The Challenger’s Playbook: Challenge the Work, Not the People

Oct 15

In Unleashing the Irreplaceable: How Multipliers Elevate Teams, I introduced the five Multiplier behaviors: the Talent Magnet, the Liberator, the Challenger, the Debate Maker, and the Investor. This article takes on the Challenger.

Many leadership frameworks position the Challenger as pushing people harder or raising the bar. In practice, that’s lazy leadership. Stretch is only needed when the bar is too low or unclear. Instead of pushing, why not clarify the bar, set it exactly where it needs to be, and enforce discipline about how new objectives are rationalized before execution ever begins?

At 120VC, the bar is crystal clear: nothing starts unless we can explain in writing how it will measurably improve customer satisfaction, team member satisfaction, or profitability, none improved at the expense of the others. That’s the guardrail. It keeps us from making short-sighted decisions, choosing speed over trust, or growth over culture. It’s how we lead, how we prioritize, and how we hold the line.

That’s why the Challenger’s role is so critical. The Challenger isn’t about driving people harder, it’s about protecting their capacity by ensuring only the right work makes the cut.

The False Challenger: A Pusher

Most leaders confuse being a Challenger with being a pusher. They assign stretch goals without rationalizing impact to things that drive real business outcomes, they assume more will lead to more. Instead, more without a clearly defined purpose leads to burnout-busy, rework, and noise.

I don’t think leaders are intentionally attempting to substitute intensity for clarity. Most leaders know how to demand. Very few have been taught how to create clarity and alignment. Even if they did… It’s easier to demand more of people than it is to get clear and aligned.

“The Pusher” creates unnecessary stretch because the bar wasn’t set or rationalized in the first place. The push feels arbitrary because it is.

The Real Challenger

The Real Challenger demands discipline before work ever starts. Their job isn’t to push people harder, it’s to protect their capacity by making sure only the right work makes the cut.

Every objective must be rationalized against the Three Pillars. If it doesn’t measurably improve customer satisfaction, team member satisfaction, or profitability, and do so without negatively impacting the others, it doesn’t start. Period.

At 120VC, there are only three ways work makes it into execution. Most of the work shows up as weekly outcomes defined in the Weekly Focusing Exercise. These aren’t random to-dos; they’re pulled directly from the 2x2 Prioritization Matrix - our one-page alignment tool that prioritizes objectives by value and effort so only high-value work makes the cut. From there, team members commit to the outcomes and block time on their calendars to deliver.

When new work is proposed, it doesn’t just appear on the 2x2. It has to be vetted through a 1-3-1, one clearly defined problem, three possible solutions, and one recommendation. The format forces clarity, proves demand, and ensures the leader and team are aligned before a single hour is spent.

For larger initiatives, we use the Challenge | Opportunity (C|O) Exercise, the most powerful alignment tool in our playbook. It requires leaders to define the change in outcomes they’re proposing, why it matters now, the risks of not acting, and how the work will measurably improve the Three Pillars. Done right, a C|O doesn’t just create clarity, it creates demand — the team leaves the exercise wanting the outcome as badly as the leader does.

Every path requires the same discipline: a crisp written definition, a clear line to business outcomes, and proof that real demand exists before work is ever considered for prioritization on the 2x2.

The Challenger enforces that discipline. They don’t stretch people thin. They protect capacity, make delivery predictable, and ensure the only challenges in play are the ones that matter.

Tools of the Challenger

The Challenger enforces discipline through a small set of tools that everyone at 120VC is expected to use. These aren’t optional. They’re the system that makes clarity and alignment routine.

The 2x2 Prioritization Matrix ensures that only high-value objectives make it onto the team’s plate, and it forces prioritization conversations before execution ever starts.
The 1-3-1 gives leaders and team members a simple structure to propose new work. By requiring one clearly defined problem, three viable solutions, and one recommendation, it eliminates fuzzy thinking and protects the team from wasted effort.
The Challenge | Opportunity (C|O) Exercise is the crown jewel. It transforms vague ideas into clear, demanded outcomes. It asks leaders to define the change in outcomes, why it matters now, the risks of not acting, and how the work will measurably improve the Three Pillars. Done right, a C|O doesn’t just clarify the work, it creates demand for it.
The Three Pillars Guardrail: Everything we do must measurably improve customer satisfaction, team member satisfaction, or profitability, and none can be improved at the expense of the others. This guardrail keeps us from making short-sighted decisions, choosing speed over trust, or growth over culture.
Focusing Exercises: The daily and weekly practices that break objectives into achievable commitments, ensure progress is visible, and make sure work in flight stays aligned with the 2x2.

