Recruiting Is Just Like Dating - Here’s Why - podcast episode cover

Recruiting Is Just Like Dating - Here’s Why

Feb 11, 202526 minSeason 1Ep. 147
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Episode description

In this episode, I explore the surprising parallels between recruiting and dating. From first impressions to long-term commitments, the way we engage with recruits is similar to how we build relationships. If you approach recruiting like dating—by focusing on connection rather than selling—you’ll build stronger, more meaningful relationships that lead to better hires and long-term retention.

Episode Breakdown
  • [00:00] Introduction – Recruiting and dating have more in common than you think! Why understanding this concept can transform your recruiting success.
  • [01:30] Recruiting Is Like Dating – The process of sorting through candidates, handling unpredictability, and managing ghosting.
  • [03:00] Why Selling Doesn't Work in Recruiting – Transitioning from a sales mindset to a relationship-building approach.
  • [05:00] The Complexity of Career Changes – How recruits weigh major life decisions and why leaders must guide them with empathy.
  • [07:30] The Slow Build vs. The Quick Close – Why recruiting isn’t about rushing but about building a foundation of trust.
  • [10:00] The Ideal First Contact – Crafting a compelling, non-sales-driven first conversation with a recruit.
  • [12:00] The Progression of Relationship Recruiting – Moving from initial conversation to deeper engagement without forcing commitment.
  • [15:30] The Power of Affirmation in Recruiting – Why affirmation is one of the strongest motivators in both dating and recruiting.
  • [18:00] Serving Before Asking – Why giving value first leads to stronger, more successful recruiting relationships.
  • [21:00] Dreaming With Your Recruits – How asking about their dreams over the next five years creates lasting loyalty.
Key Takeaways
  1. Recruiting Is About Relationships, Not Sales – Selling opportunities too early creates resistance, while relationship-building fosters trust.
  2. Slow Down to Speed Up – Just like dating, recruiting requires a natural progression to be effective.
  3. Affirmation Builds Connection – Encouragement and recognition go a long way in both recruiting and leadership.
  4. Put Their Interests First – Giving value before making an ask makes recruits more open to future opportunities.
  5. Help Recruits Dream – Leaders who help people reach their long-term goals will attract and retain top talent.

Recruiting isn’t about pushing opportunities—it’s about building trust and offering value over time. The best recruiters act like great relationship builders, leading with curiosity, affirmation, and genuine interest in their recruits' success. If you focus on relationships over transactions, your recruiting and retention will transform.

Want to build better recruiting relationships? Subscribe to my weekly email at 4crecruiting.com or schedule a coaching session at bookrichardnow.com. Let’s refine your recruiting strategy together!

Transcript

Introduction

So the big question is this, how do recruiting leaders like us who have 12 to 15 other job responsibilities win at this game of recruiting? How do we build a system that allows us to recruit effectively in a minimal amount of time while motivating recruits towards meaningful change? That is the question and this podcast will give you the answers. My name is Richard Milligan and welcome to Recruiting Conversations. Hey everybody, it's your host Richard Milligan.

You're back with another Recruiting Conversations. I'm coming to you with a rather humorous topic around recruiting, and this comes up from time to time in these conversations that I have in my coaching, and the idea is this, is that recruiting is very similar to dating. Now, stay with me here, and you'll, I think you'll connect the dots on this in just a second. One of the things I know about dating now, look, I've been married for over 25 years.

So if I still remember what it was like to date, however, flea and I dated, I think for two years. So it's been a long time since I've dated. That's crazy. That is just crazy sauce right there. I know that when I go back, I look at dating, like dating was crazy. Dating involves sorting through crazy people to get to the qualified few. Yes. And that's one way that dating is just like recruiting, right? It's like the things that happen in recruiting.

It's just, there's some things that are just nuts about it, right? People don't respond the way that they would normally respond.

