08. Cal Thomas ~ Tailwind, Inc
Episode Notes
Key moments from this episode
Cal Thomas joins Tailwind for a practical conversation about defining the right ideal client profile before scaling outbound: how to separate easy inbound interest from true ideal-fit accounts, why different account sizes deserve different sequences and sales meetings, how to test verticals without chasing a bad fit too long, why the buyer decision-making process matters more than a single decision-maker title, and how sellers can treat no as useful sorting instead of personal failure.
Takeaways
- ICP strategy should account for revenue, margin, sales cycle, comfort level, and the characteristics of the people inside the target organization.
- Easy inbound interest is not always the same as ideal-fit business, especially when larger middle-market targets create better long-term revenue.
- Different account sizes deserve different sequences, qualification standards, and required stakeholders in the sales process.
- Sellers should learn how the prospect organization makes decisions instead of relying only on a single decision-maker title.
- A no is useful sorting data when the seller stays focused on truth, fit, and the next right prospecting behavior.
Key Moments
- 0:23
Honing in on ICP while doing outbound
Austin sets up the central question: how long a team should stay with a target profile before changing course.
- 1:52
Inbound interest versus ideal-fit accounts
Cal explains why easy inbound deals are not always the best use of selling time when larger, better-fit accounts drive stronger revenue.
- 4:23
Criteria and sequences by account size
The conversation moves into different prospect categories, sequence lengths, sales meetings, and stakeholder requirements.
- 6:49
Testing verticals and buyer decision process
Cal discusses how sales cycle, risk tolerance, introductions, and organizational decision process affect whether a vertical is worth pursuing.
- 9:55
Outbound behaviors versus lucky inbound
Cal separates revenue that comes in by luck from the prospecting behaviors a seller or owner can intentionally count in the cookbook.
- 14:20
Finding ICP before asking for introductions
A story about a robotics program turns into a lesson about identifying the right profile before asking a network for introductions.
- 16:25
No as useful sorting
Cal reframes rejection as learning whether there is a truthful fit, not as failure by the seller.
- 18:04
Prospecting behavior and sales identity
The episode closes with the mindset behind cold calls, identity versus role, and why behavior matters more than any single response.
- 23:39
Final advice on fit and decisions
Cal finishes by advising teams to understand their sweet spot, best-margin clients, and how prospects actually make decisions.
Transcript
0:00 All right, we have another episode of Tailwind. Uh, this one's kind of special
0:08 because we uh somehow are named after the same thing as Kyle Thomas' training practice. Uh, so it's going to be a very
0:15 Tailwind focused episode, right? Uh, today, uh, Cal's been a Sandler trainer for the last 15 years. Um, and we are
0:23 going to talk a little bit about honing into uh ICP as we're doing our outbound and how to navigate that because can be kind of tricky. And so, you know, we
0:31 mentioned talking about this a little bit beforehand. You know, one of the things that we're working on is um doing our outbound, but then figuring out
0:40 truly what our ICP is as we're doing it and trying to figure out how long do we stay the course versus how long do we sw
0:47 like change course versus all right, is this one of those things where, you know, I should be continuing to go after
0:54 this ICP even though I've failed for two weeks to get any interest. Is that an indicator? Is it not an indicator? Um so that's kind of where we're at. like what
1:02 what are your initial thoughts as you hear where we're at in our journey of trying to figure out how to hone in our target for our cookbooks?
1:09 Yeah, that's that's great, Austin. In fact, we talked about this yesterday and and thanks for having me. And I thought was very um ironic or coincidental, I
1:17 guess, is really the right word, that our companies have the same name. We're Tailwind Strategies. I'm a pilot and a boater, and you always want a tailwind
1:25 if you can have it. And that's kind of our philosophy, which I think is similar to yours. So, that's that's kind of fun. Yeah. But I'm not a pilot or a boater.
1:33 So if we get into real nautical terms, I'm gonna let That's okay. We'll skip the technical stuff. So question about ICP of a
1:41 client. They call it technical the TCP target versus ideal ideal client profile.
1:47 And I love that you picked that as a starting point. I don't want to say fail too many times.
