E36: Fail Fast, Fail Forward: The Key to Thriving in High-Pressure Sales and Leadership with Alex Palmer

Eating the frog traditionally is referred as doing the hardest thing first or doing the most impactful thing first. For me, this comes in a few different ways. You can use it as a rep, you can use it as someone looking to go into leadership, you can use it in a few different ways. I think as a rep, you think, what's the hardest thing to do every day? Most people will tell you it's pick up the phone and make X number of dials, because we know that's gonna produce these results. Sales is luckily quite a linear game, and your inputs regularly equal your outputs if done over a long enough period of time. For me, it always starts with eat the frog. If it's a Monday, do the hardest thing in the week to get right. If that's the biggest, most impactful initiative that you've been putting off, just get it done as early as possible. The reason why? Everything else becomes easier after that, and you have this big sense of achievement.

Alex Palmer is the head of SMB sales for ANZ. At Deal, a pre-IPO hypergrowth SaaS company that is transforming payroll and workplace mobility worldwide. Alex is an athlete. He's a coach. He's a mentor and well regarded for the impact that he brings in designing and developing high-performance teams. In today's conversation, you're gonna learn about how he has grown in his career, as well as shapes his teams through the traits that he looks for in high performers, how he coaches them, how he gets them to do hard things, and creates a psychologically safe environment, and provides radical candor to give them feedback that helps them grow. This is going to be a terrific episode. So let's jump right in. Alex, thank you for chatting with me today. Mike Wingfield mentioned you to me, and he said, you got to get to know Alex. He's a great leader. He's building great teams. And he's a story that— you wanna get to know, and I was just super impressed with the first conversation. So, I'm so glad that you're joining me.

Thank you for having me, Pri. Very happy to be here, and that's very generous from Mike. I know you've interviewed a number of great leaders, Mike, Emma, John, 3 of the people you've interviewed that I know very well. So, you're building quite a strong list here.

Thank you. Perks of the job. I love cricket, and you came to Australia to play cricket. So, tell me all about it.

Yeah, absolutely. Although my accent doesn't suggest it now, English. I've been here long enough to adopt a hybrid accent. But yeah, I came over here originally, was working in consulting in the UK, and a friend said, hey, we need an English guy to come over and play cricket for a club for 6 months, have a bit of fun, and see what happens. So, saying yes to a serendipitous opportunity has led to 7 years here, and now just waiting for citizenship. So, very, very lucky. entry to the country and I'm very happy that I said yes to that opportunity all those years ago.

Wow. Now, that's fantastic. So, you know, clearly, as an athlete, you know, people bring all of themselves into work. So tell me first, as an athlete, what are some of the things that have shaped that aspect of your life in reaching a level, you know, in sport, which is competitive? And how does that then feed through into what you do on a day-to-day basis?

Yeah, it's a good question. I know we were speaking off air about your love of cricket as well, Pri, so I'm sure you can see some of this. But for me, team sport's been pretty much the center of my life since about age 6. So for a long time now, longer than I'd care to admit, but it's been, it's kind of been the defining trait of how I've built myself, my career, and my ambitions. So for me, it just, it comes down to a few things. It's really about working as a team. As soon as you come from a team sport background, you know that you win as a team, you lose as a team, but really importantly, you commit to each other. And you commit to each other through regular practice, you train to get better, and we'll talk a bit later about development and training. But then the ultimate goal is you build a high-performance culture. It's one that manages itself, everyone knows what good looks like, and everyone strives to be that little bit better. And that can really be from sport, but mostly across business as well. So, Yeah, that's kind of how my childhood ambition of sport has turned into a bit of a business ethos now.

Terrific. So tell me about the pivot into tech sales and leading teams. How did that come about?

