CUTTER CONSULTING GROUP

[E285] Where was your sales career 19 years ago?

January 17, 2024


Reflecting on your sales career, how far have you come since you first entered the field?


Sometimes in your career and in life you need to take time to reflect. 


There are milestone days that trigger emotional memories.


Today is one of those globally historic days. But this is not a ‘here is my 9/11 story’ episode.


But it is a call to action – for you to look at where you were 19 years ago, 10 years ago, 5 years ago.


How far have you come in your sales career? Were you even in sales before this year?


And…having looked back…now look forward – where do you want to be in a year, 5, 10, or 19 more years?


Check out today’s episode that is less about sales tips and more about motivation and direction.



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  • Show Transcript

    So like everyone, I. Remember clearly where I was on the morning of nine 11. I remember what I was doing, what it felt like when things were happening and what it was like after that, even though it was 19 years ago, it's still very vivid in my mind. Like most people who experienced their own version of it.


    Now, at that point in my life, I was not even in sales yet. I was in between contracts at Microsoft and working for a totally different company doing a completely different type of project. Sales wasn't even on my radar or anything that I thought I would end up doing or being good at. I was still doing everything I could to not have to really deal with people, especially not having to try to convince people to do anything or change anything or buy anything.


    It was not even in my mind at any point. Then, a year later, I was in my first sales role. I was doing residential mortgages as a loan officer. And that's literally where it started in 2002. And like most who got into sales or are in sales, no real structured training scripts plan, learning the hard way by losing deals, messing up conversations, making mistakes, just the classic way of learning things the really hard way.


    Then fast forward to 2011. I had been in sales and sales leadership roles at four companies by then and had just left the world of sales again to work as a government contractor. So 9 11 2011 was my first day in Iraq that then marked the beginning of many deployments that spanned over four years, the next four years.


    And keep in mind, if you don't know my background, my story, my bachelor's degree is in marine biology. That's how much I didn't think I was going to be in sales or dealing with people. That's what my bachelor's degree is. Then I ended up in sales and then I ran away from sales completely. Now, during that time, I had enough kind of space and time away from sales and business to reflect on what was at the intersection of what I was good at and what I enjoyed the most.


    And that is when I decided to set the aspiration of being consultant. Coach and trainer to help others succeed. Now I tell this background story as a reminder that we never know where life will take us. If you're in sales right now, just starting out or struggling to succeed, or maybe you've plateaued in your results.


    Remember that life is long for now, today, reflect on where you were in life 19 years ago, or 10 years ago, or five years ago, just as a reminder to take stock of how far you've come, whether it's in sales. Or in life, one of the things is to look where you're going. And we'll talk about that next. But one of the things that I've also done recently, just to take stock of how far I've come in life and even in recent ventures is I actually have a progress wall, which is small achievement steps and things that I've done, not talking big certificates and awards, just various things that I've done over the last few years.


    To help remind me of that progress and where I have come from and where I'm at now. And I recommend doing that as well. Take stock, like I said, of how far you've come, whether it's in sales or it's in life, it's in relationship, it's health, it's business, whatever that looks like. And if you're in sales, that one is huge because a lot of times you get stuck or you get depressed.


    And I know so many people who struggle with the mental wellness side of sales because in the moment. It just feels like a challenge and it feels like a struggle and it feels like failure or you're winning and things are great. And then the winning stops in that period, right? You just hit a dry spell or a slump, or it's just in between deals.


    And then that's when the devil is in your head, trying to convince you that you're not successful. And so it's always important to take time to reflect back and look at how far you've come, what you've done, what you've accomplished to remind yourself what you're capable of doing and what you've proven that you can do in the past.


    Then, and here's where we want to go next, is I challenge you to take stock on your current goals. Do you have goals? A lot of times people, they're just going through life without goals. Sales people generally have some kind of goal, but is it written down? Is it documented? Is it somewhere that you see it all the time?


    Is it clearly in your mind? And then what's more important, and this is where most people fall short with their goals, is do you have a big why behind? Why you want to achieve those goals and why it's important to you. Do you know why you want that? And money is important. Money is valuable, of course, but money is energy and money is something that leads to other things.


    So why do you want that? And what's the deepest, most powerful, emotional reason internally for why you have that goal that you've set. And the more important that is to you. The more you'll push through these barriers. And then do you have a timeline for when you want to achieve those goals or that goal?


    Whatever that looks like. Don't let another five years slip by without you being intentional on where you want your sales career to go. If your company provides support and training uses many of those resources, you can, I see a lot of salespeople who have resources. They have. coaching or accountability or training or mentor available at their company and they're just not using it.


