Latest / Better Together / Transforming Leadership Through Strategic Hiring with Jason Crawford
Transcript
- Meesam curingbusy: Hey everyone, and welcome back to another episode of the Better Together Podcast. I'm your host for today, Sean Sunsvold, joined as always by my partner in life and business, Kelly Sunsvold. I am crazy excited about today's guest, Jason Crawford. Jason is the founder and chief hire officer at HireOptions, a company that helps business owners grow with clarity. by connecting them to high quality, values aligned, executive assistance, and operational talent. What's unique is that Jason's work goes deeper than just building teams. With a background in coaching and a strong grasp of mindset, pace, and personality dynamics, Jason uses his unique combination of skills to help leaders find the right support that truly fits how they're wired to work. In this episode, Jason will share the story behind the business, including the bold move he and his wife Amanda made to relocate to Columbia and build a fully remote life. We talk about what it means to lead with intention, how to stay grounded when you're carrying a lot, and why the right kind of support can change everything. Jason, welcome to the show. Thanks for being here, man. Thank you. Thanks for the intro. I appreciate that. Now I'm super excited. Yeah, more than welcome. I truly meant every word of it. But let's start off here. You know, just tell us a little bit about you and higher options. What problems were you trying to solve when you guys started the company? We, was trying to solve a problem that I dealt with in my life. Really from like 2010 to 2020, it was hyper pronounced. There was so much stuff that I wanted to do from a business perspective, from kind of a civic perspective. I was always overwhelmed. not a real high attention to detail type of person. And so I get bogged down in the details. And when I ended up hiring an executive assistant back in 2016, 17, my life changed. It was like I had 50 % or a hundred percent more capacity to do what I wanted to do and to manage all these things. I just, I fell in love with the concept and I realized the potential that it could have. When I was sitting there in 2023, figuring out what I was going to do with my life, I sold a company in 2020 and was on the biggest high of highs. And then three years later, All the things that we had tried to do and we thought we were going to be able to really propel ourselves forward actually didn't work out. It was a real beat down for us. And we were in a situation where were cash flush. And then all of a sudden we've been draining these down, making investments that weren't paying off, taking a really big risk. I mean, really big swings for the fences and it didn't work. And so I had to have this talk with myself. Where did I serve people in the business community? at the highest, one that was in business to business. That's where I really spent 18 years of my life and crushed it. And then there, what could I do? And just the idea popped in my head. I want to do a better job of getting CEOs in ⁓ small to medium sized businesses, ⁓ executive assistants. Because too many times when I talk to people, even with what I'm doing now, but prior to that, they're like, yeah, that never worked out. I couldn't sort out what I needed to do. And I realized that there was a process problem in that generally, that the reason it didn't work was, was not because the concept doesn't work because it always works. We needed to fix that process. So I decided that was what I wanted to crack. I wanted to be the best in the world at finding people executive assistants. And when I talked to people, I just, found still so many CEOs of large companies weren't utilizing this and we needed to, you know, it just propelled me to get into that and to figure out how I could make it. you know, really pop. So that's what took me there. Yeah. Yeah. And it's interesting for those listening, Jason and I actually, and Sean, we met each other through a client that we, that Gold Bear has currently. And so connected us, we met Jason, actually hired our first EA through Jason's company and through higher options, which has just been a fantastic experience. And so we got to actually experience that matchmaking. process. So walk us through that process and share with our listeners your process of matching the business leaders with the right support staff. And then what makes it different than like the traditional staffing models? Cause it was definitely different. Yeah, it is. It's a, it's a little more work. Cause some companies they'll do kind of a light intake and then they start throwing warm bodies at you. And that can work at times, but in, in my past 25 years, I actually haven't been that great at hiring. So it's kind of funny that I'm in charge of a recruiting company. What I did a few years back and then what, you know, this, ⁓ this partner that you're talking about made a big difference in our hiring process is they de-risked the hiring process. So we use Active Index as probably 70, 80 % of our process. And very few people are willing to put that much onus on something or they don't believe that Things like psychometrics and behavioral analysis predict success. And I'm here to tell you they absolutely do in most roles. Deniably