Carly Ries
One of the most valuable skills in solopreneurship is knowing who to work with before you commit. The wrong client or contractor can create months of stress, constant churn, and endless prospecting to replace relationships that never should have started. In this episode of The Life-First Solopreneur, Carly Ries and Joe Rando share how to vet clients and contractors so you can build long-term, low-drama working relationships.
Start by doing your homework
Vetting begins long before the discovery call. When you clearly define your business, who you serve, what you do, and what products you offer, bad-fit clients rarely make it far. If your ideal client owns a restaurant and a dental practice comes knocking, that mismatch is a signal worth respecting rather than rationalizing.
Why personality matters as much as deliverables
For service-based businesses, the working relationship is the product. Carly shares how one consultant uses a personality test and a thoughtful questionnaire, not to judge the answers, but to observe how prospects respond and whether their style is compatible. Joe leans on the gut check built from decades of experience, along with tools like personality surveys and intake forms to assess fit before signing.
Red flags to watch for
A few warning signs come up again and again. Watch how a prospect talks about past providers, notice whether they seem panicky or urgent for results from day one, and pay attention to early freebie requests. Joe also shares a costly hiring mistake that taught him a lasting lesson, if someone is rude to the waiter, believe them.
The payoff
The better you get at vetting the right people upfront, the stronger your business becomes. You reduce churn, cut down on constant prospecting, and set yourself up for long-term engagements. It all starts with being diligent from the very beginning.
Listen to the full episode on Apple Podcasts, Spotify, or YouTube.
Episode Transcript
Carly Ries: Ever signed a client and known by week two that it was a mistake? On today's episode, we're talking about how to vet clients and contractors before you commit so you can skip the churn, the stress, and the endless prospecting. We get into personality tests, gut checks, the red flags to watch out for in a discovery call, and why the freebie ask on day one tells you almost everything you need to know. If you want to work with people who are actually the right fit, stick around, this one's for you. You're listening to the Life-First Solopreneur, the podcast for those in pursuit of a life first business.
I'm Carly Ries, and my cohost Joe Rando and I spend every episode with solopreneurs who are proving there's a better way to run a one person business and experts who are helping make it happen. We like to say life first, then business. So let's get right to it. Joe, I'm kinda laughing at me bringing up the topic of this episode. Like, I have the expertise in it when you, not even arguably, are probably the best at figuring out which people to work with. I am the baby on the team and we've been working together off and on for a decade. You have worked with Stacy, our community community manager for over thirty years. I mean, Shelley and Tricia, you know how to get people to stick around and how to work with people and all that. So I don't even know why I'm talking during this episode. I feel like this should be a solo episode for you.
But, basically, the point of this whole episode is how to vet clients or contractors before you sign with them. Joe, before I dive in, I have my thoughts. But I am laughing that I even think I compare to you on this topic. Any 2¢ to kick things off?
Joe Rando: I like to think about clients and contractors, you know, employees, contractors differently. they're totally related, but I do think it's good to have a kind of a slightly different perspective on each. I mean, the first thing, starts with doing the homework. And going back to defining your business.
What do you do? Who do you do it for? what are your products? What are the products that you're offering? And if you have all that stuff down and then you stick to it, you're not gonna be in a situation where you're going to easily come across the wrong client.
I mean, there's obviously the personality issues and things that are going to be, different for everyone that you talk to. But if you don't start out with a very clear idea of the kind of people you work with, and what I mean by that is, your target customer. If your target customers are people that own restaurants and somebody comes along with a dental practice and says, I wanna hire you. You should be thinking hard about that because again, and it goes back to the last episode of the problem client. Now all of a sudden they're special, they're different, and you're doing other stuff and it's not efficient. so the idea is to get that homework done of defining, who your customer is, what it is you do, what your products are. And then when you start to evaluate working with someone, and they evaluate you, you have those pieces in place. And if those don't fit, there's no need to go further.
I mean, that's kind of the blocking and tackling, as my dad would say, of the situation. Get those pieces down. Then, to me, I'd like your opinion, Carly, because you're much more of a people person than I am. But, from there, to me, it becomes an issue of personality. If they need your product the way you serve it up, and they're the kind of people that you're serving, then, are they the right kind of person and are you the right kind of person to work together?
Carly Ries: Yeah. And I think in this scenario, we're talking about, service based businesses. where you're actually gonna have that working relationship with the client and with you.
Joe Rando: If I'm selling dog toys and, you know, I don't care.
Carly Ries: This is purely if you have a working relationship with somebody.
Joe Rando: Which is kind of who we talk to.
Carly Ries: Exactly. That's our audience. it's funny you said that , so I have a friend of mine. She's a consultant. She has her own business.
And one of the things that she does with her clients is she sends them the Myers Briggs assessment. She sends another personality test, like something based on color. I haven't done this color test. But there's a color test and then a questionnaire that's like, what's your favorite movie? What's this? What's that?
And she doesn't look at it for the answers. Like, Joe, you would say, Star Trek is one of your favorite things. I would say Tommy Boy is one of my favorite things. Obviously, we want to have The same answer.
Joe Rando: Tommy Boy is pretty good.
Carly Ries: It's great. It's the best, if we're being honest. But she looks at how people respond. It doesn't even matter if she likes Tommy Boy or not or Star Trek or not, but it's how they respond to these questions that kinda gives a feel for it.
Joe Rando: What do you mean? Explain that. Like, how they respond to the idea of having to answer the questions or how they respond to the questions specifically?
