Sales success is limited by fear of rejection, risk avoidance, and an unwillingness to tolerate the negative outcomes required to win more deals.

In this episode of SalesTV, Caspar Berry, keynote speaker and former professional poker player, explores how salespeople think about risk, rejection, and decision-making under uncertainty. Most people associate risk-taking in Sales with failure, loss, and hearing “no.” Instinctively, they work hard to avoid it. But in reality, success often requires accepting a predictable number of losses and understanding how probability shapes outcomes over time. In a sales environment that rewards wins and discourages failure, this creates a natural bias toward risk avoidance, even when it limits better decisions and long-term opportunity.

We’ll ask questions like -

* Why do good salespeople keep losing?

* What should salespeople do when they’ve done everything right and still lose the deal?

* What are the long-term consequences of consistently avoiding risk in sales?

* What can salespeople do about buyers who are afraid of losing?

Caspar Berry is a keynote speaker on decision-making, risk, and uncertainty. Drawing on his experience as a former professional poker player and entrepreneur, he has worked with organizations including Google, IBM, KPMG, and Barclays, helping teams understand how people assess risk and make decisions under pressure. His work focuses on how probability, loss, and uncertainty shape real-world choices, including those made in sales environments.

Join us Tuesday at Noon ET/ 9am PT.

This week's Guest was -

• Caspar Berry, keynote speaker and former professional poker player

This week's Host was -

• Rob Durant, CEO, ISP US

Transcript of SalesTV.live Mid-Day Edition 2026-04-14

Rob Durant [00:00:00]:

Hello and welcome to another edition of SalesTV Live. Today we're examining why good salespeople keep losing. We're joined by Caspar Berry, former professional poker player turned keynote speaker. Caspar helps enterprise organizations like Google, IBM and Barclays understand how profitability, excuse me, understand how probability, loss and uncertainty shape real world choices, including those made in sales environments. Caspar, welcome.

Caspar Barry [00:00:39]:

Thank you very much indeed for having me.

Rob Durant [00:00:41]:

Oh, it's our pleasure. So, Caspar, I've only got you for a limited time. I want to jump right into it. Why do good salespeople keep losing?

Caspar Barry [00:00:54]:

So, you know, we've had a few conversations before this and I'm very insecure and British and I don't want to be here saying I know exactly how to sell and what sales people are doing wrong. I look at it all from my perspective, but from my perspective there's a very, there's a very particular answer to that question, and that is that salespeople see themselves as salespeople, which makes sense, but don't tend to see themselves as resource allocators or investors. And they are. They're allocating their time every single minute, every day. They're investing their time, money, I'm sure, energy, passion, dedication, credibility, standing, status, respect. All decision makers across the whole range of business and life. We're all allocating scarce resources under uncertainty. There are certain skills and things that we can learn to do that better and worse.

Caspar Barry [00:01:50]:

And I would put forward the idea that a lot of salespeople are much more concerned with the skills of sales than with maximizing returns on investment as resource allocators. And whereas I'm sure salespeople will agree with me, in other departments of a business, people can kind of, they can hide. Right, because their results aren't so visceral. Right. We all know bad people promoted to high office in sales. Your results are there for everyone to see. It's so much more obvious whether you are a good resource allocator or not.

Rob Durant [00:02:26]:

So I want to dig into that a little bit. Tell me more about what you mean when you say a good resource allocator. And how is that different from sales skills or really any profession skills?

Caspar Barry [00:02:41]:

Yeah, so, so here's the, here's the relevance. You know, you introduced me as a former professional poker player again. Actually, poker is. You've got sort of, I don't know, general management down here, right? You've got sales here and you've got poker right up here in terms of how obvious and, and revealing your results are as an indicator of how good you are. Allocating scarce resources, sources, right. In poker, broadly speaking, it's pretty much everything. So in order to be a successful poker player, you have to learn this skill. And if you don't, you won't be a good poker player.