Yeah, the pivot into tech sales was, again, quite a lucky one. It came through a friend who also works in sales that I played cricket with. I loved Australia so much, I said, hey, I'll come back again the next year if someone can get me a job. I've worked in sales for quite a while before I came over to Australia as well, but he found me a gig at Uber looking into SMB sales. So super high volume, pre-IPO tech company. I probably didn't grasp the opportunity or what it was before I joined, but after 6 years at Uber, I can tell you it was a pretty lucky— again, you make your own luck to some degree, but a pretty lucky opportunity. And for me, I love talking to people. I love getting to know their story, and I love getting to hear what keeps them up, hear what their problems are, and figure out how we can solve things. So, tech sales was a bit of a no-brainer. And then in terms of industry, why tech? Things that are fast, things that are growing, things that are always changing, kind of like sport. You can't always set out a plan. You just got to adapt to your environment and find a way to win, which is something that I really enjoy.

And in terms of those 6 years, tell me, you know, you started in SMB in, in a sales capacity. Um, by the time you left, tell me a little bit about that progression. What did you do? What happened at Uber?

Yeah, a lot happened. So 2018 Uber, you go back to an SMB sales motion. It was high volume. Um, we were starting to bring in structure, rigor, um, and data, data discipline. in order to build solid reporting metrics ahead of an IPO. Fast forward to leaving in 2024, earlier this year in about May, Uber is a $150 billion behemoth that is building new lines of business worth $1 billion plus in a matter of years. So, you talk about a company that started, I probably joined in its teenage years, it was just figuring out who it is, and really starting to build its own personality, to then becoming a fully fledged adult, grown up in the world, and really knows where it wins. And how to play in areas that it's going to win. So, for me personally, that looked like starting in SMB, moving into leading teams, informal team lead roles, to IC roles. We'll talk about maybe how to get from IC to leadership a bit later, and then progressing upstream. So, learning the skills of SMB, mid-market, enterprise, but also across sales and account management. So really learning the full commercial 360 and figuring out how to genuinely best solve for customer problems, and culminating in leading some teams across SMB and mid-market towards the end.

That's fantastic. What were some of the key shifts that you saw in yourself going from a competitive individual contributor to actually leading teams? Because there is a definite A change of priorities once you start leading teams?

Oh, yeah, there is. I think for me, it was the biggest change, I think, is as an IC, you can control a lot. There is a lot of things at your control, and your inputs equal your outputs. As a manager, there's sometimes a layer between what you can control, what you want to control, and what you've just got to give up and say, you know what, that's just got to be how it is. I think for me, the main change was figuring out how to get the best out of people and figuring out how to build a culture of everyone buying in together and everyone achieving together. Sales can get quite a bad rap for lone wolves, people maybe taking leads or other behaviors like that that aren't quite what we look to build. But for me, it was really a case of how do I coach and enable these people in a way that gets the best out of them? Easier to have a group level. When you've got 50 or 60 people in an org, you have to do it very differently to if you're managing a team of 4 upmarket. So very much adapting your styles, your methods, your frameworks to the situation at hand. Great example at Uber is actually a skip-level manager of mine. He brought in an agency called Winning by Design for 50 or 60 reps to build the base level. The base level was very varied. The top performers were great, the bottom performers not so. So this really raised the bar, brought us more predictable and consistent revenue, and was a great way to, I guess, enable people at scale. The follow-up activity to that at a manager level would be, how do you do it individually? How do you keep the top performers growing up? How do you really get them promoted up and out of your team and to achieve bigger and better things?

That's fantastic. So, you know, let's fast forward to your current role at Deal, which is another hypergrowth organization and, you know, going places. So tell me a little bit more about your current gig, you know, the organization, and how do you structure, you know, high-performance teams by design?

