May 28, 2022
E58: Beat Boredom with Jordan Benjamin

On today’s installment of the RRH, former Hubspot human and founder of MyCoreOS Jordan Benjamin and I dig into one of the most pervasive mental traps of selling: boredom. And how to beat it.

Topics Discussed: 

On today’s installment of the RRH, former Hubspot human and founder of MyCoreOS Jordan Benjamin and I dig into one of the most pervasive mental traps of selling: boredom. And how to beat it.

  • Boredom is a mental trap (3:46)
  • How to beat boredom? (9:05)

Resources Mentioned: 


[00:00:00] Amy: Uh, what's up human. Welcome to the revenue real hotline. I'm Amy Rahab check.


More importantly. I'm excited. You decided to do. Today. I know you've got a ton of options and I appreciate you. This is a show about all the hard and uncomfortable conversations that arise while generating revenue and how to think or rethink what you're doing, why you're doing it. And then of course, how to execute differently.


And like I said, I'm happy you decided to come along for that. Don't forget to follow the show wherever you listen. So you can be notified each time a new episode drops. And do me a favor friend. Don't tell anybody about the shell. Let's keep it our little secret. I'm Amy Rahab check. This is the revenue real hotline enjoy.

Conversation Start



[00:00:57] Amy: Oh my gosh. Jordan Benjamin. Welcome to the revenue real hotline. Thank you. Thank you. Thank you for making time for us today. 


[00:01:04] Jordan: I am excited to be here. I think there is a lot of power to what you're talking about. 


[00:01:10] Amy: I love that. I love how I have an audio record about that excitement. You know, if we, if I push the envelope too hard, I've made point is back at this moment.


Just, just do me a favor. Just hold onto the sentiment, sir. 


[00:01:22] Jordan: I love 


[00:01:23] Amy: it. Oh my gosh. Okay. So tell him, why don't you tell us a little bit about you and the work that you're doing right now. 


[00:01:29] Jordan: Yeah. So I stumbled into sales a bunch of years ago and had been at HubSpot, uh, after getting laid off twice from two startups within about six months of each other. Uh, decided to follow my girlfriend to Boston and joined the HubSpot team.


And they were about 700 employees. I think we're like 5,500 now pre IPO, uh, and had been working in the sales round there for quite a while. Um, coaching different businesses. But my deep passion has really lied around a yoga instructor. I've been practicing meditation and mindfulness for many years, and digging into a lot around my own personal development performance.


Uh, and how do others do that? And so I've spent a lot of time helping other teams think about, you know, how do they manage mental health? How do they be resilient and bounce back? Uh, with my own business called my CoreOS on my podcast, peak performance selling where I love basketball. Beyond the tactics into some of these like real conversations, uh, that have actually impacted our lives.


So that's where I've got my hands in a few different cookie jars right now, 


[00:02:32] Amy: bunch of it. Okay. I'd love that. I, you know, it's funny. I didn't realize that you were at HubSpot until today until I was like taken into your background. Just didn't even cross my radar. Now what's interesting to me is that in the past, that would have been something that just like jumped out right away.


But the only thing. That I have up until this, I would say earlier this week associated with you, Jordan is you're one of the mental health advocate champions, right. In this space. And it's been an absolute pleasure, right. To watch what you're producing, to listen to what you're producing and to know. The impact that you're having given how few of us there are still at this point.


And so on the off chance, you haven't heard it yet this week. Thank you, sir. Thank you from my heart to yours. Thank you. Thank you. Thank you. Okay, so you're very welcome. You're very welcome. 


[00:03:20] Jordan: Always welcomed that I think most people don't hear that enough. So I think there is just more of that needed in this world is call out when you see people doing right, it will reinforce that in your.


And become super helpful. So I thank you 


[00:03:34] Amy: as well. You're very welcome. And this is, this is really why I started a podcast. I have the kudos to whom I deem where they, which is very different criteria. Um, but anyways I kid, all right. 

Bordem is a Mental Trap



[00:03:46] Amy: So Jordan, one of the things I'm like on the fence about telling you why I'm asking this question or like telling you after the fact then in this moment, I think I'm going to lean to towards after, right?


So just know that there's, there will be a reveal at the end of the. But you wrote a post today on curiosity and specifically boredom, and I'm going to read it to our audience or to, to the audience here, if you don't mind. Okay. So listen, her friends, this will be in the show notes, but I'm just going to read Jordan's post. Again this is from today, which is January 18th. As of recording. When was the last time you were truly curious about something. For sellers, especially after a year or two things can get boring. You feel like you've had the same conversation over and over again? You know what they're going to say before they say it. You've already got your response ready. This is an easy way to get lazy, lose deals, and be bored. What would it be like if you went into each conversation curious, just like it was your first. If you chose to be curious, You would most likely listen more actively come up with more value and added responses. Build more trust. Find more joy in each conversation, learn more. It's up to each of us to choose our reaction to any situation. Curiosity wins, blah, blah, blah. Be more curious X mission points. 


