02. Tim Bryson ~ Sandler
Episode Notes
Key moments from this episode
Tim Bryson joins Tailwind for a practical conversation about modern top-of-funnel sales motion: why decision-makers still answer the phone, how low-quality AI outreach is changing buyer behavior, why meaningful conversations matter more than raw activity counts, and how teams can use data to diagnose whether a slump is caused by behavior, attitude, or technique.
Takeaways
- Phone outreach still works when the message is human, relevant, and well-practiced.
- AI can support prospecting, but lazy AI-generated outreach makes bad selling worse.
- Raw activity counts are less useful than measuring meaningful conversations and outcomes.
- Sales teams should diagnose funnel problems with data, not gut feel alone.
- Teams can learn faster by talking to the market before they feel fully ready.
Key Moments
- 0:16
Unlearning sales head trash
Tim opens with the Sandler idea that sales requires people to unlearn old rules about talking to strangers and asking about money.
- 3:58
Meeting prospects where they are comfortable
The conversation turns to matching outreach channels to how prospects prefer to engage, while keeping conviction in the value of the call.
- 6:46
Measuring meaningful conversations
Tim explains why activity counts are incomplete unless teams also track whether outreach creates real outcomes.
- 10:31
Diagnosing funnel health with data
Tim and Austin discuss why more top-of-funnel activity is not always the answer when conversion is breaking later in the funnel.
- 13:53
Why sales matters before perfect marketing
Tim argues that a business can survive without perfect marketing assets, but not without the ability to sell.
- 18:04
Learning before you feel ready
The episode highlights how calls help teams test new markets, products, and assumptions before waiting for perfect readiness.
- 20:17
Real outreach examples
Tim shares real examples of cold and lukewarm outreach turning into useful sales conversations.
Transcript
0:02 I do have one I guess I do have Oh, sorry. Say again.
0:06 I do have one oneliner that I sometimes use that you can record and then keep or not keep. How's that? Let's do the oneliner.
0:14 All right, Austin, thanks for having me.
0:16 Tim Bryson with Sandler. You know how your parents taught you um not to talk to strangers and not to ask about money?
0:24 I'm in sales and that's what I do all day every day.
0:27 We got to unlearn a whole bunch of stuff like the head trash, right? That's right. Yep.
0:32 I'm I'm kind of learning. I'll get there one day. You are doing just fine, sir.
0:37 Yeah. Appreciate it. All right, let's get to the first one. Uh, good or bad, what trend in the top of funnel motion is catching your eye right now.
0:45 I forgot to ask you how long you want my answers to be. Do as long as you want them to be. Okay.
0:52 Good trend. I I find this hilarious.
0:56 Austin, there's a recording in our archives from like a while back, I think the '9s,
1:03 where there's a sidebar conversation as the guy's going up to take the stage and the conversation is, "Oh, cold calling is dead. Nobody answers the phone anymore." They were saying that back in
1:12 the 90s, but you know what I'm finding prospects are doing right now? They're breaking the rules. When I call them, they answer the phone. What the heck?
1:23 And you know what's even weirder?
1:26 I share my 30 secondond commercial which I've practiced for a while at this point. So it's it's been crafted. It's
1:33 been refined. But literally so I think I was telling you about the guy I called through top sale uh two months ago who
1:41 said I quote I share my 30 secondond commercial and how I work with business owners similar to him. He goes, "Man, I've been looking for somebody like you
1:50 potentially." and he did some assessments and we're meeting again on Wednesday.
1:56 Yeah, there was a bit of relationship equity that I knew a guy that he knew kind of thing, but he answered the phone. I'm like, dude, what is your problem? You
2:03 know, nobody decision makers don't answer the phone. Tell that to the CEO that answered when I cold call him the other day. Like, what's going on? But it's it's funny.
2:13 Have you noticed it like become more late like more like reception like lately? because so
2:21 I had huge gaps in mine and so like at the beginning it was just like that's all they I had phone numbers that's all I had
2:29 right and then I took a break from being a seller and I did it again for a little bit and I sucked and I needed training hence working with you guys
2:35 and so my experience has been only in this age of AI where it seems like everyone's happy to pick up the phone I don't know if you've actually like seen
2:43 it up and down up and down so I've seen two things recently that I think are fascinating ask any business owner you know how many
2:51 emails and LinkedIn messages they've gotten in the last week versus how many phone calls 99 out of 100 will tell you they have
3:00 gotten five to 10x more LinkedIn messages and emails at least than phone calls so the funny thing that happens is
3:08 when they answer they're suspicious and then I say something that convinces them I'm a real human being and they're so
3:16 happy to talk to me because I'm actually a real It's hilarious.
