E182: Positive Mindset with Libby Gill – Part 3 of 3

January 8, 2024


How do you define positivity in your life, and how does it impact your overall well-being?


This is the third segment of the conversation I had with Libby. 


In Part 3, Libby and I talk about:

  • Self-awareness is key
  • Libby’s Hope Theory
  • Positivity for success



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Connect with Libby on LinkedIn


Libby’s Bio:

Libby Gill knows change. She grew up on two continents and went to eight different schools before putting herself through college waiting tables. Starting her career as an assistant at Embassy Communications, a television company founded by the legendary Norman Lear, Libby survived three mergers to emerge as the head of publicity, advertising, and promotion for Sony’s worldwide television group in just five years. 


After her first career heading communications at media giants Sony, Universal, and Turner Broadcasting, Libby founded LA-based Libby Gill & Company, a leadership consulting and executive coaching firm. She guides individuals and organizations to lead through change, challenge, and chaos by deeply engaging employees in a shared future-focused vision of success. 


In her consulting, coaching, and keynotes Libby helps her clients:

 Reframe change as an opportunity for massive growth

 Re-energize your best performers to reach their full potential

 Reinvent your corporate culture to embrace ambiguity


Her clients include Abbott Medical, ADP, Disney, Ernst & Young, Facebook, First American Insurance, Hyundai, Microsoft, Sony, Sutter Health, Viacom, Warner Bros., Wells Fargo, as well as non-profits and small businesses. A global speaker, Libby has delivered keynote presentations on three continents and in 36 US states for organizations including Acura, ADP, Bank of America, Capital One, Cisco, Disney, Honda, Intel, Kellogg’s, Marriott International, Medtronic, Royal Caribbean Cruise Lines, United Healthcare, Vanguard, and many more. 


Libby is the author of five books, including the award-winning You Unstuck, Capture the Mindshare and the Market Share Will Follow, and Traveling Hopefully. Her latest book is The Hope-Driven Leader: Harness the Power of Positivity at Work. A former columnist for the Dallas Morning News, Libby has published book chapters and peer-reviewed articles for numerous journals and trade publications. Business leaders including 
Zappos.com CEO Tony Hsieh, Stephen M.R. Covey, Dr. Marshall Goldsmith, and Dr. Ken Blanchard have endorsed her work. Currently, she is co-authoring a book about Rice University’s Doerr Institute for New Leaders with former Brigadier General and Director of the Institute Thomas Kolditz, Ph.D. 


A frequent media guest, Libby has appeared on the CBS Early Show, CNN, Inside Edition, NPR, the Today Show, and in BusinessWeek, Time, the New York Times, Wall Street Journal, and many more. Libby lives with her husband in Los Angeles and is the proud mother of two millennials sons and step-mom to a step-daughter and step-son.


Libby’s Links:

Website: https://libbygill.com/


Her Books: 
https://libbygill.com/books/


Twitter: 
https://twitter.com/LibbyGill


Facebook: 
https://www.facebook.com/meetlibbygill/?eid=ARDsv9uLoyb6ydPiTE7c3FWQucwW5VT6lY1kZObvuVbR2QYh3Moo4aBZep8Xma0qTbgBnGeAxlmNCM_N


Youtube: 
https://www.youtube.com/channel/UCzRyNbIN3VEQ-CFdqyJFPZA?view_as=public


LinkedIn: 
https://www.linkedin.com/in/libbygillleadershipexpert/

  • Show Transcript

    Jason: Welcome back to the sales experience podcast. Welcome to part three of my conversation with Libby Gill. She is a force and I appreciate so much what she’s doing in the world. Focusing on positivity, leadership coaching. Make sure to subscribe to this show so you can get all the future episodes and if you haven’t, make sure you check out parts 1 and 2 of my conversation with Libby because it’s just a continuation. We’re just on this train and at the end, she’s going to share her links, make sure to check out her information and support her in whatever way you can and get support from her. She shares an interesting quiz that she has on her website that might be useful. So stay until the end and here you go. Part three.


    Libby: That to me is fascinating. I started to be a marriage therapist and I grew up in a family of strengths and thought, you know, they’re just pretty nutty. I don’t don’t want to do that. There wasn’t a positive psychology back then or I would have done it, but, and so I went the other way, but I’ve always been fascinating. On the marriage of brains and the workplace, how does, how we think affect what we do and choices we make and how we act with others?


    Jason: Yeah, and I think really the big key is if self awareness of who you are, most people aren’t, but even as a manager is being able to discover self-awareness for somebody else. It’s like you’re saying somebody might be on the autism scale or anxiety, they might not know it or understand what’s driving them, right? Their anxiety and their brain is driving the questions and the needing to know and needing to control everything. The manager views that as a pain in the butt, but when the managers can learn how to assess that and see it not as a way to judge and then pigeonhole people, but to see it become aware and they’ll go, okay, be empathetic to where it’s coming from first and then second, how do I get that person into the right place? Whether it’s in sales or it’s in another team within the organization based on their skill set and the way their brain works. How do I point them like a weapon? At a different thing that then makes them happy, benefits the organization, benefits the customers and so on.


