Arm yourself with some expert-approved team-selling knowledge: why it’s a vital tool, how to do it well, and when to forego it.
May 29, 2024
Years ago, I took a few improv classes in D.C. Not super original, I know, but they were FANTASTIC. They sharpened my creative competence in a very new way (I’m not the first person to observe this effect). One thing our instructor said to us was, “Don’t try to be funny.” This came as a surprise to me. All the good improv I’d seen was funny. But the funny, he taught us, came from collaboration, from the unexpected directions a scene might take when several brains join forces.
He said another thing that’s stuck with me ever since. He was quoting a famous improvisational actor, if I’m remembering correctly. It went something like this: “Treat everything your stage partner does as the most brilliant decision ever made, and your scenes will be the better for it.” What’s so fresh to me about this statement is its insistence that it’s not just the quality or content of a partnership, but the very act of respectful and enthusiastic collaboration, that can elevate a project. I don’t think I’ll ever forget that insight. I don’t think you should either.
I don’t need to connect the dots for you on how improv relates to team selling. I do, however, think it’s worth taking a closer look at a strategy—some might even say philosophy—that gives off an unassuming vibe but is, in fact, invaluable.
To understand the ins and outs of team selling, I didn’t have to look far. Asad Ali, our SVP of Sales and Consulting at Maestro, could not be more qualified to speak to this strategy. He won’t say this, but he’s a goldmine of insights into management, negotiation, and many of the subtler aspects of sales that are hard to put into words—though not for him. He’s not only an expert in the profession (having casually managed multiple startup companies from their nascent stages all the way to acquisition), but he’s an expert educator, with experience teaching thousands of business students at the George Mason University Costello College of Business. Not to brag, but I got a free (and ungraded) crash course.
First, let’s back up.
It’s just what it promises on the label: multiple people from the same organization or “team” collaborating on a deal with the end goal of a sale.
There are a lot of reasons why an organization might choose to go the team-sales route. One, Asad explains, is to mirror your prospect’s organizational choices. “If they’re involving their legal department, tap into somebody from your legal side that can be on the call to at least listen and to take notes.”
“Another approach,” says Asad, “is a top-down approach.” If a deal runs cold, he will sometimes reach out to Maestro’s CEO, Will Fuentes. If Will has a relationship with that company’s CEO and can connect with them “executive to executive,” he might start a parallel conversation to bolster Asad’s efforts with something along the lines of, “Hey, Asad’s been working with so-and-so and the deal’s kind of stalled. What can I do to help move this along?”
These are not just pleasantries. “We’ve seen this reinvigorate a sales process,” says Asad.
Team selling has another advantage. It’s a great way of displaying your group’s (hopefully eclectic) skill set. This applies to both large and small companies. In his startup days, Asad used to refer to this as “peacock feathers”—brandishing your abilities, “showing them how big you can be.”
In some ways, team selling begins before there’s even a team. There are things you can do in advance of other members (on either side) getting involved, in order to facilitate a smooth encounter down the road. If you’re working with a single individual at your prospect company but know that their colleagues will eventually need to come on board, instead of saying, Can you get your customer service team on the next call? Asad recommends having some language prepared that they can use in an email to their own coworkers, or even writing the email for them (with their permission). Ask them how they prefer to communicate. Get a sense of whether they’d like to keep things small for the time being or are eager to invite others to the table.
However effective team selling can be, it’s not always the answer. In fact, there are situations in which bringing in another member could pose an obstacle to a deal. You want to respect your prospect’s way of doing things. It’s possible they’re relishing the one-on-one time with you at this stage of the process. “You don’t want to force a team if that’s not appropriate at the time.”
Asad likens it to not cc’ing colleagues on every email—as well as courtship. “It’s like you’re dating somebody and it’s still earlier on, where you don’t want to propose, ‘Why don’t you bring a friend, and I’ll bring a friend…’” Sometimes, it’s good to take a wait-and-see approach to a deal that seems to be moving along nicely.
When you do opt for team selling, remember that two or three people do not (necessarily) a successful team make. So how do you choose the right partner or partners? “Knowing how the other person flows is extremely important,” says Asad. For example, if he’s on a call and chooses to deliberately use silence, and his teammate flails about trying to fill that silence, they’re not successfully supporting Asad’s efforts. They’re undercutting his strategy, well-meaning though they may be.
A good flow between partners is particularly important when it comes to question time—assuming you’re fortunate enough to make it to that point. In those situations, “it’s a bit like dancing. You want to have the right partner when you’re getting out there, so you don’t embarrass yourself or embarrass your partner.”
And that’s where it starts to remind me a lot of improv. You are your partner’s greatest asset on stage, and they are yours. You build each other up. You balance one another’s strengths and weaknesses. You do what any good team does. And then you knock it out of the park—together. Don’t take it from me. Take it from someone who’s sold companies, landed deals, and has dedicated time to teaching others how to do the same. Here’s how Asad puts it: “Some of the best pitches I’ve ever been a part of—successful pitches that have worked out in my favor—have more often than not been with somebody else in the room.”
https://www.lucidchart.com/blog/what-is-team-selling
Whether you’re team-selling or going solo, we have lessons, assessments, and coaching that can help. You can reach us at mastery@maestrogroup.co.
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