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Outsider Insights | What We’re Hearing from CEOs Right Now — And Why AI Keeps Coming Up
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 |
| AI accelerates clarity. It doesn’t fix broken data. |
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.
Why Your Messaging Isn’t Converting (and How to Fix It)
Thu, Aug 14, 2025 — After working with organizations of all sizes— from small businesses to Fortune 500 giants—one difference stands out: large, successful companies consistently invest in clear, concise, and emotionally compelling messaging that motivates their customers to act. Small and mid-sized businesses (SMBs) often start executing marketing and sales tactics — SEO, SEM, email campaigns, publicity, trade shows — before they have compelling messaging. Their messaging is often focused on what the company does, rather than what motivates the customer.
Beating Industry Benchmarks
Fri, Jul 18, 2025 — In my previous blog, I discussed a fast way to assess relative marketing performance, and covered proven approaches to improving six industry benchmark-based Key Performance Indicators (reach, share, engagement, loyalty, pipeline, and progression) that can boost overall marketing effectiveness. Today, I’m going to review some of the key findings from recent research around Marketing benchmarks. I’ll select key metrics from each of these three benchmarks and their implications for optimizing marketing performance.
Rapid Marketing Performance Improvement
Mon, Jun 23, 2025 — With tariffs, the Middle East and trade tensions increasing the odds of a near-term recession and persistent inflation, it's more important than ever for CEO’s to increase marketing’s overall performance and the ROI of every marketing dollar spent. I created the Marketing Performance Index and Assessment to help CEO’s and their organizations quickly assess relative marketing performance. The Marketing Performance Assessment is an objective way of quantifying the impact of Marketing.
Growth Hurts. Let it.
Wed, May 14, 2025 — “Don’t Risk Too Little. Don’t Rescue Too Soon” – the growth lesson I learned outside the boardroom. My son once played striker in a school tournament. With minutes left and his team trailing, he broke through the defense and had a clean look at the goal. He hesitated, and the shot went wide.
Tariffs and Your Next Chapter | Selling Through Tariffs: Avoiding the Pricing Traps
Tue, Apr 8, 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.
A CEO’s Guide to Marketing Performance | Measuring Performance (and Underperformance)
Thu, Feb 6, 2025 — Part 3 of A CEO's Guide to Marketing Performance In the marketing world, performance is the difference maker - not experience, expertise, effort, or endurance, just results. This article is about how to address underperformance in the three major measurement components (Market Presence, Brand Strength, and Pipeline Health), and six key performance indicators (reach, share, engagement, loyalty, pipeline, and progression).
A CEO’s Guide to Marketing Performance | Metrics Matter
Thu, Jan 9, 2025 — Part 2 of A CEO's Guide to Marketing Performance Metrics matter now more than ever. As a six-time CMO over a 16-year career, I’ve tracked dozens (actually hundreds) of metrics and found that many measures are ultimately meaningless or only matter to marketers.
A CEO’s Guide to Marketing Performance
Thu, Dec 12, 2024 — B2B marketing is broken. The root of the issue lies in a need for more understanding of the complex nature of marketing. Marketing involves navigating a multi-dimensional equation to guide prospects from unawareness to consideration and purchase, a complex, non-linear journey with varying durations. Yet, stakeholders often seek results based on simplified, discrete metrics like “Just get me a 5x pipeline!”