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6 Sales Tips to Prospect, Sell and Retain More Clients

Sales Training World · 2026-07-02 · 16 min

0:00--:--

Key moments - from our scoring

Substance score

25 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality5 / 20
Guest Caliber3 / 20
Specificity & Evidence8 / 20
Conversational Craft3 / 20

The Ryan Dorn Business Show introduces a faster-paced weekly format with six focused segments targeting sales professionals. Dorn emphasizes timing strategy for outbound emails, recommending delayed delivery tools to match prospect schedules rather than sender convenience - whether contacting contractors at 6-7pm or doctors at 5am or 9pm. For prospecting, he advocates recording personalized Loom videos for website leads to differentiate from competitors and track engagement. On AI productivity, Dorn identifies telltale signs of ChatGPT-generated content (em dashes, formal language) and recommends using the "/human" prompt prefix and disabling m-dash formatting for more natural-sounding outreach. His retention idea centers on Starbucks B2B gift cards as a low-cost customer appreciation touchpoint. Addressing a listener's CRM frustration, Dorn reframes CRM adoption as essential for time management, marketing automation, and forecasting - suggesting training and attitude adjustment rather than abandonment. Finally, he introduces the Pomodoro Technique (25 minutes work, 5-minute breaks) with emphasis on true task disengagement, not context-switching, to prevent sales burnout.

Key takeaways

  • →Send emails at times optimized for prospect behavior (6-7pm for contractors, 5am-9pm for medical professionals) using delayed delivery tools, not when convenient for you.
  • →Use Loom video responses to inbound leads as a differentiation tactic and engagement tracker that competitors aren't deploying.
  • →Eliminate obvious AI tells from ChatGPT by using the '/human' prompt prefix and explicitly disabling em dashes before sending outreach emails.
  • →Implement Starbucks B2B gift cards as an affordable retention gesture beyond standard customer service to build lifetime client relationships.
  • →Adopt the Pomodoro Technique with physical task disengagement (not tab-switching) to prevent sales burnout and maintain sustainable productivity.

Topics in this episode

SalesforceAI prompt engineeringCRM adoptionDelayed delivery email strategyLoom video prospectingChatGPT em dash formatting/human prompt prefixStarbucks B2BCustomer relationship management toolsMedia OS

Questions this episode answers

What's the best time to send sales emails to contractors and business owners?

Time emails for when your prospect is most likely to be available and checking messages - typically 6-7pm for field contractors, 5am or 9pm for doctors/dentists depending on their schedule. Use delayed delivery tools to write at your convenience but send when they'll engage.

How can you make your prospecting stand out from competitors?

Send personalized Loom video responses to inbound leads immediately, introducing yourself and setting calendar links within the video, which tracks opens and differentiates you from text-only competitors.

What's a quick way to make ChatGPT emails sound more human?

Use the '/human' prompt prefix before your request and explicitly tell the AI 'please do not use em dashes' to avoid the telltale formatting that signals AI-generated content.

Why should sales professionals use a CRM if they hate it?

CRMs serve as time management and forecasting tools that guide your daily workflow through lists and task prioritization. Most successful salespeople rely on them for marketing automation and deal tracking; consider getting more training rather than abandoning the tool.

How can you prevent burnout while prospecting all day?

Use the Pomodoro Technique: work focused for 25 minutes, then completely disengage from your computer for 5 minutes (walk outside, refill coffee, get sunlight) before resuming. True task disengagement, not context-switching, prevents brain burnout.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

Six tips crammed into 16 minutes sounds dense, but almost every tip is surface-level common sense: send emails when customers are awake, use Loom, learn your CRM better, and do Pomodoro breaks. The one slightly novel tactical nugget - using /human in ChatGPT to avoid M-dash tells - is buried and unverified. No insight requires a B2B operator to update their mental model.

Are you emailing at times that are good for you or at times that are great for your clients?
customer service is expected. Retention are the things you do beyond customer service to keep your clients for a lifetime

Originality

5 / 20

The Pomodoro technique is decades old and widely known, Loom for inbound video responses is a common sales playbook staple, and the CRM section offers zero contrarian framing. The /human prompt tip is marginally novel but presented without any evidence it works as claimed.

the Pomadoro technique is work on a task for twenty five minutes, then come off of that task for five minutes
you need to be doing things that are different than everybody else

Guest Caliber

3 / 20

There is no guest. This is a solo host monologue. Ryan Dorn introduces himself as a 'billion dollar sales coach' but provides no verifiable credentials, named clients, or demonstrated results anywhere in the transcript. The listener Q&A segment involves a pre-selected email from a listener, not a practitioner guest.