Caspar Barry [00:03:16]:

But what does that mean? It means you will literally lose your own money on a daily basis, right? In sales, you know, you still get paid an income, you've probably still got leads coming in. You know, we all know bad sales people who can just keep it ticking over. So there's a certain amount of hiding. And as I say, when we get down to general management, you can hide behind all sorts of things. But, but we're trying to be good resource allocators. Right, and what does that mean? It means overcoming the very specific decision making biases, resource allocating biases that are inbuilt, that are hardwired into most of us as human beings not because we're flawed, not because we're quotes on quotes, emotional or they tend to be associated with sort of emotional biases, but because we are human and we were hardwired to survive essentially. Right? So what is the first and most obvious of those emotional biases? It is that we, we don't want to fail because failing occupies the same part of our brain as dying, right, or getting injured. And so we are risk averse, broadly speaking, as a species.

Caspar Barry [00:04:13]:

That does not mean to say that every salesperson is risk averse or every human is risk averse. We're all different and different people have different skills. But most of us, most of the time are avoiding pain. And in sales, if you're hardwired for avoiding pain, that means not losing. That doesn't necessarily mean winning or maximizing returns on investment. During this little chat, you know, I'm going to introduce a concept called negative metrics. It just means outcomes that we don't want. Again, as salespeople, as fathers, as motivational speakers, none of us want negative outcomes, none of us want bad gigs, none of us want sales that don't go anywhere and therefore we want to try and avoid those.

Caspar Barry [00:04:53]:

And one of my big points is that actually embrace tracing negative metrics is not necessarily a bad. A friend who was a sales guy in the city selling insurance, broadly speaking, and they actually did a very interesting sort of, you know, assessment of, of their different sort of sales returns and the different people in the office and the two people who outsold the others by a long way. Number one was the person who made the most approaches and sales calls and experience the most rejection. So that's one example of the negative metric. And number two, but still head and shoulders above everyone else, was the person who made the least approaches and got the least sort of no's. But he put the most amount of time into researching the prospects. Right? Something I call a J curve. You put investment in before you start to get a return on that investment.

Caspar Barry [00:05:49]:

And that's another kind of negative metric. It's the one we associate with learning and growing and change and all those kinds of things. So again, as salesperson people, we don't necessarily think about those. We know that we do have to make outbound calls and we know that we're going to get no's, but we don't necessarily sit down and do the maths behind that. One final one to say is, as poker players, we know that we've got a certain amount of limited, scarce resources. We know that we're going to get a certain number of opportunities presented to us in the form of poker hands. In your case, the sales case, it's prospects. And as poker players, we know, because people have done the maths before us, that broadly speaking, we should say no to 85% of those.

Caspar Barry [00:06:31]:

Could be 94%, could be 68%. But we know that we should be saying no quite a lot of the time because each opportunity, most opportunities that get presented to us do not have a good, high, positive expectation. So a salesperson's more natural inclination would be to go for every opportunity that becomes available to them. If we did that in poker, we would make a loss. And that's just another example of how in sales, I'm not saying that we don't do this at all, but none of that has anything to do with the skill of selling of, you know, persuading people to buy something. But it's all about the mathematics of trying to maximize returns on investment. And it's how someone who might be really good at selling actually might be working. And this is the key term inefficiently.

Rob Durant [00:07:16]:

Wow. A lot there to unpack. And I followed, but I want to dig into a couple of things there. So I heard good salespeople are losing not because they are hearing no from prospects, but because they are not saying no enough. Is that what you were saying?

Caspar Barry [00:07:40]:

Let me be clear. These are. You've heard me use this phrase before, but I think it's crucial. These are tools, not rules. Let me just divert into a 30 second story. So after playing poker professionally, I got a job as a commentator on, on a TV show because the poker boom in 2004, 5, 6 happened. And there were, there was a, there was a demand for people like me who had an understanding of poker and media. Right.

Caspar Barry [00:08:03]:

And during that time, it was actually from 2005 to 2009, I did it. We, we got a lot of emails from people who wanted help with their, their poker game. And their thoughts changed a lot, by the way, from results to process. And that's one of the key messages here. But my key message for them was that I'm trying to give them tools, not rules. Because unless I'm standing over them playing poker, obviously I'm not standing over anyone watching this as they sell. I don't know what the exact situation is. And selling like yachts is probably different to selling, you know, banging out insurance policy.