1:52 I think that's what um a lot of my newer clients are missing. I give you a great example. I was with uh one particular
2:00 client yesterday and they get a lot of inbound stuff which is awesome but their inbound stuff is down at this end what I
2:09 in my practice call the squirrels and we've got squirrels uh deer moose and elephants. That's just what we made
2:18 up for size and characteristics. We're very very clear on the characteristics.
2:21 I'm okay with a couple squirrels. I don't spend my time there.
2:25 I also don't spend my time on the giant whales and the great big ones. I spend my time in the middle on the deer and
2:32 host. But I'm very clear on that. So, one of their challenges was, "Hey, it's pretty easy. Uh, they close in a couple
2:38 of days. It's this many dollars and if I go over the middle ones, they're going to take four to six months to close." And there was a little bit of a pause.
2:49 And then she said, 'I know you're gonna you're gonna say some Sandler thing that's going to make me think differently. And of course, and you're a Sandler guy. I said, what what do you
2:58 think I would say? And then she told me, right, Sandler 101 or 2011? She said, well, if I start that and it's a five or
3:06 four month sales cycle, you know, I've got 10 in a funnel and I close 50% as most of them do. Oh, now I'm closing
3:16 four or $5,000 deals, but still regularly and I'm doing more outbound.
3:21 It's harder. It's more It's It's less comfortable, but they actually make I think it was
3:28 3.2 times the revenue, right?
3:32 So, they kind of have their ideal client profile. They're going easier to take the inbound stuff because it closed
3:39 faster. Now, when I put that up against their mortgage and the bills that they pay at the business, they're going to work a little harder. Not because they
3:47 didn't want to, but it's just they didn't process that ICP. So, I'm glad you brought that up first. Yeah. So when you're looking at those, you know, the
3:55 different sizes, are there some se still like key characteristics for that customer where it's like like the
4:03 inbound squirrels are pretty much the same one, but it's like for you know a sloppy like example like but it's like a
4:11 five person shop and they really want to go after like the bears 30 person shops but those are just going to take a little bit longer even though it's the same industry and a similar fit for what they're doing. It could be.
4:22 It could be.
4:23 And there's all kinds of ways to slice it and dice it. So, we've got one and they're they're equivalent of a squirrel is uh it's x amount of dollars. Not a
4:31 lot, but it, you know, pays the electric bill. That's a good thing. Yeah.
4:36 But I'm also only going to spend this much time. It's a three uh a three-piece sequence.
4:42 So, I'm going to close the file after three attempts, not chasing it. If they want to come back, great. On the other
4:49 ones, uh it's it's a 9 to5 uh item sequence. Yeah.
4:55 And the sales meetings are very different. We have a discovery call, which in Sandler terms are bonding, a rapport, an upfront contract, and some
5:02 pain indicators and a yes or a no to have another conversation. The next one we're going to need to pay.
5:09 The next one we're going to right and and the ones in the middle, um probably a sequence of five or it's a warm
5:16 introduction. By the way, my whales, I don't chase any unless I'm introduced to somebody with a C in the front of their title. Mhm.
5:24 Because it just takes too long and it's not I can close two or three in the middle in that amount of time. Right.
5:30 But yes, they all have a very clearly defined set of criteria. The ones in the middle, we know what the first, second, and
5:38 third sales meeting looks like and who must be there. So, we're very clear on that on the process and who needs to be
5:46 in there. Very short story marketing client and in their second meeting for their their bear and their moose, their
5:55 talk track literally is typically what happens next is the chief marketing officer and the CFO come into that meeting. How do we make that happen?
6:03 Now, they say it a little more nurturingly than that, but it's being crystal clear and sticking with it. You know that one. So
6:11 as so in this situation it sounds like like they have a very specific ICP and now it's just like where do you where
6:18 you focusing energy? How much energy is then going to be like the right acquisition cost for what you could potentially get? Um, what about people
6:27 who you work with that are maybe still trying to figure out like the right vertical? Like that's that's going like,
6:34 okay, like we're getting this interest, but it's scattered, which is not an effective outbound strategy. It's fine for inbound.