    So if that's you and you work at a company, check and see what's available. Your company is in business to succeed and win and they want to support you. They're there for you. A lot of. Times. It's so amazing how salespeople think they have to do it all on their own, or they're used to struggling on their own and trying to figure it out on their own.


    And companies want you to win. They don't want you to lose. They want you to win. And then of course, if you're self employed or you work in as a leadership role, Then you're going to have to go outside of that. And if your company doesn't have those resources, then where can you find them? Where are they available in your non work time?


    Read, study, work on perfecting your skills. I'm telling you, especially this is where you look at your progress board and your life, take some time reflecting. You can get a lot done in the next five, 10 or 19 years. And I'm not saying life will take you on a straight path, but on emotionally historic milestone days like 9 11, it's a good reminder to look back, then look forward.


    And I'm telling you, this is what's fascinating about today, is it's very rare that the whole country, and most of the world, can all simultaneously remember back to exactly what happened on one Particular day. And for many people, depending on your age and your generation, that is 9 11. And that's why 9 11 is such an important, interesting day because everyone has an emotional attachment to it in one way or another.


    And more than just focusing on that, which I think it's always good to remember, and reflect, and then focus on better future. It's also one of those good emotional reminder days to help you focus on what you want to achieve in life. Because you can look back and know pretty much every year on 9 11 where you were, and maybe in memory and in milestones.


    And so that's why it's so important. That's why I want to use this episode and support you more than sales training tactics or lines to use or mindset or other things like that for you to use this day. And this podcast as a way to figure out what support, what training, what coaching, what wisdom you need to achieve your goals so that you can then move forward.


    And down the road, you're achieving what you want if you're not currently. And so how can you use this? Utterly tragic anniversary for our country as a reminder for this year and every year to make the most out of your time available. That's the question I have for you is how can you use this as the day where you reflect backwards and then forward every time and to shift your sales career into something amazing.


    Something positive and something that's just forward charging in the direction you want to go. So that's it for today's episode. This is just personal. Remember to appreciate each and every day. Remember to spend time with those people you care about and remember to live the life you want and To get there and to do it by helping others get what they want.


    That's it for another episode of the Sales Experience Podcast. Thank you so much for listening. If you find yourself on iTunes, can you leave the show a rating and a review? It helps other salespeople and sales leaders find the show, and please subscribe to the show and share episodes you find valuable with anyone you know in sales.


    Help me on my mission of changing the way. Sales is done. And if you're ready to work together, go to Jason cutter. com. Again, that's Jason cutter. com to find out how I can help you or your company create scalable sales success. I will see you on the next sales experience podcast episode, and keep in mind that everything in life is sales and people will remember the experience you gave them.


