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When to Disappoint Others

Here’s a story about first time I got a gig through LinkedIn.

Jennifer worked at a ~~ prestige beauty company ~~ and needed a consultant to revamp the 100-slide PowerPoint about the state of the prestige beauty industry for their upcoming conference.

I said yes, even though (1) the deadline was tiiiiiight, (2) I don’t really love doing this kind of design work, and (3) I don’t know jack about the prestige beauty industry.

The pay was structured as a flat dollar amount per completed slide.

Jennifer sent me the deck from last year that “just needed to be updated” (famous last words).

Each slide had at least 100 different elements on it – dozens of textboxes in 4 point font, photos arrays of expensive neck creams. I very quickly saw that the reasonable dollar amount per slide was going to equate to far under minimum wage, with all the work it would take to redesign even a single slide.

I spent a whole weekend in my office, cranking out remakes according to what I knew to be best practices for slide design.

Sent it off to Jennifer Sunday night.

She freakin hated it.

Her email was something like “this is not prestige, this is not elegant, this is not beautiful.”

That hit me like a gut punch.

I took another shot at it, still without any real idea of what prestige, elegant, and beautiful would look like to Jennifer.

I’m sure I fell short. I sent off the next draft, which, at this point, was like the day before the conference. I never heard from Jennifer again, despite my follow up emails.

I had disappointed her.

The right time to disappoint her would have been back when she slid into my LinkedIn DMs. I should have said no. The project wasn’t a good fit. The answer should have been simple.

Or, I could have asked for a sample slide so I could get a sense of the scope of the work. I woulda opened the sample slide, laughed out loud in my office, then politely declined the job – disappointing her.

What do those two opportunities have in common?

They come before the contract is signed.

The best time to disappoint someone is before you sign official paperwork.

We risk damaging our reputation and wasting everyone’s time and energy when we don’t engage in a thorough discovery phase before we ink signatures.

In order to honestly engage in a discovery phase, you’ve gotta know what work you will and won’t do. What lights you up and what’ll be a slog. Who you love to work for and who you don’t need to support.

Those distinctions are blurry at best when we’re desperate for work or flattered by the ask.

You need clarity about your focus and purpose to enter into a discovery phase. (You also need a list of client red flags to look for.)

Most of us skirt this. Because we want to “remain open to new opportunities.”

But clarity about your focus and purpose brings you strength and confidence.

You might think, what’s the harm? You only lost one weekend of your life saying yes to Jennifer.

Not so, my friend. I lost my time, my energy, and I risked my reputation. And as an entrepreneur, time, energy, and reputation are all you’ve got.

So now I know better. I asked for a sample to get a sense of the scope. It’s part of my discovery process.

Let’s trade stories. How did you disappoint a client, after the contract was signed? And what changes have you made to your discovery phase as a result? Shoot me an email.

Being Strung Along

The thing about being strung along by a “potential client” is that you often don’t know it til it’s too late. Let’s look at what happened to a couple of my students and let their hindsight become your foresight.

No work without a contract.

Sometimes we make it easy to string us along. Like when we agree to work we wouldn’t normally do, for the promise of a future contract.

One of my previous mentees (let’s call her Trudy) accidentally set herself up for being strung along. She realllllllllly wanted to partner with this organization. It woulda been a big fish to add to her portfolio.

In her early conversations with her point of contact at this org, they seemed super eager to work together. So much so, that the client asked Trudy if she’d be willing to jump in on some small tasks (warning sign #1) at a low (warning sign #2) hourly rate (warning sign #3).

Trudy didn’t know me then, so she said yes. The client said it would just be temporary while they write up the bigger contract and get it in place.

Did Trudy ever advance beyond low wage task labor?

No my friend she did not.

And she was too embarrassed about the scope of her work there to ever include this client in her portfolio.

The client doesn’t know what they want.

Another student of mine (code name: Blanche) got stuck in a months-long string-along with a potential client because of “decision by committee.”

Similar to having too many cooks in the kitchen, decision by committee is an excellent way of slowing progress to a casual stroll through I Don’t Know What Do You Think Land. Have you and your partner ever entered into starvation because neither of you could decide what you wanted to eat for dinner? Like that. But with ten partners.

Blanche had a typical initial meeting with this client to lay out the possible solutions she could offer to the problems they were experiencing. They seemed to have come to agreement about the way forward. Blanche went home and waited for a contract.

And waited.

Blanche checked in but by this point, the finer details of the conversation had been lost, so the potential client asked Blanche to write up the plan in a proposal (note to Future Blanche: Write and send the proposal immediately after the initial meeting.)

Blanche sent the proposal and waited.

And waited.

When she checked in again, the potential client said the team needed to really think about whether the proposed solution would solve the right problem. Could Blanche meet with the whole team and help them talk through their problems?

I’m gonna skip to the end of Blanche’s tale: Blanche dealt with so much waffling you’d think she could open an IHOP franchise. This client liked the idea of working with Blanche (or, at least, of having a consultant) but couldn’t ever make a decision about where to start.

I actually suspect they didn’t have the funds to invest in the right solutions but didn’t want to say that to Blanche’s face, so they just let it playyyyyyy out.

Look, some clients really do take months of nurture before the project comes to fruition and you get that sweet contract in your hands. You’ve gotta relationship build. They’ve gotta convince some team members to swipe right on you. Procurement processes and vendor onboarding – the creepy evil twins staring at you blankly at the end of the hallway of consulting life – can take a long, long time.

You’ve gotta learn how to tell the difference between when they really do need time and when they’re stringing you along. Here’s how I tell:

Check-ins should advance the plot.

If you’re not hearing a reply after you send a check-in email, wait a week and send another. We all have those weeks from hell where we can barely breathe. But if you don’t hear anything after the second check-in, move on with your life.

When you do get a reply, it should include some decision or action or next step with a date attached to it.

Like “My team and I have a meeting to discuss this project next Tuesday and I’ll get back to you then.”

or “I have a few more questions. Can we schedule a Zoom to discuss?”

These are check-ins that advance the plot.

If your check-in gets a reply like “Thank you for checking in!” or “We’re still thinking about it.” you’re being strung along and it’s time to walk on by.