CUTTER CONSULTING GROUP

[E274] Tales of a new CRO, with Darryl Praill (Part 4)

January 17, 2024



Do you hold your team accountable based on company values?


Do you hold your team accountable based on company values? The behavior of your sales team is determined by your company’s mission and values. 


Aligning with teams in different apartments creates a seamless and effective approach to your business. This is where understanding the vision and goals to improve productivity is by contributing their strengths to tie results together. 


Technology plays an important role in today’s businesses. Taking the ability to analyze and track data can direct your business to additional strategies, but also help to further your process on current and future trends on how a salesperson is performing. 


Learn about what it takes to ensure that your company has a clear set of values for your team to make the right decisions, achieve company goals, and define your brand character.


Book your free Sales Power Call with Jason

Enroll in the Persuading Like A Professional Online Mini-Course

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Connect with Jason on LinkedIn

Connect with Darryl on LinkedIn


Darryl’s Bio:
Darryl Praill is the Chief Revenue Officer at VanillaSoft, the industry’s most established Sales Engagement Platform. As an accomplished award-winning marketer, a Sales World Top 50 Keynote speaker, a 2020 top 10 SaaS Branding Expert, a Top 19 B2B Marketer to Watch in 2019, a social media influencer, a category-leading podcaster, and a serial entrepreneur. Darryl has raised almost $100 million in venture capital, acquired, merged and taken companies public, been hired and fired, and worked for companies of all sizes



Links:


• VanillaSoft

Twitterhttps://twitter.com/vanillasoft

LinkedInhttps://www.linkedin.com/company/vanillasoft/

Instagramhttps://www.instagram.com/vanillasoft/

Facebookhttps://www.facebook.com/vanillasoft/

 

• Darryl Praill

Twitterhttps://twitter.com/ohpinion8ted

LinkedInhttps://www.linkedin.com/in/darrylpraill/

  • Show Transcript

    Jason: Welcome back to the sales experience podcast. Welcome to part four. The final part of my conversation with Daryl Prill. If you have been following along and listen to all the episodes, we are going to wrap it up here with basically his tips, his suggestion on what a CRO actually what a CEO should do in bringing in a CRO and how to set that up.


    Lots of good value. Make sure to support him, his podcast, his work that he's doing in the sales and marketing community. And of course, subscribe to this show, share this with anyone, that's in a marketing role, a sales leadership role, a CRO, as well as CEOs who want to grow this. Please share this message.


    And of course, if they need help, if there's anyone you know out there that needs help, let me know. I would love to chat with them as well. Here you go. Part 4. Enjoy.


    Darryl: You want reps to do butt, butt, butt. You want reps who are hungry and chasing deals and they want to be king of the hill. You want that.


    I continue to refine.


    Jason: And that's what I'm always telling clients and various managers and owners I deal with is that theoretically, if you have a really good salesperson on your team, as long as they're aligned with your culture and their intentions, and it's a good fit for your values and the company's values, you've got to understand and appreciate.


    When they're pushing back, when they're selling you, when they're overcoming what they think are challenges or objections coming from management, because that's what you want, right? You don't want them to be an order taker pushover on the phone with prospects. And so you also can't expect them to not.


    Bring that into meetings and conversations when they want to try to get their way. They're a salesperson, right? You nailed it.


    Darryl: That's exactly it. And I remember having this conversation with my CEO and it was a really, we had many times to your point, I would use an abbreviated version.


    I would say to David, I would say, David, I need more Oracle reps. I need my reps to be more Oracle and he's you sure you want that? They're all I make. I know exactly what you're saying because it's a cultural thing, right? Because I'm using Oracle as a cliche. Maybe Oracle is much better now.


    But the Oracle I grew up with in the last 20 years is very cutthroat, very aggressive very type A. And push, push push, push. Because they're selling enterprise software. It's six and seven figure deals and eight figure deals sometimes for ERP, etc. So they're playing hard to win.


    And they will step on you if they view you as no longer adding value to go up one. It's a mix. I want more Oracle reps, but I want integrity and character. I'm not sure that mix exists, personally, but we're working it.


    Jason: And what you want is Oracle reps, integrity, doing the right thing, empathy, but also powerful closes who also just take your orders and run with them and don't push back on you.


    Darryl: And if you just heard what Jason just said, send your resume to me right now.


    Jason: Darryl at Vanilla Soft. com. Is that what it is? I'm listening. Please reach out to him. In thinking about all this and looking at this challenge that you have and this mission and kind of the fun part. Companies out there, one of the fundamental issues I see and because this started with the presentation that you were doing.