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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?
By Jason Cutter February 17, 2025
The Abundance of Options Today we all have lots of options. While writing this I could speak into my phone and order whatever I want. I can get food delivered before I finish writing this article. I could get a TV delivered to my door before I wake up tomorrow. When someone wants to buy something, they are armed with as much information as they want to access. They can research, read reviews, and watch videos about a product or company. The Shift in Power to the Buyer Because of this, the power balance of sales has shifted away from the salesperson and company to the buyer. Knowledge is power – and they now have all the knowledge they want. With knowing that they have ultimate choice of what to buy (internet and globalization has led to the ability to order anything you want from anywhere…so you are no longer limited to the stores you can drive to and what they have on hand), it means that everything is a commodity in their minds. Nothing is unique or special. Everything is interchangeable. Does the Sales Experience Even Matter? So, this means the sales experience doesn’t matter anymore. There is no reason to put effort into the sales process, the conversations with potential customers. No value in spending time trying to ‘help’ people – since they just view products, salespeople, and companies as interchangeable. You are not special, so there is no benefit in caring. They will walk into your store, and they will decide what they want. They fill out your online for, and they decide if they answer when you call and how the call will go. They walk up to your event/booth, and they decide how the interaction will go and if they want to listen to your elevator pitch. They will let you know if they are interested in moving forward. They will let you know how they want to buy. So, like I said above, there is no real value anymore in the sales experience. Or could it actually be valuable? Is it possible that all that matters IS the sales experience? If people feel they have ultimate information and control of the buying process, how do they decide on what to buy and who to buy from? When I search on Amazon for a product type I have never purchased before, how do I pick? When I want to go shopping for garden supplies for the house, how do I pick where to go? When I need to buy a new fridge, who will I hand my money over to? The cheapest place with terrible service? The place with reasonable prices and great service? The Sales Experience Shapes the Decision I choose based on the sales experience that I will receive. With everything else being equal, I (and I believe most people) will select the place to shop at or the products to buy online based on the experience I receive. To me all that matters is the experience. While I am trying to buy something. Once I receive it – ensure it does what I need it to do. With the feeling of unlimited choices, it can actually be harder now to buy something that in the past. People get into analysis paralysis more often. Which means that for consumers to buy something new they need help. They need a professional salesperson. They need a sales experience that matches their expectations. They want a guide who will help them make the right decision for them, with an experience that goes above and beyond what more people receive any more when they walk into a store, call a company’s toll-free number, or visit a website and have to fill out a form. If you want to succeed in sales – the only thing that matters is the sales experience you provide.
By Jason Cutter February 13, 2025
The Balance of Effort in Sales The blogs this week have been about the other person going most of the way. Whether it’s a prospective customer and your salesperson, where the salesperson truly can’t want the deal or make most of it happen for that customer to truly be successful. On the path for that prospect to becoming a customer, they should go at least 51/49. Whether it’s your team and their manager, the manager can’t want the team to succeed more than the team actually wants it for themselves. It’s not scalable for the coach (manager) to run on the field every play to win the game for the salespeople. What about sales ops processes and systems? What about the tools available to the sales team and the ones that are classified as sales enablement? In a reversal of philosophy, I believe the sales ops processes should go 90, the team should only have to go 10. Why Do We Need Salespeople? Let’s start where it matters – what is the point of having salespeople? I know many owners question the need and desire to have salespeople. They are hard to manage, tough to deal with, always want more money (potentially for doing less work and closing less deals), and are very resistant to change. Of course, that is a generalization. Of course, there are salespeople who don’t check those boxes. However, having worked with a lot of teams in a lot of industries, that generalization isn’t completely wrong or unfair. So if there is even a small part of that which is accurate, why would we even mess with the messiness of having salespeople? Of needing to employ and manage humans? The Human Element in Sales We need them. That’s why. Even in 2025, AI and technology has not successfully replicated the requirements of sales – which is about helping a human (prospect/customer) make the right decision and move outside of their comfort zone to buy something new. It still takes your human (salesperson) to persuade that other human. It’s why I say all the time that its not B2B, B2C, Retail, SaaS, etc. – it’s H2H. Sure, people can buy something online or even in a store without speaking to someone. But if it’s a considered purchase where there are options and decisions to be considered – it still takes a human being involved. That means ultimately your human (salesperson) has one job, and one job only – persuade the right prospective humans to buy. Minimizing Distractions for Salespeople Everything outside of that mission, task, focus is a distraction that takes away from their highest and best use. Imagine if we had a surgeon who had to prep the room, prep the patient, schedule the surgery and meetings, and do all the parts of the surgery themselves. Nope – they show up for the surgery and do what they do best. Then they take off their gown, gloves, and walk away to get cleaned up and move on to the next thing. Your goal as a sales ops leader is to support the team with systems and processes that allow them to focus on the one thing you need them for. The human part. It would be amazing if they could show up, talk to people, and make sales happen. Of course, there is more that they (and any professional) need to do before, during, and after the sales conversation. But your goal is to minimize all that. Every hour that your salespeople aren’t selling or doing sales-related activities, they aren’t moving revenue forward. The Ultimate Goal of Sales Ops What processes can you put in place that go 90 percent of the way, where the salesperson can do the last 10 percent? An example would be building an email campaign that runs automatically, and when the right people reply, the salesperson gets involved in getting that person from email to phone call. Another example would be your CRM serving up people for the salesperson to call – leads or anyone in the sales pipeline flow – with all the backstory, research, data, intel needed for them to review it then take action. What can you put into place that takes away as much distraction and effort from your sales team such that they can focus on the one thing you need to focus on – other humans?
By Jason Cutter February 12, 2025