Yeah, it's, it's probably the equivalent to joining Uber before the teenage years. And growing at a pace that is actually far quicker than Uber. So, Deel is in this place at the moment where it's a nascent industry, it's competing with behemoths in payroll, in HR, in a variety of SaaS-led verticals, and it's growing sort of triple digits year on year, at a pretty large ARR base. So, the kind of challenges you have are, you might go through a period where A current set of processes or standards have got us to today, but now you need to redefine what's gonna get us to tomorrow and beyond. So, I think that really starts with, one, building a culture, but two, hiring. So, when you come in as a new manager, you've gotta assess the talent you've got, the abilities you've got, and then equally add to it in the right way. So, for me, it's a case of, I now know where we're at as an org. I know what's going to take us to the next level. But most crucially, we know what bar raisers are going to be like. And this isn't just behavioral bar raisers, people that are going to bring values and personalities that are going to build the team up. But this is also skills. This is also disciplines. And this is also, you know, who and what succeeds in these roles and these kinds of conversations. So, Deel is at a very exciting time. The thing I enjoy most about it is its chaos, and it's chaos in a fun way. Chaos because every day is different, every day has a different challenge or problem, but there is always a solution to it. You're never chasing your tail figuring out how to, it's just picking from a variety of options and then executing, which is quite a refreshing place to be for a sales rep.

Fantastic. So I heard you say some really interesting things around the skills and traits. I'd love to build a practical, applicable scorecard for my listeners, because we get a lot of sales leaders who listen. We also get a lot of sales reps who listen. So, tell me, in your book, what are some of the key traits that you look for, and why are they important?

Yeah, it's a great question. And I'd probably direct listeners to ping Mike Wingfield, because I know he's got an excellent scorecard for interviews that removes a lot of bias as well, which is tough to do in an interview process. For me, and this is focused on more junior sales, so think your SMB mid-market account execs or account managers, so more geared towards that slightly earlier career rather than your mature enterprise sellers. I think I'd preface this with, what do you wanna do when you're hiring? Are you looking to hire a bar raiser? Are you looking to replace some attrition? Are you looking to de-risk a hire to ensure continuity? I think your Scorecard should depend on what you're looking to hire for and your reasons why. For me, at the moment, for deal, we are growing. We are always growing, which is a nice place to be in, especially in this climate. And for junior sales talent, anyone can have a great resume. If you're in a certain company like a Salesforce, I associate that with you have gone through this enablement. You are likely great at medic as a qualification framework. You likely use sonder in your discovery and objection handling, and you likely do things in CRM in your CRM system. systems very well. However, that's not the full story. If you're looking to get people that don't just do the role, but they do the role and have a progression opportunity, or can go further within a business and within your teams, I look for some more soft skills. So, those soft skills for me would be EQ and IQ. I think when you're in a customer-facing role, to be empathetic, and then apply intelligent solutions, that is a very important skill, not only because it helps the business, but because it genuinely leads the client to have their best-case solution for them. So, really taking a client-led mentality. 2 other skills, one comes from business, one comes more from the sport background. From business, curiosity. People like yourself, Pri, people that ask good questions, people that are interested to learn and meet and understand. You're always gonna get good results in sales if you ask great questions, and then you're gonna find out information that you can use to solve problems and make things more productive for the client down the track. Final one for me would be drive. I think in a sales role, especially lower stream like SMB, where it's a monthly game, there's a more degree of volume, you need to have that drive. And for me, I I'm a big analogy fan. So instead of, instead of me having to light a candle under someone every single day to get them to move, I want to find people that have their own candle, they figure out how to create their own energy. So that would be the soft skills I'd look for. What kind of skills would you look for, Priyam?

For me, I think I would look for, I look for people who have ownership, because I find that The greater the degree of ownership they have on their journey and their career, they are more likely to take responsibility of solving any ditch that they find themselves in. So if they can't get enough people on the phone, they'll make more calls. If they can't get enough people to engage in a conversation, they'll improve their openers. If they aren't getting enough information to create a compelling value proposition, they'll ask better questions. So every Every stage you kind of get stuck at in that process, people with ownership are likely to figure it out. And high ownership people will defeat people with low ownership any day, in my opinion. I remember specifically telling some very experienced reps that I've had to let go, saying that You can be a Ferrari, but if you don't have any fuel in the tank, we aren't going anywhere. So essentially, ownership is a very big one for me. And obviously, number 2 is curiosity. If the person wants to do all the talking and no listening and doesn't want to learn and is not you know, learning and improving. You know, we didn't get to it, but you talked about the 1%. I love that. You know, there's always room for improvement, right? So those are the 2 things that I look for. Yeah.