Mister Revenue, here your billion dollar sales coach
I speak forty to sixty times a year at sales meetings, just like all of you have

Specificity & Evidence

8 / 20

The episode does name specific tools (Loom, Media OS, Magazine Manager, Ad Orbit, Workbooks, Salesforce, Dynamics, Claude) and gives concrete time windows (5am/9pm for doctors), which is above average for this content tier. However, there are zero conversion metrics, zero case study outcomes, and no named client results to substantiate any claim.

some of the CRMs out there would be for example, media OS, Magazine Manager, ad Orbit workbooks
doctors dentists, if you have to sell to them, that's like five am or nine pm, depending on the type of dentist or doctor that they are

Conversational Craft

3 / 20

This is a solo monologue with no interview dynamic whatsoever. The single 'listener question' segment is answered without any follow-up, nuance, or pushback - the host literally tells the questioner to 'have a little change in attitude' and move on. There is no guest to challenge or probe, and the host does not challenge his own claims.

David says, Hey, Ryan, I hate my CRM. It is a waste of my time
I'm sensing the negativity and your hatred in the email that you sent, and it's no problem

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

friends26sales18email15send13david13five8love8show7chat7starbucks7brain7minutes7help6perspective5reply5prospecting5

Episode notes

Welcome to the new weekly format of The Ryan Dohrn Business Show, hosted by Ryan Dohrn, Mr. Revenue and your Billion Dollar Sales Coach. In this fast-paced episode, Ryan shares practical sales training ideas you can use right away to prospect better, sell smarter, retain more clients and stay focused. This week’s topics include how to use delayed delivery and send later tools so your sales emails reach prospects at the best time for them, not just the best time for you. Ryan also shares how to use Loom video messages to stand out when new leads come in and create a more personal sales connection. You will also learn how to avoid sounding like AI in your emails, including why long em dashes can make your message feel robotic. For customer retention, Ryan shares a simple idea using personalized Starbucks gift cards to stay top of mind with clients. In the listener question segment, Ryan explains why top salespeople use CRM tools for time management, forecasting, follow-up and sales automation. Finally, Ryan shares how the Pomodoro Technique can help salespeople reduce burnout, improve focus and keep their brain sharp.

Full transcript

16 min

Transcribed and scored by The B2B Podcast Index.

