustrated about it, or spend an hour updating your headshots and remove that barrier.
Your 55-year-old boss is judging your headshot. You might as well make sure they like what they see.