    Libby: Wouldn’t it be so awesome if everybody thought that way? I’ll tell you, when I was in entertainment, it was still a, you know, there’s somebody cheaper and younger than you are, so don’t let the door hit you on the butt on the way out. Thanks. And it really felt like that. And I did feel like I had to, you know, put on the suit of armor to go to the office every day and it was wearing, it’s changed to some degree. And once I got out of that, I saw a lot of companies where people really cared about, you know, are my people thriving? Are they growing, are they developing, do they have the right training or coaching? And that was to me was that was a revelation that was a breath of fresh air. And that’s about the point where I said, Oh, I’m going to take the skills that I had and apply them over here. And I always had a team of young green people. And my job was to, cause what we did was very labor intensive. You send somebody out to the set of, you know, law and order and married with children to babysit a news reporter for three days. I wasn’t going to do that. So you had to train these young people to become real professionals. And I love that. How do we turn them into leaders? How do we make them better at what they are? And that was the fun of it.


    Jason: So let’s segue, cause this seems like a perfect place cause I really wanted to talk about one of your projects, one of your focus, which is the positivity and the power of positivity and your hope theory. And I think what’s interesting, obviously the world needs more positivity and most people feel that way, yet it doesn’t happen. There’s this weird barrier between we want it to be positive, we want our team to be excited, we want our employees to be happy and positive. Sometimes that’s where that stops. It’s just a nice thought.


    Libby: Yeah, it’s kind of a, wouldn’t that be nice if, but it’s too much trouble and there’s no bottom line, a reward, which in fact I think there is. And there’s been a lot of demonstration of that. Now. I discovered this, I wrote a book called traveling hopefully years ago and it was sort of about my journey of in life and work and I grew up in a family with an alcoholic parent, a mentally ill parent. It was a Rocky road for a long time for me. And I kind of grew myself up at age 18 and the day I started my first real job working for Norman Lear’s production company, which was really cool. He’s the all in the family and all those great sitcoms. My stepmother committed suicide and so there was this huge disconnect with work and family and you know, it’s just a mess.


    Libby: And so I wrote that book and it was about hope was kind of the idea of tomorrow is going to be better and I just believe that in my gut, Tomorrow is going to be better. This is a really bad day, but tomorrow is going to be better, a little better, a lot better. I don’t know, but I’m just going to keep moving forward. And that was my mantra. I was just what I believed. If you had hope and you had the right tools, so it just became hope and tools became sort of my inner mantra. And then later as I became a coach and I did tons of research and reading as I still do, I know you do as well to see what’s going on out there, you know with other thought leaders and experts and books. And I discovered hope theory, which is comes from science and comes from the medical community and positive psychology.


    Libby: And it simply boils down to having a vision of the future that is lofty and ambitious and ideal, but also grounded in reality. Like, Oh we can get up here, but there will be bumps along the way. If you’re setting the bar high, it’s not going to be easy, but it is attainable. And when you can paint that picture of for people and a lot of great leaders do this. We’re going way up here, not going to be easy and the next six months or the next two years or the next whatever, we’re going to hit obstacles and we’re going to have to overcome them together because this vision is important and we’ve got that strategy that’s going to take us along. And that’s really what hope is. And the word itself comes from old English, the word hope Aeon, which means to leap forward with expectation.


    Libby: And that just caught me, I just thought, yeah, that’s it. That’s it. It’s that belief. And there are some amazing studies about people that identify as hopeful, their mortality. They live longer. I mean they, they can self cure. They’ve got, and I’m not saying you can cure all diseases, but their outcomes medically are much higher because it’s not just a mind over matter, but in fact physiologically they release brain chemicals like endorphins and enkephalins things that boost their immune system and suppress pain so that they can in fact go through painful rehabs and treatments. And so it’s really fascinating what our brain can do and literally healing ourselves, making ourselves better. Can you look at those people who do, you know, swim channels and it’s like, how do you do that? Well, they believe they can do it and by gosh they do. And that’s why the mile, you know, how the mile that people run gets and sports teams, I mean, come on, I got to change all the rules in baseball and basketball because everybody’s so much better than they were a year ago or a decade ago because they’ve got, they see it and they just get better at it.


    Libby: In fact, when athletes or musicians practice their sport in their heads, like you know, you’re on a piano practicing your concert or shooting free throws, the same part of your brain activates that it would if you were actually in that event.


    Jason: Yeah, I mean I’ve seen that in the like, you know, reports that show MRI readings of somebody thinking about that event and how active their brain is. And it’s all that hope. And I think what’s interesting too as you’re talking about the hope and kind of the struggles in life is bumpy, but one more day, you know, tomorrow will be better. The thing that I learned and I try to remind everyone as if you’re listening to this podcast right now, I guarantee and can save for sure that you’ve survived 100% of your bad days, right? If you’re here right now in this moment, you have made it through everything that life has thrown at you so far by definition. And so you know that I love marrying that with what you’re talking about, which is you know it. Depending on what you’re going through right now, tomorrow will be better, like to hope that tomorrow will be positive.