Caspar Barry [00:08:37]:

So it's horses for courses, but as a tool, not a rule. Yes, it's, it may well be that the salesperson themselves should be saying no more often in sales speak, qualifying more leads, doing more of that pre conversational time, for example. Yeah, Just, just understanding that not every sales meeting that they've got in the book is, is necessarily worth going to. Our time and resources are incredibly scarce and precious, and how we allocate them in the sales process, I would argue is going to determine our results as much as our ability in the room.

Rob Durant [00:09:14]:

I get that. And from a sales perspective, so often we feel like the leads that we've been provided are the scarce resource. Even a good lead is hard to come by, though. And not all leads are created equal. So if I'm applying what you're telling me as a tool, not a rule, I am evaluating the viability of that lead, and then I am determining whether I want to allocate resources to that, as in pursuing it, calling, following up, and so on.

Caspar Barry [00:09:56]:

Yes. I mean, here's a good poker analogy with that. Um, let's say I make a bet of $10,000. Right. And let's say there's only a 20% chance that they'll call that bet of $10,000. That's, that's, you know, when you were talking about the viability, the quality of this lead, the likelihood that they're going to buy. You know, you use the word in my introduction. That's probability.

Caspar Barry [00:10:19]:

Right. That 20,000. Sorry, that 20% of $10,000 gives me what we call an expectation or value of that bet of 20% of 10,000, which is $2,000. Right. And at a basic level, salespeople should be thinking exactly the same way, because 20% of 10,000 is worth more than a 90% chance that someone would call my $1,000 bet. Right. So this leads to a conceptual misunderstanding of poker. Poker is not about getting people to fold, like bluffing, so you can take the pot.

Caspar Barry [00:10:55]:

It's not about betting enough that they call in poker. And this is not where it translates to sales in their opponents to make a mistake. So either folding incorrectly or calling incorrectly. Okay. With a view to maximizing that concept of value or expectation. So 20% of 10,000, they're going to fold 80% of the time. So it's going to look like I failed. Right.

Caspar Barry [00:11:17]:

But that is better than 90% of 1000. So in a way, salespeople should be thinking the same, which is what is the value of this opportunity in terms of probability, likelihood to buy, and total value of sale? And I'm sure many of them do. But being really brutal with ourselves about that in Boker is how we get better. I just want to say one other thing, because we're talking about taking risk here. I used to know a guy in poker in the early days of the Internet who used to have a home gym that he used to work out on. As I'm sure many of your viewers will know, there was still is. You get software to crawl all the different games. So you're watching, you're gathering statistics on lots of different players.

Caspar Barry [00:12:04]:

And his software was looking, as software should, for rich people who were bad at poker. Right. Because they are the best people you can play poker with. Right. And every now and again, one would come online and literally in his home gymnasium, his machine would go bing bong. And he would go and sit with those people, and he wouldn't play at the limits that he played for with general poker players. Right. In other words, he put his time and energy, as a very sort of amateur computer programmer at that time, into finding bad players and opportunities.

Caspar Barry [00:12:40]:

And again, I'm not saying salespeople don't do this, but I think that's interesting because I think generally in business, not just sales, how much energy do we put into being a better poker player, better salesperson, versus how much energy do we put into finding people who are less good at poker than us in sales terms, Finding inefficient markets where the pickings are rich. So it's very easy to complain about the quality of our leads or the quality of the market that we're playing in. But what we're doing is we're busy, so we feel like we're, you know, productive. But are we as productive as if we were Actually spending that time looking for completely different situations, maybe selling completely different products, but maybe selling the same products in different ways or to different people.

Rob Durant [00:13:28]:

Got it. You mentioned a term that was new to me the first time I heard it and I'm sure it's new to our audience. Negative metrics. Can you unpack that for us a little bit?

