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:

1. Meet with buyers who fit our ideal customer profile

2. Effectively ask them for a one on one sales meeting

3. Figure out what the buyer’s biggest challenges at work are

4. Frame our product as a solution to those specific challenges

5. Directly ask the buyer to sign a sales contract

6. 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.

That means hiring junior people or adopting technology/AI to tackle low value tasks. For sales teams, that could be list building or prospecting/coming up with target lists. For legal teams, that could be contracting workflows and email/approvals. It’ll be different depending on what function you lead, but the general principle remains the same.

Once you’ve outsourced everything else, what should remain is the “magic” work that can’t be easily scaled/replicated. As a leader you need to protect the magic, and—importantly—take the time to deeply understand how & why it works.

At the legal tech startup, we ended up hiring & firing a ton of account executives. In the end, leadership decided to try something unprecedented for them. Instead of hiring veterans from the outside, they decided to hire from within.

The thinking was that the most effective junior sales reps (who were largely responsible for scheduling appointments) were likely also those who had domain knowledge, sales drive, and culture fit. This seems obvious in hindsight, but at the time—the conventional advice was to always hire from the outside. Which is what we did.

That was partly how I ended up being promoted from BDR to account executive in record time. It didn’t escape leadership that I had domain experience as a former lawyer. But they saw that I also had the potential to convert leads to signed contracts, just by watching me generate appointments for other account executives. The same was true of one of my colleagues—a tenured BDR who wasn’t a lawyer.

The two of us were promoted to jobs that were stacked in our favor. We ended up outperforming external hires, and ended up moving up quickly. It accelerated our careers, all while enabling the company to reach higher and higher levels of revenue.

Look—the lesson isn’t that you can never scale the magical part of your workflow. Eventually you will need to operationalize it. However, your solution will very likely be highly unique to your company and the market it serves. It won’t come from a cookie cutter playbook from investors, ie. “just hire a bunch of sales reps” or “just use legal AI to outsource all the work.”

Takeaways

To sum it up, scaling requires you to deeply understand your workflow and make calculated bets on what’s most easily outsourced. Protect the magic at all costs, and be creative about how to scale that side of the house.

Before I wrap up the article I do want to provide some qualifiers. For example, it may be that your organization has an accelerated timeline to scale, such that it’s necessary to simply add headcount/technology. In that situation, I would simply make sure to assess your tasks in parallel. Hire/outsource, but try and understand what is happening in real time to identify bottlenecks quickly.

Another example, you may believe that all tasks in your team’s workflow are magical and cannot be outsourced. If that’s how you feel, I’d suggest that you take a deeper dive into how your team members spend their day to day. There’s definitely going to be admin/logistical bottlenecks that benefit from a junior resource or technology—it’s just not obvious.

In the end you may find that scaling/operationalizing processes doesn’t actually require a ton of resources. It just requires re-designing workflows and daily schedule; and perhaps even the org chart.

Good luck!

1. Sometimes they weren’t aware of these tasks, but other times they simply hated doing it. For example, getting first meetings with ICP was often the most important thing, but for weaker sellers, they shied away from going out there and hunting for meetings.