Episode 135: 3 Questions You Must Ask in Every Salesperson Interview
30 Sept 2025 · 18 min
Ben Wright shares three interview questions that separate strong salespeople from weak ones: ask about grit through stories of sustained effort, honestly assess whether you'd buy from them, and call references asking if they'd hire them again. Mid-career reps often lack experience selling through downturns.
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Hi everyone, I'm Ben Wright, successful entrepreneur, corporate leader and expert sales coach to some of the most talented people our.
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Right where you need to be. Welcome back to Stronger Sales Teams, the place where we provide real world and practical advice to help you develop super powered sales teams. It's amazing how as every week goes by, I think I'll run out of things to talk about with sales teams and something amazing or so impactful to a team's journey will pop up. And away we go again in a terrific learning curve. And I'm more than happy to share that because I think what it shows is that the sales landscape is one about continual learning. In fact, learning is a habit. It's a lifelong journey for people that are genuinely good at most professional careers that they undertake. In fact, most things in life, it becomes a lifelong journey. But often in sales, it gets overlooked. The importance of making sure that you are continually training and retraining on topics that are really important and impactful to how you build your team. And what's come up in the last week for me are lots of questions around hiring, around hiring, not just salespeople, because I work with businesses outside of sales, but certainly predominantly around how to get the best people on board into your team. And I think that's come from two areas. Number one is we are seeing a definite slowdown in the global economy, which means sales teams and salespeople in general are having to work a little bit harder to get that sale than they did in the past. And what's happening here is that we are seeing more and more salespeople come unstuck. If you like salespeople who aren't prepared to make the effort needed to really thrive in difficult scenarios or difficult economic climates, but also salespeople who've never actually experienced a slowdown. Right. If we have a look at the last true slowdown look, it's different in everyone's books. For me, it's been about 15 years since globally sales was reasonably difficult, yes, we've had patches, we've had periods of maybe one year, maybe 18 months across that journey. We've had a little bit post Covid, right, of some hangovers. We had a little bit in the early stages of COVID a few months there where things were difficult. But by and large it's been 15 years since we've had a real, real global slowdown. And I think a lot of industries are experiencing that now. And whilst I wouldn't say we are in a global slowdown, there's certainly the signs of that. And I'm seeing more and more industries find that sales cycles are lengthening, number of decision makers involved in deals are lengthening. The time it takes us to contact and to work with our customers is lengthening. It's harder to get potential customers on the phone. But all those things that are very much prevalent in more difficult economies, we're starting to see the signs of that. So here we have people who are up to 15 years in their sales career, which is starting to get towards late 30s for university trained salespeople. Late 30s where we're seeing people have never really had to operate in difficult economic climates. So for me, what's happening here is a little bit of self selection. People are opting out and going to look for new sales jobs, but also a little bit of force selection where businesses are starting to cut the fat, cut sales people who are not performing and actually not even necessarily replacing them. Perhaps they're rolling two, three, four roles into a smaller number of roles. Perhaps they're getting rid of one and not replacing. But certainly salespeople that are not performing are coming under the microscope now more than they have in, I would say, at the very least the last five years. So as a result we're seeing more hiring and I'm having more questions from sales leaders around, well, what do I do next? How do I find the person that's really right for my team? I know how to hire, I've done interviews. But in this climate, when a good percentage of my workforce hasn't actually dealt with difficulty economic scenarios or difficult or slowdowns in global performance, how do I actually make sure they're going to be up for the challenge? How do I make sure that if I bring them into my team, they are going to fight like their life depends on it to bring in sales to this business, and I think that's where we're landing today, is three areas that I'm really encouraging. Leaders in general, but also sales leaders to Focus on when it comes to the hiring process. Now, today's going to be really short and sharp. It's a nice punchy topic. But I wanted to make sure I got these three things out for people that are hiring. Because if you can move the dial on these three things, it really does make a big impact in the quality of people you hire, the enjoyment that they have in your business and in the end, the tenure. Right. The time they actually spend with you and the results that they drive. So the very first area I'd like to start here is around how do you recruit for skill in difficult economic climates when someone actually hasn't evidenced that in their career? Well, the first thing that I recommend here is you need to be aware of it. So just acknowledging that people who are in up to their mid to late 30s may not have experienced difficult sales climates before allows us to really focus in on it in our interviews. It allows us to start to ask questions around. Too many times in your professional career where you've had to really, really struggle to get sales, where you've had to work overtime, where you've had to go that extra mile. Right. Where things haven't gone your way. I think very