Caspar Barry [00:13:43]:

Yeah. So I referred to it earlier on when I, when I used that ten thousand dollar bet versus the one thousand dollar bet. If I make the ten thousand dollar bet, my opponent, let's imagine I've got four aces, by the way. So let's imagine I'm going to win this hand. It's just a question of how I maximize my overall returns. What I want to call the net effect, okay. If I make the $10,000 bet, my negative metric is going to be a lower call rate. So over the short term, in sales terms, they're going to say no more often.

Caspar Barry [00:14:18]:

In poker terms, they're going to call more often. That's a negative metric. But what's the net effect? The net effect is that each time I do it, the value, as I've already shown by that calculation is greater. And therefore the net effect is that I'm making more money and I'm making a higher return on my investment. So this has resonance throughout all areas of business and life for a very specific reason, and that is that when you move into that space, it is an unexplored space because other people are reticent to embrace negative metrics because they're risk averse. Okay? So for example, in ice skating, Jeff Colvin discovered that the young ice skaters who seemed to win all the gold medals, who wanted to correlate against something in their life, wasn't their upbringing, wasn't their parental profession, wasn't their ability to succeed at lots of other things. Some correlation with hours spent on the rink. Because practice makes at least perfect, if not permanent, if not perfect.

Caspar Barry [00:15:22]:

But the single strongest correlation was with the number of times they fell over during practice.

Rob Durant [00:15:25]:

Right?

Caspar Barry [00:15:26]:

Because those people were trying to do new and different things. Why didn't everyone do that? Well, because falling over is painful, right? And not just painful in ice skating terms. And I would argue that all negative metrics are painful in a way. But if anyone's ever tried to get better at golf and gone to the driving range and got all the equipment out, that people say you look like an idiot, right? If you, if you start doing what they tell you, which is swing without a club, just try and hit it 30 yards because the guy behind you is driving it 240 yards. And again, you look like an idiot. Right? So that's not pain, but it's this kind of, why would I be trying to do these things I can't do at the moment? And difficult things. And that's an example of self improvement when I can just do the easy thing.

Rob Durant [00:16:18]:

Right.

Caspar Barry [00:16:20]:

That's not what people mean and talk about when they. When they say there is no such thing as failure, only feedback. And I kind of hate that phrase. Not because it's not true. Right. I've given an example there of personal development, but the feedback there is the value. All right? So we have to respond to the feedback. I'm falling over.

Caspar Barry [00:16:41]:

I'm not doing it right. I'm not doing it right. I'm doing a bit better. I'm doing a bit better. And now I'm starting to see succeed. I'm starting to succeed and now I'm perfect in doing it right. So there, the feedback is the value. But here's another example.

Caspar Barry [00:16:51]:

Ryanair, when they were the fastest growing airline in Western Europe, also had the highest number of passenger complaints per mile. Now, that's not no such thing as failure. Any feedback they weren't learning from each passenger complaint they had. I'm sure that they were a little bit. But that's not the point. That's not why that strategy worked. That strategy worked because by embracing that negative metric that very few companies are prepared to embrace, because most companies want to do the best possible job, they don't want to do something that they kind of know is going to get higher number of passenger complaints. They were able to explore a place in the market that other people were reticent to explore.

Caspar Barry [00:17:33]:

So these are examples where the negative metric being prepared to do things which are painful and unpleasant and difficult in all sorts of different ways, way beyond the physical, although it can be physical, actually leads to a higher net effect as a result. And in sales, let me just give the most perfect example. Perfect, but just a good visceral example of that. Listen, when I sell, I have sold in the past. I'm not a good salesman, you know, I'm not wearing a cap saying salesman here. I want to be liked, okay? Because I'm a human being and I want to make friends with people and I want them to follow up on LinkedIn and all that kind of thing. But what if that's just not tools, not rules, just not the right approach in this situation, in this market, with this product, with these potential prospects, what if the Negative metric is, you know, being quite aggressive and quite visceral in ways that a lot of books don't necessarily teach in 2026. But what if that is the most profitable way? It's a negative metric.

