By: Natalie Johnson
Strategy has become the safest job in corporate leadership. A deck gets built, a plan gets approved, targets get socialized, and the person who authored it moves on to the next initiative before anyone discovers whether the project works. The gap between the plan and the P&L is where most companies quietly lose money, and it is seldom a strategy problem. It is an execution problem that nobody owned. Elaine Joggerst, a growth operator who built and sold her own company to a positive exit, argues the distinction is not semantic. The leaders who produce results are the ones who take the first swings themselves, before the organization commits time, money, and headcount to an approach nobody has stress-tested in the real world.
The Case For Taking The Practice Swings Yourself
Joggerst describes a working method that runs against how most senior leaders are trained to operate. Delegation is treated as a mark of seniority, and executives are encouraged to set direction and hand the mechanics to someone else. Her approach inverts that. “Even when I’m given a strategy to work with, I prefer to take the practice swings myself first,” she says. “It allows me to see what works with my own two eyes, learn from the experience, and then teach the team how to make it work. Along the way, I can refine the approach before investing more time, money, or people into it.”
The payoff is not just better information. It is credibility. A leader who has personally run the process knows which parts of it are awkward, which assumptions break under contact with a customer, and which steps the team will quietly abandon the moment the pressure rises. That knowledge cannot be acquired from a status report. It also changes the economics of failure, because the refinement happens before the budget is committed, rather than two quarters into a program that was flawed from the first slide. Companies rarely fail because they picked the wrong direction. They fail because they scaled an unvalidated process and called it a strategy.
Finding the One Constraint That Makes Everything Else Easier
Most diagnostic work inside organizations produces a list. A new leader arrives, interviews the team, and emerges with 15 things that need fixing, all of them true, and none of them sequenced. Joggerst’s value is in the sequencing. She has seen the same failure patterns repeat across very different businesses: as head of partnerships, she recognized product development dragging past where it should; in another role, customer service and onboarding were eating disproportionate time. At a closet company, the diagnosis was immediate. The standard operating procedures had to be built first, and only then could the customer relationship management (CRM) system be updated.
That order matters more than it sounds. Updating a CRM before documenting the underlying processes creates an expensive system that encodes confusion. “Years in business and consulting have taught me to look at how work actually gets done, where things get stuck, and what’s creating unnecessary effort,” Joggerst says. “The trick is figuring out what to tackle first so everything else has a better chance of working.” That last thought is the whole discipline. Fixes are not independent. The right first move makes the next five easier, and the wrong first move makes them harder while consuming the political capital needed to attempt them.
There is a second structural precondition she treats as non-negotiable, and it is one that spreadsheets never capture. A new program or revenue line has to be wanted. “There has to be buy-in, openness to the idea, and a shared belief that it can bring meaningful value to the business,” she says. Her method is top-down by design: align the right leaders, then find the people who will champion the idea alongside her. “I can build the plan, but it takes a team to bring it to life. When people believe in what we’re building and understand the value it brings, that’s when the real work and the results happen.” Plans imposed on organizations that do not want them do not fail loudly. They get slow-walked into irrelevance.
Why Agentic AI Will Expose Operational Blind Spots
The pressure to move agentic AI out of isolated pilots and into core operations is now sitting on most operating leaders’ desks, and it is where Joggerst’s execution discipline becomes most consequential. A successful pilot is not a mandate to deploy. “Moving from a pilot to core operations takes more than a successful test,” she says. “You have to understand the process you’re changing, know where human intervention is still needed, and make sure the people responsible for running the business understand what’s changing and why.” Her preference is unambiguous: test, learn, fix, and measure before scaling. “AI should strengthen execution, not disrupt it.”
Underneath that caution sits a sharper point, and it is the one most organizations are not ready to hear. Automation does not fix broken processes. It accelerates them. A company that cannot describe, in operational detail, how work moves through the business is not in a position to hand any part of that work to an agent. Joggerst’s prescription is deceptively simple, which is why so many overlook it. “Everyone who can should be walking through their organization’s processes and confirming how the business runs, not just what the manuals say,” she says. “You need to understand the business as it operates today before you can successfully introduce AI into how it operates tomorrow. You can’t improve or automate what you don’t truly understand.”
That is the uncomfortable implication for leadership teams racing to deploy. The documented process and the real process are rarely the same document, and the difference between them is where automation projects quietly fail. Walking the floor, tracing the work, and confirming where humans still need to intervene is operator work. It does not look strategic, and it will not present well to a board. It is also the only factor that determines whether the AI investment produces results or an expensive, well-governed mess. The companies that stay ahead will be the ones whose leaders are willing to do it themselves.
Joggerst shares insights on growth operations, strategy execution, and building revenue programs that hold up in practice on LinkedIn.