    Libby: Well, and you know Jason, I just joined the board of, this is near and dear to my heart, but of a, an organization, the nonprofit board called the DD Hirsch mental health services and they developed the first suicide prevention center and call line in the United States. They are world leaders in this and in fact they’ve done it. It’s a repository of research about mental health and suicide and they have studies about people who’ve attempted suicide. It’s almost but not succeeded. It’s nearly a hundred percent of people who say, the minute I try, I did whatever I knew it was a mistake and I wanted to live and we do have this inborn thing we want to survive. And when you can get beyond the mere survival and get to that level of, you know, the Maslow’s pyramid of self actualization and life gets really exciting, but it doesn’t get that way overnight or necessarily early. I mean it was, I was into my thirties before I even thought all this stuff was doable, but I know it was worth giving it a shot. And then life started to get fun and now it’s, you know, this is what you hope. It’s better than ever. As you grow older, things are more fun and more exciting and richer and that’s the way you want to keep going forward. 


    Jason: Now for people who are in sales, this is obviously a sales related podcast. They may be wondering like what the heck are you guys babbling on about with the mind and hope and positivity. But it all connects back to where we first started about which is the mindset, especially in sales because sales is 100% a mental game, right? So first you’ve got to stop running from the tigers and lions and bears that you think are chasing you when you’ve got to pick up the phone and call that person back. So you’ve got to get past that. It’s all a mental game. It’s struggle, it’s fear, it’s concern, it’s doubt, it’s self awareness. And so all of that is the hope and the positivity and knowing like, okay, I’m going to make one more call. And then I think the biggest lesson for this is is taking what you’re talking about and then tying that into the kind of the empathy and projecting out and remembering that everybody in life is going through something at this very moment.


    Jason: It might be at the tail end, it might just be starting, they might be in the middle of it. I’ve been in some situations where like internally I am just on fire because stuff is exploding in my life and I’ve got to kind of set that aside in public face because that’s not person at the grocery store, you know, they don’t need me lashing out at them. Right. And hearing about it. And so as a salesperson, a lot of times I take it personal and just always remember if you’re going through stuff, everyone else is going through stuff and just do your best and make it positive and hopeful for them and everybody you’re dealing with and try to make their experience better. And which will, by default, I mean I know one of the things I heard was if you’re in a funk and you’re feeling depressed or anxious or worried about things, one of the best things to do is to go do something for somebody else and give to somebody else. And if you’re in sales, it might not seem like, okay, well I’m gonna sell somebody to make money. But like if you can give them the gift of you helping them and being a professional and consulting them in some way and helping them achieve a better situation for them, you will then get that gift in return.


    Libby: You hand them the right product or service and a good experience doing it, then you’ve absolutely improved their day and your own sales people. It can be very high stress profession as you will know. So I also think you’ve got to find that repository of how do you replenish, how do you rebuild whatever it is you need to do. Cause like you said, you’re 100% on, but on your off times really nurture yourself and find whether it’s sports or fitness or spiritual, whatever it is, music that refills that so you can come back to the workplace and back into that feeling good about yourself and handling and managing that stress.


    Jason: And it’s interesting because we’ve talked in the past and prior to this and there was something you had said about being an extrovert and kind of in that, especially like I think you said a situational extrovert where it’s depending on what you’re doing if you’re on stage or speaking to a group or speaking to a company. And it’s funny because I’m that same way, like with the group, I’m one way by myself, I’m different and there’s a term that I heard which is called ambivert, which is not an extrovert, not an introvert. And there’s a lot of people in sales who feel like they have to be an extrovert, but it’s not who they are. Or they can do it and then they feel bad because they’re like, otherwise they just melt into nothing. But I think it like you’re talking about that self awareness and understanding and knowing who you are in this situation and then what you need to recover and recharge your batteries and then go back out there and play the game again.


    Libby: Do it again. Yeah. And just finding the joy in the little moments to this, you know? Yay. I closed the deal. I made a sale, I had a good day. There was no traffic, whatever that is that you can at the end of the day say, yeah, I did my job, I felt good about it and tomorrow’s going to be even better.


    Jason: And when it doesn’t go your way, just understand like you said, tomorrow will be tomorrow could be better. Positive. That’s great. Well I, you being on the show, this has been fascinating cause I love, again, I always love talking to somebody who started out in their career in one place. Right? So you’re in media, you’re in PR. I mean that’s, you want to talk about sales, that’s some sales stuff right there because you’re, you’re the ultimate spin master. And I think, I know in another life I could’ve been in PR because that same spin that you do in sales or with products and services and management, like sometimes you’ve got to spend some really bad news in a positive way for the team. It’s all PR. And so I appreciate that. And this has been fun. Where’s the best place for people to find you? The work you’re doing reach out to you. Where’s that at?


    Libby: Just go to my website, libbygill.com L I B B Y G I L L and I’ve got a really fun thing. We didn’t get to it, but I’ve got a leadership assessment if you want to see what kind of leader you are and on four different scales, we’ll see where you fall in each one and what that means. And it’s, it’s really relevant to sales folks to see. I’m this kind of a leader on this kind of a communicator. So that’s fun and always happy to hear from any of your listeners. Just shoot me an email. All my contact stuff is on my website.


    Jason: Perfect. And what would be like outside of what we’ve talked about, what would be one thing you’d want to leave everyone with or have everyone focus on?