Caspar Barry [00:18:37]:

It's not something that people want to do. I certainly wouldn't want to do it. But if I was a salesman and I wanted to achieve the highest net effect, the highest results, maybe that's the right way to do it. Precisely because other people are issuing it. That's what the negative metric and the net effect are.

Rob Durant [00:18:54]:

Got it. So it's not about avoiding being told no, it's about embracing the no and learning from it. Developing past that.

Caspar Barry [00:19:09]:

Yes. But again with. With the caveat. Two caveats. Number one, tools, not rules. That might be right, it might not. But the second caveat is moving away from the concept of learning being the be all and end all. Listen, let's say.

Caspar Barry [00:19:24]:

Let's say. Let's say in poker, we make the right play. The heart doesn't come, or the spade or the club, or the what's the other one diamond, and we don't make our flush and we lose the hand. Right. Was it the right play if the mat. If the underlying maths was right, could have been a brilliant play. Could have had a huge value. Right.

Caspar Barry [00:19:47]:

As an expectation, as I referred to before. What do we do in that situation? There's no autopsy. There's no learning to be had. We did the right thing. The heart didn't come. Everything was right. Were there things that we could have taken from the person's body language? Yeah, yeah, yeah. All of that's great.

Caspar Barry [00:20:03]:

Learning from the past, whether we fail or succeed, that's all great. But there are situations in poker where the learning is not the integral part of the negative metric. So no such thing as failure. Any feedback is. It's a. It's a cliche. It's not helpful.

Rob Durant [00:20:18]:

It's.

Caspar Barry [00:20:18]:

It may well be, as a salesperson, that we do absolutely the right thing. We don't make the sale, and there is nothing that we should change because we were doing it, you know, 96% bang on, dead right. There are just things in life, and poker is a very visceral example of it, but I think sales is a really good example of it as well, which we just can't control. And sometimes there's no lesson to be learned.

Rob Durant [00:20:41]:

Let's flip the script. Why do buyers equate no decision with avoiding risk? And what can salespeople do about buyers who are afraid of losing?

Caspar Barry [00:20:57]:

Good Question. And again, you and I have sort of talked about this. So let's, there's so much to say, but let's try and think about it. Calculation that I talked about 20% of 10,000, 10% of 1,000. That is a mathematical codification that poker players have learned of the most natural decision making. Okay? Because what it does is it says there's an upside. What are we going to sell in this scenario? Think of something that has a visceral example. Let's think about employing someone.

Caspar Barry [00:21:40]:

Let's think about employing this salesperson, right? So I'm a buyer. So there's an upside of this bringing this salesperson in, which is a potential amount that they could sell per month, per year. But there's also a probability of that, right? Because obviously not everyone who comes in is going to do the job perfectly. A lot of the time as salespeople, we think about selling the upside. We don't necessarily think about addressing the person's probability assessment. Now we do. There's lots of things that we do all the time. Listen, you talk about sales and marketing.

Caspar Barry [00:22:12]:

What is branding? Lots of things. But one of the principal aims of branding is to increase the buyer's probabilistic assessment that they're going to get the promised upside. So you know the, the best brands, McDonald's, Coca Cola. I pretty much know that I'm going to get the promise. I know that I'm going to get what everyone else is talking about. I know what I'm going to get, what I had before. And that consistency is absolutely a key part of the brand. And that's what elevates my probabilistic assessment.

Caspar Barry [00:22:50]:

And so mentally that changes my perception of value of, of this thing. Because if I had a choice between a McDonald's and a little burger house that I've never heard of, right? I could be a stranger in America. And that could be fat burger or in an hour, which my two favorite chains, right, Brilliant. They're going to be a better experience than McDonald's. But I'm British and I've experienced McDonald's and sometimes I may just go for the safe option because fat burger, in and out to a stranger tourist on the west coast have also a percentage, a downside. Right now we need to move away from, from, from that example here because the downside is really crucial. And the downside is what, what could go wrong here? So there's a necessary downside, which is my, which is my, which is my, my purchase price, right? So the salary of a theoretical Salesperson. But there's also a what could go wrong here? Right? And that also has a probability.

