Any highly performing team is the sum of its parts. Driving success in sales teams is about recognising the right traits and talents, and building a deep understanding of what makes people tick. Here, Jake Webber-Cadby of Inforcer talks about the vital characteristics needed to be successful in sales, and how sports has influenced his career.
Many of us grew up dreaming of playing professional sport, however, the harsh reality soon starts to hit home as to how hard it is to achieve!
As a young lad, I spent hours each day kicking a football against a wall outside of our house, with the dream that one day it would be a penalty kick at Wembley. For me sport was everything, and my entire mood for the week would be shaped by the full-time result each Saturday morning.
Looking back, I certainly feel for my parents as I was a miserable little s**t each time we lost.
At the age of 12, I turned my attention to golf, after getting hooked on the game following a round of pitch & putt with my best mate. Like football in my earlier years, golf became an obsession of mine, with 90% of my school summer holidays being spent at Taunton Vale Golf Club.
Again, it was the dream that one day I would be putting to win the Masters at Augusta that kept me going back for more. Golf is one of the few sports where you are in direct control of the outcome and being able to see incremental improvements each week becomes addictive.
After winning the British Colleges Championship at the age of 16 at St Andrews, I truly believed I could pursue a career in the sport. Fast forward the clocks and I’m sitting here aged 29 having been selling into the MSP space for the past six years. Would I change anything? No! The reality is I wasn’t good enough to make it as a Professional Golfer, but the mindset I developed has served me incredibly well in my career so far.
So, what is it about Sport & Sales that makes it such a perfect match? I’ve broken it down into three common characteristics I believe they share, which I use as part of a hiring framework today.
Obsession with improvement
The thing many of us all love about playing sports is the fact you can ALWAYS get better. Whether it’s improving your swimming stroke, refining your tennis serve, or increasing your swing speed – we all love the feeling of improvement.
How does this translate into sales?
Through the dozens of interviews, I have been a part of over the past couple of years, here are the common themes to look out for to help identify a top performer:
Are they a student of the game? Similar to a budding golfer who watches countless Youtube videos on how to improve their technique, you want salespeople who are hungry to learn. Do they read books, listen to podcasts, work with a mentor, or complete extracurricular courses outside of work? These are all great signs that they genuinely want to reach the top of their game! You can lead a horse to the water, but you can’t make them drink.
What are they currently working on improving? In the interview process, ask them what they are currently focusing on with their manager. Ask them: ‘If I gave you this job today, what is the one area I could help you improve?’ If they provide a solid answer here that is a positive sign. Something along the lines of: ‘I’m currently working on my discovery questioning, as I often do not dive deep enough into the customers' pain points which hurts me later in the sales cycle’.
Driven to win
I don’t know many people who enjoy losing but it’s surprising how few truly care about winning.
I’m a little old school and don’t agree with the: ‘it’s the taking part that counts’ mindset. Competitive people sometimes get frowned upon due to the fact there are many bad losers in the world, and I’ll be the first to admit that there were times when I was a petulant youngster and may or may not have broken a tennis racquet or two. If channeled in the right way, being competitive can provide you with an edge in both sports and sales.
How do you determine this in an interview process?
Are they sharp on their numbers? Like a top striker who can reel off all the details of every goal they have scored over the past three seasons, you want a sales rep who knows their numbers inside out. Why? This shows they were always looking at what they needed to do to reach the top. Better yet, they can tell you exactly where they finished on the sales leaderboard across multiple years. I’ll never forget the 31st of December 2022, when I was beaten at the last minute by Paul Hochberg, to become the top-performing ConnectWise sales rep globally. That was a tough one to take (although he deserved it!) – Why? Because I wanted to be number one.
Drill into what gets them up in the morning. There is no hiding from the fact that great salespeople are driven by their commission plan. Run a mile if they don’t question you on the commission structure during the interview process. If they are more focused on securing a hefty base salary, they probably aren’t the best fit for a sales role. Usain Bolt woke up every day striving to beat his previous PB 100-meter time. The best Sales Professionals wake up every day with a plan of how they are going to beat their previous best commission cheque.
Resilience
There is no denying, sport and sales can both provide a brutal and lonely reality at times. The massive highs of winning are often far outweighed by the thousands of failures experienced along the way.
You only have to read the great Michael Jordan’s quote to resonate with the pain that comes with reaching the top. There were hundreds of points during my sporting days where I questioned what the hell I was doing. Practicing five-foot putts in the middle of January on a frozen green whilst my teeth clattered together, just why? The same goes for sales! How many no’s do we hear before we get to a magical yes – A LOT! People must think we are crazy, making 50 calls a day to get through to one decision-maker who may or may not entertain a two-minute call with you. But like any of the best understand in their respective profession, each failure is one step closer to the euphoric feeling of success.
How do you know if someone is resilient?
How have they dealt with pain? Unfortunately, everyone in life experiences some extremely painful moments – some more so than others. What truly defines someone is how they get back up from these moments and continue being the best version of themselves. This is where I tend to get a little deep during interviews and ask questions like: ‘What is the worst thing that has happened to you both personally and professionally, and how did you deal with those situations?’ If they don’t want to share the details with me that is fine, but often this will allow me to get a feel for how they react to adverse experiences. I look for people who turn pain into fuel and hunger to go on and achieve more in their lives.
What have they achieved outside of work? This is where sports can be a great indicator of resilience, as anyone I have ever met who has played at a high level tends to have this characteristic in abundance. With that being said, there are many people out there who do not play sport, that are also extremely resilient. What are some of the other signs of resilience? I tend to look at things like academics as although it’s not the be-all and end-all, completing a tough degree is an emotional rollercoaster and often says a lot about someone’s mindset. Appreciating higher education is not always accessible due to the sheer cost associated, what else can be a sign? You want to look for times people have had to push themselves outside of their comfort zones. Things like running a marathon, teaching themselves a new language on Duolingo, climbing a mountain, or doing a less-than-desirable job to earn some extra cash as a youngster (pot wash for me).
A high performing sales team share many of the same characteristics as a high performing sports team.
I highly recommend reading the book: ‘Legacy’, which focuses on the culture of the famous New Zealand ‘All Blacks’. Here are a few of my favourite quotes from the book which really resonate with the way I view the relationship between the two disciplines:
The strength of the wolf is the pack, the strength of the pack is the wolf.
Leave the jersey in a better place.
Improving 100 things by 1%. By finding the 100 things that can be done just 1% better, you achieve marginal gain which creates an incremental and cumulative advantage in performance and results.
Although I am biased towards sport as it’s something I’m very passionate about, the same can be applied to several other activities/skills such as playing an instrument for example. The overriding message I am trying to get across here is mindset is everything when it comes to a career in sales! How you develop that mindset is individual to each one of us.
With hiring the right people being such a challenge, I’d love to hear other people’s perspectives on what they look out for during an interview process, as I and the team at Inforcer will be hiring rapidly over the next couple of years.
You can reach out to me at jake.webbercadby@inforcer.com
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