6:41 Anyone can come to anyone for that, but if you want to get targeted, you got to have like the right focus. You got to be honed in. um when you're navigating that
6:49 with one of your clients, how do you go about like the experimental phase of that depends on your tolerance and your sales
6:57 cycle and I mean there are so many variables but I'll just give you a quick example of one one guy very technical guy fantastic business uh medical device
7:06 manufacturing and also he had a lot of clients in the education in in higher education.
7:16 The founders of the medical device companies can make a decision with a couple people, right?
7:23 Think about the decision makingaking process in an institution of higher learning, right?
7:29 They have to find the funding. They need to get the approvals. There's a whole political will that has to change. So he will do that if introduced in at a very high level.
7:40 And and that's I think that's one of the failings in I had a question yesterday.
7:44 One of the failings why a sales cycle say take take so long or longer than they should.
7:49 First and foremost, we don't get clear futures date time on the calendar for the next conversation which as you know in Sandler is non-negotiable or it's a no.
7:59 Right. Right.
8:01 Uh or they don't we don't understand how the prospect how that company makes decisions and it's not decision maker
8:08 it's decision making process and that's our job to learn it. It's not their job to tell us. It's our job to ask them the
8:16 questions. And that I find that is one of the biggest after people have been a client one year, two year three, they start to get really good at that.
8:28 Yeah, that makes a lot of sense. I guess uh to your point about it being like complex like yeah it's gonna totally
8:35 depend on so much context of like maybe you have resources to mess around with an ISP for a couple years just to learn about it and maybe you don't and maybe it's not the right fit for your product.
8:45 Um I guess like for a specific like our what we ran into we spent about a month going after uh benefits producers and we
8:55 were having these conversations. We were getting in with like you know seuite or like right below VP level people having conversations and I mean it we spent
9:03 about a month doing it mostly cuz I'm stubborn which is probably really the issue but every time I talked to them they're like you know we just rely so much on
9:12 inbound and referrals we have no interest in doing any outbound and I would get like one out of 10 conversations somebody may show a little
9:19 interest in outbound but a majority of the conversations were just our business model isn't aligned with that. And so like I I cuz I'd find the people and I
9:28 was like, "Well, let me just see if I maybe talk to like the wrong 10 people to start. Maybe the next 10 people will have a different story." But then by the end of the month, I was like, "No, the
9:36 story is the same. I'm going to have to like find a needle in the hay stack during my outbound to in order to find the people who even would consider us as
9:44 part of their business model versus like maybe we're a bad fit or maybe they like an alternative or competitor. That's to me a totally different data set than we don't even care about that motion.
9:55 Yeah, that's true. That's so we're we're in a little bit of the same business to some extent, right? I don't go generate leads for anybody. Um, but we're mostly
10:02 an outbound organization other than referrals because we have a very intentional model of asking for referrals. Um, and those are the only
10:11 ones. I mean, not the only ones that count, but in our, you know, the Sandler cookbook and your prospecting plan in there, I can't count the ones that just come to me because I was lucky.
10:21 I'll count them in my revenue happily. Yeah. that that's I'll take them all day long.
10:26 Um, but it's the ones that I ask for that count in my behaviors.
10:30 So, a lot of my early on questions to either owners of companies, um, which by the way are often sales managers and I need to remind them of that.
10:40 If you're the owner and you have people that sell for you, you're a sales manager and sales managers have to do some behavior. I mean, they don't have to, right? And if they don't want to,
10:49 then they won't work with us, which is fine. Uh, but I will ask early on, tell me a little bit about the behaviors of your sales team.
10:58 And often they don't really know what that means. Um, they do good followup.
11:03 Well, I don't know what that means, but are they do you what's the percentage of inbound leads they get versus the self-generated leads, which is usually what they call them?
11:13 And if if it's mostly inbound, right, we used to call it, David Sandler called it sitting aggressively sitting by the phone waiting for it to ring.
11:22 I don't know about you. Mine doesn't ring that much for people who are dying to bring me in to do training.
11:26 I wish I wish it rang more often, but it just doesn't.
11:30 But then we wouldn't be very we wouldn't practice and hone our skills, right, Austin? So, yeah.
