CUTTER CONSULTING GROUP

E128: Time To Reflect Back & Plan Ahead

January 4, 2024


How do you typically manage the balance between taking a break during the holiday season and maintaining momentum in your sales career?


When you are in sales and sales management, it can be tough to give yourself a break. Usually taking time off means not making any money.

However, during this holiday season, give yourself some time to enjoy a break. Whether its with family or along, traveling or at home.

In this episode I talk about giving yourself a break during the holidays, as well as how important it is to reflect back on the last year (and the last decade), as well as looking forward.



When you set your goals for the upcoming year, make sure to also create a list of who will you need to become, what you will need to learn, and how you will need to grow in order to achieve those bigger, different results.

Merry Christmas and Happy New Year from The Sales Experience Podcast


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  • Show Transcript

    Hi and welcome back to the sales experience podcast. My name again is Jason Cutters, so glad that you’re here, so thankful that you’re downloading this podcast. Hopefully with the goal of improving your sales experience for yourself, for your team, for your customers, for your prospects. I wanted to make a really quick short episode today. It is Christmas 2019 if you’re listening to this, the day it came out, Merry Christmas. If not happy holidays, no matter when you’re listening to this, and I just wanted to make a short episode. Kind of touch on something here that I think is important to always remember is that this time of year, especially if you’re in sales, things tend to slow down. Now there’s some of that happens when sales reps kind of give up and think that it’s going to be slow and they kind of create that self-fulfilling prophecy.


    Then there are other times where it’s just slow because your clients are not there. Your prospective customers are not there. Whether it’s business to business, business to consumer, they’re just not around. They’re not thinking about it. There’s not much you can do about it. And you’ve just got to understand that and then give yourself a break. And so this is a little reminder I wanted to record and share is to give yourself that break. It’s really tough, especially as salespeople and sales managers, cause you always feel like you got to keep going. You can’t give yourself that time off. If you stop, then everything stops and your pipeline is going to dry up or your income is going to drop. And sometimes you don’t feel it right now in the moment you’re going to feel it in a month or two months when a, you know, you slow down now and there’s less to work on down the road or fewer people that you’re nurturing or talking to.


    But this is a good reminder. Always make sure that you give yourself some time off, whether you’re spending time with family or by yourself, traveling, staying home, you know, always understand that it’s good to give yourself a break. And this time of year can be pretty stressful. You know, a lot of times I see salespeople who are stressed out about the holidays, about money. I know I have been there, I have been there where during this time of year I have been very stressed out, very worried, very concerned about money and where things are going to go and where I’m at right now at this point in the year. And then going into the new year. I’ve also spent times around the holidays where I’m not worried and not stressed because I’m doing really well. Money has been there and the success has been there and things feel like they’re on a roll in the holidays feel much better cause there’s that momentum.


    And so I’ve seen both sides and I’ve dealt with both sides and I’ve also spent holidays where the money might not be there. The success, the direction, the future might be uncertain. Don’t know where things are going to go. And I’m still not worried about it because I know that it will all work out. And this holiday season, just remember what the great philosopher Bobby McFarland says, don’t worry, be happy. So enjoy the holidays and relax. Now, if you’re in sales and you have some downtime during the Christmas season, like between Christmas and new years, I strongly suggest and would love for you to take time to review how this past year went. How did 2019 go? Spend an hour writing out what happened just right out of basically a play by play of what happened throughout your year in life, relationships, finances, health, spiritual, all of those categories. Just write out how the year went. Just take your time and just replay that kind of like we talk about with sales where you want to listen to your calls or have someone watch your interactions with your customers and then give you that feedback to, same thing you want to do at the end of the year.


    Just take some time. Spend some time. Most people don’t spend any time planning their life or setting their goals or really doing anything right. If you look at the amount of time people will spend planning a vacation, it’s usually far more than people spend planning out their life or what they’re going to do, their strategies, where they’ve been, what’s working, what’s not working, and if you look at how much time people will spend watching TV shows or binge watching series or movies online on Netflix versus how much time people spend on themselves and getting where they need to be, then you’ll notice that if you can carve out some time, spend it on recapping and looking at it, not for anyone else, not to share with anyone else but just for your own head and then see where you’ve been and then appreciate how far you’ve come.


