Boston, MA Headshot Photography Fail

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A few months ago, I was approached by someone from a Boston-based medical-tech start up, asking me to help update their CEO’s headshot. The idea was that the marketing team wanted to showcase just how “bad ass” their CEO was and wanted their brand to have a youthful, dynamic feel.

We went back and forth over details, agreed in principle, and set up a phone call with their CEO to schedule the session and their marketing rep sent me a copy of their branding-guidelines. The guidelines listed specific color combinations (particularly blues), displayed a retro 80s neon vaporwave vibe, and generally aspired to embody a certain hip “cool” factor.

It all looked very rave-themed.

Much of my photography is centered on creating high energy, dynamic, and colorful images of people and events with saturated colors, strong contrast, and expressions that full of life.

This all sounds like a good fit, right? Because they made a lot of sense to me as a potential client, I was excited to proceed so the very first thing that I did was ask, “Do you have your own contracts/paperwork or would you be okay with mine?” It’s always good to know where things stand right away.

Their reply was pretty encouraging.

“For this kind of contract – it’ll be best to review yours! Haven’t contracted with photographers much yet :)”

Great! So, I sent them a contract after scheduling the on-location headshot session for their office in Boston and let them know that I’d be looking forward to their initial payment and I’d be ready to go on the day we agreed to. Easy peasy.

A day or two later, I received their first bit of push back.

“Legal got back to me and was hoping you could use our 1099 contract with the model release – can you have a look at the attachement (sic) and let me know what you think?”

Red Flag #1

Why is it a red-flag? They had earlier wanted to see my contract first then immediately asked if I’d consider theirs, instead.

Remember, “red flags” are not necessarily deal breakers. They’re just areas of incongruity for you to pay closer attention to. Besides, I was willing to look it over and consider it in the first place, so I asked them to send it over for me to review.

There are very specific things that I look for in someone else’s contract and, after reading theirs, it raised more red flags because I immediately felt that they might not value photographers (or any other vendors, really). I felt that it was generic and seemed to be expected to cover any and all of their 1099 contractors.

Seriously, why would a photographer, with copyright issues to consider, need the same contract as an SEO?

Without getting too deep into legal drivel, the following red flags stood out to me immediately:

  1. Section 4, Relationship of Parties: It was not specified if this was “work-for-hire” relationship or not? This is a huge copyright red-flag.
  2. Section 12, Injuries: Did they mean any and all injuries? Physical, mental, emotional, etc? There was also a clause requesting to be added to my insurance “naming the Recipient (them) as an additional insured party.” Were asking to be added as “additional named insured” (based on “naming the Recipient”) or were they asking to be added as “additional insured” instead? Not a major red flag but I felt it was worth asking because it was phrased poorly.
  3. Section 13, Indemnification: Basically, it was very one-sided and very broad about who takes on risk and how much. According to their contract? Me and all. Another enormous red flag.

After reading it through and taking notes, I offered to use theirs if they were willing to address the concerns I had. I also let them know that I was willing to add specific clauses that addressed my concerns as an addendum to theirs, especially since much of our respective contracts happen to be full of standard boiler-plate bullshit.

Of course, as an obvious option, they were always free to use mine since it already covered those specific issues.

Their reply was breathtaking.

“While I can appreciate the level of detail you have put into your contract, and the review of ours, our Legal team typically works with health insurance companies and physical therapists not photographers. In the past, the photographers we have worked with on small projects have executed very simple contracts and with this new small exercise our Legal team does not want to overly complicate such a simple exercise as a corporate headshot session. I am waiting on approval to just use your contract since going back with redlines is something that my team will not accept due to their workload and this supposedly being a small and simple relationship. Will get back to you by EOD Monday! I am imagining we should be able to use your contract but need to get signoff.”

Huge Collection of Red Flags

How many red flags do you see?

Sometimes an encouraging thing can become an instant red-flag because there’s now an incongruity with things you’re getting told. Before telling me about the other photographers they’ve worked with “in the past” being willing to work with “simple contracts” and “small projects” (and, to me, it shows), they told me they haven’t “contracted with photographers much yet,” remember?

Because I certainly remembered.

Anyway, and unsurprisingly, their rejection email followed shortly afterwards.

“Hey Adrian! 

Unfortunately the team has asked me to engage with a photographer that will not take such legal bandwidth due to the stage we are at and our internal review processes. Apologies for the late change, hopefully you can find another project to fill the time on Wednesday!” 

Rejection Email

Not gonna lie, I laughed at “legal bandwidth.”

Photography client rejections are par for the course and they never sent an initial payment. No big deal. No big loss.

Thankfully, our interaction gave me some very valuable insights to my own marketing efforts (which I may go into more depth another time), so all was not lost. SEO works and my portfolio stood out enough among a sea of other cookie-cutter photographers to get their attention. That’s all that matters to me, when all’s said and done.

Anyway, for giggles I decided to check up on their website to see what changes, if any, were made to their headshots since their rejection back in October.

This is what I found, as of Friday, Feb 2, 2024:


There’s a lot to unpack here so I’ll just point out things that I noticed right away.

For starters there’s the overall color palette. It’s not consistent at all. Their headshots may not be following their own branding guidelines but at least the brick-wall background looks passable. I’m also pretty confident that jaundice-yellow wasn’t part of their brand guidelines but at least it’s a complimentary color. What else? Tilted buildings outside the office. Dark eye shadows. Blown highlights. Uncomfortable expressions.

There’s more but I’m sure you get the idea.

I won’t bother to criticize their actual updated website because that’s an entirely different set of issues that are sticking out to me.

So, what’s the point to all of this?

I suppose that it would be in poor taste for me to criticize a prospective client after negotiations didn’t pan out and, in most cases, it isn’t something I typically do. I felt, however, that there was something of value to be extracted from this exchange for other photographers who will end up experiencing a similar back-and-forth. We all do.

For starters, photographer to photographer, I can assure you that we will all collect a lot of client-hell stories. It’s inevitable.

Secondly, you must be willing to learn something from every interaction. Have your own contract ready to use and understand what the sections, terms, and clauses mean! Look out for red-flags that indicate just how little they may value your work.

Finally, be willing to push back on all of them to protect yourself because plenty of clients will not value your photography, no matter how good you feel your photography is. Instead, they want cheap, inexperienced hungry, and easy.

That’s okay. Do you and keep taking photos!

If you’re a potential client, remember, it’s not so much that “you get what you pay for,” but more that you will always get what you value and that will be reflected, for better or for worse, as part of your “branding.” It goes far beyond just bad photography or failing to use your own brand guidelines (what’s the point of having them if you don’t follow them?). It also reflects how much you value your prospective vendors, contractors, and freelancers. Believe me, we do talk about our client-experiences among each other.

In summary, what red-flags are you running up the flagpole for all to see and is your brand okay with them?

So, Dear Reader Who Stumbled Across This Opinionated Blog-Post:

What does a collection of bad headshots tell you about a company? What kind of priorities do they demonstrate to you? What kind of red flags, if any, do they set off?

There’s a comment section down below, waiting for your input!

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