Larry EllisonEveryone looks up to Jeff Bezos, Mark Zuckerberg and Reed Hastings, but who do the senior IT leaders of midmarket organizations admire?

I have been in the tech industry for a long time. I have had the good fortune to see firsthand many industry giants at work and up close. It was amazing to witness. Early on in my career, I became fascinated with these individuals. People like Bill Gates, Steve Jobs, John Chambers and Larry Ellison, along with the founding fathers of the indirect sales channel.

Sure, the tech titans always got the headlines, but if weren’t for those tech-focused entrepreneurs who figured out how to sell all their innovations to customers, the Larry Ellisons of the world would never have been as successful. Thus began my fascination with such leaders, who I often had the chance to interview as a tech journalist or watch on stage during their numerous product launches or keynote presentations.

Today, many in the industry closely monitor the movements and words of Amazon’s Jeff Bezos or Facebook’s Mark Zuckerberg and Netflix’s Reed Hastings. These are all worthy individuals to admire and learn from.

This brings me to an important question. Who do the senior IT leaders of midmarket organizations admire?

I often wonder if they admire anyone. Sure, there are lessons to be learned from accomplished business leaders of Fortune 500 companies such as Ken Langone or Howard Schultz or investors like Warren Buffett. But what midmarket CIOs and senior IT leaders yearn for is someone closer to their work so they can gleam useful wisdom. That could be a mistake.

I was always in awe of IT leaders of large enterprises. Back in the day, the CIOs of such giants as GM, Merrill Lynch or HP were individuals who could crisply articulate their strategy and demonstrate the value they delivered for their organizations. The fact that they could manage vast empires with hundreds, if not thousands, of employees made them all that more interesting.

They could make or break suppliers and partners simply by choosing their application, server or IT solution or say that a particular product fell short. Because of their positions, they were sought-after speakers, hobnobbed with industry leaders and their names turned into brands that hopefully would make their positions more tenable, given the pressure and risks they face.

That’s still the case for the big-name CIOs of today’s leading organizations, right? Yet these leaders of enterprise IT shops are often not those admired by the men and women driving IT strategy for their midmarket company.

I was always perplexed by that. Oftentimes, midmarket CIOs will say they cannot relate to their enterprise brethren because they are worlds apart. But by dismissing these individuals and their insight, midmarket CIOs miss some valuable lessons. Enterprise CIOs understand their role is to lead, not necessarily do the work.

Midmarket senior IT leaders—many of whom I admire for their accomplishments—want advice they can apply to their day-to-day jobs because they are forced to do the work while figuring out ways to lead. That’s a difficult challenge for anyone. It remains the biggest struggle of the midmarket CIO. These individuals want to grow as leaders, yet they often lack the resources or staff to get out of the day-to-day mindset.

I am not sure what the answer is, but I do know after many years in this industry that you need role models and, yes, idols who can help you do your job better. I often bring this topic up during our conferences and meetings with midmarket CIOs and have yet to hear with clarity on just who inspires them. It is a topic worth thinking about more deeply because while your peers can help identify best practices, you need people on your list who can advance your career, strategy and thinking.

Who do you admire? Let me know by sending an email to