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Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this new series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
Beyond the Buzzwords: How CEOs Can Build a Truly Resilient Business
Wed, Oct 22, 2025 — In every keynote, article, and boardroom conversation, “resilience” gets tossed around as the Holy Grail of leadership virtue. But resilience is more than just surviving economic turbulence—it’s about turning disruption into a competitive edge. Too many CEOs treat resilience as a slogan rather than a strategy. Real resilience is built in advance, not claimed during a downturn. It starts with clarity regarding where you are in the economic cycle, where you’re headed, and how to align your people and resources accordingly.
The Cost of Waiting: Why “Doing Nothing” Is the Most Expensive Strategy
Tue, Oct 7, 2025 — When markets shift, many CEOs adopt a dangerous mindset: Let’s wait and see. On the surface, it feels prudent, even safe. But hesitation quickly becomes the costliest default in leadership—a form of self-sabotage and an expensive compromise. Economic shifts don’t pause until you’re ready. By the time you’re confident the upturn is real—or the downturn has arrived—it’s too late to act decisively. Competitors who moved first have already secured the best opportunities. And you’ll be left wishing you had not waited.
Becoming the Issachar CEO: Leading with Foresight in a Time of Uncertainty
Tue, Sep 30, 2025 — It’s not every day that a C-suite leader turns to 1 Chronicles for advice, but there’s something here for us. 1 Chronicles chapter 12 describes each of the tribes of the nation of Israel as they moved their allegiance from the house of Saul to the newly crowned King David. The scripture recounts an impressive array of warrior clans ready to fight for their new king, until it reaches the tribe of Issachar, described in verse 32 as “men who had understanding of the times, to know what Israel ought to do.”
From Recovery to Recession: A CEO’s Guide to Thriving Through Economic Shifts
Tue, Sep 9, 2025 — When markets shift—and they always do—the winners are those who don’t wait to react. They move first, and fast. No matter which of the four cycles you’re currently experiencing, one constant remains true: waiting for things to be more favorable is a bad strategy. Additionally, doing nothing is not an option. Companies that anticipate, plan, and act in alignment with their current business phase can maintain resilience, capture opportunities, and outperform competitors who simply “wait it out.”
What Can Chester Cheetah Tell You About Your Brand? Part Two
Fri, Aug 1, 2025 — We’ve already discussed how to define a brand in part one. Now, we are going to explore why the C-suite should care about its brand at all. It’s not just numbers, although that certainly is the end game. Remember that brand is the business. Like the business, brand is about being effective, meaning carving a position with a market that is highly productive financially and competitively, and efficient, meaning serving the market in as cost-efficient manner as possible. Brand helps maximize and expand return on investment.
What Can Chester Cheetah Tell You About Your Brand?
Fri, Jul 18, 2025 — Imagine an argument about whether Chester – yes, Chester of Cheetos fame – should be 2D or 3D. The debate raged in almost every corner of Frito-Lay headquarters at the time. There were strong opinions on both sides and an even more provocative discussion about the brand’s target audience. At the time, two of every three bags of Cheetos purchased were consumed by adults, not tweens and teens. So, the debate was fair, if inconvenient.
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part Two
Thu, Jul 17, 2025 — In Part One, we established the critical groundwork: vision clarity and deep market understanding. Now it’s time to convert strategy into results. This section of the playbook takes you through the essential steps to build, activate, and scale your go-to-market initiatives.
When the Founder Is the Rainmaker: How to Scale Without Losing the Spark
Mon, Jul 7, 2025 — In many founder-led businesses, the founder isn’t just the leader—they’re also the best (and often only) rainmaker. They land the big deals. They have the trusted relationships. They know the pitch inside and out because they are the pitch. It works—until it doesn’t. As the business grows, this model creates a bottleneck. Every new opportunity depends on one and only person. And it’s the same person every time. But there’s a downside. When that person is also responsible for running the business, mentoring the team, and shaping the vision, something eventually gives.
AI Isn’t a Replacement—It’s an Accelerator: How SMBs Can Use AI to Elevate Human Performance Across the Organization, Part 2
Thu, Jun 26, 2025 — AI as an Executive and Organizational Force Multiplier In Part 1, we explored how AI streamlines execution in outward-facing functions like marketing, sales, and customer service. Now it’s time to turn inward. In this second half, we’ll examine how AI empowers internal operations, drives better financial strategy, and helps executive leaders see farther and act faster—without sacrificing the human qualities that make a business thrive.