These tools make the Challenger’s job simple and powerful: don’t let noise through the gate. Protect capacity. Ensure that only the right work, clearly defined and demanded, is executed with precision.

The Payoff

When the Challenger enforces this discipline, execution becomes predictable. Once an objective clears the gate — whether through the 2x2, a vetted 1-3-1, or a C|O — it enters the flywheel of execution. Weekly outcomes are defined, time is blocked, progress is visible, and blockers get removed.

The result is clarity, alignment, and demand baked in before the first hour of effort. Teams don’t waste cycles on noise, they don’t burn out chasing stretch goals that don’t matter, and they don’t spin in rework.

The Challenger protects capacity through discipline. They ensure that only the right work makes the cut, so when the team leans in, they know their effort is driving measurable improvements to customer satisfaction, team member satisfaction, and profitability.

The Challenger doesn’t push people harder. They give the team the confidence that if it’s on the 2x2, it’s worth doing, and it will get done.

Your Next Move

Stop challenging people by piling on stretch goals. Start challenging the work.

The next time someone proposes new work, demand discipline before you commit. Run it through a 1-3-1 or a C|O. Make sure the definition is crisp, the demand is proven, and the impact on the Three Pillars is clear.

If it doesn’t make the cut, don’t start it. Protect capacity. Save your team’s effort for the work that matters, the work that measurably improves customer satisfaction, team member satisfaction, and profitability.

Series Note

This article is part of our Multipliers series. In the anchor, Unleashing the Irreplaceable: How Multipliers Elevate Teams, we introduced the Multiplier foundation — autonomy, collaboration, and empowerment — and the five behaviors that bring it to life: the Talent Magnet, the Liberator, the Challenger, the Debate Maker, and the Investor. This follow-on delivers the Challenger: not about pushing people harder, but about enforcing discipline so only the right work makes the cut. Upcoming articles will continue to break down each Multiplier behavior into actionable systems leaders can use to elevate their teams.

J. Scott

J. Scott is the CEO, founder, speaker, author, instructor, and location independent entrepreneur who’s recognized as an expert in transformational leadership that gets sh*t done #GSD.

J. Scott, a talentless, real-life anti-hero who doesn't just talk the talk, he walks the walk. Growing up in the streets of Los Angeles with less-than-ideal parents, J. learned early on that actions speak louder than words.

After dropping out of high school at 17, J. joined the Navy and learned firsthand that grit and courage could overcome any lack of talent. He embraced every opportunity to learn and eventually became a Naval Rescue Swimmer, jumping out of helicopters to save lives.

Rewind, two decades ago, J. founded 120VC to help people, leaders, and teams get things done that really matter. He's uncovered some universal truths along the way: organizations are optimized for the results they're getting, and to get different results, humans need to perform their jobs differently.

But here's the kicker: humans crave success in all areas of their lives, and nobody knows how to be successful doing their job differently. That's where leaders come in - to help people feel safe to experiment and slay new ways of working.

J. Scott is the epitome of the anti-thought leader, proving that leadership isn’t about being the most talented or successful person on the team. It’s about helping your team members define and deliver success. If you surround yourself with talented people and inspire them to reach for THEIR potential, the leader doesn’t need to be talented. They just have to play for the team. J. Scott is a regular guy who's proven that actions speak louder than words.

Jason has spent over 20 years leading global transformational efforts for DirecTV, Trader Joe’s, Blizzard Entertainment, RIOT Games, Sony Pictures, ResMed, AAG, Universal Music Group, Remitly, and others.

He is the author of two Amazon-bestselling books “It’s Never Just Business: It’s About People” and “The Irreverent Guide to Project Management, An Agile Approach to Enterprise Project Management.”

Jason is a sought-after keynote speaker, with 5-star reviews for his unique, people-centric, and outcome-obsessed approach to change that has generated breakthrough results and created meaningful jobs.

His passion to mentor and training a new generation of leaders led him to start the Transformational Leadership Academy where he leads a 14-week certification program.

In 2020, Jason launched the 120 Brand Community, featuring Brick and Matter CO, BAMCO, a brand accelerator transforming how brands can go to market, and Next Jump Outfitters, an overland guide and e-commerce business transforming how people balance work and play as digital nomads.

http://www.jasonscottleadership.com