Recruiting Is Like Dating

People ghost you. People ask you all kinds of weird and crazy questions. One of the things I know about dating is that dating requires everything of you. It just does. And I think I know a lot of people that have just grown weary of dating because it's just too hard, right? Recruiting is very similar. I always say this. I think the recruiting leader has the most difficult job in the world.

I say that with a lot of empathy, setting that role for 15 years, almost in one side, one industry set in that position for almost five years in another industry. And one of the things that I know is that it's just difficult. It's a difficult juggling the leadership piece because you already have a current team in place and all of the things that go into Keeping that team in the place. You want to keep them where you're serving them. You're leading them.

You're providing Something that's substantial to them so they can accomplish their dreams and their goals It just takes a special person to be a recruiting leader. It takes a special person to be a recruiter In addition to being a recruiting leader. So I know that it's very similar to dating because dating is hard. Dating is crazy. Dating requires a lot of you, but here's some perspective on this. A lot of people think of recruiting like selling.

Now I spent a lot of time in a career as a sales person. And so I've been through training with like spin selling.

Why Selling Doesn't Work in Recruiting

I've read a lot of, if not most, of the Sales books out there. And one of the things that I struggle with as a recruiting leader is actually not trying to sell someone something like that's actually very difficult to move away from, because look, I got to grow my team. I've got to increase my numbers, whether that's volume or units or contracts or whatever metric it is that you're growing. If you're in sales, you're really hyper focused on that.

And there's this transition that I think all great recruiting leaders go through where they move from being a salesperson to being a relationship builder. And that's where I think that recruiting is like dating. I think if you'll see recruiting like dating, it will give you a better perspective on recruiting. And let me just give you some of the reasons why this is true. Think about all the moving parts for someone when you're recruiting them.

I've moved from one company to another company prior to having my own company. And one of the things that I know is just even in a conversation with my wife around changing companies, the things that came up were, are we going to have to change our primary care physician? Are we going to have to change the kid's pediatrician because the insurance is different? Are we going to have to start over with a new copay? What's the new dates of our paychecks?

Is the prior company going to actually pay me the money that I think that I'm owed? I'm changing platforms as a salesperson. And so I'm going to move from one platform that I know and one support team that I know I'm going to move towards another platform that I may not know. And I'm going to move towards another support team that I do not know. And so there's just, that's just a couple of like big things that you evaluate. And the list goes on.

We start to evaluate all the moving parts for someone, you recruit them into your organization. You're really asking for wholesale change.

The Complexity of Career Changes

And so it is a lot like dating because like in dating, like you're dating someone, like when Lee and I were dating, we got three to four months into dating and we were both pretty convinced like this is going to turn into, into this forever and ever till death do us part thing. And so there's a lot of. Energy and effort that goes into that next part of really getting to know each other and really trying to figure out what is it? What is the happily ever after look like?

I think that most people in recruiting have some sort of fantasy about going on a first date proposing and then writing off to the writing off into the sunset. And that's just not the way recruiting works. We can't treat it like that. Because we are asking for people to make really large changes in their life and we need to treat it more like dating. In reality, here's what it really looked like for Lee and I when we were dating.

It's, I'm not proud to say this, but Lee and I actually met in a bar. So there you have it. For any of you that are, Like young enough that you're like I don't have my forever and ever till death do us part person and you're actually going to bars on a regular basis and your mom and dad are saying you can't find the right person in a bar.

What I know is that you can actually find two very lost people trying to get found in a bar and that was Lee and I. And so in first interactions are obviously like their synergy there. Like she's a beautiful girl. I'm an extremely attractive dude. Nah, I'm just, that's supposed to be funny. You have this short exchange where it's like, Hey, I like you. I'd like to get your phone number. And then you follow a progression.

It isn't, you imagine the person that was like, Hey, I'm just going to skip over this first part and the second part and this third part, this fourth part. I just want to get straight to this conversation of, Hey, can we get married? And it's, hey, that's really weird. And for those of you that have happened, that had that happen on your first date, I just want to say, I'm sorry because that, that had to have sucked for you to have been put in that situation because that's just weird.

