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Outsider Insights | You Built Something Different. Your Messaging Made It Sound the Same.
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.
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.
Go Time? Or Just Another Head Fake? How Mid-Market CEOs Should Move Forward Now
Wed, Jun 25, 2025 — Six months ago, we diagnosed a condition gripping mid-market companies across the country: Waitflation. Leaders were holding back—not because of financial hardship, but because of economic ambiguity. Interest rates were high, forecasts were fuzzy, and confidence was low. The result? A national game of “wait and see.” Now, as we enter a volatile summer, it’s time to ask: Is it go time?
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part One
Mon, Jun 23, 2025 — Every CEO knows this nightmare scenario: Your team spent months crafting the "perfect" go-to-market strategy, only to watch it crumble during execution. Resources hemorrhage, timelines slip, and while you're still troubleshooting internal alignment issues, competitors are capturing the market opportunity you identified first.
AI Isn’t a Replacement—It’s an Accelerator: How SMBs Can Use AI to Elevate Human Performance Across the Organization
Fri, Jun 20, 2025 — We’re in the midst of a generational shift—one where artificial intelligence is reshaping how we work, how we serve customers, and how we think about the roles of humans in business. But here’s the reality I’ve seen across dozens of companies: AI is not a silver bullet, and it’s not a pink slip. It’s a power tool—one that requires a skilled operator, a clear use case, and the right safety measures in place.
Winning the Fraud and Cybersecurity Race: A Go-to-Market Blueprint for Competitive Edge
Thu, Jun 5, 2025 — Fraud and cybercrime have become a systemic, trillion-dollar drag on the global economy—but the fight to turn the curve is more than a market opportunity. Over the past few years, I have worked alongside cybersecurity and fraud-management teams in government, banking, and payments, and nothing is more satisfying than seeing a new solution stop a romance scam or prevent a pensioner from losing their life savings.
Waitflation: The Hidden Cost of Economic Paralysis
Fri, Apr 11, 2025 — The New Economic Fog We’re not in a recession. Not in a boom. Inflation isn’t gone, but it’s no longer spiking. And yet, everywhere you look—executives are hesitating. The markets are twitchy, customers are cautious, and leadership teams are frozen in Waitflation: the tense, uncertain space between reaction and resolution.
Tariffs and Your Next Chapter | From Cost Burden to Market Edge: Turning Tariffs into a Competitive Advantage
Fri, Apr 11, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
From Crisis to Competitive Edge: Leveraging Digital Transformation in Tough Economic Times
Wed, Apr 9, 2025 — In today's unpredictable economic climate, small and medium-sized business (SMB) owners face numerous challenges, including fluctuating market conditions, supply chain disruptions, and evolving consumer behaviors. These uncertainties can be daunting for business leaders striving to maintain stability and growth. However, by reframing economic downturns as opportunities for transformation, SMBs can leverage digital technologies to not only survive but thrive amid these challenges.
Tariffs and Your Next Chapter: Turning Disruption into Go-to-Market Growth
Mon, Apr 7, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.