3:21 Very, very wild. Um, I think I think it's going to vary by size of company, by industry to some
3:28 degree, I found, but also I've seen people respond from all across the place. And then, ironically, there are
3:37 some people still that would never do not answer the phone. got another guy who I'm talking to, doing
3:45 some work with, who even after he knew who I was, didn't answer the phone, but he responded to the email.
3:52 And I think that has to do with his personality. The dude's a PhD data scientist. He loves communicating over email. Yeah.
3:58 So, I ask people all the time, would you rather be comfortable or make money?
4:04 So, why don't you meet your prospects where they're comfortable? And if you don't know, then call, email, LinkedIn,
4:11 drop by, networking event. I don't know because I don't know what they prefer.
4:16 So, I'm going to show up where I think they might be because I want to meet them where they are. Yes.
4:23 And I will say part of that is having the conviction, having the belief that what I do is
4:31 valuable to them. And if that's in my head as I'm calling, they're going to feel that. And if I'm nervous and I'm scared and I'm hoping they don't answer, they're going to feel that, too.
4:40 Yeah.
4:41 That it has to be well executed has been my experience. And obviously, I'm getting better every day at that. And I can still get better sometimes. But no,
4:50 I've been um to your point about being like uh you know, nervous or not really wanting to like have the person answer the phone and all that jazz. I used to
4:58 feel like I was interrupting somebody's personal space and I've been working on that head trash of being like you know what as their role as this person who's
5:05 a CEO or a sales leader you know a leader in their organization they should expect calls and then to be Sandler about it also give them the opportunity
5:13 to say no thanks and just like leave it at that but like it's helped me so much with like the ability to just pick up the phone to just reconfigure how I'm
5:21 thinking about it and just being like this is an expectation I have to be polite and but I'm not interrupting their personal space. I'm engaging them in their professional role.
5:31 It is a red letter day for my prospects if they choose to answer the phone and have a conversation with me. Yeah. Yeah.
5:37 I have to carry that belief because we know sales is an emotionally violent profession.
5:43 Yeah. That might have been why I quit the first time. Um any bad bad trends that you want to highlight or is the good and the bad kind of like part?
5:52 I mean I I alluded to it. Yeah, I kind of thought, you know, the bad trend and again, email's not dead either. Wellcrafted,
6:00 thought out, and intentional. Can you use AI to research what pain points you should highlight so it's more tailored and customized to the persona? Yes.
6:09 Should you copy and paste what the AI wrote? No. Yeah.
6:13 I have started unsubscribing from newsletters because I see that the the tells like you had AI write this, didn't you? No thanks. delete, unsubscribe.
6:25 Yeah, that's the biggest bad trend that I'm seeing is, you know, bad selling is still bad selling.
6:31 Yeah, makes sense. All right. So, uh when uh you're going your dayto-day or, you know, over whatever like time period, how are you monitoring your top
6:39 of funnel health and like what are things you're watching out for that saying change something? For sure.
6:46 Well, sometimes if nobody's calling me, then I call Austin and say, "Hey, can you give me a new number?" I think I'm showing up as spam. But aside from that,
6:54 um, two things, you know, you've heard us say in Sandler a hundred times, success is the activity, not the result. So, if I'm if
7:02 my activity number isn't where it needs to be, of course, my pipeline is going to be thin. But the other thing I monitor relentlessly is um what I call
7:12 what I would call a meaningful conversation. You answer the phone, I share my 30 secondond commercial, and you either say, "Yeah, that actually
7:19 sounds relevant." or you know, go pound sand. I never want to hear from you again. Hang and hang hang up on me. To me, a meaningful conversation is we got
7:27 to an outcome. You told me yes, you told me no. Maybe you came to an event that I'm hosting or we got to something specific. You told me no, but you gave me a referral.
7:37 If I'm doing, you've probably seen this.
7:39 I've seen sales people. Well, I did 250 interactions today. Well, how many conversations did you have? Three. Okay,
7:47 then your activity wasn't the right activity.
7:50 So, I'm monitoring not just the activity count, but the conversations. And one of my buddies reminded me a long time rule in Sandler is if I can have 10
7:59 conversations a day, that's a really healthy metric. Do I get 10 every day?