11:36 No, it it's definitely interesting. I I think the whole idea of uh um an owner at any point in time not being part of
11:44 the sales or maybe maybe not making you know 30 dials a day or something but still very involved in the sales process
11:52 you know especially if you get a whale coming through the door that owner's got to be involved in that conversation but now what what the right amount is based on their team skill set that's going to
12:00 change but right I feel like you know that's something that I took an entrepreneur class when I was in graduate school And like, you
12:09 know, it should have just been like a sales class. Like that would have been the real like, yeah, I learned a bunch of great stuff and like I started to learn that entrepreneurship is being a
12:17 seller, but like that should have just been, you know, maybe just like a Sandler class for a year of just learning how to sell the process.
12:25 I'm very happy that we don't teach sales in college. I'm I'm good with that. So, you don't think it should be taught in college?
12:31 Well, of course it should. I'd rather them come to me, but you know.
12:34 Oh. Oh, okay. Yeah. Sorry. Sorry. I messed up. No, no.
12:38 Yeah, it keeps your your business model alive a little bit. For sure.
12:40 Yeah. Yeah. Yeah. Now, if if we could take if we could teach uh teenagers and I coach a couple teen kids of clients
12:49 and the stuff that they're able to do that their peers can't do because it's a mindset shift. It's a behavior shift and it's having guts and not worrying about
12:57 the rest of the world, what they think, right? Self-esteem, self-worth, self-concept, all that stuff. Boy, if we could develop that in kids' be a
13:05 different world. But we're not going to go down that.
13:08 I mean, why not? I'd be really curious what you mean. I like Do you think that they're like more assertive and like staring their own way and like, you know, setting up conversations?
13:18 Really great client, probably one of my favorites. I've got a few favorites. And uh um we do a couple goal setting programs throughout the year. You've
13:26 you've been in them, I'm sure. And uh uh this woman, she's a COO of her of a goodsized company and she took the goal
13:33 setting program home with her and did it with her 12-year-old son. Mhm.
13:39 Kind of an introvert, kind of shy, kind of 12. Yeah.
13:43 He's now 15, the leader of his um robotics program. Mhm.
13:51 in three sports.
13:54 Um and the whole and and he's the nicest normal kid that you'd want to talk to.
14:00 Now, am I going to give goal setting full credit for that? Of course not.
14:03 That's good parenting and it's other stuff. But um but we know it made a difference. We know for sure it made a difference.
14:10 So we this person recently asked, he said, "Can you connect me with some businesses?" I'm gonna bring this back to our topic. I promise, Austin.
14:18 Oh, no. No. This is great.
14:20 Can you can you give me um some contacts because I know you have a big network um of people you think would sponsor our program or participate, right?
14:29 Materials, time, and money. I said, "Absolutely. You deliver your ideal client profile.
14:36 You figure out through tools that I know you have access to and you give me some names and some examples and I will introduce you all day long after you do
14:45 that and identify your ICP." and they looked at me like they're in the heads of but they did it and now they know.
14:54 Yeah. Well, and and that I love that example especially with like you know what is
15:01 outbound other than starting a conversation that's just an honest one to figure out if there's some sort of relationship to have or if not and all
15:10 good. And for a 15-year-old to go to somebody and ask, "Hey, we are trying to do this." Like, let's put on this, "Do
15:18 you have anyone that you can refer to me?" Like, at 15, I would have been like too worried, too scared, had the wrong headspace. And now this kid is like, if
15:27 he can figure out that that's exactly what he's going to do with business, which I'm going to be extremely surprised if he can't, he's gonna have so much success. and no matter what kind
15:34 of like department he wants to work in or whatever, he's just he's already built the confidence, the knowhow to go out and start a conversation that helps
15:43 him get to an end goal. And I'm ass sure and like a very polite and friendly and you know professional attitude. Um it's
15:51 incredible and and the thing that came to me and I he taught me this. I didn't I mean we teach this in Sailor, but he asked me a
15:59 question. I gave him the kind of talk tracks for a sailor cold call or cold conversation.
16:04 You know, this probably isn't for you, but we're looking for engineering companies who are worried about um developing young talent, having new
16:13 engineers, all those things. And you know, we run the robotics club, but I don't know if those are things you
16:21 think about. And the guy's like, "Yeah, of course I do." Yeah.