Yeah, I like those, Priya. I like those. And I don't know if you've read Extreme Ownership by Jocko Willink, but that seems to be a popular one for anyone that likes accountability, extreme ownership, and all the likes. And I think just to add to your Add to your mantra there. You might have heard of the— I think it's an American presentation that talks about ducks and eagles. Have you come across that one before?

No, but I can immediately relate to— I've heard one about chickens and eagles. And tell me, tell me about it.

It's likely the same. We actually had it as part of our sales enablement team presentation for the Deal SKO recently. And it talks about how In your team, you're going to have ducks who might just sort of waddle along. They might get to the 100%, but they're never going to be able to soar high and move upstream and advance. You really want to build a team of as many eagles as possible, but you equally need to train the ducks to be able to get to a certain bar of achievement, attainment, and ultimately keep them progressing. So, I think it's a really important one when you're hiring. to filter candidates out that will never be able to get to Eagle status, as you will here. And I think some of those soft skills of EQ, IQ, curiosity, and drive enable people to, to develop upstream in their career, especially coming from an SMB or mid-market lens. Wow.

The, the Harvard Business Review had done a study of salespeople, fairly large one, and they had categorized 3 groups, which I liked as well. It was called trailblazers, core performers, and laggards. Trailblazers were those who were going to move 1 or 2 levels up. They were really going to open up new territories. They were going to do amazing things. But they could, as much— without the right circumstances, sometimes these people can flame out and go elsewhere. You had core performers who typically would get between the 80 to 100, 110.

Mm-hmm.

More consistently, but may not be trailblazers. And then you had laggards. And those are people who have found their way into sales, maybe no longer have the mojo. You know, they've lost the mojo. But basically, you know, you will find that managers tend to get— average teams have a third, a third, a third if they've got— and the whole thing is that you've got to keep replacing the laggards with core performers and trailblazers because not everyone who walks through the door is going to be a trailblazer.

So.

Yeah.

That's a good analogy. And I think you've managed a lot of sales teams and you've done it for a lot longer than I have as well, Priyesh. So, you'd know this better than I, but you're always gonna have times where individuals or teams are gonna have a rut. And it's a case of during a period that is a downturn, whether that's self-induced or a macro environmental or other, how do you get everyone to get as close to their objectives as possible? Mike talks about the 100% at 100%. That's the ideal situation, and that's what we all strive for. In an instance where that is unlikely for one reason or another, how do you really continue to enable, empower, and motivate people to get towards those? And just make sure that if they take any risks, they're okay. There is a safety net. If you're doing the right behaviors, we can keep you moving forward, and we can keep you progressing towards what the individual and the team targets are. Yeah.

And for anyone who's wondering, who's this Mike that we keep talking about? It's Mike Wingfield, who we both, Alex and I, regard really highly. And he has done an episode with me early on in the day. So go and take a look at the chat with Mike Wingfield, and I'm sure you'll come away with some great actionable items. All right. So Alex, you've talked about eating the frog. Tell me more about eating the frog and what you see in that high-cadence SMB mid-market motion.