    Libby: Oh, that’s such a good question. I think there’s a statement. It was the quote that I used to title my book traveling, hopefully. And it’s a Robert Louis Stevenson quote and he said to travel hopefully is a better thing than to arrive. And it’s just that sense of as we go through the, you know, the good and the bad and the ugly as we go through it. We’ve got to find some joy and some beauty in it and service to others. And you’re right about that. Nothing makes you feel better than that.


    Jason: And when you’re joyful, not just happy, which is conditional but joyful, you can get through anything you see the best in every situation or understand that it will always get better. So thank you for that. And Libby, thanks for being on the show.


    Jason: And for everyone listening, obviously we’re going to put her links in the show notes. You can go to cutterconsultinggroup.com to find that, check her out, make sure to reach out to her if you have any questions, needs check out that leadership assessment, which is great. And as always, keep in mind that everything in life is sales. And people remember the experience you gave them.


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By Jason Cutter August 27, 2025
Most businesses struggle to grow their sales teams. At some point, they give up on looking for rock stars; they just need a team that shows up every day. In fact, research shows that 52% of sales leaders list recruiting as 'very challenging,' and average sales rep turnover hovers around 26% annually. That means for many leaders, the hiring process feels like a revolving door of wasted time, lost revenue, and constant stress. Here’s how to achieve scalable hiring results without having a massive hiring team and a huge job marketing budget. What Most Companies Do They need to hire salespeople. Maybe it’s one. Maybe it’s their very first salesperson. Maybe they need 10 more. So they: Write a job post about all the things the job involves and who they are looking for, and the type of experience they feel is important Put it on Indeed and/or LinkedIn They get hundreds and hundreds of applications They freak out – stressed at the thought of going through all those submissions They have someone on the team spend hours/days going through all the submissions. Have them call and email everyone whose resume fits what they think they want. A few people respond. So they call again, to ‘check in’ on the candidates to try and get more to respond. If that works, they have dozens and dozens of candidates ready for the first interview. Someone has to then take a week’s worth of time blocks away from their actual job to do first interviews. Most of the candidates don’t show up to the call/meeting. A few candidates make it through to the second interview. The boss or sales manager takes these. Two out of the three show up. Offers are sent to the two. One takes another job because the process took so long. The company ends up with one new hire The company repeats the process over and over again, feeling like the best they can do is one to two new hires after each complete cycle of hiring madness. And it is madness. It is also the definition of insanity – doing the same thing, running the same hiring process out of some playbook that no one can point to its origin or actual stats of success. Recent surveys confirm this frustration: more than half of leaders admit they lack an effective hiring process, and many acknowledge that their comp plans don’t even align with the results they want. The result? Slow hiring, bad hires, and retention issues that eat away at growth. Most companies struggle with filling their sales team, with both quantity and quality. They probably run the hiring process like they run their sales process. They default to old-school business thinking that the only way to hire is to just get experienced salespeople to join the team. But there is a better way. I have spent over 15 years being tasked with keeping teams filled with salespeople. Whether it was for inside sales in a call center environment or work from home, to retail environments, from consumer products and services to B2B, from within the United States to offshore, this framework works, even if you have failed in the past to try and scale your hiring efforts. In working with small and large teams, the key is the balance of quality and quantity. Humans will always surprise you. I have seen the ideal candidate – on paper – be completely ineffective in the role. I have seen reps with very little experience, whom we took a chance on, completely outsell their experienced co-workers. The experience of everything that goes into hiring over 800 salespeople, this framework is designed to help you succeed no matter the size of your hiring team. Here’s how to create a scalable hiring process that doesn’t require a large recruiting team and without losing your mind wasting time on candidates that aren’t a good fit. Step 1: Hire Traits, Not Just Resumes Did you know there are three different types of salespeople? The Newbie, The Entrepreneur, The Sales Veteran (email me, and I will send you the ebook that breaks them down). First, make sure you know what you need on the team, who you have the bandwidth to train, and if you need someone that follows your playbook (do you even have one?) pretty much exactly, or are you okay with them just ‘doing what they do best’ without much structure? Next, you need to figure out the mindset traits you find most successful. A business friend of mine, a long time ago, taught me: “Hire the smile, train the skill.” Given enough time and patience, you can teach anyone how to do anything. But it's really hard to teach someone a different mindset. Most people are who they are when they are applying to be a part of your company. Here is my list, in order, of mindsets that I know are successful for sales (in any sales role, any industry, any company): This aligns with broader studies: while past performance can matter, attitude and coachability are consistently ranked as stronger predictors of sustained success. Leaders who over-prioritize experience often miss the hidden talent right in front of them. Openness Curiosity Creativity Persistence Authenticity As I tell my clients, most leaders think they just need more reps who are ‘persistent’. They blame a lack of sales results on the team not asking for the sale enough or doing enough follow-up. The problem with biasing the screening process for persistence is that if you don’t care about the other traits, you will end up with a team full of persistent assholes who don’t listen to you or their prospects, don’t care to learn anything new, and don’t try to come up with new ways to move people to the close. They just see every prospect as a nail and sales is a giant hammer in their hand, where