8:04 Nope. Is that what I'm what I'm monitoring? So, if I get 25 in a week, okay, I'm looking at it's probably one of the things actually that triggered me
8:12 to say, "Hey, I feel like I'm not getting a lot of call backs. Can we look at this?
8:16 And then after that going down the funnel is from conversation to discovery and so forth. But
8:24 even though I want to look at my leading indicator because that's what I can control, I have to look at my outputs because if I'm not seeing the output,
8:31 then I got to figure out, okay, where is it breaking down?
8:34 Yeah. Yeah. I like that. I I used to try to pin it on like I still do, but now that you're saying this, it's like how many meetings am I getting for next
8:42 week? basically and you can only control so much of that but meaningful conversations you can control that part
8:49 because you might just get the wrong 10 people that day right and I can control in the sense of if I'm
8:58 consistently not getting 10 a day either I'm not calling the right people or I'm not calling enough
9:05 you know and again I'm a huge fan of data driven decisions I shouldn't say again because I didn't say that before
9:12 um data driven decisions. Like I might have a gut feel for what I think I'm doing, but if I don't have, you know, CRM, top sales, something that's showing
9:21 me here's what my conversion rates were, then I it's 2026. There's no reason we should be going on gut feel when we have more data than we've ever had in history.
9:32 Yeah, but gut feelings are great. They're fun. Okay. Gut feeling.
9:38 No, it's an art and a science. Yeah, that feel has its place. Yes, but it's not a not it's it's two sides
9:47 of the A railroad needs two tracks. I don't know where that fits somewhere, but I'll just throw that in as a freebie if that's all right.
9:54 I like it. I like it. I mean, in my opinion, you can't improve what you don't measure. And so, if you're not measuring it, there's no way to improve it.
10:01 You can think you're improving it, but you don't know because you didn't measure it. So then you're just always in this, you know, railroadless like track where
10:10 you're just kind of wandering in the wilderness and you need to put some sort of like data on it and then you can make up decisions off that. But data probably helps more
10:19 which actually that was my answer to your next question. So go ahead and answer ask your next question because that's that tactical tactical tangible
10:27 move to break your team out of an unhealthy slump or yourself out of an unhealthy slump.
10:31 Either one for sure. Yeah, that's look that's that's a big part of it is what is the data saying, right?
10:37 Um the it is in my opinion completely unhelpful
10:44 if my problem is conversion from top of funnel to middle of funnel, middle of funnel. The solution is not more top of funnel activity. M you know if I'm
10:54 having a bunch of conversations that aren't moving to next steps or if I'm doing those 200 interactions and I'm getting three meetings I don't need 300
11:01 interactions. There's probably something wrong with my conversion rate. Yeah.
11:05 So and then when I look at the data so maybe I I hope we're recording calls to some degree. I hope we're you know we've
11:13 got emails tracked in CRM. We can see who's opening all those things. look at the data and then I would analyze the
11:20 data through the BAT triangle. So, behavior, attitude, technique. If you spend any time around sailor, you'll hear us say this a hundred times, but
11:27 it's another great um lens to say, okay, you know, is it if it's technique, it's just I'm not reversing when I should be
11:36 or you know, they say I'm all set. I'm all set and I'm like, okay, thanks. You know, that's a technique problem. I need
11:44 to I need to have something to respond there. But if it's, we talked earlier about, you know, if I've got my parents on my shoulders going into a sales call
11:52 saying prospecting call saying you shouldn't ask about money and it's not polite to talk to strangers.
11:58 Yeah, I didn't say that right. But you know what I'm trying to say. I know exactly what you mean. Yeah.
12:01 Right. It's a it's a huge attitude problem and I can make all the calls in the world. Yeah.
12:05 And I'm going to get stalled. But again, if the data says I'm just not doing enough activity because I'm I I don't have time quote
12:14 unquote. I love that one. or it's not comfortable, I'm scared, but I'm not doing the behaviors. You know, I want to know what's the root cause of that
12:22 slump. And then we'll troubleshoot it through behavior, attitude, technique.
12:27 Yeah. And then the last thing just not to cut you off, but the thing I was going to say, the other thing I say about the railroad analogy
12:34 is hopefully nobody here listening struggles with this, but I sometimes see
12:41 sales people that default to networking because it's easier. Now, this shows up a little more maybe in inerson context than like the outreach that we're
12:49 talking about, but you know, it's always easier to call somebody and say, "Hey, do you know anybody that maybe I should call?" and and hope for those warm intros.