    Two marketers about aligning and that, classic sales versus marketing battle. And so I'm hoping their sales leaders, organizations, owners listening to this and they're inspired and going, okay, what we need is that let's evolve to a CRO who can tie everything together. Or even if it's not a chief revenue officer, it's a something revenue.


    Ops head at any scale.


    Darryl: I'll go one step further, right? Cause what you're saying is a thousand percent correct, but not every company is big enough or ready for a CRO, right? Fair enough. Okay. Some of you guys aren't going to I'm about to say, Mr. Or Ms. CEO, if you are big enough for a CRO, but you need alignment between your sales teams and your marketing teams.


    It's incumbent upon you to do that. You are the CRO, even though your title says CEO. Stop abdicating. Stop letting the kids try to figure it on their own. That's my harsh medicine for the day.


    Jason: And it's so true, right? Like people always ask me, how do you fix that? I said, it always starts at the top. And I think I've never thought about it that way, but the organizations where there is sales versus marketing is because the CEO has abdicated.


    They're off playing chief executive officer. And they're allowing the chips to fall where they may. And then everyone's egos and personal stuff and just people, humans being humans, gets in there and there's no mediator and there's no umbrella kind of leadership.


    Darryl: I get it. You look at president Trump, right?


    President Trump has this public state approach that he likes conflict in his leader. So when he's got his lieutenants, he wants them in the oval office to be scrapping over stuff. Okay, he's the CEO in that picture. That's his style. We can sit back and reflect and say, does that work? Personally, I believe scrapping in private is perfectly cool and acceptable.


    But once you open that door, we're all on the same team. We've determined the play we're about to execute. Nobody deviate from the playbook, right? That's why I point, if you don't have a CRO, it's up to the CEO to play that role to make sure that everybody's aligned. Because if you rely upon the sales leader or the marketing leader to come together on their own, chances are it's not going to happen.


    One will want to, most often. The other one Won't, or they'll want to, but on their terms, which are completely self serving, they're not looking for a compromise. They're not looking for a compromise. They're looking for I win, you lose. And that doesn't work out.


    Jason: One thing I've seen is that sales people worry about only being able to win if they use manipulation tricks, tactics, and hard closes.


    So they end up struggling to close deals. Make their quota or earn the kind of money that they want to make. If this sounds like your current situation or maybe you want to make more money in sales without feeling like you're selling, then my upcoming book called Selling with Authentic Persuasion will help.


    In it, I'm going to take you on a journey to transform from order taker to quota breaker. If you're ready to become an authentic persuader, crush your goals and create success in your sales career, then go to Jason cutter. com again, that's Jason cutter. com and pre order the book today. I had a Maya Conant on the show and she's a CRO.


    And one of the things that she brought up is that what happens like when she started out is. There was history right between sales and marketing a meeting a year ago. John didn't like Kim's idea and said something negative and hurt somebody's feelings. And now that baggage is there. And even if I want to be friends with you and align us, then something happens.


    Feelings get hurt. It creates a rift. And then nobody knows why that rift is there. It's just this feeling and this vibe. And sometimes bringing in something new can help because they don't have the history. They don't care. I don't care if somebody hurt your feelings a year ago. Like we have a mission.


    Let's be successful.


    Darryl: And that's also though why I created the RevOps team. Like we already had marketing ops and sales ops. I'll put them all together. And it was specifically so that we had data. So in your example. Maybe there's bad blood between two individuals a year ago, and no one knows how we got here, but here we are.


    We can either replace them, spot on. Sometimes those people are irreplaceable because of their tribal knowledge or what have you. Okay, no problem. It's like a child. Then what I need to do is I need to change their behavior, and I need to make sure, for some, it's a timeout. For others, it's corporal punishment.


    I'm going to, whatever. For others, it might be, I'm taking away your iPad. Who knows? The data that you get from the RevOps, eliminates the he said, she said, eliminates the interpretation. I can say, no, look at here is your leads that you've given sales, Mr. Head of Marketing. And I can tell you that the lead quality sucks or blah, blah.


    I can, here's the numbers, right? So you can point at sales all you want to, but you're not free here. You got problems. And then I can turn to sales and say, they don't feel gloating at marketing person over here. You're attrition, you're ramp time, whatever it might be. Here's the data. The data doesn't lie.


    So the data becomes the arbiter. And that's why I love having data. And I'm not smart enough to pull that data together, but I'm smart enough to get the people who are smart enough to pull that data together. Even to the point that they send me wonderful charts and everything. And most people would take the charts and they themselves would open it and peruse it.


    Yeah. I'm not that guy. It's in the charts and I say, okay, let's have a meeting. Walk me through the chart because I don't want to assume I know anything. I want to hear the story behind the numbers.


