May 5 2026 | By: Tracy Allard
A good headshot should do more than make you look nice. It should help you get where you’re trying to go.
That might sound a little dramatic for a photo, but it’s true. Your headshot is often your first introduction before you ever walk into the room, answer the Zoom call, submit the proposal, or shake someone’s hand. It is already speaking for you. The question is, what is it saying?
A lot of people assume headshots are mostly about choosing a backdrop, deciding whether to smile with teeth, and hoping for one image they don’t hate. And yes, those details matter. But they are not the most important part.
The most important part is understanding what the image needs to do for you.
A photographer who is thinking strategically should be asking smart, useful questions before they ever pick up the camera. Things like:
What industry are you in?
Are you using this for LinkedIn, your company website, speaking engagements, press features, or something else?
Do you need to match the look of an existing team or company brand?
Are you building a personal brand that needs to stand apart from your current employer?
Are you trying to look more polished, more approachable, more authoritative, more current, or perhaps a little bit of all four?
Because those answers change the image, quite a bit, actually.
Someone in finance may need a very different look than someone in wellness, law, real estate, tech, or media. A corporate team headshot may need to feel consistent and polished. A business owner or speaker may need more variety, more personality, and images that work across multiple platforms. Someone submitting for podcasts, publications, or conference bios may need horizontal crops with extra room for text. Someone updating LinkedIn after ten years probably needs a very different image than someone actively pitching themselves as an expert.
That’s not overthinking it. That’s using your headshot on purpose.
And then there’s the bigger question that often gets skipped:
Where are you professionally right now, and where are you trying to go next?
If you are job hunting, your headshot may need to help position you for a stronger next step, not just reflect where you’ve been. If you are hoping for a promotion, stepping into leadership, speaking publicly, writing articles, launching a business, or shifting into a more visible role, your image should support that move.
It should look like you belong in the room you want to be in.
That doesn’t mean you need to look stiff, overly serious, or like you borrowed someone else’s personality for the day. It means the choices made during your session with posing and expression should be intentional and aligned with your goals.
A good photographer should be helping you think through all of it based on how the images will actually be used, not just what sounds flattering in theory. Maybe your role calls for something clean and polished. Maybe it needs to feel warm and trustworthy. Maybe you need one image that says “confident executive” and another that feels a little more approachable and conversational for speaking or content creation.
That’s where a thoughtful headshot session becomes really valuable.
Because a strong headshot is not just about looking like yourself on a good day. It is about looking like the version of yourself your audience, employer, clients, or industry needs to trust.
If your photographer is only talking about backgrounds, lighting, and whether you want to smile, they may be giving you a perfectly decent photo. But there’s a good chance they are not giving you a useful one, a useful headshot should work for you.
It should help you look credible, current, capable, and aligned with the kind of opportunities you want more of. It should feel like you, but the most effective version of you for the audience you are trying to reach.
That takes more than a camera and a clean backdrop, it takes good questions and that's where my 30-year international sales management career delivers value.
So if you’re booking a headshot session soon, pay attention to what your photographer asks before the session even begins.
Because the right questions usually lead to the right image, and the right image can do a lot more heavy lifting than people think.
Tracy Allard of Penny Whistle Photography is a Master of Photography, Photographic Craftsman, and Certified Professional Photographer, holding the M.Photog., Cr.Photog., and CPP degrees from the Professional Photographers of America (PPA), designations held by fewer than 2,000 photographers nationwide and a hallmark of consistency, technical skill, artistry and professionalism.
Penny Whistle specializes in both on-location and studio photography providing pet, family, and high school senior portraits as well as corporate headshots and commercial photography services in her studio located in historic downtown Carrollton as well as on location in Coppell, Grapevine, Southlake, Flower Mound and surrounding communities in Dallas – Fort Worth, Texas.