standard questions that most people are reasonably comfortable with asking. But where you can't find that evidence in someone's CV or someone's experience, which the feedback I'm getting from sales leaders is common. It's not just every now and then sales leaders are coming to me saying, hey, I'm actually having trouble finding salespeople who have had to sell in really difficult times. Where I'm encouraging these leaders to go is to dive into the topic around grit. Sometimes we'll say getting scrappy, but I prefer to say grit. Right. Evidence from this person when outside of their professional life they've needed to show some real grit in getting things done. This could be areas like health and fitness. The sporting field is a terrific example where they've got teams that have just not been performing well. What they've had to do about it. My father in law's football team won every single game this year, but they just lost their grand final on the weekend by a significant amount. That team who they played had to really show some grit to work out how to beat this team that had knocked them off twice in the one year. How to bring it in a higher pressure environment on grand final day, but also how to have the belief in themselves to do it. So being able to evidence grit, really, really important in salespeople dealing in more difficult climates so how do we do it? We start to have a look at their performance in sporting pursuits, where they've had to experience it at a personal level. I really love digging into difficult times during people's education, where they've had to fund themselves through university, where they've had to move away from home, where they've had teachers that didn't like them, where they've had issues in the schoolyard that might have rolled into their studies, or issues at home that might have rolled into their studies, right? You start to really dive into. Tell me some times where you've really had to dig deep and make things happen and what was the end result? What did you learn and how do you roll that into your life moving forward? So we've certainly got. Show me some grit around your health and fitness, your sporting performances. We've certainly got some grit around your studies and education, and very much there's an opportunity here around personal lives. Now, we need to be really careful that we're not diving too deeply into people's personal lives. But for us, in the question that says, hey, are there times in your life when things haven't gone your way? There are times in your life where you really need to put the bit between your teeth and go extra hard to make things work for you. Are there times within your life where we've actually needed to show some resolve to make things happen or work for you? Right? What were they? And when people share these, you can often get a really powerful insight into how they've had to grow and develop as people. My family, we come from a divorced family, like many families around this world, and we had some really challenging times through that. We had some times when, you know, as a student, I was really picked on, right? Particularly years kind of 8, 9 and 10 before I grew, right. When I was a little bit small, right? Once I grew, it became a bit easier. But where I was picked on and I. And it was really distracting for me when I was studying, right? Where I had to show some grit. We've had times in my life when I couldn't get to sport, right? And I had to make my own way there. And there was a tram and then a train or a bus or whatever it may be, right? And just times when I get injured and have to make returns that were really lengthy, right. I've dealt with stress reactions in my tibia on and off for 20 years now, right? So most people who can evidence grit will be able to tell you about it in an interview because it's etched in their memory, and it's often really impactful in the formation of how they live life. So I'd really encourage people who can't find evidence of grit or thriving salespeople through difficult economic times to actually go outside the square and look for that grit in other parts of their life. So that's number one. It's quite straightforward. But for every leader I've spoken to about it so far, they've actually welcomed it and said, you know what? I know that, but I haven't been focusing on it enough. You've sharpened the axe. You've got me aware of it, and I'm going to go and run away and get that done. So that's number one. The second one, and this is a deeply personal, deeply personal judgment call you need to make when you're interviewing salespeople. And this is around, would you buy from that person? I have made so many mistakes across my sales career of hiring people that I wouldn't necessarily buy from myself. And it's only once that person has left the business that I recognize and acknowledge this. But it's certainly a mistake I've made more than once. And the reason I've made it is because I get attracted by wanting to give that person a go. Perhaps they're someone who has a story of showing great determination and grit. They've overcome some really strong challenges in their life. And I just feel like if they apply themselves to this role, they can make it happen. But I walk past that piece around likeability, around, are they able to build relationships with people where someone will trust them, like them, they don't have to necessarily actually like them, but respect them and want to do business with them. And unfortunately, I just have seen it too many times where people have experience, they have the right iq, they have the ability to work hard, they can show grit and resilience, or they even are perfect for your industry when it comes to their subset of experience. But unfortunately, they're just not people that can build relationships and in the end have people buy from them. So my really strong encouragement when it comes to the second part of hiring, right? The first part being look for grit. The second part here is around asking yourself that honest question, would you buy from them if you can't give it a hell? Yes, an instant, yeah, I'm in. Damn straight I'd buy