It's awkward because dating really follows kind of a progression. I get your phone number. I call you, right? Have a short conversation or a minute conversation with you. And then we set up an actual date. This is what Lee and I did. We went on date. We left the date. Date went well. And I said, Hey, can I call you again? And can we go out again? And we have a second date and a third date and a fourth date. And then way down the line, right? Conversations getting better.

We're getting to know each other. That leads to something else. Maybe you say, I love you, right? All of these things take place when you're dating.

The Slow Build vs. The Quick Close

So I think the best recruiters really look at. Recruiting like that. So you follow my progression. Here's one of the things that you know, is that like we do a lot of research. So I don't ever blindly call someone if you're in the mortgage industry. Mobility RE is a great tool that you can use to actually do research and know your vault, know the volume and units of the person that you're actually going to call, know who they're doing, who they're doing business with.

I can see the list of real estate agents that you've actually done loans with. That's great information that leads into a better conversation. So I'm going to do a lot of research. And then when I call you, I'm going to have my phone script memorized, like memorized, like when I call you with my phone script, it's going to sound so authentic and so conversational that even when you object, You're not, you're gonna have a very difficult time saying no to me.

Okay. So my phone script says something along the lines of, I've done a bunch of research on you and in my research, I see a lot of similarities between your core values and my core values. And because of that, I'm reaching out to you, understanding that in this industry, most people transition on average every two to three years.

And one of the things that I know is that if something happens, a trigger of it happens where you are and you decide to leave, you'll probably have a short list of leaders that you know, and you trust, and you'll pick up the phone and call them. And so with that said, one of the things that I would like to do is just get to know you not to try and recruit you in this moment, but to try and make the short list of leaders that you would call and say, Hey, things are changing over here.

Can we have a conversation? And I realized that the only way I get to that short list of leaders, you'd be willing to call is to try and build a relationship with you. So that's what I'm doing. I'm calling you today. Say, Hey, no recruiting allowed, but I would like to get to know you. And I would like to find out if we've got similar value systems. And then if down the road, things change, you know how to reach me. That's a great phone script.

What I found is that about 30 to 40 percent of people that use that phone script on or something along those lines of that would actually say yes to that. And you have to start dating with that first date or with that first conversation. Okay. So we set that up to something bigger.

Now, if you're more in a regional role and you're listening to this, one of the things I would encourage you to do is set up that first meeting in like a 10 to 15 minute phone conversation that makes a lot more sense than actually. Taking an entire day out of your calendar to go and get with somebody. Go spend 10 to 15 minutes on the phone. And so my ask in that phone script is going to be this.

Look, I've got 10 to 15 minutes now to talk to you, but I realize I'm calling you in the middle of your day. So I'm happy to schedule it for later this week, but I would love to snack to

The Ideal First Contact

10 to 15 minutes just to get to know you. Would you be willing to say yes to that? I'm available on Thursday afternoon. What's your schedule look like? That a phone script works really well. Okay. What am I doing? I'm actually just setting up the next thing. The next thing that seems like a natural progression in dating. And then what I'm going to do is that 10 to 15 minute phone call, it's going to be great energy. I'm going to find out everything I need to know about you.

I'm going to leave you wanting more. And so I'm going to say, look, I promise to keep this to 10 to 15 minutes. We're up our time's up right now. I would love to get together with you face to face. Okay. Now, I'm going to pause there and say, you're going to already know whether you want to get face to face with this person or not.

So we're not always going to get face to face with somebody, but what we will do is we will, if we sense that there is alignment, that we've got some similar values that we're going in the same direction, like it's someone that I, I'm 50 50 minimally now that I know I would love to have you on my team. Then I'll actually say. Look, I think a great next step would be for us to grab lunch and just to continue conversation again. No recruiting allowed. Okay. No talking about marriage allowed.