if they can just hit enough nails hard enough, they will win. [Don’t believe me? Ever heard the phrase ‘sales is just a numbers game’? That is this mindset in action.] The last part you want to define is what type of company culture you have and what personality is a good fit? Is it a fun environment? Does everyone like to joke around? Is it all serious and focused? Is it mission-driven? Do you actually have defined, stated core values that you care about? The answers to these questions will help you determine culture fit. One area that organizations will fall short in their selection process is ignoring culture fit and just wanting people with certain experiences on their resume or skills to help sell more widgets. If not careful, it can lead to bringing someone on board who might be an excellent, technical salesperson (meaning…technically they can do the job), but they are a not a good fit for the team. “The best reps don’t just sell your product — they sell it your way.” It’s not enough to just hire for experience; you need team players. Step 2: Treat Recruiting Like a Sales Funnel Now that you know who is open to bringing on board, what that winning combination could look like, it’s time to start building the hiring process. In sales, the initial key to success is attracting the right leads into your funnel. This is the job of marketing. Not just in the steps they take, but the messages they put out there to the world. Like fishing, putting out a hook with bait on it where the right fish that is interested will want to take that bait. Marketing should be doing the same thing for your revops. Your hiring team should be doing the same thing with the job posts and the hiring process. Your goal is to write a job post, like your marketing team writes their content, in a way that your ideal candidate would read it and say “holy crap, that is me!” Part 2 is to build in some hoops. One area that I see pretty much every organization fail at is building and managing candidate lead flow. They put a job post out there, get a shit ton of candidates, go from excited ( “We have so many candidates, we will definitely find all the reps we need!” ) to despair ( “How the hell are we going to get through all these resumes, and then what about all the interviews?” ). So many orgs are not ready for the flood of applicants. And did they even want that many applicants? If you haven’t noticed…recruiting is like sales. Well, to be specific, everything in life is sales, and selling, and persuasion. So building a recruiting process is like building a sales process. Sales teams think it would be great to be flooded with leads until it happens, and so much potential business falls through the cracks of inefficiencies and bandwidth limitations. This is why we want to put in a) hoops and b) templates for our hiring process. Let’s start with hoops. Think about it: in sales, 63% of managers admit their teams do a poor job managing the sales pipeline. If you can’t expect discipline in pipeline follow-up from a candidate during the hiring process, you certainly can’t expect it once they’re in the field. The hoops should be similar to what your prospects have to go through to become a customer. The logic is that your salespeople will run that process with their prospects, so you need to identify those sales reps who are naturally built for it. It’s similar to Alex Hormozi’s take on hiring – that what is more important than the years of experience someone has, is evaluating and selecting for traits like intelligence, work ethic, adaptability, and coachability. This is what we want our hoops to do – help the candidates show us what they are really made of. Some hoop examples: Do you require your sales team to use scripts? Yes, yes, yes…I know…salespeople shouldn’t use scripts…scripts are bad…scripts make everyone sound robotic…scripts are the problem. Bullshit. You are wrong if you think that. Alright…soap-box-moment over…back to scripts. If you require your reps to use scripts…let’s say for an intro, elevator pitch portion, compliance/disclosures – then one valuable hoop to put in place is to make your candidates memorize a short script in the hiring process. There are many ways to do it [email me, I can give you some examples of how, when, and what for this hoop], but it is an amazing filter for candidates. This is how you filter out the people who are not open/curious (remember, my top two sales success mindset traits above) – because they will decline your requirement to memorize the script. Or they will take the script, say they will work on it, and then disappear into the wind, never to be heard from again. And…that is the perfect result. I promise, no matter what fantastic story they spun on their resume or tried to present to you in the interview…their resistance to this step is all you need to know. Truly. The ones who say, “ Sure, sounds good, I will memorize this and get back to you, ” are the ones you want. Not because they are actually good at memorizing things – because I know I am terrible at it – but because they are willing to do it. A tiger can’t change its stripes. Is it a short sales cycle or a long one? If it is more than a one-call close, then you want to put hoops into your process that will help differentiate the short-term commitment versus long-term commitment people. Some salespeople out there are just too impatient to handle making follow-up calls, delays by stakeholders, and rejection after long sales cycles. They need immediate gratification. (and here is a contrarian thought…they are probably also single…because how someone is with work, they are in their life. If they can’t handle long sales cycles and long-term relationship building in a sales role, they probably aren’t very good at it in their personal life. And that’s okay…there is nothing wrong with that mode. The question is – is that what fits your sales cycle/length/mode? If you need reps who can do more than build enough rapport to sell someone something in the next 20 minutes before never seeing them again, then filter those people out by adding layers to your hiring process that extend the length. Now, I am not saying that if your sales cycle takes an average of six months, that your hiring process should do the same, but it should be relatively long. Definitely don’t interview people and then have them start the following Monday. Is there a lot of follow-up in your sales process? Do you expect your team to actually manage their pipeline of valuable leads to ensure they close? Then you want to build in a hoop that requires candidates to follow up with you. We want to test them on how well they will treat their future sales pipeline. If they won’t even follow up with you on their progress in the process, then they aren’t the type of salesperson who will follow up on their