something from them. Then I'd really encourage you to think about if they're the right person. If you're not sure, ask others in your team to meet with them as well. Right. At the end of the day, we don't all get on with everyone we meet. I've certainly had that challenge across my life. But when we have multiple people who actually look at the lens of would you buy from someone? We'll generally come up with a pretty common consensus around if they're the right people for our business. Now, I will say before we go on from here, that doesn't mean they're bad people, but it might just mean for your business at this point in time, they aren't someone that's right for your team. So as leaders, we've got to be able to make that emotional call, right? Lean into our gut, into our intuition, and make that judgment around whether or not people would actually buy from this person. So, number one, all about looking for grit. Number two is all about being prepared to ask yourself if you would buy from them. Okay? So we've evidenced that people have that grit, they have that ability to, to work hard, wear the rubber off their shoes, and really hit the pavement, right? We've established that they're buyable from, they're likeable, they're trustworthy, and we think people would actually engage with them. The third part here is how we validate our decision, right? How we look at the judgment calls that we've made or that our team have made on a very limited number of points, right. A few hours interview, perhaps. We've spoken to people that they know who have been introduced. Right. We've seen some of their work. Right. But they're really limited touch points. Right. How do we take that from our judgments and get some external, objective validation? Referees, right? They're the obvious answer here. And, and most people, most leaders that I work with will do referee checks. However, the very vast majority of these actually approach referee checks as a formality rather than a chance to really validate that assumption around whether or not that person is the right one for their role. And for me, there's one question that I was taught about 10 years ago that I've never, ever forgotten, and I ask with every single referee check, and that is, would you hire them again? So we're looking to hire a candidate. We've got our referee there. I don't always open with that question. I like to try and build a little bit of momentum in the referee checks. But certainly before I end, the question comes out, would you hire them again? And for me, there's three types of responses. No, A pause followed by a response, and then a yes, right? A no. We clearly need to dig into why not now, sometimes the no will be for reasons that aren't important to us. Right. They lack the skill in a certain area being the most important. But often when we ask the no, it comes down to cultural themes. They were late. I couldn't rely on them to consistently follow up with customers. Their written communication skills were not strong enough. And we need to make a judgment call on those nos, if they're skills we can supplement or are prepared to work with or are too impactful indeed to whether or not we'd like to proceed. So that's the first one. The second one is a pause followed by a no. I'd encourage you to follow that same process. Ask why. Right. But then the really big one here is a pause followed by a yes. They're the ones I want to really dig into because for me, I want to understand why they hesitated. Right? Yeah, sure. It's easy to move on and say, great, you'd hire them, no problems. But that's where I like to ask and say, hey, there's a slight pause there from you. Is there something you needed to think about? That's where these conversations can open up. Again, they dive back towards a lot of those reasons why it's a no. But often for this person or the referee we're talking to, they were able to overcome them. Right. So in those first couple of responses, they're all about making sure that we are deciding if the reason they wouldn't hire someone is impactful to us or if we can manage those ourselves. Right. But most importantly, we're getting external validation. Now, the last piece here is when we get a yes, I think it's equally important to follow up with a question that says, hey, if you did rehire them, are there any areas you'd want to see them upskill on? Are there any areas maybe they didn't perform as well and that you'd like to see them improve on? Now, you might have already asked that question earlier, but for me, it's the would you rehire them? Question that gives you that objective feedback that is very difficult to build yourself on a short engagement with these potential candidates. So there's three things from today when we're hiring people, particularly those up to their late 30s, who likely haven't had to go through really difficult selling periods. Right. And I'll asterisk this with that. Of course, there are. There are going to be a huge number of people that have dealt with adversity, but as a general theme, I find there's certainly less of it than more experienced salespeople, right? So the question here is around understanding, grit, making sure that they are able to fight through the difficult periods to get results. The second piece here is when we're going through with our customers making that judgment call around whether or not you'd buy from them, are they likable? Are they trustworthy? And the third piece and really important piece is to get some third party objective feedback around the question would you hire them again? Three areas, very practical, very easy to roll out, shouldn't overwhelm anyone listening, but will absolutely move the dial when it comes to hiring people for your business. So I hope they really worked for you today. I hope you've been able to write them down. I hope you've got some scenarios where you can use them. If not, put them in your black book for the next time you are hiring someone. And between now and next week, please keep living in a world of possibility and you'll be amazed by what you can achieve. Bye for now.
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