    And then what you want to do is you want to look ahead. What do you want to create in the next year? What do you want to create in 2020 what are your goals you want to have and that you want to shoot for and go after? Whether it’s sales, whether it’s business, whether it’s finances, life, relationships, spiritual, maybe it’s health related. What are the things you want to do and not in a new year’s resolution way where you get excited, you start out strong. And then next thing you know by February you’ve already given up and you’ve gone back to your routines. But what kind of things are you actually wanting to go after and create in your life? And then if you also want to take this to the next level, look back at the last decade, right? We are about to finish the decade of the 2010s and so look back at what you went through in the last decade.


    Where were you 10 years ago versus where you are now? What did you go through? What ups and downs, career, relationships, what was yours like? I know that I did that recently and look back the last 10 years, and I’m not necessarily further ahead than where I wanted to be, but based on everything that happened in the last 10 years for me, I am so thankful to be at this point and moving forward, having gone through everything I have as I go into this next chapter right this next decade. And then figuring out where you want to be in this next decade. If you can look out that far, sometimes it’s really tough, especially if you’ve been like me where if you look back, there’s no way you could have predicted where you aren’t now relative to where you were five years ago, 10 years ago, maybe one year ago.


    And so to look out 10 years for most people is really challenging because they cannot fathom or even imagine what that’s going to be like in 10 years. But put some time and effort into it. Figure out what that would look like if you had your way, if you got what you wanted, where would you want to be in 10 years at the end of the 2020s where do you see yourself? What would you love to have be do and relationships, business, finance, all of those things. Where would you want to be? And then when you set your intentions on that, you set some goals around that. You will move that direction. Now, of course life is going to toss you around a bit and we know that and if you’ve been through life at all, you understand that it does come for you from time to time and kind of mix up your plans.


    But just focus on what you want to create in this next year and this next decade. It’s so important and always remember that wherever you are in life right now, you can change that and no matter what age you are focused on the fact that no matter what’s happened for you, with you to you or not happened for you, with you to you, there is still so much life left. Like I am 44 right now and I feel like I am pretty much at the halfway point. I feel like I’ve, this is halftime. I’ve spent 44 years on the planet and here I am the next 44 years. Who knows? So I don’t feel like, Hey, my life is over, I’m getting old. And you know, I feel like literally there’s so much time and space ahead of me now that doesn’t mean that I don’t want to create anything and I’m not going to work hard because I know I’ve got too much time left.


    But it means patience that I know I will create things in the next 45 50 years, 60 years. Who knows by then and that I want to work hard now and I want to do lots of things and create lots so that I can see what amazing things will happen. So if you’re listening to this, that’s my kind of Christmas end of the year goal setting, help you focus. Also, if you’re in sales, set some parameters and some guidelines and some goals around what it is that you want to create in your sales career. And keep in mind there’s the sales itself, like how much do you want to make? How many sales do you need to do in this next year to hit those goals? If you have that in mind, you know what that is. Assuming you don’t change careers, change companies, but also what is it that you need to do?


    What do you need to learn? Who do you need to become to hit those goals? Because always remember that where you are now and everything that you have now is a result of who you are. If you want something bigger, better, different, greater relationships, finances, business, whatever that is, then you have to become something different. You have to learn new skills. You have to change your mindset. You have to change your focus, change your habits, right? Everything that you have now is a reflection of who you are. If you want something different, you have to become different. What kind of courses can you take? What kind of books can you read? Podcasts? Can you listen to experts? Can you listen to what kind of training programs can you go through? What is it that you would need to add to your toolbox as a sales professional, as a person?


    So fixing your mindset or changing the way that you view the world and yourself, your goals, and what is it that you need to do? So it’s one thing to set a goal and say, I want to make X next year. It’s another one to say, okay, I want to make X. What do I need to do differently? Who do I need to become? How can I get there from where I am now? What do I need to add to myself to get there? So hopefully that helps. Again, Merry Christmas, happy holidays whenever you’re listening to it. And may the new year be great for you no matter what. 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 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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