no questions asked, full stop in an administrative and executive assistant role. We can predict levels of success by their traits. So that's number one. We, we get candidates and well, let me start back. We look at the client. And we get the client to take the behavioral analysis. And that's something really different that most people have never seen because part of these matches are who are we matching this person with? Yes, we have one or two ideal profiles that we search for, but every now and then we have to make fine tune adjustments based on the manager, based on the leader. And that is, don't think I've ever seen it or heard from it because everyone I do it with, they're like, we've never done that. We've never gone through that. I'm working with five staffing companies. and no one has tried to pair up based on my behavioral patterns. And so that's huge. We get the client done first. We understand who they're gonna be working for. And then we go out and then we use that process for the candidates. And what's really cool in Columbia though, when we get down to, yes, we've matched these behavioral traits, which if we wanna go into what makes a great EA, I can summarize that real quick. But here, when we get through that process, we're finding very talented people, people that have great education. great background in a variety of businesses, but the job market's tough here. They're not able to leverage their education and then they want to go, they want a pinnacle job and that's these jobs in the United States. So we're able to pair up highly talented people with the right behaviors with the right person. And that combination is different. You know, whenever I've used recruiters and staff and companies in the past, they haven't done anything like that. And it generates results. It's, it's amazing. And it even, I just, I think maybe you guys kind of saw this too. We get to predict where the friction points are going to be. And we start working on those early on in the relationship and say, Hey, keep an eye on this. Think about that. The EA, you know, in y'all's case, Hey, I'm working for two different leaders. Are there some things that I should keep in mind? Yes. This leader works this way. Every time you're working with this leader work that way with that leader. This leader works this way. And what happens a lot of times in all employment is we're using bias to figure out how to make that work. where with us due to active index, we're using science and it says, is how this person ⁓ clicks. This is how this person clicks. Let's use that when we're engaging and it makes the world a difference. So long answer to what our process looks like, but that's what we do. would say as someone, you know, like when we went through that process and even the follow-up that you gave after, so we hired our EA in June and you know, you. had emailed us some follow-up support stuff, I think in the fall. we, so we got to know her a little bit. Obviously Sean and I know each other pretty well. And I was like, Whoa, this nailed it spot on. you know, it was like the different personalities. just, it just nailed it. So there's definitely something to that science that really helps the process just to make it smoother, but also just a better work experience. And what we found, especially in the executive assistant realm, One big mistake that people commonly make, I made it forever, is we hire people that we like. You know, we'll look at the resume and all the resumes great. And I really liked this person that can come later on down the road, but let's ensure they have the right behavioral traits because that predicts success more than resumes. Nowadays resumes are, fabricated and polished with AI. They, they tell a different story. Sometimes per job they're, they're working that up. The traits don't, the traits are what get demonstrated. And so when we have that nailed down, we know how that's going to work. ⁓ but you know, again, you're a classic example. When we don't hire people that we love, then we also have to give some tolerance and patience for appreciating the way that these traits are and how they show up. But then you realize, ⁓ my gosh, this person is like twice as productive. The one that I've ever had, I'm excited, you you get excited, then you get closer to them and those, that rapport and relationship builds. But we have to have patience and likewise, those, those EAs have to understand who they're working with. Entrepreneurs beat to a different drum and we're pulling people out of corporations. They work for managers. They've got really structured environments and we train them or we bring to their attention, Hey, the entrepreneur may not call you back. not cause they don't. you know, like your value, they're just so busy. They're working on all kinds of things and we need you to help bring ⁓ order to their chaos. But we let them know that they're not ⁓ being ignored or undervalued. And we show them the profile and why they respond that way. And it really helps them build confidence. Okay, I got that now. Now I see that or someone's not abrupt. They're just intense. And you again, you may be able to tell that, but some people read abruptness, especially in another culture as rude, as short, not interested in me. And we're like, no, that is specifically