16:25 He didn't say, "Where do I sign up?" He said, "What if people say no?" And I said, 'You'll get more of those than you get yeses. And he just went, oh no.
16:33 Yeah.
16:33 So he said, "So I'm going to fail at this a lot. You're not going to fail. People are just going to say no to you.
16:40 Is that failure?" And he said, "No. When you lose a tennis match because somebody's really great, is that a failure?"
16:48 No, it's actually not. So if we can change that mindset, then they fail early. And we we hear about this in all the leadership books and everything
16:56 else, but fail fast, fail off, and fail fast. If if we can get these teenage kids that fail and understand that it's
17:03 not real failure or that they've they've done that, then boy, when they're 20, 30, 60, Yeah.
17:10 And the world's going to be a better place.
17:12 Yeah. With a lot more like interconnected relationship with folks because like that's what it is. And I mean, I think that was like one of the things when I first started having to do
17:21 like my own cold calling is like not understanding that a no has nothing to do with me and just purely like I mean it could be something as like I just
17:29 caught them on a bad day all the way to legitimately this isn't going to help their business. That doesn't mean anything like it just not every business is going to work with every business.
17:38 Not every solution is for everything. So when somebody says no, they're just clarifying, hey, their reality is that this isn't the right thing for them at
17:46 that time. Cool. That that's just a good sort.
17:51 All right. So much of saying the rules, you probably know them. Sales is a conversation between adults to get to the truth.
17:58 Right. Some will, so what? Some will, some won't. So what? Someone else is waiting.
18:04 Yeah, that's true. And I have a I have a a new addition to our team. uh who's who's
18:11 become a really is understanding Sandler and the mindset and doing the behaviors not great at them yet but that doesn't matter right technique will come along
18:19 and I'd asked him I said what is the point of thoughting behavior and let's go since you brought it up
18:27 Austin code calls what's the point of doing cold calls I'm not going to put you on the spot put him on the spot and he said I know the answer to this
18:36 and as you know we just wait in silence for people to answer their own question he said, "The point of making the calls is to make the calls and complete your
18:44 calls." I'm like, "Boom, tell me more." And he said, "Well, in the beginning, when I'm not great at them, people are going to
18:52 hang up or they're, you know, most Sandler cool callers don't get hung up on, but they may get a no. I don't want to continue the conversation." You get a bunch of them. Mhm.
19:02 And he said, 'But if I'm getting those, I need to change my technique or my mindset or I need to do something or I just need to change something because I
19:09 know they work in combination with other things. But the point of doing your prospecting behaviors, they'll bring it back again.
19:18 If they're directed at your ICP, your ideal client profile, and you've got good technique, and you've got a belief system, and you're
19:26 willing to suck it up and go, "Yeah, people are going to say no." There's a bunch of yeses in there. I mean, I can certainly 15 years later, I can
19:34 certainly attest to I got way more nos than yeses, but you know, we gota we got a pretty decent fun business. I
19:41 have no complaints, but it's you just you just got to do it. And it stings a lot less after you've done it a couple hundred times.
19:48 Yeah. And I think also once like I think when you first start doing it, it's just impossible to be like, I'm going to take on the mindset of like no doesn't feel
19:56 good, but that's okay. Like you have to actually feel it too, right? Like there actually has to be like the moment of like I I got to know. Let me just think
20:04 about that. Sit with that emotion of getting the rejection and then have the good, you know, training that tells me it has nothing to do with me. They've
20:12 already forgot about me in like the next 30 seconds. We're probably not a fit based on the conversation or maybe I just need to improve and say something
20:19 better. Sit with that. Make another dial. And then like after you made a couple hundred dials and that's happened now you can go all right now now it
20:28 really does roll off my back. Whereas at the beginning it's like let's not pretend like it really is rolling off the back from the start.
20:35 Absolutely right. Right. We have a a Sandler thing called IR theory is is your identity versus your role. Mhm.
20:43 So, how I feel, my beliefs in myself, self-worth, self-concept, self-esteem versus how other people in the world
20:50 view me as performing in my role or even I I mean, we've all had a bad day with a a spouse, significant other, kid or or
20:58 sibling or golf course or something, right? We've all had a bad experience, but that can't define who we are. So
21:05 society tells us that how you perform in your role depend determines how you feel. It depend determines how uh what
21:13 you're going to do, right? That's your identity is your performance and your role is how you're viewed in the world.