own leads. Or, they just don’t care that much about this job. Either way, this is a perfect filter to remove those candidates from your pipeline. If you want my ultimate filter process/scripting for this hoop – email me with the subject “ candidate follow up, ” and I will send you what I have done to successfully apply this filter. While that might look like a lot of hoops and processes to build out, it doesn’t take much to both eliminate the candidates who are not a good fit and allow the ones who are to raise their hand so you can pick them. Remember, no matter how desperate you may feel you are – needing to fill your sales team today, it’s never worth bringing on bad hires, especially in a sales role. The cost of their onboarding, training, combined with the cost to your leads (aka – the wake of revenue and reputation destruction that is caused by terrible sales reps speaking with your hard-earned, expensive leads is almost immeasurable) is not worth it. Fight the urge and bad business advice to just get butts in seats. And I guess that you are here reading this because you have already tried that mode and it failed. And with annual sales turnover costing companies millions, every wrong hire creates a hidden tax on growth that most leaders underestimate. Mads Faurholt-Jorgensen spoke about it in his TEDx Talk titled “ How To Master Recruiting ” with a focus on hidden talents over resumes. He called it the “whispering talents” – and in sales, we want that person who just automatically does the sales activities with the right mindset that fits your organization, sales process, and target customer type. TL;DR Most companies hire salespeople the same broken way: post a generic job, drown in resumes, waste hours interviewing, and end up with one shaky hire. It’s slow, costly, and sets teams up for turnover. The fix? Stop hiring based on resumes alone. Instead: Hire traits, not just experience (openness, curiosity, persistence, authenticity). Treat recruiting like a sales funnel by writing magnetic job posts, adding “hoops” that filter out the wrong candidates, and testing real-world behaviors like follow-up. This approach flips hiring from chaos into a scalable system—so you attract the right reps, faster, and avoid the expensive revolving door. In Part 2 of this series, I’ll show you exactly how I scaled this process to hire 50 salespeople without the chaos—complete with templates, filters, and lessons learned. Don’t miss it. And if you think that there might be some ways to improve your hiring process, contact us and we can do a free Hiring System Assessment to determine where the biggest impact can be made to help you fill your sales team.
By Jason Cutter February 26, 2025
How Can You Predict The Future Of Sales Ops? One of the keys to sales success is to be able to predict the future – what that other person is thinking, what they might say, what they will experience, how they will feel about the product/service. But what can you do – from a sales ops leadership perspective – to predict the future in masse of all the potential customers that will flow into and out of the sales process/funnel? That is a really tough one, but it is doable. Meeting Prospective Customers Where They Are The key is to always meet the prospective customers where they are and with the experience they hope to find. It’s a common theme now in these articles because it’s important AND widely disregarded – your potential customers do not care about you, your sales team, your company, your industry. They don’t care about your stats, your testimonials, your logos. They don’t care about your mission statement or your values. They only care about themselves. They also firmly believe that there is currently unlimited choice for any product/service, which means that everything in their mind is a commodity. Easily replaceable and interchangeable. Nothing (other than iPhones…which you can only get from Apple) is special to consumers unless they feel like it should be special. Are You Still Making It All About You? There is a good chance you are still running a marketing, sales funnel that is all about you. I bet if I looked at your company’s website that from the top down it’s all about you (the company). How great you are. What you do for people. What you have done for others. I bet if I tried to speak with your sales team, I will be made to go through your process whether I like it or not. Maybe fill out a form and wait for a response. Or made to call into a toll free number, even though I don’t want to talk to someone yet. Or made to use a chat widget on a site to get started. I bet when I speak with your sales team, 70-80% of the conversation will be about them, your company, and how amazing you all believe you are. This is all fair. No one starts a company to be mediocre. The goal is to provide value and make money. The missing piece, again like I said above, is no one cares about your goals. They only care about themselves. Predicting What Customers Want From The Sales Experience Back to your mission as sales ops leader – predict what massive amounts of prospective customers are going to want from the Sales Experience. It’s why I wrote about it last week and even offered up a book for free to help in any way that I can. To succeed at your mission, you have to stay ahead of the curve of what the public, and specifically – your buying demographic, psychographic, and valuegraphics, want from that experience. Key Questions To Shape The Sales Experience Do they want to call, text, email or chat? Probably all of them…so can you offer each one? (Don’t make someone decide if they want to go through your hoops…remove all the hoops) Do they need to see pricing online – should it be available and transparent? (In most cases, yes) What sales process will be ideal for moving the most people through the sales conversation to a successful outcome? (More discovery, empathy, active listening. More front-loaded about them, not you. Use the Authentic Persuasion Pathway as your model) Who are the decision makers? Is that individual going to decide or do they need to check with others for approval? (Set them up for success, and don’t force them to make a decision in the moment – you will just lose the potential sale) What type of follow up do they want and need until they make the buying decision? What type of post-purchase follow up would go above and beyond a) their expectations and b) what others in your industry do? If there is an ‘onboarding’ stage after the sale – how can you make that actually customer centric and successful? (It is rarely both) Can You Stay Ahead of the Curve? Remember – evolution is natural. The buying public is always evolving their desired sales experience. Can you predict the future of what they want so that when they encounter your company it matches what they were hoping to find – both in the experience and the solution to their need?