Yes or yes. If you're recruiting, you're nodding your head right now because that's what you should be doing. But it's not what the entire market does. Okay, let me tell you what the entire market does. They literally act like they're trying to get married on the first date. And that's just awkward. And it creates tension unnecessarily. And you miss out on opportunities because that's how you recruit.

So natural progression is like the normal phone conversation I hear or the normal phone scripting I hear is, are you open to a better opportunity? And to that I say, I just threw up on the mic because that is just awful. What you're doing is you're really forcing yourself into a very small segment of the market to try and appeal to those who are unhappy and already looking for another opportunity. And that's a small part of the market.

The Progression of Relationship Recruiting

If you're a recruiting leader and you're recruiting successful. People that already have a book of business that already have these referral partners, places that they're getting business from. These people aren't walking around looking for their next opportunity. Typically, it doesn't mean that you don't run into those situations, but for the most part, my data, the data that I see says that close to 95 percent of those people that were after they're good where they're at.

You call them, they'll say things like, I'm not interested. I'm happy where I'm at. I'm not making a change anytime soon. Those are all the things that they will say. So, you trying to show up and throw up your better opportunity on them does nothing to progress you towards the finish line. So it's an awful way to try and recruit because it diminishes the results that you have.

It diminishes the results that you have in terms of the number of people that you can put into your process and into your pipeline to build relationship. Okay, and so that's what we want to focus on is getting those people in a process of building a relationship with me because here's what I believe. I think that great leaders, they have this intangible thing that a lot of people want to be, that a lot of people want to align with.

They have this thing, the it factor, where If you, if you were to meet with someone and you were to present them your it factor, now let me just pause and go, you may be going, what's the it factor? And what I would say is that the it factor is, you're clear on your vision, you're clear on where you're going, clarity, clarity. That's important. And the other part is what's your value system? What do you believe? What are your core convictions?

And if you don't know those, you probably don't have the it factor. So work on your it factor. But if you have the it factor, and then you can storytell those. And if you're wondering what I'm talking about right now, and you're lost, go back to a prior podcast that I did on storytelling. I talk a lot about that. But if you have that it factor, if I put you in front of people in large numbers, you are going to win In the large numbers at scale.

I really believe that and so our process is better when we invite people into a conversation that's a non recruiting conversation because I remove the tension. If I'm the needy guy that wants to get married on the first date, nobody wants to date me. If I'm the guy that is not needy but is most interested in pursuing you, okay, that's a key component to dating. We pursue, let me just add a tagline to that, with integrity. We pursue with integrity. Many people pursue with a lack of integrity.

What I know is that a lot of people are just trying to sell something. And when they try to sell something, there's a huge lack of integrity. Like I've gone to organizations that sold me on something. And then within the first couple of weeks realized that they were pivoting and everything they sold me on, they already knew they were going to change. And they changed that. And my income was reduced by 60 percent in literally the first few months that I was with them. That's a lack of integrity.

So when we date someone we pursue with integrity, if the end result is the forever and ever till death do us part. If you lack integrity. I can already point to where this is going to go. This is not going to end well. Like this person is not going to stay loyal. They're going to feel like you lack a core value system. They'll move away from you and they might stay for a year or two years or three years.

But early on, what we know that data says is that it's 68 percent of people say that they determine whether a company 12 months. So if you don't honor the things that you say you're going to do, guess what? They will stay, but they've already determined that they will leave.

The Power of Affirmation in Recruiting

So, when we date, yes, we pursue, and that's an important part of that. When you date, here's another thing that you do. You are overly affirming. Now, let me just pause there for all you dudes out there that, that are married. Like, how we date is really how we should be married. Now, this isn't a podcast on marriage, but Don't get me started. If you want a place to start, go check out the Forty Day Love Dare. That's an unbelievable book. It's a rhythm for me.