12:58 It's more it's scarier to call somebody that's actually a prospect and say, "Can I tell can you don't know me? We've never met, but can I share with you what I do?" Because I'm risking rejection.
13:06 Yeah.
13:07 But if I'm in a slump and I haven't made any calls to, I don't know, industry associations where my prospects hang out or influential people that know the
13:15 people I'm trying to reach, I have no problem with 10 5% of my outreach being to those people to unlock that door because it's a little variation, right?
13:27 indirect and direct prospecting. The train needs both rails to go down the track. I just have to remember it's always easier to def it's often easier to default to the networking piece.
13:37 Networking has to be earned. They have to show me that they're worthy of building that relationship. Nice. That was a free.
13:45 Um so what's your favorite counterintuitive fact about topofunnel activity?
13:53 I this go I'll key off of the actually the the indirect prospecting thing.
13:57 Yeah. is there's tons of content and tons of resources about inbound leads
14:03 and marketing and lead generation and um referrals and you know and those are all super important stuff and I know a bunch
14:12 of people that run really successful marketing companies and that's important but also true Austin you know as a business
14:20 owner is it possible to run a business without marketing yes yes is it possible to run a business without sales.
14:29 No, not at all.
14:30 No, I know. And that's my favorite my favorite counterintuitive fact is it's easy when I'm from a startup. Well, I
14:38 got to set up a bank account and set up an LLC. I need an attorney and I need a website and I need a logo. Okay, yes, at some point. But what we forget is if you
14:48 get all the leads in the world and you have a great website and you can't get more strangers to give you money and buy your stuff, it doesn't matter. And my
14:57 favorite thing about about top ofunnel activity is you can make a lot of progress and make a lot of money if you
15:04 do it before you think you're ready, which trust me as a as a historically overanalyzer lifelong planner is scary
15:13 as all get out to pick the pick up the phone before I think I'm ready. Yeah.
15:17 And then they tell me no and I still have all four limbs and I didn't die. What the heck?
15:24 So un not ready and like the sense of like you don't feel practiced enough.
15:28 You're still feeling a little raw and like the presentation the 30 second but just going for it learning on the like learning reflecting not being maybe necessarily.
15:36 Would you rather I I ask sales people this all the time. Would you rather have 10 okay conversations with potential
15:44 clients or two really good conversations?
15:48 I'm going with two really good personally. But what would you recommend? Most people say that.
15:52 Yeah. But what gets you more reps? Uh yeah, the 10, right? And by the way, I'm not saying don't practice. I'm not saying be bad at
16:01 what you do. I'm saying, yeah, if you get out there, and it's by the way, it's great if you are if you happen to be a startup listening to this, you can say, hey, can I ask you your opinion
16:10 about something? We're just like we're doing this thing like we're trying to get this started. Like would you even buy something like that if it was you?
16:16 And then I can make it about somebody else and not about them. And then they sometimes say, well, what about me? I don't know. Did you want to talk about you? Right.
16:24 But yeah, you can't. And again, I maybe I'm just speaking to myself there, but I know for a long time I was like, well,
16:32 I'll call that that or what about this moving from squirrels to rabbits to deer to bear. I'll call that bigger company
16:39 when I'm ready, when I'm good enough, when I'm worthy enough. Goes back to the head trash, right?
16:45 Um, and then you call a he didn't he didn't go anywhere, but I through top sale I got a CEO of like a$2 billion
16:52 dollar company answered the phone. That was weird.
16:55 Yeah, he was busy and he never called me back after that, but he answered the phone. I don't know.
17:00 You never know if it's just the right time. Who knows what you could have landed there, right?
17:04 Yep. I was just talking to my little sister and she has this idea that she wants to roll out and she's like, you know, all excited and she's talking
17:13 about like should I get an investor and that way I don't have to work for a while. And I was like, you know, maybe
17:20 maybe on all that stuff, but how are you going to get customers? Like that's the first thing you should really be answering. And then it's like if you
17:27 just picked up the phone and called like 500 people, that's going to be more valuable than any code that you could write at this point in time. and just
17:35 call 500 people and even if you don't have the thing even started yet, you'll know a lot more and you'll be a lot more ready to either say yes, this is a good
17:42 idea or no. And so like when you're saying like are you even ready like if you're talking to a startup, I'd say before you even launch or do anything.
17:51 Just like go call 500 people and see what they say and then that'll tell you if you should do it or not.
