Your last team photo day went badly? 9 questions to ask before you book again

If your office had a bad photo day once, nobody wants to do it again.

Maybe the photos came back weeks late. Maybe half the team hated theirs, and nobody asked them first. Maybe a retake request went unanswered, so the team page still shows people who left.

You are not alone. When we read 283 Google reviews of photographers across five Prairie cities in October 2026, one Calgary office wrote that it had a really bad experience with headshots before, so the team was wary going in. An Edmonton client wrote that their photos didn’t look like the samples on the photographer’s website, and retakes were ignored until they left a bad review.

The photos themselves are rarely the whole problem. The process around them is.

Here are 9 questions to ask before you book anyone, with what a good answer sounds like. I have added my own answers too, so you can hold me to them.

1Can I see one complete job, not just your best photos?

Why ask: Every portfolio shows the 10 best photos from 10 different shoots. You need to know what a whole team looks like when it comes back.

A good answer: “Here is a full set from one team day.” Or a link to a client’s team page, with their permission.

My answer: Ask me and I will send a full team set, with the client’s permission. You can see examples on my corporate headshots page.

2Is your price on your website?

Why ask: A price you can see is a price you can compare. In September 2026, we checked six Regina corporate photographers. One showed a price.

A good answer: A clear price per person, with what is included, before you have to call.

My answer: Yes. $149 for a single headshot, $79 per person for teams of 8 or more, plus PST. I explain how it adds up in what corporate headshots cost in Regina.

3Does each person get to see and choose their photo?

Why ask: This is the question that matters most to your staff. A headshot goes on a public page, next to their name. An employee writing to Ask a Manager said they would rather have no photo than a bad one. (Ask a Manager, 2017)

A good answer: “Everyone gets their own gallery and picks their own.”

My answer: Yes. Everyone gets a private online gallery and picks their favourite.

4What happens if someone doesn't like their photo?

Why ask: It will happen. What matters is what comes next.

A good answer: A clear retake policy. Who pays, how fast, and how to ask.

My answer: If a shot isn’t right, I reshoot it free.

5When exactly will we have the edited files?

Why ask: “Soon” is not a date. Speed came up in about a fifth of the corporate reviews we read, so it clearly matters to buyers.

A good answer: A number of business days, in writing.

My answer: Proofs in 2 business days, final retouched photos in 3. Up to a week for bigger jobs. Same-day delivery is $99 extra if you are on a deadline.

6Do we get full-size files, and can staff use them on their own LinkedIn?

Why ask: This one causes a lot of quiet frustration. One employee wrote to Ask a Manager that their company headshot could only be used on LinkedIn and the company website, and they only got a small file. (Ask a Manager, 2015)

Under Canada’s Copyright Act, the photographer usually owns the copyright unless you agree otherwise. (Copyright Act, s. 32.2) So the usage rights depend on what you agree.

A good answer: Full-size files, and a plain sentence about where you can use them.

My answer: Corporate clients get full commercial use for the company. Files are sized for LinkedIn, web and print. Staff can use their own headshot on their personal LinkedIn.

7What happens if someone is away on the day?

Why ask: Someone is always sick, on holiday, or in a meeting that ran over.

A good answer: A catch-up session in the same setup, so the photos match.

My answer: I keep the backdrop, light and crop on file. A catch-up slot matches the rest.

8Can you match these photos for new hires next year?

Why ask: A team page goes out of date the day someone new joins. If the next photographer uses a different background, the page looks patchy.

A good answer: “Yes. I keep the setup on file.” Or “Send me your current headshots and I’ll match them.”

My answer: Yes. Send me two or three of your current headshots and I match the backdrop, light and crop.

9How long does each person take, and what do you need from us?

Why ask: This tells you how much of the day your staff will lose, and what you need to prepare.

A good answer: A number of minutes per person, and a short list: a room, a power outlet, a schedule.

My answer: About 5 to 7 minutes per person. I bring the backdrop and lights. You need a meeting room and a power outlet. A team of 20 is done in a morning. My team headshot day guide has a sample schedule.

Copy this email to send any photographer

Hi [name], we're looking to book team headshots for about [number] people at our office in [area] around [date]. Before we decide, could you let us know:

1. Your price per person, including tax and travel.
2. Whether each person sees and chooses their own photo.
3. What happens if someone doesn't like their photo.
4. When we'd receive final files.
5. File sizes, and whether staff can use their photo on their own LinkedIn.
6. How you'd handle people who are away on the day.
7. Whether you can match new hires later.
8. How long each person takes, and what you need from us.
9. A full set from a recent team job, if you can share one.

Thanks!

Comparing two quotes side by side

Once the answers come back, put them in a table like this. It makes the choice obvious.

Question	Photographer A	Photographer B
Price per person, all in
Who picks the photo
Retake policy
Delivery date
Usage rights
People who are away
New hires later
Time per person

If one column has gaps or "it depends" in every row, that tells you something.

Red flags to watch for

• No price anywhere, and no price on the first call. Fine for a custom event. A warning sign for a standard team day.
• "We'll pick the best one for you." Your staff should have a say.
• No delivery date. If they won't commit before you book, they won't after.
• Vague answers on usage. Ask again, in writing.
• Only one or two photos in their portfolio look like what you need. Ask for more.
• Slow replies before you have booked. It rarely gets faster after.

What a good photo day feels like for staff

When it goes well, your staff barely notice it happened. They walk in at their time, get told where to stand, laugh a bit, and are back at their desk in a few minutes. Two days later, they pick their photo.

If you are weighing up an AI headshot tool instead, I compare the two honestly in AI headshots or a photographer?

If your team was nervous last time, my guide on what helps, and what to wear is written for them.

If your last photo day went badly, tell me what went wrong when you get in touch. Late files, no choice of photo, retakes that never happened: whatever it was, I'll tell you plainly how I handle it, before you pay anything.

Frequently asked questions