    Jason: They thought worthy of my seat. And that was the thing that Maya actually pointed out too, was. The data is important.


    It eliminates all that, right? It's no longer subjective. It's very objective. It's very direct, but then also her point, which was fascinating. And it's what you're talking about, too, which is the transparency of the data and the more live the data is, the less the data can be manipulated or stories being told or spun to protect somebody's position instead of here's the numbers.


    Now, Let's have an honest conversation so that everybody can win.


    Darryl: And that's part of the reason we are, we're implementing salesforce. com because we didn't really need it. My whole sales organization lives in vanilla soft and does a bang up job, but we have a federated tech stack. So sports got Zen desk, success has got churn zero.


    Accounting's got NetSuite, marketing's got HubSpot, sales has got vanilla soft. All right. You know what? I'm just gonna put salesforce. com across the top and everybody can plug in. And now I've got one. Holistic view and at the same time I can also log in and I can see, Oh, somebody's late on their payment or somebody's had 42 support calls.


    I wonder if they're not happy. Look, success is pointed. This guy's got a net promoter score of five. We should be doing something about this, that kind of stuff. So it was again. So we had a single record of truth that everybody can see for that wonderful word that Jason used.


    Jason: Final thought, final comment.


    What is the one thing you would want? Let's say a CEO who's going to put in a CRO position, right? So they're at that part. They've evolved. They're ready to go. They want to put in a CRO. What is the one? Because I'm sure you have 94. What is the one suggestion or tip or thing that they should know? To help that CRO position be successful, not just the person, but the position.


    Darryl: So if you're going to implement a CRO that has a heavy bias towards one discipline, sales, then don't put in a CRO. Because there's, make them the VP of sales. Because they're a default to what they know. Alright, I mentioned I've been a VP of sales, hadn't carried a bag in 10 years, so that's a bit of a risk.


    I know marketing, I'm in the sales community, I talk to sales leaders, I talk to industry analysts, I talk to the reps. I have pretty good ideas. No one person will ever be perfect. Clearly, I'm better marketing than I am in sales. But I've got enough of a balance, and I understand the process, both sides, that I can be Switzerland.


    I can be neutral. I can hold each team accountable and make sure this friction is gone. The challenge is, too many CEOs think they understand the craft. They think they understand marketing. If you talk to them, in their world, marketing is just press releases and great parties and trade shows. That's it.


    Or they think they understand sales, even though they themselves have never picked up a phone in their life to make a phone call. They actually do a cold call, right? You want somebody who's got foot in both camps, who is knowledgeable enough and experienced enough, or at least educated and informed enough.


    Know them minded enough to know what they don't know and get those answers before they make a decision. If they're going to default and bias to what they know, if they only bring one skill to the table, they should not be CRO. That means you have to really interrogate them, make sure you understand, do a great background check.


    That also means you need to be honest with yourself. If you think you know marketing, you think you know sales, but you've never picked up a phone, you've never actually done anything other than have your name appear in a quote in a press release, then you need to get outside experts to supplement your knowledge to vet the CRO candidate.


    And frankly, as a CEO, that's what you should be doing. The pressure's not on you to have all the answers. The pressure's on you to resource the answers and then to lead by example. So that's my advice.


    Jason: I love it. That's perfect. That's a great place for them to start and really makes sense. Especially the biased part.


    As far as where people can find you, I know the best place historically, except recently, has always been LinkedIn. Anybody that wants to find Daryl, it's Daryl Prail, P R A I L L. Go to LinkedIn. You were super active. You've taken a CRO mental hiatus because of how busy you've been. You've disappeared from there, but there's a lot of great content, especially if people want to go historically.


    Also, people can email you. Daryl. Prayle at VanillaSoft. com. Is there anywhere else where you're active right now? Any good resources?


    Darryl: I'm active on Twitter, too. You can go to my own website, DarylPrayle. com. The simplest method? Just go to Google, type in Prayle, and you'll find every location that I've ever been at.


    You'll also find a Prayle from Alberta, Canada, who apparently killed her mother. No relationship to me, but it's a great story. So it's a win.


    Jason: There we go. Lots of good stuff. And you're in Canada as well. And so it makes sure it's the Canadian press. Something about that. I don't know. You got it. Yeah.


    Darryl, thanks for being on the show again, coming back and with some new information, new kind of experience. Super excited to see what you do, but thanks for being on the show.


    Darryl: Jason Cutter, killing it in the hallways. Thank you, sir.


    Jason: 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 jasoncutter. com. Again, that's jasoncutter. 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 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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