Yeah. So, eating the frog traditionally is referred as doing the hardest thing first or doing the most impactful thing first. For me, this comes in a few different ways. You can use it as a rep, you can use it as someone looking to go into leadership, you can use it in a few different ways. I think, as a rep, you think, what's the hardest thing to do every day? Most people will tell you it's pick up the phone and make X number of dials, because we know that's going to produce these results. Sales is luckily quite a linear game, and your inputs regularly equal your outputs if done over a long enough period of time. For me, it always starts with eat the frog. If it's a Monday, do the hardest thing in the week to get right. If that's the biggest, most impactful initiative that you've been putting off, just get it done as early as possible. The reason why? Everything else becomes easier after that, and you have this big sense of achievement. You tick it off on your to-do list. you mark it off your Notion, whatever your productivity tools you use are, but it makes everything else seem more manageable. And I think for the ICs listening into this, the people that would get your 40 or 50 dials done before lunch, you know the rest of the day is gonna be easy after that. Whereas if you put it off till 3:00 PM onwards, you know it's gonna be a tough afternoon in store. And from a management, or from a IC going to a management level. I had a manager at Uber who had me as a 2IC, very informal role early on back there, but the dilemma is, do you get the job without the experience, or do you get the experience without the job? So, it's a bit of a chicken and egg when you're trying to move from IC to leader. So, our agreement was that I would eat the frog on his behalf. So, this was, If he had to do forecasting, enablement, initiatives that might take away from bigger strategic, move-the-needle things for the team, there were things I could help with, pick up the experience for, and just get done. So, I think anyone on the call that's looking to move from an IC to a leader, how do you pick up the experience without having the job, so that when you are going for the job, you de-risk yourself as a hire, because you've already done some of that? We'd love to know, Priya, how did you move from an IC to a leader?

For me— thank you. You're putting me on the spot as well. For me, the opportunity really came— I grew up playing a lot of sport. And I found myself captaining my football or soccer team, depending on which part of the world you are in. But basically, and I found that essentially, the common pattern was from if you manage yourself well, that is self-leadership. You get to move to peer leadership. That means your team, a few people, could be 3 people that look to you as someone that they're going to take some advice from. And if you're a good peer leader, you can then become a team leader. And I found that whether it was in sport or whether it was at work, being a rep that performed well, and I had to— I often did it wrong. Until I got it right. And as soon as I started managing my day well, and I started managing my week well, and I started having good months and good quarters, and I made club— it was my second year, I didn't get it in my first year because I had to work on— and I became a good rep, there were people who were looking to me on how— and that's what led to progression into leadership roles. So that became easier. But you've got to, you know, you've got to work on yourself before anyone else is going to take a chance on you. So my other mantra is you've got to grow on the inside to grow on the outside. You know, you've got to have personal development, which will then bring leadership opportunity, income, and so on and so forth.

That's, that's good advice. I appreciate, appreciate you sharing as well. It's It's always interesting to me to hear everyone's different path and different journey, because there's no single pathway. It depends on your company, it depends on the time, it depends on the lay of the land. But you mentioned something really interesting there, which, for anyone specifically in tech sales, iteration, trying things. You're not gonna succeed a lot of the time, but how do you fail fast and fall forward? You just got to iterate fast and often, and ultimately, you'll get to the right direction or find the right outcome.

Absolutely. And that's with your call scripts, your call rhythms, that's with your objection handling, that's with every single thing. So, one more thing before we wrap up. Tell me about 2 things, actually. I could keep asking you questions, but I am Mindful. Tell me about creating safety, creating an environment where people are doing hard things and eating the frog and making it safe for them to try things and fail and get up again.

Yeah. And maybe before answering that, I'd love to hear your thoughts, Pri, on what do you think was the scariest thing as a rep? Like, what did you have that little bit of anxiety over that your manager was gonna ask you, or that if you did something, there was gonna be a ramification?

Let me start by taking a step back and saying there was a time when I failed a test. And I had my grandmom ask me, did you do your best? And I lied and I said, yes. But as I walked away, my conscience caught up with me. And my conscience, I had to go back and said, actually, I didn't. I didn't prepare. I didn't do my best. And that's the same with your manager. If I've done my best, I really have done my best. And if there's things that I need to work on. But if I've been slacking off, I haven't made enough calls, I haven't tried to do it better, then we have a problem. And I think that creating a safe environment to say, okay, I've got things that are happening in my world, but I'm going to fix it. And I think that creating an environment that if I bring my honest, authentic self to say, I'm gonna do my best, I'm gonna fail, and my manager's got my back. That was, you know, you can call, you can do whatever you want in that environment where you feel safe.

