Nope, not doing it. Feels gross.

Apr 27, 2026

It’s cringy.

It feels gross.

We were having a good discussion in a FB group I’m in about how to follow up when a ‘yes I want to go forward’ prospect doesn’t sign the engagement letter and send payment like they said they would and now it’s days later. 

(Short answer, the #1 way to correct this is review the engagement letter in the meeting and get it signed and collect payment then – even if it’s on Zoom.)

What has been foremost in my mind since yesterday is WHY are we so resistant to this in the legal field?  Maybe in other fields too, but I know the legal field, and I know it’s so prevalent here. 

Every time I recommend tying up the sale in the meeting I get HUGE pushback. And attorneys are honest.

“Nope, not doing it.  Feels gross.”

“I would never. That’s pushy.”

And there’s no judgement here – I get the discomfort. I feel it too.

And I want to shine a light on it.  Because when someone says YES, I want to protect my family. I’m ready to do my estate planning finally so I have peace of mind my family will be ok. Why do we hesitate? Why do we feel so ‘wrong’ and ‘gross’ if we say great, let’s get started. Here’s our engagement letter. Let me take a few minutes and go over it with you so you understand all the legal talk and know how it protects you.

(Many attorneys think of an engagement letter as a CYA for them and it is. It ALSO is protection for the client.  It clarifies exactly what they are hiring you to do for them, not just to protect the law firm, but so the client is clear what’s included, what isn’t and there aren’t surprises or disagreements later. I use it as a tool to close a deal – it’s part of helping a client feel comfortable proceeding.) 

But it’s heavy, it’s legal talk, it has lots of scary language especially for people not in the legal field. Legal professionals live and breathe by ‘scopes of work’ in engagement letters – we have to. The rest of the world doesn’t. 

So, you have this great meeting, you talk about beautiful, important things like family and legacy then later that day you drop a heavy, scary legal letter on them to review and sign on their own. Why do we do this?

 “Because I just want to educate people I don’t want to sell them.”

Helping a client understand an engagement letter and get going isn’t selling. It’s helping them through the process of getting started on what they just said they wanted.

I’m in the car buying process right now which I abhor. But I do really want and need a new car. No, I don’t want to spend the money. No, I don’t want to go talk to a bunch of salespeople but not because they are selling me – I need to be sold to because I need a car. I don’t want to talk to them because I don’t want to deal with the ambiguity and the feeling that I am being taken advantage of. 

We aren’t doing that to clients here. We are having them sign the required engagement letter and support them in understanding it versus emailing it to them to navigate on their own. 

And once I decide on my car, and I agree to the terms of the deal, I will be super mad if a salesperson says great, go home now, I’ll email you all the documents to review on your own!

No, I’m spending money. I’m making a hard decision. I need this car. Don’t make me do it alone. Don’t leave me to stall and talk myself out of it.

It’s not gross or cringy to get the prospect across the finish line when they say they want to proceed. It just feels that way because WE make it uncomfortable. Our egos say, eww I’m putting myself out to be rejected. Either way you are – it’s just if they say no, I’m not ready to sign in person or ghost your emails after…

And really, truly, if helping people is important (and all the attorneys I know tell me it is) then why do we duck and cover when the moment comes to truly help them move forward.

If they want to say “I’m not ready” they will. It’s like when your server comes and says ‘would you like dessert’ – you don’t get mad. You just say ‘no thanks.’

It’s not gross. It’s not cringy. Those are really hard judgmental words we say about ourselves.  It’s uncomfortable and scary.  And that’s ok. But there is nothing gross or cringy about helping people make a decision which will protect their family.

Often the best way forward is to shine the light on the truth – it isn’t pushy or gross. It just feels yucky to YOU. Do it. And learn that no one is going to be offended because you asked them to review and sign the engagement letter with you and make payment. At worst, they will say let me think about it. At best (and most will), they will do it and be thankful they are on their way to protecting their family.

(Saying goodbye to my Jeep – you were a fun ride.)

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