Keeping the magic alive
How to scale your team's impact without destroying what makes it so effective
The main professional challenge I’m focused on these days is how to operationalize work that is both valuable and difficult without losing the “magic” that makes it all possible. I’m writing about it here because I think it’s something that law firm & legal department leaders also grapple with—especially if they are part of a high growth organization.
Background: I’ve spent a lot of time at startups watching them struggle with this challenge when trying to scale sales/revenue. There’s usually one or two Evangelist-Sellers who have driven most of the startup’s early success. They usually fit a common profile: deep domain/subject matter expert, great at building trust with sales prospects, and extremely creative in getting the deal done.
However, as the startup grows and revenue targets increase—there’s top-down pressure to add even more sellers. That leads to hiring a large number of new employees who fit a very different profile than the Evangelist-Seller. For example, it may be a sales professional with limited/no knowledge about the industry. Generalizing broadly, these sales professionals tend to be process oriented & disciplined but lack expertise and aren’t as adaptable to fluid scenarios.
I’ve witnessed this play out at multiple startups/scale-ups. Struggling to scale is a necessary growing pain of any fast-growing company. After seeing how it’s played out and having contributed to some of these teams—I’ve developed a framework on how to tackle these challenges.
It’s a 3 step process that hopefully can be applied to your own situation.
Step 1: Break down valuable work into its most essential pieces
The first step is to take a step back and deeply understand every little thing that goes into the larger process. At one legal tech startup, I saw how our top Evangelist-Seller, “Greg” generate revenue effortlessly. After watching Greg work his magic for a few months, I was able to roughly divide his day-to-day into 6 types of tasks:
Meet with buyers who fit our ideal customer profile
Effectively ask them for a one on one sales meeting
Figure out what the buyer’s biggest challenges at work are
Frame our product as a solution to those specific challenges
Directly ask the buyer to sign a sales contract
Provide technical guidance post-sale to increase usage
These six individual tasks weren’t obvious to anyone who wasn’t looking carefully. When I asked Greg to break down his process, he said he didn’t really have one. “You just gotta know the product cold,” he’d say.
But when you watched Greg work deal after deal, you could see that product knowledge wasn’t the secret sauce. It was something else. Greg didn’t necessarily take the same approach every time, but somehow he’d always complete all 6 tasks. The newer/weaker sellers on the team often skipped/omitted one or more of these tasks.1
The question then became, which of Greg’s 6 tasks could be outsourced, delegated, or automated—and which ones were most valuable, and should remain untouched.
Step 2: Figure out where the magic happens
How do you figure out what task is most valuable? By process of elimination. In short, you should try to delegate & automate everything, and see where you run into roadblocks. You’ll find that most tasks can be outsourced—but maybe 1 or 2 cannot.
That’s where the magic happens.
At that legal tech startup, it took a while to figure out which one of the 6 tasks was most valuable. Right after we raised a large round of funding, company leadership suddenly found themselves with a huge amount of resources to increase sales. Here’s what they did:
Try and outsource tasks 1 & 2—more meetings with ICPs—by doing two things: (a) hiring BDRs (full-time staff to generate sales appointments) and (b) increasing investment in new marketing channels.
Try and outsource tasks 3-5—selling effectively—by hiring new account executives and provide rigorous sales training for them
Try and outsource task 6—post sale technical guidance—by hiring new customer success managers (ie. account managers) and provide rigorous technical training for them.
Within a month or two, we saw a flood of meetings and increased capacity for post sale technical support. However, revenue continued to stall. As it turned out, tasks 3-5 were not easily outsourced. And it was a bottleneck to new revenue. Turns out that it’s quite difficult to find account executives to effectively convert leads to signed contracts.
That was the first time I realized that that’s likely where the magic happens. Looking back to Greg, the reason why he was so effective was partly because he had a unique mix of the right personality & temperament, domain knowledge, and sales drive—to maximize conversion rates from leads to closed contracts.
When we tried to hire from the outside to replicate Greg, it was incredibly difficult. You needed domain experience to address buyer’s challenges. But you couldn’t just rely on a technical expert, you needed someone with sales drive to connect challenges to features, and boldly close the deal. Even hiring from competitors didn’t solve the problem; they were always flawed in some way.
As a result, by process of elimination, we recognized that account executive hiring was the big bottleneck—and likely where the magic happens.
Step 3: Protect the magic while outsourcing everything else
It’s likely that you have a sense of “where the magic happens” in your own team’s processes. Once you discover & validate it, don’t try to immediately outsource it. Instead, your first step should be to aggressively outsource everything else.