The Danger of Doing Too Much as a Sales Leader Alright – so maybe they don’t need to go 90. In true servant leadership mode, you would go way more than 10% of the way to your team. But you have to be careful, as a sales leader. The inclination might be to do it all for them. To help them close their sales. To make excuses for them to your leadership as to why they aren’t closing more sales. Especially considering the very high likelihood that you are a sales manager because you were a great salesperson in the role that you are now managing. And there is a slight chance that you are a player-coach…so you are leading and selling. This can make it really tough not to want to run out on the field to win the game each time. But that doesn’t scale. That doesn’t lead to increased results. You can only sell so much as one person. Creating a Culture of Ownership So, you need to have people on your team that are coming to you. What does that look like? The pinnacle is a salesperson who doesn’t close a deal, comes to you right away and asks for feedback. They want some critiques as to where they could have done things better, different that would have led to the desired result – a closed sale. That takes a healthy level of ego by a professional who has the ultimate growth mindset. They know there are always ways to improve. They want to improve. And they are willing to risk their ego (and the internal, protective, primal part of our brain that doesn’t want to risk our place in the tribe) by asking for feedback that could be negative. Whenever you can, encourage that type of response. Ensure that the team knows that the team itself, and you as their leader, is a safe space – where the goal is to improve, grow, win and that everything done to support each other is done in that mode. They truly have to feel safe to share their mistakes and to get support in learning how to do more, better. Feedback That Drives Growth Part of this takes team and individual meetings that are actually filled with positive support. That doesn’t mean it’s always positive, motivational fluff. It’s not even about the shallow strategy of the feedback sandwich. Its about being real, honest, and empathetic – meaning “I see you are here, I know you want to be there, I will help you get there – even if its hard and it means saying hard things.” It should never feel mean or abusive or like an attack. But you can give some really direct feedback that will sting that ego I mentioned, but the person will know the intent behind it. The second part is hiring this type of person. Hiring people for the team that wants to win, grow, succeed. And they know that you don’t get better by being coddled, sheltered, or protected. You want people who don’t like the thought of perpetually living safely in their comfort zone. And they are excited about the opportunity to be a part of a team that pushes everyone, empathetically, outside of their comfort zone. Are You Leading or Just Managing? If you find yourself as a leader having to push your team, or going to them most of the time, or most of the way mentally – then they see you as a manager not a leader. They see you as someone who manages them, pushes them, and wants them to do things they don’t want to do. I have written some blogs here that go into what your role should be – as a leader, not a manager. Pulling people along with you, inspiring people, and supporting yourself with a team of people who want to win. Not just those that want to show up, do as little as they can and hopefully go unnoticed (yet – complain about not making enough money and how the comp plan isn’t fair, or the leads are bad, or their schedule means they can’t be successful.) Make sure your team knows that they need to come to you – at least 51/49. They should be asking for help, guidance, training, feedback, and support more than you are having to push it down onto them.
By Jason Cutter February 3, 2025
If you have seen the movie Hitch, then you know the scene. Will Smith’s character (Hitch) is trying to coach Kevin James’ character (Albert) on how to finish out his upcoming first date. He is giving him pointers, one being that if his date fumbles with her keys at the door, it could mean she wants a kiss. So Hitch wants to see if Albert knows what to do – for a good night kiss. Hitch gives him the advice “you go 90 percent, and then wait for her to go 10%” which Albert then asks “wait for how long?” Hitch: “as long as it takes.” Albert leads in, Hitch is holding back to see if Albert will wait, and then Albert goes all the way and gives him a kiss. Hitch gets upset, and says “You go 90, I go 10 – you don’t go the whole 100%.” The Sales Analogy Kissing our prospective customers is not acceptable (just ask HR!). But the concept is the same. You don’t want to ever make 100% of the effort for your prospective customers. You don’t want to be the one who is doing all the work. Fundamentally, it is not good practice to want the deal more than the other person. When you go your 90, you need to wait – as long as it takes – for the prospect to go to their 10. And I would say that you want to go somewhere between 10-49, in reality. How Successful Sales Professionals Balance Effort Successful sales professionals know how far they have to go to meet the prospect where they are, while also knowing how much effort the prospect needs to put in to show they are committed. Where most salespeople get in trouble is they get desperate. They want the sale (kiss) more than the other person and they go the full 100%. Of course, persistence is important. And you won’t get what you don’t ask for (although…if you have followed me for any length of time, you will know I am very against having to ask for the sale). But you also have to ensure that your prospects actually want what you are selling. And they want it for their reasons and their motivations. They are driven to pursue your production option(s). They must go 10, 40, 60% of the way to you. The Pitfall of Chasing Your Prospect Just like courtship and relationships – if you find yourself chasing and one-sided-pursing the other person then it means you want it more than they do. It also means they own you. You are essentially begging them for the relationship – convincing, manipulating, begging, bribing, persuading your way forward. Which means they consciously and/or subconsciously know that they are in control. Because if they say no, you will keep pursuing and offering solutions. In sales – that looks like a salesperson who is calling, emailing, stalking a prospect – making offers, offering discounts and trials, and trying to find any way to make deal work. They are going 90-100% of the way for the prospect, not requiring them to go anywhere towards the agreement. This will end terribly. If they do decide to buy – taking the discount, free trial, taking the sale bait – they will not be happy (since they weren’t bought in for their reasons), they will look for reasons confirming why they didn’t really want to buy anyway, and they will know that they own you. Your company will have to convince them on a regular basis to stay in the relationship. The Right Balance for Customer Ownership You fundamentally need that prospective customer to come to you. Not 100% where you are just an Order Taker. But potentially 51% of the way – so they want it more than you. The more you can get them across that 50/50 threshold, the more they will be a satisfied customer. But remember – at 51/49 – they still need persuading, they still need to understand the value of your product for where they ultimately want to be in their life/business, and they still need your support. They lean in the right amount, you lean in the right amount = sales magic!
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