21:22 My belief is the behaviors and the things that I do determine how I feel about myself.
21:30 Yeah.
21:31 Right. the the the role performance. And here's the technical part. If on a scale of one to 10, I see myself as a a six
21:40 through six, seven, eight, meaning I don't get out of my comfort zone a lot.
21:44 I'm afraid I'll never be that good. I'm an at least or worse. In New Jersey, we call them losers. You can't do that on on a video. Right? And if I'm getting
21:53 out of my comfort zone and I view in my mind without a big ego that I'm an eight, nine, 10, then I can start to perform in roles better than I could if I don't see myself that way.
22:03 Yeah.
22:04 So I think I think society's got a little bit got it a little bit backwards and psychologyy's probably got it a little bit better. Well, you know,
22:13 to the point of like being in the high school and what you're learning, you're learning more of like compliance and read this book and then fill out this
22:22 book report and you're not learning these emotional intelligence building activities like, hey, if you guys have a robotics club, you don't ask your dad to
22:29 go ask somebody to do it. You go out and you have a conversation with adult and start building your own selfworth. And then if you start doing that, then it's
22:37 like, okay, now like you're becoming self-sufficient. you start to understand the difference between, you know, who you are and what that activity is.
22:45 You're going to be way more uh open to it because you haven't overlearned like this whole like just fall into your role that society tells you thing. You're going to be like, "Oh, I'm going to try
22:53 this stuff out. I'm also 15. If I say something dumb when I'm trying to get some some materials from a robotics like company, like eh, whatever."
23:01 Yeah. You don't need grace for saying something dumb when you're 15. You know, when you're 16, not so much. But yeah, I think we should all get grace for saying something dumb as long as we're willing to admit it.
23:11 I do it every day. Ask my wife every day. But it doesn'tffect it doesn't affect my identity side.
23:18 Yeah. Well, we're humans. We're going to make mistakes.
23:21 Exactly. That's We're not We're not trying hard enough. That's for sure.
23:25 Yeah. Well, K, we had a a upfront contract that this would only be a 30-minute meeting total. We're two minutes over. My apologies for not
23:32 managing. Um, do you have any final parting thoughts before uh we end the session?
23:39 Aside from the psychology stuff, I would go back to um understand your ideal client profile. What they what it really is, what's your sweet spot? What makes
23:48 you the most revenue uh and the best margin? I don't think it depends on vertical necessarily. I think it belong is characteristics of the people in the
23:57 organization. That's a takeaway. Um, and the other is learn as much about and ask questions about how they make decisions.
24:08 Yeah, the decision-m process can shed a lot of light on whether or not it's worth going all through. It can also help you figure out how to to play the
24:15 game of how do we go to the right people and talk to the right people in an organization. Because even just like going to the wrong person who maybe is
24:23 not interested in it, maybe if you talk to this person instead and had paid more attention to what your you know your initial you know champion or uh you know
24:31 contact was saying like not forcing it at that organization. Um right make a difference or the minds or or I might make a
24:39 decision right there to say nope not a fit none I'm saying no on your behalf let this call it a no move on.
24:47 Yeah I mean that's a hard one for anyone. Everyone wants to get through.
24:50 Yes. But that's not necessarily the place to get to. At what cost? That's the question. Yeah.
24:56 Hey, thanks for asking me tough questions. I always like when people stump the Sandler guy. That's awesome.
25:01 I don't think I stumped you, but thank you for answering them. I thought those were all great. Really appreciate you taking the time and uh I wish I had
25:08 better way to send us off. Give us a good nautical sendoff for the podcast. Oh boy. On the spot.
25:17 Uh there's there's your one stump question, but it has nothing to do with Sandler.
25:21 Well, that's okay. Um couple of things is a boating term. Uh ships were not
25:27 built to stay in a calm port, and the other is watch the weather and
25:34 don't do anything stupid, which does relate to prospecting, by the way. Yes. Thanks. That was a stumper. You might have gotten me there.
25:42 All right. Appreciate you, Cal. Thanks.