Are there differences in leading a one person organization compared to an organization of fifty? "Absolutely," says Robert Sher, Founding Principal of CEO to CEO, a company that improves leadership and business skills of CEOs in middle-market companies. Learn more what Robert has to Say on American Dreams.

About Robert Sher

Robert Sher is founding principal of CEO to CEO, a firm that improves the skills of chief executives of mid-market companies who are navigating major shifts in their business or marketplace.

Robert has published extensively on the successful leadership traits of CEOs of mid-market companies. He is a columnist for, has written a book ("The Feel of the Deal") and numerous articles for such publications as, the Silicon Valley/San Jose Business Journal and the East Bay Business Times. He also publishes his own newsletter, The CEO Insomnia Factor.

CEO to CEO has worked with chief executives of such companies as GoGrid (a fast-growing and pioneering cloud computing firm), GSC Logistics (the largest third-party logistics firm serving the Port of Oakland), Triangle Software (a GPS traffic software firm) and Hanson Bridgett LLP (a San Francisco-based law firm).

CEO to CEO improves the skills of CEOs navigating major shifts in their business or marketplace. We help these executives improve their capabilities in three areas: leadership skills (including defining and maintaining a high performance corporate culture); business skills (e.g., competitive analysis and planning); and interpersonal skills (e.g., managing relationships with investors, board directors, and the management team).

Unlike consulting firms that are brought in to solve company problems, we are former CEOs of mid-market companies who equip CEOs with the skills to address those problems. And while executive coaches largely help CEOs improve their interpersonal skills, we develop business acumen and leadership acumen in addition to personal acumen. Lastly, where university programs teach CEOs in classrooms, we bring the education to our CEO clients so they can use their new skills to solve pressing issues.

Articles and Books by Robert Sher

Midsize Companies Must Prioritize Ruthlessly - Harvard Business Review

The world is littered with the hollowed-out shells of firms that tried to do too much and spent too big trying to grow too fast. Many of those firms were midsize companies; they didn’t have the resources of the big firms to sustain setbacks, nor were they scrappy like most small companies, making do with the resources they had...

Tinkering with Strategy Can Derail Midsize Companies - Harvard Business Review

Many leaders of midsize companies – especially if they’re the founders – are constitutionally inclined to see new opportunities around every corner. And they love to pursue them, deadline commitments or old strategies be damned. They forget that the strategy which took them from small to midsize has already proven itself a winner. But a new vision is always more exciting to them than the present one. So they begin tinkering with their core strategy, burning up resources while their companies wander off their tried-and-true growth path...

Midsized Firms Can’t Afford Bad Bets - Harvard Business Review

CEOs of midsized companies who make big bets can lose the farm. The executives of Fortune 500 companies might be able to lose the same bet with impunity, and the founders of venture capital-funded startups are only renting the farm (with the VC’s money) anyway. But for a midsize company, an ambitious investment that you don’t have the wherewithal to execute on can be fatal...

Mighty Midsized Companies: How Leaders Overcome 7 Silent Growth Killers - New Book on Amazon

Midsized companies are often overlooked by Wall Street and mainstream media outlets, though they are an integral part of national economics. Thus it’s important for national economic success to have a thriving midsized company sector. But that is not easy to do, largely because the factors that throttle growth of midsized companies can be quite different than those of their smaller and larger business brethren. Some of these factors are well known, but others can creep up on management teams and go almost unnoticed until it’s too late...

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