that person and embrace that. And when we do and realize that's just who they are and who they're being, you're going to get this random call and they're going to show you their soft side. And, and you'll realize that they do care about you a lot, but we get in our head, but the science keeps us from getting in our head. And we've seen some really amazing. relationships spawn from that. That's awesome. You know, as being a leader, you we've, you and I both, you know, we've worked in corporate America. We've come to the, the entrepreneurship side. We've gone through, you know, the process of hiring people, you know, in both environments. And I think there's a lot of opportunity when you're an entrepreneur, because you're so busy that you, you maybe hired the wrong person or. ⁓ you're not hiring the right support. So I'm curious, like what do most leaders get wrong when they're trying to find support, especially an executive assistant or some other type of operational help? few things that I see again, especially in a small to medium sized business where we're a smaller team, every higher counts. A lot of us would prefer to have this tight knit group. And, and I again, I think that can come with low friction and alignment and everything else, but We're trying, you we like this family environment. So we hire that person that we like as opposed to filling in gaps that we have. First off, be hyper clear with ourselves. What are my gap and hire to those gaps clear we are on. And again, my gaps were, I am so big picture that I struggle to even communicate with people on the ground, executing people in the trenches. And when I was told that. That was quite helpful that I'm probably not going to be able to modify that at a really high level. So either I have to radically slow down and change my communication, or I have somebody that communicates to, the people that are executing for the, for our teams. But it was a radical acceptance of, I thought I was a great communicator and I'm not. I enjoy this type of stuff, but communicating details. is a massive deficiency for me. And so I own that now and I chain, you know, I'm working toward that and I, you know, I'm making up for those differences. So we got to hire to our gaps. We got to who we are first and we got to hire toward our gaps. ⁓ and that is then understanding that people on the team again, you know, we just look at these profiles and we understand that that's why they're there. Cause we also, the one mistake that I see a lot of times on teams is There, there's a specific pattern of people that ended up on this team and the next person they hire is toward that pattern again, toward the gap. And it's just easy to get into that routine. So by mapping that out, by using psychometrics and really understanding that that's the, that's the single biggest gain is believing that science over skill and, and, ⁓ technique and everything else is going to provide you the best results. I think that there are one to 5 % of people in this world that are hiring that can do it in their sleep and literally can pick the diamonds in the rough. And then there's the rest of us and we need help to cut through the noise and start with science and behavioral traits. And then, you know, get to this next part of cutting through the noise. But, ⁓ so those are things, and then a little technical one in an administrative support and an executive role. We think that. people try to hire unicorns. get all the time. Like I want someone who can assist me in my email and calendar and just kind of, know, the, the dailiness, the, Dan Martell executive assistant, but then they want them to do accounting. Then they want them to do marketing. Like literally today I saw all things marketing. We're hiring an executive assistant, not a marketer. A marketer is good at marketing and all things marketing. And so we have to really pay her back. And I think that's where some of the failures occur. They, they hire somebody and they're like, they're going to do everything. That is not going to work. We really want to figure out what moves the needle over the next 90 to 180 days and then pair the support person based up on that. And it may be thinking you need an EA and you really need a marketing coordinator because so many businesses need that support. Or we separate that. We first get ahead of ourselves on the executive assistant side. And then later on we realized, yeah, we do want to backfill with a finance person, with a marketing person. So JD's read wrong all the time, especially in support. And then lastly, the one thing that I realized that really people need to stop and take care of is wording in JD's matter. ⁓ can't ask for a highly proactive person. And then the next line is. You need to follow all SOPs perfectly. Don't deviate from them whatsoever. And anything that I say, go, you know, is, you know, has to be that way. Those are completely contradictory behavioral traits. And I see them in up 90 % of job descriptions. We completely contradict the true behaviors that we want with the wording that we want. So we either alienate people away from that, or we have radically. ⁓ know, unachievable expectation. we, that part of our coaching process is we just go through the JD and we're like, do you really expect this? Do you expect that? My