1 - >

Speaker 1: What's going on? Friends and fans, Welcome to the new 2 - > Ryan Dorn Business Show. Mister Revenue, here your billion dollar 3 - > sales coach, and we've got a new show format for 4 - > all of you. So it's going to be a lot 5 - > faster paced, and we're going to be moving up to 6 - > weekly updates. Friends on YouTube, Spotify, iTunes, wherever you connect 7 - > with us online. So get set friends, new format, new 8 - > fast paced. Here we go. All right, friends, here comes 9 - > your quick sales tip of the week. Friends. I say 10 - > to folks all the time, if you're not using delayed 11 - > delivery and send later thirty forty times a day, you 12 - > need to be asking yourself this question. Are you emailing 13 - > at times that are good for you or at times 14 - > that are great for your clients? Think about this. Maybe 15 - > you're in a business where you're having to sell services 16 - > to contractors or people that are out in the field 17 - > all day, and you're a salesperson that sits in the office. Well, 18 - > you've got to be asking yourself, what's the best time 19 - > to potentially reach that business owner. Is first thing in 20 - > the morning, is it at lunchtime? Is at after six 21 - > o'clock at night? You do you and you need to 22 - > figure that out. But once you do. From a sales 23 - > strategy perspective, you want to use delayed delivery or send 24 - > later to write your emails at a time that's good 25 - > for you, but have them hit the customer at a 26 - > time that's good for them. Now, in order to do that, 27 - > you're gonna need to know a little bit about the business. 28 - > My dad is a contractor. I know that you don't 29 - > want to email him at noon. That' says one time 30 - > to sit down and get a little break. But I 31 - > do know from his business and the way that his 32 - > day kind of rolls, probably you're gonna be more than 33 - > likely going to get a reply to an email, say 34 - > at six or seven o'clock at night. Oh Ryan, that's 35 - > people's dinner time. I don't necessarily care whether it's dinner 36 - > or not. I want to hit their inbox at a 37 - > time that I think the chances of them applying are 38 - > gonna be higher. So if you don't like that, it 39 - > doesn't work for you. Maybe it's eight o'clock at night. 40 - > Maybe it's six o'clock in the morning. Like for examples, 41 - > doctors dentists, if you have to sell to them, that's 42 - > like five am or nine pm, depending on the type 43 - > of dentist or doctor that they are. So you've got 44 - > to be asking yourself, friends, am I sending email at 45 - > times that are good for me or times that are 46 - > good for my client? From a sales strategy perspective, you 47 - > should always have emails hit your customers at times that 48 - > are good for them. Now, if you don't know that 49 - > what time is good for them, watch when they reply, 50 - > or just analyze their business a little bit, or go 51 - > into chat GPT and say, hey, here's the type of business, 52 - > here's where they're located, tell me about their day, what 53 - > does a typical day for them look like, what's a 54 - > great day for me to potentially reach out to them, 55 - > and what's the best time to send them emails? And 56 - > even good old chat GPT will help you out as well. 57 - > All right friends, that is your quick sales tip of 58 - > the week. All right friends, Now it's time for your 59 - > prospecting tip of the week. All right. When I'm prospecting, friends, 60 - > one of the first things that I'd like to do 61 - > when a lead comes in from the website is I 62 - > like to record people of video and send it back. Now, 63 - > the tool that I use to do that is loom Loom. 64 - > So if you're not following it. That's Lima Oscar Oscar, 65 - > Mike Loom and Loom is a web based application. It's 66 - > a Chrome extension. And when the lead comes into me, 67 - > I immediately pop up Loom and I say something like, Hey, 68 - > my name is Ryan Dorn. Thanks for submitting a lead 69 - > through our website. I wanted you to be able to 70 - > put a face with a name. I'm very excited to 71 - > share with you what we're doing to help other customers 72 - > of ours be crazy successful. So when we have an 73 - > opportunity to meet, hopefully pretty soon, I'm going to give 74 - > you some case studies and examples of businesses similar to 75 - > you that have had some really great success with us. 76 - > If there's something specific you need, please drop me an 77 - > email back. Here's my phone number eight hundred eight six 78 - > seven five three oh nine. If you'd like to text 79 - > me and set up a meeting, love to do that. 80 - > But in the email I sent is my calendar link. 81 - > I'd love for you to jump on my calendar at 82 - > a time that's convenient for you. I look forward to 83 - > working together with you. Then I send the email, include 84 - > it included inside of the email that I send, and 85 - > I find that i'd love it because I can track 86 - > and see when they open up that video. Here's what's interesting, friends, 87 - > from a prospecting perspective, what are you going to do 88 - > differently today than everybody else, all of your competitors. What 89 - > are you gonna do that's different. Whether it's an agency 90 - > or it's a private company, whatever you're gonna do, you 91 - > need to be doing things that are different than everybody else. 92 - > And that's why I love to use video as a 93 - > part of my prospecting process. All right, friends, let's move 94 - > on to your sales technology tim of the week. You know, 95 - > it's a dead giveaway when you're using AI if you 96 - > send an email to somebody that includes those long M dashes. 