Okay, so now speaking of curiosity, Jordan Benjamin, why was it that prompted this post? Like I need some deets here. What got you writing about curiosity and boredom in particular? 


[00:05:20] Jordan: Well, there's probably three things that go into that. Um, one, sometimes I find myself sitting in the conversation saying I know exactly what you're going to tell me. And I'm staring out, not really paying attention. And realize that is not really how a professional would act or. The other one, uh, the one that really kind of prompted me as I've been spending some time with little kids lately. And getting a chance to watch how they operate in the world, how they look at everything with this sense of wonder and curiosity. I realized I just don't do that in many of my processes. And somewhere along the way that had kind of just left my psyche. And so I think watching those kids and how they operate. And then last one is I talked to a lot of professionals that, you know, if it ain't broke, don't fix it. Or things have been working well enough where they're scared to make a change or where they're scared to even open their mind to a new idea.


And I'm a huge fan of Carol Dweck and her growth mindset, always thinking about how do we learn and challenge and grow. And it's so easy to say, well, I'm already good at this thing, so I don't want to change. I don't want to, or I know it can't do something else when we haven't ever actually examined it for ourselves.


So I'm going to use one word and it's one of my favorite words I've ever heard. And it's a, he passed CECO. And it comes from poly or kind of what predated Sanskrit from the Buddha. And essentially it means, and this is teaching from the Buddha. It's like go search for yourself. Many of the just read something and take it as gospel or hear something, but we don't actually go explore. We don't actually go try things for ourselves to see what really resonates. And I think that's where this curiosity has really been a foundation for me to say, this is how I can find fulfillment in my role, how I can sell better, truly be a professional and also just stay engaged. 


[00:07:21] Amy: Yeah. So yes, to all those things.


And what I would add to that is that when we're able to show up in conversations and convey curious, Think about what that feels like on the receiving end. Right. And think about the experience that you're giving to your buyer when you truly are fucking curious about what they have to say, which is by the way, next to impossible to.


Holtz, discloser. I'm working with Andy Paul on his book launch rate sell without selling out, run into with the new strategy called the launch team. And the second pillar on sell without selling out is curiosity. So it's been a subject that's been on my mind, Jordan for awhile. 


Okay. Now, back to why I brought this up, I'm working on a book. And it's the operating title now is called sell well, right. Wellness. And essentially it's like how to avoid the mental trap. It's sucking the best of us. Okay. And now when I think about one of the bigger traps that eventually got me, boredom Was it. When I left though, the biggest reason was because I was born. I mean, like I, I was working in law firms and I had a big meeting downtown. I was living on the upper west side and I was literally putting the deck together and the cab ride on the way down. And I was like, you know, Okay, so I'm going to pause there.


I'd like to talk about this of, from a mental health perspective. It's so it's great to be curious. It's great to have that beginner's mind. It's great to keep an open mind when we, when we go into new conversations with different people, right. With the knowledge that there truly is something here to learn, even if it's what not to do.

How Do You Beat Boredom?



[00:09:04] Amy: Or how not to think, but that said, how do we combat that boredom? That is fucking real. Oh, by the way, you are allowed to curse on the showcase you had to notice. Um, but yeah, what say you, sir? 


[00:09:15] Jordan: So for me, this concept of curiosity also came from one of our early sales trainers and leaders at HubSpot, Andrew Quinn, who talked to me about an attitude of curiosity.


And I think there's this really nice foundational element when you think about, you know, showing up to something with an attitude. And a specific attitude of this curiosity concept. And so for me, I think it comes back to this story that we tell ourselves, like so many of us have stories running through our brain.


And if I sit there and show up every day saying I'm just punching the clock, I need to talk to these people to get their money. Life becomes really, really boring. But yet if we see an opportunity to add value, to uplift others, to give back, now all of a sudden we see a purpose that goes beyond ourselves. That is much more empowering and inspiring.


And so if I'm there realizing that most of the people that I talk to every single day, I have more broad perspective across an industry across how other businesses operate then that individual person does. And so I've got a ton of value to add. And so I can actually help them run their business better, sell better, move, more effective if I can show up fully. 