I appreciate you sharing that. That's good. And you're right, doing your best, I think, is definitely one part. I think there's a few sides to Risk. As an underlying value here, for me, one of my main leadership principles is creating an environment of psychological safety. Sales and tech is fast. There is commission. It can be not just fast on an emotional level, but on a financial level. So, there's a lot of impact for the people you're managing, both on an emotional, a financial, and a wellness level at times. So, for me, Risk has— if it's risk, it's got to be calculated and it's got to have material upside. Um, risk cannot be a gamble and a 50/50 roll of the dice. Um, for me, I think it starts with what does good look like. So if you're going in a situation where you want to risk offering a certain set of commercials to a client to try and incentivize them to do something that, that is beneficial to you or the business, Sure. But what does good look like for them? Are we in line with the client expectations? Have we followed our decision-making framework? Have they followed their buyer's journey? Have we controlled the controllables before we take a calculated risk? So, for me, it's just setting the standard of what does good look like, and then also setting the expectation that if you follow these set of processes and procedures, I want you to be autonomous and to have the ability to make these decisions by yourself. But know, if you get things right and you succeed, I'll be your biggest cheerleader. I'll put you up on the pedestal. I'll make sure everyone knows your name and sing your praises. But if you fail, and it's a calculated risk and you've done the right thing, I'm your safety net. I'm going to catch you before you get to the bottom. I'm going to catch you on the way down when you're transitioning from maybe doing okay to slightly weaker, and you're trending in the wrong direction. So, um, that is great, but it starts with creating the culture of what does good look like as an expectation, um, operating with candor, which is calling a spade a spade, and just making sure that everyone is transparent and, to what you said, accountable for their own success.

Let's finish on that, those 2 words which you talked about, radical candor. Tell me more. What does radical candor mean to you? You talked about calling a spade a spade. But how— what I'd really like to understand, how do you keep caring for the individual? And how does radical candor actually enable that?

Yeah, it's a good question. Just to preface this, I have not read the Kim Scott book. And I actually never had before I came across the term. I came across the term Radical Candor as feedback from a manager. When I was at Uber, I wrote, I think it must have been a wrap email or something, but the language, it wasn't how we're speaking. It was very formal, very, maybe overly formal, maybe using too long words and trying to sound too much a certain way. And my manager at the time challenged me and said, hey, who wrote this? That wasn't you. Why, who wrote your email for you? So, challenging the authenticity, and it was a bit wishy-washy, didn't quite get to the point. So, his feedback of saying, that's not you, why are you communicating like that, was a good reminder to say, just be upfront, honest, and just call a spade a spade. If performance is good, tell it, why is it good? If it's bad, why is it bad? And I think as a As an IC and as a manager, if you proactively communicate why things are going to be good or why things are going to be bad, you can have any hard conversation in a much easier and controllable way. I think if people are not upfront and are not transparent, it can lead to, can lead to maybe skepticism on agendas or skepticism on, is what they've said correct? So, I think as a, Specifically, as a manager, leading with candor and leading with honesty, good or bad, in a pretty concise and transparent way, helps you have hard conversations. It also helps you with good conversations. Final anecdote on that would be, at Uber, had a team member who was looking to get promoted, but they'd missed out on a couple of rounds. Why? So, we sat down and had a really frank conversation on, here are the areas you are missing, here are the areas you're hitting.

Yeah.

Here is what you need to do in this timeframe in order to be in the conversation. The ultimate outcome was maybe a bit of disagreement at the time, but ultimately led to that person getting promoted and getting a good outcome. So, personally, that comes from sporting dimes. In sport, you don't have time to sugarcoat things. It's real. You've got milliseconds or seconds to deliver feedback. It's got to be to the point, constructive, and progressive. So, yeah, candor is my default and has been for a long time.

Alex, this has been so useful and it's going to help a lot of sales leaders and a lot of reps who join in and listen to this conversation. So I want to thank you for your generosity today, and it has been very good. Thank you.

Been a pleasure chatting to you, Priya. Thank you for having me.

Thank you.