97 - > Do you know what I'm talking about? Like chat shept 98 - > is notorious for this. It'll polish up an email for 99 - > you and then they'll send the email to you and 100 - > it's kind of like a long dash in it that 101 - > technically is called an M dash em like an M dash. Well, 102 - > that's a dead giveaway or using AI because AI does 103 - > that all of the time and most humans don't. So 104 - > there's a couple of things you might consider doing. One is, 105 - > when you're asking for a reply, use the cheat code 106 - > forward slash human, forward slash human. Use that cheat code, 107 - > and you're going to put that before your request, So 108 - > you do forward slash human. Okay in the prompt box 109 - > on any AI tool and then you're gonna say, polish 110 - > up this email for me, colon. Insert the email text 111 - > and the reply it's going to give you friends is 112 - > going to sound more human, or it should. Now, if 113 - > you don't like those long dashes, I definitely don't you 114 - > want to use the phrase in the in the new 115 - > chat box when you do work for me, Please do 116 - > not use an M Dashins are fine, but M dashes 117 - > definitely don't want you to do that. Please remember that 118 - > for the future, and what you're gonna find is that 119 - > the bot will remember that. Now, if you move from 120 - > chat GPT over to Claude or you add claud on 121 - > to your AI tool set, just don't forget that. You're 122 - > going to need to take your data and that information 123 - > from chat GPT and either import it into claud or 124 - > make sure the rules that you define and we'll talk 125 - > about those in other shows. The rules you define for 126 - > chat GPT or claud make sure you copy and paste 127 - > with those rules in as well. All right, now it's 128 - > time for your retention idea of the week. Friends, I 129 - > just came across this, didn't know that it existed Starbucks 130 - > b to b dot com. So this is a website 131 - > where you can go and order customized Starbucks cards that 132 - > you can send to your customers. As most of you know, 133 - > I try to be a retention machine. Never forget, friends, 134 - > that customer service is expected. Retention are the things you 135 - > do beyond customer service to keep your clients for a lifetime. 136 - > So I'd love for you to check it out Starbucks 137 - > b toob dot com. I'm not going to necessarily get 138 - > paid or something for it, but I really want you 139 - > to always be exploring new ideas. So here's what I 140 - > would do. I would write a custom note. You can 141 - > send the Starbucks cards electronically to people they tend to 142 - > really like that. You can also get hard copy hard 143 - > printed ones if you wanted to hand them out at 144 - > a trade show or something like that. Now, if you're 145 - > like me, I've got the Starbucks app on my phone, 146 - > I like to get them electronically. I just add them 147 - > in to my app. But you might want to check 148 - > out Starbucks BtoB dot com and if anybody from Starbucks 149 - > watches or listens to the show. Love to have you 150 - > as a sponsor of the show as well. It's very affordable, 151 - > I promise. All right, Now, let's move on to your 152 - > favorite part of the program, and that is your listener 153 - > questions of the week, So send those in ryanat Ryandorn 154 - > dot com. All right, so here's one we grab from 155 - > the grab bag. David from Oakland, and I'm guessing it's 156 - > probably Oakland, California, is what I'm guessing. All Right, David says, Hey, Ryan, 157 - > I hate my CRM. It is a waste of my time. 158 - > Why do so many sales organizations they rely upon their CRM. 159 - > Why is this such a big deal, David, I think, Well, so, 160 - > first of all, the big thing, David is that typically 161 - > professional salespeople are going to use a CRM just help 162 - > them to remember the things that they did yesterday or 163 - > the things that they have coming up. For those of 164 - > you that don't know what a CRM is, that's a 165 - > customer relationship management tool, and every industry tends to have 166 - > ones that tend to stand out from everybody else as 167 - > a lot of you know, I do a bunch of 168 - > work in the media business, so some of the CRMs 169 - > out there would be for example, media OS, Magazine Manager, 170 - > ad Orbit workbooks. They all work inside of the media space. 171 - > Now there's some ones that are more generic, if you will, 172 - > and are bigger, like Microsoft Dynamics and Salesforce things like that. 173 - > But David, I'm sensing the negativity and your hatred in 174 - > the email that you sent, and it's no problem. I understand. 175 - > What's happened here, David, is that someone has not helped 176 - > you find value in using your CRM. You see it 177 - > as not being valuable. So let me share with you 178 - > two or three ideas that you might use to make 179 - > your CRM a lot more valuable to you. What I 180 - > like to do is like to use my CRM as 181 - > either a starting point or a way for me to 182 - > guide my day. I use my CRM really as a 183 - > time management tool. So I'm going to go into my CRM, 184 - > and any competent CRM like the ones I just mentioned, 185 - > any of them, will do this. I want to create 186 - > lists in my CRM, So on Monday, I'm working a 187 - > particular list. On Tuesday, I'm working a particular list. Use 188 - > the CRM to help me really maintain focus. Now with 189 - > my CRM and many that are out there, not all 190 - > of them, but many They have marketing built in to 191 - > the CRM. Just recognize friends that. For me, I want 192 - > a very smooth, easy CRM to use. Sometimes that's hard 193 - > to find, so I need to get more training. So 194 - > if you feel like your CRM is hard to use, David, 195 - > just get more training on it, whether you're using help 196 - > videos or whatever. But I also like to use the 197 - > CRM to drive my marketing efforts. So I'm going to say, hey, 198 - > I need to send an email every three business days 199 - > to this particular list inside the CRM, and I set 200 - > up that sales automation and that's super valuable to me, David. 