By Jason Cutter February 25, 2025
How do you, as a sales leader, help your team become Oracles that can predict the future? [make sure to read the Selling Effectiveness article this week https://go.sellingeffectiveness.com/LI.2.25.AM ] There are five ways to facilitate their Oracle-ness. Be Present in the Moment First, you have to get your salespeople to be in the moment. The challenge that most salespeople (and…humans, for that matter) experience is they are always thinking ahead. Salespeople default to thinking about what they will say next. The next part of their script or process. The next question they want to ask so they can get through discovery. The next part of the agreement they need to discuss and review. Their mind is too busy thinking about what they are going to say and do next, that they aren’t present. As weird as it sounds, if you want to predict the future you must be present. I have said this for decades: the moment you no longer need to think about what you are going to say/do next and can actually be present with your prospect and truly listen to what they say (and don’t say) – you will become a sales professional. Master Active Listening Second is Active Listening and paying closer attention. It’s actively listening…it’s taking what I mentioned above and putting into place. First step is to be present, second is to actually listen. For what they say. For what they aren’t saying. For changes in their tone. For when they are talking to someone on the side – who are they talking to, and is it about your sales conversation? If you sell in person, reading their body language and facial expressions. You must help them develop an almost sixth sense of listening (and yes, I know hearing is one of our senses…but this goes beyond hearing…it’s truly, deeply listening). Ask Better Questions Third, is to help them ask better questions. So many people in sales ask the discovery questions they are required to ask in order to check the discovery ‘box’. Or, they have done sales long enough they know all the answers, they think they know what everyone wants and why, so no reason to even ask questions. [Note – this type of salesperson thinks two dangerous things: 1 - everyone is the same and wants the same thing, 2 – people like to be sold to.] When your team asks better, deeper discovery questions with a focus on uncovering the what and the WHY, they will get better answers. Remember this – when you ask the right questions and you listen close enough, each prospect will tell you EXACTLY how to help them buy. Build Up Experience Fourth, build up experience. If you want to predict the future it comes from enough experience to know the probability of what will happen. For example, when I am in a season of commuting from home to an office, I am the type of person that can predict exactly what will happen on the freeway. Which lane is always faster around certain exits, which lanes always slow down, how much leaving five minutes later can make the drive suck a lot more. How do I know what will happen on a freeway with hundreds and hundreds of random people? Because of experience (and the fact that most people are just going through the motions in life so they become predictable). The more experience your team has with sales scenarios, they more they can predict the future. I generally see that it takes about six months for most people in a new sales role to have seen enough scenarios where they can start to know what will come next before it happens. Trust Intuition The fifth and final trait to help them with is intuition. One definition of intuition is “a thing that one knows or considers likely from instinctive feeling rather than conscious reasoning.” It’s that feeling you get when you know something, even if you cannot explain it. It’s what Malcom Gladwell wrote about in Blink! It’s what we do very well as humans, even if we don’t listen to it. The more you can help your team tune into their intuition and listen and trust it – the better they will do in helping persuade that other human. This goes back to the first suggestion – about being present. When your team trusts they know what to do and say next and they are mentally living in the moment with that prospective client, they can let their intuition guide them. Conclusion When I do trainings, public speaking, facilitating meetings, interviews, and sales – this is my main key to success. I trust and know that I have the experience to handle whatever comes my way in the present moment, while also knowing the destination I am heading towards. I can be present, let that experience and my intuition guide me instead of getting stuck in my head and worrying about what I will say next. Get your team to do some or all of these five steps – and they will become an amazing Oracle.
By Jason Cutter February 25, 2025
The Oracle’s Role in The Matrix If you have seen the Matrix movies, starring Keanu Reeves (as Neo), then you are familiar with an Oracle. In the movies, the Oracle knows what will happen. She has seen it, and it is predestined. In the Oracles mind there is no such thing as free will. In the first Matrix movie, Neo goes to visit her and knocks a vase off the shelf, and it hits the ground and breaks. Right before he hits it, she says “Don’t worry about the vase.” Neo says, “How did you know?” Then the Oracle responds with “What’s really going to bake your noodle later on, is would you still have broken it if I hadn’t said anything.” Becoming an Oracle in Sales Your mission as a sales professional is to be an Oracle for your prospects and clients. To know the future. Then be able to see around corners, as they say. Which means you know what is going to happen before it happens, because you have enough experience that you have become a psychic. You want to be able to predict, with amazing accuracy: What will happen next What will happen after that What issues will pop up What your prospect/client is thinking before they think it What concerns they might have before they have them Eliminating the Fear of the Unknown During your presentation/demo you want to set the expectation of what is going to occur next. Remember, humans fear the unknown. They want to avoid risk as much as possible. Your sales presentation is risky and dangerous and very unknown. They don’t know if you have good intentions or not. Are you going to persuade them? Are you going to try to manipulate them? Are you going to overcharge them? Will you actually care about what they need and want? Dealing with salespeople is so scary. Yet they still need and/or want something, so it’s the dangerous game they must mentally play. Guiding the Buyer Step by Step When you explain what you are going to do in part 1 of your process, and then what