Having grown up in Hawaii, there’s nothing that gets me more stoked than surfing. 

Even though my current location precludes me from paddling out, the fundamental principles I learned from surfing apply pretty seamlessly to my life as a sales leader—from scaling a team, mastering the art of the wipe out, and enacting change while boosting team morale. 

So gather around and let’s talk story.*

Scaling a team

Lately, I hear a lot of sales leaders from every industry discussing how to build and scale sales teams because it’s a hard thing to do right. 

I like to compare my strategy for scaling a team to the first thing a surfer checks before heading out: weather conditions.

Just like the tide and the wind can make or break a great day out in the water, the market, the trends, and the type of reps you hire all affect how well your team scales. 

First, take a good look at the trends of your organization. Assess how many leads you have vs. how many prospects you expect to get. Be honest with yourself. If your team is closing mostly $10,000 deals, aiming to close a million-dollar deal is going to take some time and commitment. 

You can’t surf Pipeline on the North Shore (arguably the most difficult surf spot in the world) after your second week on the board. You’d feel like a failure, and at worst, be discouraged from your goals forever. 

Another crucial aspect to scaling a team is knowing how to hire the right person for the product you’re selling. Iconic surfer Skip Frye famously said: “Surfing to me is like playing music. You play different melodies with different boards.” 

I’ve met reps who are incredible at selling in one industry but because of the different sales motion and strategy in SaaS/tech, don’t find the same success in that industry. Like matching your board to your style, look for reps who have experience selling complementary products to your company’s offerings, who are familiar with your customer, and who will take to your sales motion and strategy quickly.

Celebrating failures to create innovation

Whether you’ve ever surfed or not, if you’re in sales, you know how it feels to get worked. It’s not fun. Losing a deal is tough, but there’s an art to celebrating and using failure for your team’s good. As Laird Hamilton puts it: “wiping out is an underappreciated skill,” and I couldn’t agree more. 

I’ve had a long-standing tradition throughout my career of gathering my team to share our most embarrassing mess-ups in a meeting called ‘Fo Real Friday. On ‘Fo Real Fridays, we have a few laughs and razz each other a bit over some of the most embarrassing stories shared, but most importantly, the fact that we get vulnerable enough to recount our failures helps us learn from each other’s mistakes while creating connection and unity among the team.  

But sharing and celebrating failures can go even further. 

Barring a mistake made by the rep, I’ve found that losing a deal usually comes down to one thing: product fit. If the sale is lost because of product fit, too many sales leaders don’t train their reps to dig deeper and ask the customer probing questions like, “If we were to change X aspect of the product or add X feature, would you move forward?” 

The very best sales leaders master the art of training their reps to determine exactly what a customer’s problem is and why your product couldn’t solve it when they lose a deal. Those reps then immediately know to relay that information to sales leadership, and leadership takes it to engineering and the executive team so they can innovate and improve on the product based directly on customer feedback. 

The goal? To create a “failure feedback loop” that spurs innovation and results in a product so valuable that reps rarely, if ever, lose a deal on price. And if we can’t negotiate a reasonable price that reflects the product’s value, we move on rather than shoving a bad deal through. If the customer can’t see its value, they’ll churn out down the road anyway. 

So sales leaders: know what’s going on on the front lines. Know what customers are saying. Create a feedback loop and watch the customer, your team, and the company all win together. 

If you’re gonna bitch, bitch up

Surfing guru Mickey Munoz has a philosophy that I think applies very well to sales: “There are no bad waves, only a lousy attitude.” 

Sure, it’s normal to encounter challenges and have gripes. But if you know me, you know that there’s one thing I always tell my leaders: If you want to bitch, bitch to me or complain to anyone above you, but never, ever bitch with your reps. Always bitch up. Otherwise, you’ll kill the team’s morale and erode their trust in leadership. 

Yes, build a strong relationship with your team. You can and should empathize and relate with them, but good leaders know this is never done by joining them in their complaints. Instead, validate their feelings by letting them know you hear them and that you have their backs by taking their complaints and feedback up the ladder where leadership can enact change.

But as a leader who asks their leaders to bitch up, you also have to be ready to take it. Otherwise your team can’t bring their feedback up the chain and everything below you becomes a cancer. Put your ego aside and thank them for bringing their concerns to you, even if it’s tough to hear. 

No matter what, when it comes to building a sales team, watch the weather, turn crashes into lessons, bitch up, and most importantly, enjoy the waves. 

*“Talk Story” is a Hawaiian expression that means “to chat informally” or “to shoot the breeze.”