201 - > So what I'd be looking for is, what are things, David, 202 - > that you find valuable in your sales life, and then 203 - > get yourself trained or find the right CRM or whatever 204 - > the circumstance is, find that to be able to help 205 - > you really guide your sales day. David, I use a CRM. 206 - > I'm pretty good at this, and almost every superstar I 207 - > know out there uses their CRM in one way or 208 - > another to be successful. Now I need to admit to everybody, 209 - > David included. Do I have some Google sheets floating around 210 - > out there to keep myself organized as well. And the 211 - > answer is yes. But if my CRM went away, which 212 - > I'm sure that it won't, but if it went away, 213 - > I'd kind of be in a tough situation because I 214 - > include my forecasting in that I keep all my notes 215 - > inside of it. I mean, it is really is my 216 - > partner in sales crime. So I'd encourage you, David. Probably 217 - > what you need is to get more training, and probably 218 - > what you need to do is, maybe David, no offense, 219 - > have a little change in attitude, get excited about it, 220 - > and find some value inside of your CRM. All right, 221 - > keep your listeners questions coming to ryanat ryandorn dot com. 222 - > If we don't list them, list them and answer them 223 - > back here on the show. More than likely we're going 224 - > to send you an email reply. Well if we didn't 225 - > get if you didn't get an answer, I didn't receive 226 - > the question, So make sure you resend if you've already 227 - > set one in. All right, friends, Last, but definitely not 228 - > least on the show is one of my favorite segments 229 - > that we like to call brain work tip of the week. 230 - > As a lot of you know, mental health is something 231 - > that's a personal passion of mine. Why is that, because, friends, 232 - > I see so many salespeople that are stressed out to 233 - > a point where they want to quit their job and 234 - > do something else. Don't quit your job, find a job 235 - > that you really enjoy. Sales is wonderful, but also just 236 - > recognize you do need to do some things. Have some 237 - > techniques to make sure that your brain doesn't get too 238 - > burned out. One of my favorite techniques that a lot 239 - > of you have heard me talk about before is the 240 - > Pomadoro technique. So go on YouTube and find some videos 241 - > on the Pomaduro technique. My understanding is it was invented 242 - > by a stressed out MIT student. They're in Cambridge, mass 243 - > and that person was really struggling to stay focused. So 244 - > the Pomadoro technique is work on a task for twenty 245 - > five minutes, then come off of that task for five minutes, 246 - > and then work your next task for twenty five minutes, 247 - > and then take a break for five minutes and keep 248 - > repeating yourself four times and then take a thirty minute break. 249 - > One of the secrets, though, friends, is say I prospect 250 - > for twenty minutes and take a five minute break. I 251 - > have to come off of task like I have to 252 - > leave my computer and go do something else. If you 253 - > just change tasks, you're not giving your brain enough time 254 - > to potentially catch up on that. So you want to 255 - > be thinking about the Pomadoro technique and what can I 256 - > do to stop my brain from burning out so fast? 257 - > And that is actually coming off task. Now. A lot 258 - > of you are like me. You work remote, and so 259 - > what you can do for that five minutes is go 260 - > outside and walk the dog. I mean, don't be gone 261 - > for an hour. I'm not saying you should take a 262 - > jog and be gone for thirty minutes, but get up 263 - > from your desk, Go refill your coffee, switch from coffee 264 - > to some good Macha tea or something like that. Go 265 - > and find yourself something to go, grab some sunshine for 266 - > a minute, to go outside for some fresh air. But friends, 267 - > I think from a brain perspective, you're always going to 268 - > be a lot more successful friends, if your brain is 269 - > firing on all cylinders. All right, friends, So that's our 270 - > new format every single week where you do a quick 271 - > sales tip, a prospecting tip. We're gonna do some sales tech. 272 - > I'm gonna give you some retention ideas. Answer listener question, 273 - > then give you from my perspective, some brain works, some 274 - > mental health advice. So if you would down in the 275 - > comments let me know if you like this new, fast 276 - > and furious format, because we're gonna always be making changes. 277 - > You asked for it, and so we are delivering back 278 - > what you asked. Friends. As I always say, sales friends, 279 - > if it was easy, everybody be doing it and they're not. 280 - > We're not crazy, friends. This is a great career. It'll 281 - > feed your family for a lifetime. Hey, friends, I speak 282 - > forty to sixty times a year at sales meetings, just 283 - > like all of you have. Love to have you invite 284 - > me into your annual sales meeting or at your training conference. 285 - > Love to work with you and your sales team. You 286 - > can always learn more over at ryandorn dot com. All right, friends, 287 - > mister Revenue's signing off and we'll see you next week.

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