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Outsider Insights | Agentic AI: What CEOs Need to Know Before They Invest
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this 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.
| Executive Takeaways |
| Gen AI assists. Agentic AI acts, and requires a higher level of organizational readiness. |
The Evolution of B2B Selling: Focus on Helping Customers Buy
Thu, Jan 15, 2026 — Many B2B companies are experiencing longer sales cycles, declining win rates, and increasingly unreliable forecasts—not because their sales teams are ineffective, but because their customers are struggling to buy. Executive Takeaways B2B buyers face overwhelming complexity, not a lack of information. Long sales cycles and no-decisions often reflect buyer indecision, not sales failure. Winning sellers focus on boosting buyer confidence, not pitching products. Helping customers buy is now the key to competitive differentiation.
Outsider Insights | Beyond the Sale—Why CEOs Are Turning Attention to Retention and Expansion
Wed, Jan 14, 2026 — Outsider Insights Across Chief Outsiders, we talk to hundreds of CEOs every month. In this 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.
Outsider Insights | What We Learned Helping CEOs Grow in 2025
Mon, Jan 5, 2026 — Outsider Insights Across Chief Outsiders, we talk to hundreds of CEOs every month. In this 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.
Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Mon, Nov 3, 2025 — 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.