Caspar Barry [00:23:50]:

What's the probability that this person is going to leave her under a legal cloud? What's the probability that this person is going to cause me reputational damage or harm? And we're doing assessments of that probability as well. So if we're trying to change a buyer's propensity to buy and sell, we need to work on all four of those things. This is 70% of the answer. We need to change what the upside is. That's great. Sales does really good work in that we need to change their assessment of the upside. We're less good at that, but we're still tackling it. Let's try and tackle it really overtly.

Caspar Barry [00:24:28]:

The third thing is we need to change their perception of the downside. What could happen, what could go wrong in addition to the price which we know they've got to pay. And then it's about the probability of the downside happening. And a lot of the times, you know, buyers are just risk averse and there is a downside. And even though we could minimize the chances of that happening, they're still inert. They don't cross the threshold and buy. And that leads to the final part of it, which is that at the moment of buying decision, our prospect has two options available to them. They're at a crossroads, right? One of them is to buy and the other one is to not buy.

Caspar Barry [00:25:08]:

And here's the advantage of not buying is that it gives them complete certainty. There's all this potential upside and advantage to buying, but if I don't buy all of those probabilities, they all fade into the background. I don't have to deal with likelihoods and potential upsides and potential downsides. And so this is always going to be safer because I know what my future is going to look like in the short term by not buying. So how do we finally move them from that place to that place, given all the uncertainty and probabilities and volatility and ambiguity that this place is going to involve with almost any purchase, but particularly non run of the mill purchases, food, gas, rent, etc. It is to project them into a future where not where the decision is not do I buy or not buy, but do I buy or never buy? Because now I'm faced not with the prospect of uncertainty versus certainty and safety, but some uncertainty versus genuine long term downside. Greater uncertainty, greater loss, never experiencing the upsides that this, you know, risky, potentially dangerous, difficult, what's going to happen option presents to us. So that's my answer to that final question.

Caspar Barry [00:26:41]:

How do we move people from that place of crossing the threshold using these techniques? It's to address those four things, upside, downside, probability, and probability. But also to move away from the decision that most people have, which is to buy or not buy, and to give them a slightly different, different decision, which is to buy or what if you never buy? What if you never cross that threshold? You know, what if you never cross the room and ask these people, this woman, this man to date you, what will your life look like in that potential future? Because in many ways the uncertainty of that is scarier. Scarier than the uncertainty of this.

Rob Durant [00:27:16]:

Wow. A simple reframe, but very powerful potentially. So, Caspar, if you were to emphasize the one thing you would want the audience to take away from today's episode, what would that one thing be?

Caspar Barry [00:27:34]:

I think I'd come back to the first answer that I gave, which is to think about the fact that we are resource allocators. We don't think about it in those terms, but we are. And to maximize results means to overcome our inherent human biases in order to maximize our long term results. Because we're basically short term thinkers and our prospects are also resource allocators and they don't think of themselves in that way either. And if we want to maximize the value that we bring to their lives, because that's ultimately what sales is about, it's not trying to get people to do things they don't want to do or they shouldn't do, maximize the value to their lives. It's exactly the same process that to buy versus never buy is getting people to think about the long term. It is to train our brains both as salespeople and as prospects to escape the biases of the present created by the life and to move into a long term, to think long term and to maximize our profits, but as people, our utility. That's a terrible, boring economist word is just pleasure, satisfaction, joy returns in the long term.

Caspar Barry [00:28:54]:

And the more that we can get people thinking in those ways, actually the better decisions they make. And that's good for our organizations, good for us as people, and potentially really great for our prospects as well.

Rob Durant [00:29:05]:

Fantastic, Caspar, this has been great. On behalf of everyone here at SalesTV, thank you for today's conversation. For our audience, a replay and full transcript of today's episode along with contact information can be found at SalesTV.live/NegativeMetrics Thank you all and we'll see you next time.

Caspar Barry [00:29:34]:

Thanks folks.

Rob Durant [00:29:36]:

Bye.

@SalesTVlive

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