favorite one is flawless execution. Chad GPT must love those words, or it's like this, you graduate school and they're like, Hey, every job description you ever write, put flawless execution on because that's so like that's reality. You know, we. It needs to be like, Hey, fail forward. That's a growth mindset and something we can coach towards. And someone can say, yeah, I can sign up for that, but flawless execution people quit. They quit applying. They're like, yeah, that person's crazy. And sometimes they are, but so things like that, a broad range of things to look for, but that's what we run into. Yeah. I, one of the unique parts about your process is that mastermind that you run for the talent you place. And I know REA has taken advantage of that and that's something that she's found valuable as well. And it's not just to help them understand US work culture, but it's also to help them thrive in the relationship they have with their leaders. So what led you to create that and how has it impacted the leaders and support team? Yeah, in a few unexpected ways. I want to do that, but we. designed that it was from this story I had in Mexico. Uh, we were talking to this server helping us and she was getting her master's degree in like hospitality. And we said, that's amazing. What are you going to do with that? She's like, I'm to go around to all the restaurants in this area and consult on their SOPs and really help them perform at a high level. I was like, Oh, that's awesome. Even better. You can write one SOP and then AI can write all the next ones and you can crank these things out in 10 minutes and charge a couple thousand bucks. And she looked at me and said, what's AI? And I, I honestly started crying. I'm like, are you kidding me? You're going through the process of getting a master's degree. You are upper echelon of like drive in this world and you haven't been exposed to that. Now it was two years ago, but it was still out there. And I just realized I want to empower people out, you know, to follow our mission. want to positively change the direction of people's lives. I want to somehow play a big role in that. And we were kind of deep into AI. So I realized we need part of our program to have AI education. So when we concocted the idea, I like, how am going to serve the business and then the candidates? And then I also needed to sell against something. So when you call up a staffing company, they're going to say, Hey, we're the best culture in the world. Okay. We have all these team events for our people. have all this coaching available. We have all these classes available and. I haven't found it to always play out to be that way. I haven't seen it translate all the time. And it's also a lot to ask for the, the, the employee, the worker to have to adopt that culture fully and then have to adopt your culture fully. But I knew it was going to be something that was going to be, ⁓ it was going to be an objection. And so that's when we concocted this manager's mindset, a mastermind that we realized we needed to have something to fill in those gaps. If someone was going to say, yeah, but you don't, you guys don't have ongoing training. I'm like, yeah, we do. have a mastermind. And we train on what's relevant right now. We actually sit there and solve business problems with group think. mean, imagine having 40 different EAs in all kinds of different businesses. And one of them, part of the mastermind is, Hey, who's got a problem that we can solve as a group. And I do think that AI solves problems pretty well, but I would way rather get a solution from an entrepreneur on what's worked like that's battle tested. than AI, AI doesn't battle test stuff. And so the same thing with EAs, when you get them together, they're like, this problem comes up, whether it's a, you know, how they deal with their manager, whether it's a, a technology solution or whatever else. And the EAs jump in, you know, I had that hardship with my manager, they weren't available. And here's the way that I tackled that. And so we solve each other's problems through experience and through real time solutions. And it's, it's amazing. So I was using some techniques from entrepreneurs organization to do that, but that is why we launched out, why we ran it. The goal is to always address us work culture and to make sure they're fully prepared. Every other session is AI. We remind them if they are AI equipped, this going back to that person in Mexico. If you're AI equipped, you've got a long road and a big runway ahead of you. There's going to be so much opportunity for you, but you must stay current. Like we have. got to stay cutting edge. And that's what we wanted to deliver was that experience. And then to do something that maybe they do in Sam and Kate is I'm not so sure, but to get everybody together and let's, let's problem solve together. We've got some executives, we've got finance people, we've got EAs, we've got some marketing people. So you can throw all kinds of problems into that bucket and they get solved quick and, and good solutions that then fine, take it back to AI and maybe suss it out a little bit more, but we've, we've reveled in that. And we get amazing feedback from the assistants and really from all the personnel. But the one thing that we found out in our survey that