If you’ve been asked to organize headshots for your team, congratulations — you just inherited a project that touches scheduling, budgets, wardrobe opinions, and at least one person who would rather do literally anything else.

It doesn’t have to be chaotic. Most of the stress comes from not knowing the timeline or what to communicate to your team. Here’s how to plan it so everything runs smoothly.

Start 6–8 Weeks Out

The biggest mistake is waiting too long. Booking a photographer last minute limits your options, and rushing the internal communication means half your team shows up in wrinkled polos wondering what’s happening.

Six to eight weeks gives you time to get a headcount, compare photographers, and send proper wardrobe guidance — without anyone feeling ambushed.

Here’s the rough timeline:

  • 6–8 weeks out: Determine headcount, set budget, research photographers
  • 4–5 weeks out: Book photographer, confirm date and location, send team announcement
  • 2–3 weeks out: Send wardrobe guidelines, reserve the room, confirm headcount
  • 1 week out: Send final reminder, prep the space (clear clutter, check outlets, stage a mirror and lint roller)
  • Day of: Greet photographer, keep people on schedule

Budget by the Session, Not the Head

Most photographers price group sessions as a flat rate — a two-hour block for up to 10 people, a half-day for up to 25, a full day for larger teams. This is almost always more cost-effective than booking everyone individually.

Ask about what’s included: How many retouched images per person? What’s the turnaround? Do you own the usage rights?

The Question I Get Most: What Should We Wear?

People will ask what to wear. The answer is simpler than they think: solid colors, no loud patterns, and whatever makes them feel confident. A good photographer sends wardrobe guidelines in advance — and shows up with a lint roller, steamer, and mirror just in case.

The key is communicating early. Nobody likes finding out about headshot day the morning of.

The Room Matters Less Than You Think

You don’t need a studio. A conference room with decent ceiling height and a couple of power outlets is plenty. Your photographer brings their own lighting and backdrop — it covers whatever wall is there, so you don’t need to clear anything or find a perfect background.

What helps: let them see the space ahead of time. A quick photo or walkthrough saves setup time on session day.

After the Session

Delivery timelines vary, but two to three weeks is standard for a group of 10–20 people. Once you have the final retouched images, distribute them to the team with a reminder to update LinkedIn and your company website.

Then put it on the calendar to do again next year — or whenever new people join.

Want the full playbook? I put together a free Corporate Headshot Planning Guide with a printable checklist, email templates you can send your team, and a detailed wardrobe guide. Download it here →

Isolde Baylor photographs corporate teams on location across Philadelphia, the Main Line, and King of Prussia. 171+ five-star Google reviews. See how corporate headshots work → I come to your office with everything needed for studio-quality results — so your team never has to leave the building.