And so for me, I think part of this curiosity and engagement is a way for me to be engaged and add value and give to others because now the story in my head is about, well, here's how I'm supporting others. And by offering and giving value is usually when valuable then come back to me and return.


And so for me, as I think about the mental health side of it, this is around the stories that I tell myself and taking more control of it. Creating something that's more empowering, more inspiring And that focuses on giving versus just how much can I take every single day. He's 


[00:11:01] Amy: driven. That's pillar number four, generosity, the generosity plan.


Um, okay. All right. But still I'm going to push back a little bit. I heard nothing in there about it's a grind when you've have, are having. Near identical conversations or after you've been doing it for a couple years and you know, you're looking for new ways to spice it up. And after each meeting, it's still like there's there's and now I'm going to point out, I think it was, um, Whitney Johnson.


She wrote a book called disrupt yourself, and she was a mentee of Christiansen who wrote the innovator's dilemma that just passed away last year. Thank you. Thank you. Thank you. Over at Harvard. Anyway, so she worked with him for many years, and then she wrote this book on disrupting yourself. It hit my radar because Andy had her on his show.


And I was reading about this learning curve, right? When you're used to learning at a pace where you're just up into the right, you know, Takota silly like revenue concept when you plateau, right. It can feel. Rough in that you're customed to continuing to go up. And so I'm gonna, I'm going to ask for a little bit more, like how do we help sellers avoid this mental trap of boredom when you are truly curious when you are hungry to learn when you are in it for the right reasons about helping other people, but at the same day, you're having the same conversation over and over again.


[00:12:33] Jordan: Yeah. So I love that you pushing back on this, because I think that's where just as much as with the prospect, we actually start to find like some of the more real reasons, you know, I, I come back to this personal choice. I think one of the things that I talked with a lot of folks about is how our school system has not really set us up to be independent as learners, to take control of our own potential and opportunity.


How has human. You look at most, any other animal species, they do not have a mom or a parent figure or school administrator telling them what they have to do when they have to do it until they're 18 years old. And so we've been conditioned into this. Oh, well, somebody else has to tell me what to do. And somebody else is accountable for my learning or I got through school and like, my learning is done.


And as I work with a lot of new hires and trainees, it's like, Hey, you got through our month. One new hire training. Now things are just starting now, the learning is really just beginning. And so for me, when I find folks that are really seasoned top performers, how do you start thinking about working with somebody else?


You know, how do you start training? Because that's when we can actually learn the best as I've worked with some new hires in the last year or two, it was like, oh, there's some bad habits that I have that I really need to, uh, change or that I didn't even have awareness of when I'm thinking about, well, what would I teach somebody new in.


Well, here's what I do, but don't do that. And so I think there are a lot of other ways that we can think about, you know, training new people, uh, refining our process, or maybe it is time to find a new challenge, you know, to find a new area that doesn't have to be a new job, but is there some sort of additional responsibility that you can take on where you can flex your superpower?


You know, we all have our own unique strengths and abilities and weaknesses. I've. But if we can really look at what are our unique strengths and where can we bring that value to the, 


[00:14:25] Amy: not me, I don't have any weaknesses I have, I have mastered every there's absolutely nothing else to learn. And, you know, I know this is only your first exposure to the Ms.




[00:14:36] Jordan: It's already coming through


[00:14:42] Amy: that wraps in other installment of the revenue real hotline. I'd like to thank Mike. For being so damn real and for sharing their insights and for, of course being so much fun. And I'd like to thank you to listeners. It means the world. And I appreciate you. If you have any thoughts or comments or experiences, you feel inclined to share head straight over to revenue, rail dot.


There's a new join. The conversation feature on the right side of the page. I am all damn ears. Final thought. We are introducing a coaching aspect to the show. So anyone who's brave enough to dig into an account strategy or outbound strategy set. That's where we kick things off. Please do follow the show wherever you listen to your podcasts.


So you'll always have the latest episode down. If you want to contact me, I'm at Amy ad revenue. If you want to follow me on social, Twitter is Amy underscore Rahab check, and LinkedIn is Backslash Amy Rahab check. This episode was produced by the fabulous Nian Fiedler you rock, man.


And I appreciate you too friend. And of course, whatever you do, don't tell anybody about the show. Let's keep it at our little. Until next time, all I'm Amy Rahab check. This is the revenue real hotline, happy selling.


Amy HrehovcikProfile Photo

Amy Hrehovcik

Host of Revenue Real Hotline Podcast

Jordan BenjaminProfile Photo

Jordan Benjamin

Founder @ MyCoreOS | Host of Peak Performance Selling Podcast