blew my mind was they love it, live coming to that because they don't feel alone. And remote work life can be lonely. And we got to remember that, the company is as hard as they try. The best cultures, still it's remote work. And the one way that they didn't feel lonely is we share problems that we're having. We'll go through every person. What's a problem that you're having right now in your work. And at the end of it, we get message after message. Wow. I thought that was just me. I thought I was the only one who wasn't getting departments to respond or, you know, I messed up here or this. And then you find out four other people last week did that same thing. And that's nice that they feel human and that that it's not their fault and that they're actually are doing a great job. And so we, that's inspired us to really. And sure, have high tenants and to keep people there because we know that they feel less lonely and they also realize we all make these mistakes. This is not you. This is just part of the process and the hard work that you're putting into it. So, I, I know REA personally has taken a lot away from it. And I, know, there's been times, a couple of times she's come away from things in those meetings and it's like, and it's a solution right there. You know, she got an idea from somebody of how to make something better for us. So. You know, I love that concept of, you know, people helping people, right? And I, you know, it's, know it's kind of simplified, but it really is right. It's, it's just getting everybody together in a room and saying, how can we solve the problems that everybody's having, you know, so that everybody can perform better. Right. You know, one of the things, just kind of shifting gears a little bit, one of the things that we briefly touched on in the intro is you guys's decision, you and Amanda's decision to move to Columbia. And I know that's a very, very big part of your story. You know, I'm curious what. What prompted that decision and what kind of was going on in your life that you guys were like, this is where we need to go and here's why we're going to do it? Yeah. Yeah. It's amazing. Like one of the things that we've kind of adopted as a family is that hardships allow us to be creative. You know, when you're going through a hard time, you have to get kind of creative. Okay, are we going to move to Columbia? Okay, yes. Now what are we going to do? How are we going to live? What does this look like? Or, you know, in our case, know, Sean was laid up. You know, I, had a mountain of bills and I was like, okay, I already have a full time job. I'm going to do something on the side. And this is how Gold Bear Beanie was born. so, you know, struggle isn't bad. It, you know, pain gets us to move and often it's in a direction that we wouldn't expect or maybe wouldn't have chosen for ourselves. But it sounds like, you know, a lot of times it can be very fruitful and very exciting to see where life kind of leads out of those painful moments where you do have to kind of shift off the tack. a little. So as you've been growing higher options, what's been some of the biggest challenges that you faced? Yeah, thanks for sharing that. It's, you know, the only time I've spent a significant portion of time in another country, I was a lot younger. was in college. I spent six weeks in China, you know, and it's like you get over there and when you don't know the language, right, you definitely, you definitely feel like an outsider, right? And you watch people have conversations and, you know, look at you and you know, waiting for you to respond. And then they realize like, you don't understand what's going on. And so, yeah, that's definitely a challenge. You know, I'm curious looking back at your career and now running your own business. Is there anything you wish you had understood about leader and growth and building the right kind of support around you that. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. My, it's interesting. Like my first introduction to personal coaching was in 2017. Right. And it, it's, really changed me a lot as a human. you talk about that resiliency, you know, 18 months later, after I went through that coaching process was when my back surgery happened and our family went through all of that stuff. And I, I very much to that, had I have not gone through that coaching and that personal development to build that in myself, I don't know where our family would be, you know, because I mean, when you go from, you go to this point of like, I'm, literally laid up and I need the help of everybody else. And if I can't get to a point of really just being able to accept that, like really, really quickly, I'm going to alienate everybody around me, right? But I learned how to, you know, take those moments and speak to my own personal needs and, you know, to be able to help everybody get through that. yeah, the personal development side, just, cannot speak enough to the value of it for anybody who's listening. It's well worth the money to do it. exactly. Well, thank you so much for your time and your thoughts into this. And I hope if you're listening, definitely reach out to Jason. Even if you're thinking an EA might be an option for you, just reach out to him and just get the conversation going. So, all right, thanks, Jason.