Carly Ries: Thanks for clarifying. So they aren't, one word answers. It's like, what is your favorite movie and why? So you say Tommy Boy because it's the funniest movie that's ever been. But if they were like Tommy Boy because x y z that didn't necessarily align with what she was thinking, then she kinda deduced what their personality was like based off these fun questions, based off of the color personality test and Myers Briggs just to see if they're compatible.
Not to judge a person based on their personality, but just to see if it was compatible with hers. And I thought that was really interesting and a really fascinating way to vet the working relationship, not even necessarily the are they a good fit from an actual business standpoint? But I never heard about that before. But yes, I think personality is crucial.
Joe Rando: Yeah. I really do to. I certainly, and I think this goes back to contractors too, by the way, that personality aspect is important if you're gonna be working, nowadays, "face to face", if you're gonna be interacting with them in any way. But yeah, from that perspective, it's always been much more weirdly being the scientist guy. Mine's always been much more gut level.
You know? I mean, Myers Briggs is interesting. It's scientifically unproven and but I think it's pretty strangely accurate. I just kinda go on, I talk to people, and I just kinda go on gut.
Carly Ries: is that, over Zoom or something or, like, over coffee?
Joe Rando: I'd rather be in person, it's just better in person. But nowadays, reality is I'm working with people from all over the country, all over the world even. And, you get to know people through Zoom, I guess. like I said, it's not as good, but I think it's doable. But the main thing is, I mean, one of the things that we used to do and this was when I was actually hiring people as an employee.
One of the things we used to do was, I hate to tell you this, but we would have a prospect, and we had one guy who was really good at sleuthing social media, and find their stuff on social media. And we made decisions not to hire based on social media.
Carly Ries: Yeah.
Joe Rando: But it was because it was very, very insightful as to their personality. And so it's just one of those things where be careful what you post. But, again, I think that having a rigorous approach, I certainly can't argue with that as a way to do it. But at least having an idea of the kinds of people that you like to work with and the kinds of people that maybe you don't like to work with is very important.
Carly Ries: Yeah. I'm gonna make up this percentage, but for me personally, I feel like, the personality side of things is 50%, if not more important than the actual deliverables that you'll be giving to them and how they'll respond to that.
Joe Rando: 57.2.
Carly Ries: 57.2. How did you know?
Joe Rando: Yeah. I guess the point I'm trying to make is just that process of spending some time, getting a feeling for what it's like to work with this person, is worth the investment of time. And I know solopreneurs, who, they're willing to buy my thing. Let me get them signed up. I get it, but, can be sorry later.
And if you take a little time just to kinda say, hey. You know, my gut tells me or my surveys, whatever it is, tell me that this person is a good fit. I mean, I've seen some solopreneurs do something really cool where they usually seem to, for some reason, use, what's that one that gives a really nice looking forms? Typeform?
Carly Ries: Is it Typeform? Typeform. Yeah. I think so.
Joe Rando: And they have you fill out a bunch of questions, some of which to vet whether you're the right fit business wise. But then some personality ones that they can use, kinda like your friend does to determine whether it's the right fit. So it really is one of those things where you can gather some of that information in writing, and then maybe you have that call and talk face to face, talk about some of the answers. And don't make it on interviewing you as a client.
Make it like, a let's get together and see if we should work together, if we feel good about working together. And then they might say no. You might say no. You both might say no. Or, you both say yes, and then you've got hopefully a good match.
Carly Ries: I think the other thing is be mindful of how they talk about past providers or past companies that they've used that also provide your services because that'll be clear if it was that business or if was maybe on their side. And in that discovery call, see if they already seem like they're urgent for something. If they're urgent for results, if they're panicky. I mean, that just sounds stressful from the get go, and I think that's a red flag to watch for. I think in the beginning, if they're asking for some freebies even from the start, like, oh, will you throw this in?
It's usually a good sign, like you were saying with the gut check, that they're probably gonna continue to do that. And if they're not on board with how you do things and they already want to change some things, I mean, ask those kinds of questions too. Make sure you're up front about how you do things. And if are very set in their ways, that could be a tough relationship to navigate. I just think you need to know that.
Joe Rando: Yeah. You're right. I mean, if on day one, they're asking for freebies or anything like that, it's just a dead giveaway. Quick story. one of the biggest hiring mistakes.
This was a actual hire, not a contractor. And this guy came with a really, really high powered resume, and I was salivating. And he flew in, and I took him out to lunch during part of the interview, and he was a jerk to the waiter for no good reason. No good reason. And I overlooked it. Yeah. Maybe he's tired from the flight or whatever. Hired the guy. Terrible, terrible decision. Worst hire I ever made.
And it was heartburn for two and a half years, it was just awful. And it's one of those things you know, then I've heard other people say it since because this is going way back. It's like, if they're not nice to the waiter, they're not a nice person. And Yeah. It is those red flags, you ignore them at your peril.
Carly Ries: Yeah. Absolutely. But yeah. Anyway, I think the better you can get at vetting the right people in the beginning, the better your business will be long term because you won't have that constant churn. You won't have that constant prospecting.
You're hopefully setting yourself up for long term engagement, but it really starts with you being diligent in the beginning. That's all I got.
Joe Rando: Absolutely. Very good.
Carly Ries: Listeners, as always, thank you so much for tuning in. Please leave us a five star review if you thought this wasn't the worst episode you've ever heard. We're stealing that from Jay Schwedelson, he has a really good podcast, so I have no shame in stealing that from him. Be sure to share this episode with fellow solopreneurs who are looking to lead a life first business and subscribe to our show on Apple, Spotify, anywhere you listen to podcasts, including YouTube. And will see you next time on the Life-First Solopreneur.
You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.