17:56 Yeah. And I love that, Austin. And just to maybe confirm, if you're not a startup, it's not just for startups.
18:04 Hey, we need to break into a new industry or we have a new product that's launching or we need to call on bigger bigger accounts or we're expanding or
18:13 I'm new to the industry. I'm new to sales.
18:16 You can't wait until you're ready. Just pick up the call, pick up the phone and call somebody. Yeah.
18:22 And best guess you won't die and you won't lose a limb.
18:28 I like that's your best guess. Not not a guarantee. It's not a guarant I mean who who there's no guarantees in life but I'm pretty sure
18:37 yeah so it's it's been interesting because we were trying to break into a new vertical and the ease of which you can start a
18:44 cold call conversation by just saying hey I don't know if we're even going to go for this vertical you give me some feedback and I got tons of great insight and help from the people and they were
18:53 like they were just like straight up like hey we do inbound and referral like we don't do outbound like some some companies do but I talked to enough
19:01 people to be like this industry is full of a lot of inbound referral folks and as an outbound tool what's the point and
19:08 so like it was but it was so easy to have the conversation and like okay well we're not going to go that direction but like tons of people who are never going
19:15 to be customers gave me insight I would have never been able to get without picking up the phone which was wonderful that's how I figured out I didn't want
19:23 to be an attorney as my mentor connected me to an attorney and we had lunch and that was way cheaper to figure out than taking the LSAT and going to law school
19:31 to You probably didn't want to be a turkey, right? I'll shove into sales instead, you know.
19:37 Yeah. I think of probably in my opinion more productive and important role, but I won't go into my trauma with attorneys and my experience with them.
19:48 The final funny part of that is then the attorneys graduate law school and if they want to make partner, guess what they have to do that they didn't learn how to do in law school?
19:56 Sales. Sales. Every single time. Every single time.
20:01 Uh, all right. So, last question. What's your favorite story about an unsuspected win that you had?
20:07 Oh gosh, I have so many. Um, I mean, I alluded to the two my two per current favorites that I I referenced. So, I'll
20:15 I'll dive into them just a little bit more.
20:17 Um, so what I didn't say was the guy who like he had I don't know gone to high school with one of the guys, a previous
20:26 client. So, there was a there was a name reference which is another hack by the way. you've got relationship equity with somebody out there and then it's not a
20:33 cold cold call, it's a lukewarm cool call if you temperature- wise.
20:38 But um this guy straight up says to me, you know, I only answered and he says, "Normally I don't answer when I don't
20:45 recognize the number, but the it rang on the Bluetooth in my wife's car and I couldn't see the caller ID, so I answered." And that was the guy when I
20:54 shared my 30 secondond commercial. He goes, "Um, I've been looking for somebody like you potentially." And we did a couple
21:01 assessments. We're meeting Wednesday to talk about his one of his teams, and then we're going to have another meeting to talk about um the other team that he
21:08 has. But literally the only reason he says he answered is because it rang on his the Bluetooth of his wife's car, which I thought was hilarious.
21:16 Yeah. And then the other one that I mentioned was this um because Top Sale has a great call email call email cadence
21:24 and the um the data scientist guy responded and said this is actually interesting to me. He goes, "Do you have guarantees for like outcomes or how many
21:32 meetings you help people set?" And I wrote back and I said, "Thanks for responding. Uh I have no guarantees." Well, I guarantee I push people out of
21:40 their comfort zones and I ask them challenging tough questions and uh I can't guarantee results because I can't guarantee people implement the things
21:47 that I teach them to do. knowing that are you still open to a conversation and of course he's a you know analyst so we
21:56 had a coffee and a meeting and then he came to my talk and then we had another meeting but he reminded me of me when I started lots of questions lots of
22:03 analysis and uh eventually after telling me no at least once he uh he did three
22:09 assessments and we are um we're meeting at the end of the month to talk about what training looks like but that that
22:17 by the way was just Because, you know, I said, "Hey, I'm in this chamber. Here's some people that I haven't met that are in this chamber. Just Austin, can you put this put this list in there?" I'll
22:25 just call them and say, "Hey, we're both in the chamber. I have no idea if this is relevant to you, but you know, here's what I do." Nice. Well, hey man, I appreciate it.
22:33 That's all five questions. Those are great answers and thanks for coming on. Thanks for having me on the show. Longtime listener, first- time caller.
22:43 All one episode, now number two. That's right. Exactly. Yes.