The Delicate Art of Telling Someone They Need New Headshots

Listen, we need to talk.

As a headshot photographer in Los Angeles, I’ve seen it all. The LinkedIn profiles that make you wonder if someone’s headshot (I mean mugshot) looks like they got caught by the police driving after having one too many drinks. The corporate websites where half the team looks like they’re about to sneeze, and the other half appears to be staring directly into the sun.

But here’s the thing: telling someone their headshot needs an intervention is like telling them their baby is ugly. Except the baby is their professional reputation, and it’s been ugly for approximately seven years.

The Five Stages of Headshot Grief

Before we dive into the delicate art of diplomatic photography criticism, let’s acknowledge what we’re all thinking when we see that headshot:

  • Denial: “Maybe it’s just the lighting on my screen?”
  • Anger: “Who told them this was a good headshot?!”
  • Bargaining: “Perhaps if I squint really hard…”
  • Depression: “This person will never get hired.”
  • Acceptance: “Someone needs to stage an intervention.”
  • The Gentle Art of Headshot Honesty

    Now that we’ve processed our feelings, here are some time-tested approaches to broaching this delicate subject:

    The Diplomatic Route

    “Your headshot has such a… vintage feel to it!”

    This works especially well when their photo genuinely looks like it was taken in 1987. You’re not lying—technically, MySpace-era photography is vintage now. You’re just being… creatively truthful.

    The Caring Friend Approach

    “You look so much better in person than in that photo!”

    This is actually a compliment wrapped in concern. You’re telling them they’re attractive while gently suggesting their photo is doing them zero favors. It’s like a backhanded compliment, but in reverse—a front-handed criticism?

    The Wingman Strategy

    “I know this amazing photographer who takes really great headshots!”

    Subtle. Professional. Gets the job done without directly insulting their current situation. Plus, if that photographer happens to be me, well, what a coincidence! (Narrator: It was not a coincidence.)

    The Tech Excuse

    “Is that from your flip phone era?”

    Perfect for those headshots that look like they were captured with a potato during an earthquake. You’re blaming technology, not them. Everyone wins! (Except their current professional image.)

    The Nuclear Option

    “Your LinkedIn photo looks like 💩, my friend.”

    Reserved only for your closest friends or people with an excellent sense of humor. Use sparingly, and maybe have a good photographer’s business card ready to hand over immediately afterward. Like a palate cleanser, but for professional dignity.

    Why This Matters (Beyond My Business Goals)

    Look, I could tell you that a great headshot can be the difference between “Who’s that?” and “We need to meet them,” and I’d be absolutely right. But let’s be real here—sometimes it’s the difference between getting that interview and having your resume used as a coffee coaster.

    In our swipe-right, scroll-fast, attention-span-of-a-goldfish world, you have approximately 0.3 seconds to make a first impression online. Your headshot is often the first thing people see, whether it’s on LinkedIn, your company website, or that dating app you swore you deleted but somehow still have notifications for.

    The Great Headshot Intervention

    Here’s what I propose: Let’s normalize caring about each other’s professional representation. If you see a friend, colleague, or family member sporting a headshot that looks like it was taken during a particularly rough flu season, speak up!

    Not in a mean way—in a “I care about your success” way. In an “I believe you deserve better than looking like you’re being held hostage in your own LinkedIn profile” way.

    The Bottom Line

    Your headshot should make people think, “I need to know this person,” not “I need to check if this person is okay.” It should convey confidence, approachability, and professionalism—not “taken five minutes before a root canal.”

    So whether you’re the colleague brave enough to stage the intervention or the person who just realized they might need one, remember: we’re all in this together. And if you happen to be in Los Angeles and need someone to capture your best professional self, well… I know a guy.

    P.S. - If you’re reading this and thinking, “Wait, is this about MY headshot?”… it might be time for that intervention.

    Ready to update your headshots? Call me at 323-493-2552 and let’s create a headshot that actually helps your career instead of haunting it. Your future self will thank you.

    I have offices in Santa Monica, Culver City and Venice, but will travel all over LA and Orange County for clients.

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