Do you have the guts to ask tough questions and get tough answers or do you prefer the comfort of hearing what you want to hear through happy ears?

In this episode of INSIDE Inside Sales, Darryl welcomes Larry Long Jr., Director of Collegiate Sales at Teamworks and a sales process champion. Together, they will unearth the importance of setting up and following a sales process, being prepared to ask uncomfortable questions and hearing the bad news early on in negotiations. They also offer advice on learning how to read the room and listening to what really bothers your prospects. If you want to hear some great tips on how to obtain open, honest feedback and move towards meaningful and fruitful relationships with your prospects, don’t miss this episode of INSIDE Inside Sales


sales process

Why You Should Always ‘Take the Stairs’ When It Comes to Sales

  • Most salespeople like to talk –– and they’re good at it, too. It comes with the territory. But listening is even more important, especially when we might not want to hear what the prospect or client has to say. In short, we need to learn to read the room.
  • Sales process expert Larry Long Jr. says building relationships based on trust can help us identify problems early on in negotiations, before either side wastes time, money, and energy on a deal that won’t happen.
  • Larry shares insights on setting up and following a sales process, being prepared to ask uncomfortable questions, active listening, and encouraging open, honest feedback.

There’s always a downside to greatness, isn’t there?

With great power comes great responsibility. (Was that Spiderman, or Voltaire?)

After climbing a great hill, one only finds that there are many more hills to climb. (That’s Nelson Mandela, for sure.)

Larry Long Jr., Director of Collegiate Sales at Teamworks, likes one by Tony Robbins: The most successful people ask the toughest questions, and therefore they get the toughest answers.

Larry says that’s true not just in sales –– it applies to everything we do in “this four-letter word that we call life.”

We’ve got to have the guts to ask those questions and be willing to listen to things we don’t want to hear. The more we do that, the earlier we can identify problems to solve, make tough choices, weed out wrong-fit prospects, and generally keep our sanity (and reputation) intact.

Call it brave, if you like. But it’s pretty simple: We need to learn to read the room.

In an episode of INSIDE Inside Sales, Larry talks about the importance of setting up and following a sales process, being prepared to ask uncomfortable questions and hearing bad news when it happens. He offers advice on active listening –– and how to build trust through encouraging open, honest feedback.

‘Take the stairs’ as a sales approach

At Teamworks, the sales process happens in a series of discrete stages.

“We’re sticklers about process. There are certain milestones we have to check off,” he explains.

Because he and his team sell to athletic directors, they know that if they’re talking to a prospect at a school and the athletic director hasn’t been looped in, they’re not yet in the negotiating stage.

Larry makes an analogy inspired by the book “Take the Stairs” by Rory Vaden: “If I’m going to the gym and there’s an escalator, human nature says I’m gonna take the escalator, not the stairs. The stairs are the [sales] process.”

He has found (not just with sales professionals, but across the arts, sports –– every part of life, actually) that success is truly in the details. 

Plenty of people have “sales professional” in their job description, “but let’s keep it real, they’re amateurs,” says Larry.

“And amateur hour is painful. It makes me cringe because you’ve got to follow the process. I don’t care what process you follow, but you better have one to follow, iterate, test and measure to see if you’re getting maximum results.”

Listen so you’re heard

Have you ever chosen a word or phrase of the year? Think of it as a theme for setting goals, a way to stay focused and a reminder of what you’re really striving for. It’s a great practice for the new year, but you can choose one at any time.

Larry’s 2021 mantra is shhh and listen.

“So often, the sellers I work with don’t listen,” he says. They’re too excited to make connections, to do the demo, to have the opportunity to pitch –– and they don’t ask the customer what they really want or need.

One of the ways Larry likes to practice active listening is to ask prospects to guide them through their daily challenges.

“Walk me through your process of your morning routine. Walk me through your process of how you prepare your team for success,” he says. “And then if you listen, you’ll pick up on a lot of things. From there, you can double click, you can triple click to dig in even deeper.”

Then you can move to even deeper questions about what’s holding you back:

What’s holding you back from growing your revenue?

What’s holding you back from scaling up production?

What’s holding you back from achieving that goal?

Then … shhh-ut up and listen.

Ask now, or derail the deal

Since Larry is the process king, I ask: What typically holds salespeople back from improving their sales process and hitting their goals?

“When it comes to our prospects, we’ve got to ask the tough questions around the timeline,” he says. 

Sometimes those questions are not just hard, but they’re uncomfortable: Let’s get your CFO to the table so we can go ahead, because you told me you wanted to get this implemented by March 15.

You need to be unafraid of hearing no to that. And you need to ask it way before March 14.

Sure, the sales game is tough. You might think: I don’t wanna ask a question that might derail the deal.

Larry has a secret for you: “If you don’t ask the question now, the deal is already derailed. You just don’t know it. It was pending all this time. Your energy, your resources –– you’re wasting them.”

Sales is a match game

Larry encourages salespeople to build relationships built on trust –– “because we know people buy from folks they know, they like, and they trust.”

But you’ve got to set expectations about what that looks like in practice. It might sound something like this: I love you, and I know you love me. But to show me that you love me, if at any time throughout this process, we kinda take a U-turn or a detour, can you tell me that you will let me know? 

“Then I’m gonna shhh and listen, not just to what you say, but how you say it, because I need to make sure you’re not going to just lead me on,” Larry explains.

People don’t like to be the bearers of bad news, especially to someone they like. You’ve got to give them the permission to be honest, he adds. So you might say: Hey, you’re doing me the best favor you can by letting me know if at any time this isn’t going in the direction we thought it was.

Larry says he’s proud to be a sales professional because his definition of sales is matchmaker. 

“We’re matching our product, our service, our thoughts and our ideas with someone else’s real needs, wants, desires, challenges, hopes, dreams, aspirations… I’m doing them a disservice if I don’t ask about their motivations, if I don’t ask what keeps them up at night, if I don’t ask about what they’re trying to accomplish.”

That’s why it’s crucial to put our work in perspective.

“If you’re not doing it to serve others, I hate to say it, but it’s time for you to find a new career. If you’re a true sales professional, you’ll take pride in understanding your prospects and your clients. Come on now, holla if you hear me.”