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Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI
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.
How to Develop Future C-Suite Leaders: A Guide for Mentoring and Succession Planning
Fri, Apr 10, 2026 — Executive Takeaways Succession gaps quietly erode growth, value, and decision speed Strong companies treat succession as a continuous leadership discipline A 1/3/5-year talent map builds a visible, scalable leadership pipeline Sponsorship, mentoring, and coaching turn high-potential talent into ready leaders Ambition is the easy part. The real question is whether your company’s future CEO’s, CFOs, COOs, CMO’s and CROs are already growing inside the business long before you need them.
AI Strategy for Financial Services CEOs: Why “Good Enough” is no Longer Enough
Mon, Feb 23, 2026 — AI in financial services has moved from lofty claims about AI's use to being at the center of the growth conversation, shaping how you compete, run, and stay trusted. Margins are under pressure as customers benchmark you against their best digital experiences, whether they are opening a checking account, redeeming loyalty points, disputing a card charge, or seeking hardship help.
5 AI Trends Every CEO Must Act On
Mon, Sep 15, 2025 — Earlier this year, I shared takeaways from Mary Meeker’s Internet Trends Report, which showed how AI is reshaping business at a macro level. Building on that, Google Cloud’s 2025 AI Trends Report highlights five forces that will directly impact companies in the year ahead. AI is no longer experimental. It is restructuring markets, reshaping customer expectations, and redrawing competitive boundaries. Here are five AI trends CEOs are preparing for now:
Think Like Your Customer: 8 Cognitive Biases Every CEO Should Know
Mon, Aug 25, 2025 — Human beings like to think we make decisions logically. But research in behavioral science and neuroscience tells a different story: up to 95% of decisions are made unconsciously, then justified rationally. Cognitive biases shape every decision, often before logic enters the picture. These shortcuts drive customer responses to marketing, pricing, and branding, sometimes in ways that defy prediction.
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.
8 Strategic Moves to Grow Your Business with AI
Wed, Jun 18, 2025 — Top takeaways and action items from Mary Meeker’s 2025 AI Trends Report Generative AI is accelerating at a pace we've never seen before. ChatGPT, for example, reached 800 million users in just 17 months—far faster than the 11 years it took Google Search to hit similar annual query volumes. Tech giants are pouring hundreds of billions into AI infrastructure, making these tools cheaper, faster, and more accessible than ever before.
Why CEOs Must Be Active on Social Media: Building Trust and Authenticity with Customers
Wed, May 14, 2025 — I’ve seen firsthand how a CEO’s presence on social media changes how people view a company. Customers, employees, and potential hires want to know who’s steering the ship. When I show up online and share my perspective, the conversations become more genuine, and trust starts to build. It’s not about self-promotion – it’s about showing the real person behind the title.
Helping Clients Nail Their Target Market™ in EOS®
Mon, Apr 7, 2025 — Four Steps Every Implementer Can Use to Drive Clarity and Growth One of the most critical decisions your clients will make in their Sales and Marketing Strategy is identifying their Target Market™ — the group of people or organizations for whom they solve a clear problem, in a compelling way. Getting this right isn’t just a branding exercise. It’s foundational to the ability to set the right strategy, message, and Sales and Marketing Rocks™.
A Different Perspective on Marginal Cost Pricing
Fri, Mar 7, 2025 — I pulled up behind a Prius at a red light. A sticker on its left rear bumper, in type too small to read unless you were within a car length or two, said: “Sorry for driving so close in front of you.” A different point of view on the tailgaters that clearly bug that vehicle owner!