I try to go through that one time per year because it pulls me center. And it says, what is this all about? What is relationship and marriage all about? It's about leading my heart, not falling off my heart. It's about walking in a covenant, not a contract. It's, that's a great book, by the way, if you are newly married or not even newly married, I've never read it. Read that book. The 40 day love.

There's a phenomenal challenge to take and I would encourage you to do it, but I digress or did I digress? I'm not sure if I, if digression would be the right word to use there, but when we're dating, we're overly affirming. Okay. Now the lesson to learn to be learned here is this. The most successful recruiters that I've spent time with, guess what they are? Overly affirming. So I recently had just a, it was a 30 minute. Uh, someone got on my calendar for 30 minutes to pick my brain.

They're not a coaching client of mine. And by the way, I do regularly do that. If I've got time available, uh, give people time to give them input or advice. And this, um, wonderful lady got on my calendar and immediately I could tell like she's a successful recruiter. And the reason why is because she was overly affirming. It was like a natural gifting of hers.

And I think this does come more naturally to others, But one of the things I know that when we date, we do is that we're overly complimentary. We go out of our way to affirm the individual and affirmation. It's one of the top three forms of motivation for human beings, belonging, affirming, and then meaning. Those are the top three ways that we are actually motivated as human beings. And so to be overly affirming is something that we typically do and it comes naturally to us when we date.

But then some things happen. You get married and a lot of times we stopped doing that. And so lesson here for leaders, just in all of this, if you're listening to it, I do think there's an intersection where leading and recruiting overlaps. I think that the best leaders are the best recruiters. Like when you bring someone into your. Organization. Don't just affirm them while you're recruiting them. Affirm them while they're inside your leadership, because that's actually how you retain people.

Serving Before Asking

You can't just be a great recruiter. You got to be a great retainer of people. Now, great leaders, just as something that they do, they're life giving in the way that they affirm people in the way that they encourage and inspire people. So being overly affirming is definitely something that happens when we date. And it's something that you need to do when you're recruiting. Here's another one. When you're dating. We tend to put other people's interest before ourselves.

Now, if you're not married right now, I'm giving you some phenomenal dating tips and you can just, you can say thanks and drop me a line. That's awesome. One day when you get married, you can say, look, I learned it from a recruiting podcast. I should be pursuing with integrity. I should be overly affirming and I should be putting the other person's interests before myself. Like those things are all true. What we should be doing on the recruiting side.

A lot of people, and I had this conversation earlier today, which is one of the reasons why this is coming up in a podcast. Someone was actually asking me this question. What do you think about this sales funnel would be the best way to describe. What do you think about the sales funnel that I'm creating? And one of the things that I said was like your sales funnel simply predicated on your best interest. And what they were doing was they were creating all this company centric content.

Which was centered around all the awesome things that they do as an organization. And they were going to, in essence, try to sell that in their sales funnel that they were going to push out on LinkedIn, Facebook as their, their, what I would call a, their recruiting blueprint. And in that, what I said was, is that content's relative, but it's only relative after you've brought high value to someone, right? So you think of a sales funnel.

You've got top of the funnel content, middle of the funnel content, and bottom of the funnel content. And a lot of times the bottom of the funnel content is what is about the company, about the organization. It's more specific now as to the opportunity. Top of the funnel, the middle of the funnel content is value oriented. It's not, what is your opportunity to look like? It's not the toolbox your company has to offer.

It is your top of the funnel content is bringing things to your market that allow people to improve, that allow people to grow, that give people insights to improve their business, to improve their lives, to, to execute on these three things so that they can go get more business or develop more relationships. Or that's top. That's what I believe is top of the funnel content. And this person was actually.

Pushing content that was come join our organization that's putting their interest before the interest of the other person and so in dating dumb bass is putting the other person before yourself being selfless, right? And so one of the things that I know is true about recruiting is this, and I teach this. In my system is how are we going to give value? How are we going to create a value equation? For example, my value equation is this podcast, right?