that part is done you let them know the plan for part 2, and so on – they will be at ease in the moment. They will feel like they have control over this portion, that there is an exit they can take if they don’t want to proceed. That level of control will help them accept the risk of part 1, and part 2, and part 3. Tell them what you will do. Do it. Tell them what you did. This will validate that you can be trusted. Predicting Thoughts and Feelings The next level is being able to predict what they will think and feel before they do. You can use this information in your presentation (without telling them what you are doing). You can also verbalize it, which could sound like “I am guessing from experience that you are probably wondering about _____, so let’s cover that right now.” Or “most people I speak with ask about _____.” They will think – wow this person knows what I am thinking, he/she is in my mind! And that’s a good thing. A really good thing. Conclusion The more they feel like you know what you are doing, know what they are thinking, know what they are afraid of – the more they trust you as a Guide. Because Guides only know what they know because they have helped other Heros successfully accomplish their journeys. Your mission as a sales professional: Become an Oracle.
By Jason Cutter February 19, 2025
What does it take to build the ideal Sales Experience? Why does it even matter? Maybe you think you already have one. You are a professional sales ops leader. You have put everything you can in place to help your salespeople sell more. You have optimized the processes so that your sales team can focus on one thing – selling. But I promise – even if you think all of that is true, it’s not. The Reality: No Perfect Sales Experience Exists I have never seen any company or team with the ‘ideal’ Sales Experience and operation. And to be honest – I have never built one successfully. Why would I admit that? Because the ideal Sales Experience is aspirational and business, teams, processes, and customer needs/desires are constantly changing. So as soon as you put new processes in place, something else needs to change and evolve. The Scalable Sales Success Iceberg In my Scalable Sales Success Iceberg – there are 24 categories that, when built out, create a scalable sales machine – where you can add in an input and get way more output. I would love to see companies have all 24 categories set up and running optimally. But that’s not even possible – because, as I mentioned, things are always changing. Focusing on the Biggest Levers Here is the key – to build the ideal Sales Experience takes focus on the biggest levers. The ones that, when pulled, create the biggest and best results. There are many processes and systems that you can put in place – but those are going to get you a few percentage points of improvement. Instead of putting it all in here, I want to make you a special offer. Email me at jason@sellingeffectiveness.com with your mailing address, and I will mail you the book that I co-wrote with Nick Glimsdahl called Reasons Not To Focus On The Sales Experience. It will be your starter guide, facilitating the creation of your ideal Sales Experience.
By Jason Cutter February 18, 2025
The Numbers Game Mentality is a Losing Strategy Sales is no longer a “numbers game.” You cannot succeed, long term, by focusing on volume of activity. Making a million dials, sending a million emails, knocking on a million doors (the first two are way easier than that last one) is a scorched earth strategy that will sink your business. You can’t out-dial a bad sales process. It will lead to even more bad online reviews. You can’t out-email a terrible sales funnel process that requires people to jump through poorly planned hoops. You can’t out-knock your way past slimy tactics and bad products/services. The Danger of the "Every No Gets Me Closer to a Yes" Mindset The whole “every no gets me one step closer to a yes” mentally is dangerous. That mindset and strategy assumes that it’s a numbers game. That the only thing that matters is finding the right person who will buy from you. Potentially, no matter what you even say – they are just ready to buy. Not only will this destroy any online reputation you have it will also wreak havoc on your team. It is the fastest and best way to burn out your team. It will lead to a revolving door or hiring, training, and quitting as people realize how unfun the game is you have built and how hard it is to be successful. It will also feel like a mismatch – very few people (and hopefully even less over time) are long-term excited about the business model of calling 500 people a day in hopes of making a few sales. If It’s Not a Numbers Game, Then What Is It? It’s quality over quantity. [Now…note – it does take a certain quantity of activity to fill a sales pipeline. So I am not saying that your sales team can just sit and wait for people to fall into their pipeline with money in hand.] It’s about the Sales Experience. It’s about your team ensuring that they are providing the right and best experience for that potential customer – in a way that sets them up to get into the buying mood and mode. All that matters is the Sales Experience. How can you support your team in terms of the quantity of activity to fill a pipeline, and then the quality of interaction that leads to sales? What Does an Ideal Sales Experience Look Like? What does that look like – the ideal Sales Experience? It’s when your team understands that the potential customer they are speaking with only cares about themselves. They don’t care about the salesperson, your company or the product. They are only focused on themselves. It’s when the Discovery/Empathy portion of the conversation is the most important part. Does your team realize that everything after Discovery – when done right – is just a presentation of the solution? It’s the fact that when you combine the parts of the Authentic Persuasion Pathway (Rapport + Empathy + Trust + Hope + Urgency) that the assumptive close is all you need. If your team is having to ask for the sale they are doing sales wrong. And don’t confuse earning the right to close with asking for the sale. The Sales Leader’s Role in Creating a World-Class Sales Experience Your job as a sales leader is to ensure your team understands that the only thing – above all else – is the sales experience they provide to each potential customer. That customer knows that they have the power and the feeling of unlimited choice. Which means they will decide who to give their money to based on the experience they have with buying from a company. How can you shift your team away from the numbers game mentality to actually providing a world class sales experience to each and every person they speak with?
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