Executive Coaching

Your Team Can’t Grow If You Keep Doing Their Work

Janet Grondin, CEO of Stellar Solutions, a woman-owned aerospace engineering services company serving the defense, intelligence, civil, and commercial sectors, stepped into the role in 2021 after leading the company’s Intelligence Programs and Defense Solutions functions as VP and after 26 years in the US Air Force, retiring as a Colonel. Glenn Gow, The Scaling … Read more

Your Employees Are Already Using AI

Michael P. McCready, founder and Managing Partner of McCready Law, a Chicago-headquartered personal injury firm he launched in 1999 and has grown over 27 years into more than 20 attorneys and 13 offices across seven states, starts the AI governance conversation from an assumption most executives have not made yet: the tools are already in … Read more

Fire Yourself Before Your Business Does

Dr. Aleksandr Yampolskiy, co-founder and CEO of SecurityScorecard, a security ratings platform he started in 2014 that has raised over $290 million from investors including Sequoia and Google Ventures and now serves more than 3,000 enterprise customers with over 500 employees, describes the discipline that kept him in the seat through that growth as firing … Read more

You Don’t Need to Solve Every Problem

Clay Cowan, CEO of IRA Financial, a self-directed retirement and pension plan provider with roughly $8 billion on its platform, and previously a partner at McKinsey and Company for seven years and CMO at both Betterment and gilt.com, closes his eyes several times a week, sometimes several times a day, to ask what really matters. … Read more

The State of AI for Executives (October 2026)

This article is a summary of what many different senior executives have told me about what they are doing with AI right now. In late September, AI safety took over the AI conversation. However, I am not going to focus there. As a podcast host who speaks regularly with senior operators, founders, and investors, I … Read more

Stop Using AI Just to Cut Costs

Bob Root, Operating Partner at Southfield Capital, a lower middle market private equity firm investing in founder-owned and operated businesses, and a board member at Protos Security, takes a position on AI that he acknowledges is contentious in his own industry: cost savings is not a strategy. Glenn Gow, The Scaling Executive Coach and host … Read more

Your High Performers Won’t Scale Without Trust

Asked for the one scaling insight he wishes he had known earlier, Stevan Popovich, President and Chief Retail Officer of Cycle Gear, a powersports omnichannel retailer running more than 160 brick-and-mortar locations as part of the Comoto Family of Brands, answered in three words: trust versus performance. Glenn Gow, The Scaling Executive Coach and host … Read more

Your Managers Should Still Be Operators

Most founders answer a growth target with a hiring plan. Augustin Prot, co-founder and CEO of Weglot, a SaaS translation API company that makes websites available in any language and has operated since its 2015 launch, answered it by capping the size of his team on purpose and requiring every manager to carry operational work … Read more

AI Should Be Your Co-Pilot, Not Your Driver

Adam Harris, CEO and co-founder of Cloudbeds, a hospitality management platform operating in 41 countries and 27 languages that serves more than 40,000 properties across 157 countries and processes $25 billion in annual room sales, treats the arrival of AI as a regime change that ends the old way of operating, and he still refuses … Read more

Your Best People May Not Fit Your Next Stage

Two-thirds of the CEOs backed at the start of a growth equity investment are not the CEO when the company exits. Brian Rich, Managing Partner and co-founder of Catalyst Investors, has watched that number hold across more than one hundred portfolio companies and twenty-six years of expansion-stage investing, and he attributes the difference between the … Read more

Glenn Gow
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