Dreaming With Your Recruits

And I deliver daily content on LinkedIn. I write articles on about a bi weekly basis that gives you content on LinkedIn. You can actually go apply whether you're a coaching client or not. You can go apply my content and go grow yourself as a recruiter, right? YouTube channel, Vimeo channel. Like there's lots of ways that I bring value and all of that is focused on you. Um, I. audience. It's not focused on me. Like, I'm not here. Go. My podcast is not, and it's not sign up for my coaching.

Here's what I can offer you, right? It's, that's not what this is. And so you've got to look at, I look at this, like I'm dating you at some point, maybe a trigger event will happen. You'll say, I need a coach, right? Need another resource or as an organization, needing a recruiting strategist or a consultant. And Richard's our guy because Richard's actually given us value. So you treat recruiting like dating in this area. And then you put other people's interests before yourself.

So you give, and you give with no strings attached. In that, and when you do it that way, what happens is that people will actually reciprocate, right? It's like Brian Tracy had a law back in the 1980s called the law of reciprocity. And I think we've lost sight of that human behavior has not changed one bit. You follow Gary V calls it something different. He calls it jab, right hook, but it's value. And then you actually can ask for something, right?

But it's no different than, I think it was Robert Sindali wrote a book called the power of influence. In the 1980s, and the context of everything that I just said was true 30, 40 years ago. Just as it's true today, we haven't changed a bit. So when we put other people's best interests before our own best interests, guess what? People are likely to respond in kind. People are likely to reciprocate and all of that is aligned with dating. Okay?

So here's what I'm, here's, I'm going to leave you with the best recruiters. are ones that put other people's best interest in front of themselves. And it's not just now I can say the best recruiters, I can say the best recruiting leader. So recruiter slash leader, the best leader does the same thing, right?

So when the dating's over and you have that person in the till death do us part, Piece of this that's when the real work begins just like it does in a marriage right all the fun Fancy highlight real stuff is now over now the real work begins and I'll leave you with this I once saw a study And in the study, they were analyzing why do marriages not work? Like why do people get divorced? And I was blown away by the number two reason why people get divorced.

I think most people know number one reason is because of financial difficulties, financial disagreements. Right? We're going through a hard time financially. Someone doesn't manage money. There's a lack of money or whatever the money issue is. Most people that get divorced say that's the number one issue. But the number two issue that I saw in the survey was this.

Couples that were, that got divorced that were surveyed said that they got divorced as a second primary reason because they stopped dreaming together. I pause there for dramatic effect. And leading is a lot like dating and marriage. When we stop dreaming with our people, we really leave our people available to anybody else to recruit.

One of the most powerful questions you as a leader can ask, or you as a recruiter can ask while you're recruiting, is, what is something dreamy that you'd like to accomplish in the next five years? I'll give that to you again as a leader or as a recruiter, no matter whether you've already got someone on your team or whether you're trying to get someone on your team, one of the most powerful questions you can ask is around this dream concept.

What is something dreamy you would like to accomplish in the next five years? And then you lend an ear. What's your dream? How can I help you accomplish it? The person that asked that on the recruiting side and the leader that asked that to their team is the one that not only has success recruiting, but is the one that has success retaining when they actually help that individual accomplish it. So we use a little humor at the beginning. Yes, recruiting is like dating.

We're getting really serious here at the end. Let me tell you this over the next couple of weeks, we've teed up some phenomenal podcasts for you that I want to invite you to come back to. So with that said, Thanks for listening. I enjoyed my time talking to myself today and I appreciate you tuning in. And so until we talk again on the next recruiting conversations, thanks so much for listening to this. And I look forward to seeing you again or talking to you again on the next podcast.

Have a great week, everybody. Want more recruiting conversations? You can register for my weekly email at 4crecruiting. com. If you need help creating your own unique recruiting system, you can book a time with me at bookrichardnow. com.

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