Apr 15, 2026 · 53 min · 14 segments
Sales skills are often the missing link for firm owners who are highly technical but struggle to confidently enroll clients, and this conversation with Rob Jolles breaks down what actually changes…
Rob JollesGuestMichelle WeinsteinHostAnd I guess what would you say to someone, Rob, who thinks in sales, you have to convince or persuade? You know, when people think persuasion, it's a negative connotation too, right? Sales, negative.

There are good lawyers and bad lawyers, but I need somebody to help interpret the law, good accountants and bad accountants.

But I do need somebody as an entrepreneur to go through my books and make sure I'm doing things the right way.

So It annoys me right out of the gate sometimes because I think the sales industry is so beaten up and particularly on this topic, because not only would I wish people would just kind of lighten up and realize you're kind of bumping into maybe the used car lot where there's some great salespeople, but sometimes we can get beaten up out there a little bit.

If you have a friend who might be drinking too much at a bar, are you too afraid to ask them to put that drink down? Well, it's a life and death situation.

You know, you took a couple classes in college, but not if... really when you get audited or when you get fined, maybe then you'll wake up.
And I guess what would you say to someone, Rob, who thinks in sales, you have to convince or persuade? You know, when people think persuasion, it's a negative connotation too, right? Sales, negative.

There are good lawyers and bad lawyers, but I need somebody to help interpret the law, good accountants and bad accountants.

But I do need somebody as an entrepreneur to go through my books and make sure I'm doing things the right way.

So It annoys me right out of the gate sometimes because I think the sales industry is so beaten up and particularly on this topic, because not only would I wish people would just kind of lighten up and realize you're kind of bumping into maybe the used car lot where there's some great salespeople, but sometimes we can get beaten up out there a little bit.

If you have a friend who might be drinking too much at a bar, are you too afraid to ask them to put that drink down? Well, it's a life and death situation.

You know, you took a couple classes in college, but not if... really when you get audited or when you get fined, maybe then you'll wake up.
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