MindShare Class #3 Recap: How Great Leaders Communicate

11 Apr MindShare Class #3 Recap: How Great Leaders Communicate

United Airlines – the speech from Held en Merk on Vimeo.

This is the video that was supposed to kick off the event at last night’s MindShare program…here it is now!

Thursday night marked the third official class for the 2014 class of MindShare–an invitation-only organization comprised of first time CEOs.

This year’s class boasts the largest group the organizing board of MindShare has pulled together with 85 members!  The press release announcing the class members touts the successes the organization has seen in its 18 year history, especially the more than 700 CEOs that make up the alumni network…who continue to share information on best practices in business, company success stories, vendor inquiries and the like.

Some of the classes showcase these alums, and last night’s event featured serial entrepreneur and MindShare AlumSean McDermott, CEO of Windward IT Solutions, a consultancy focused on helping global Fortune 500 companies run complex networks and data centers. He is also the co-founder and chairman of App47, a cloud-based Mobile Application Management service.

Formerly, Sean was founder and CEO of RealOps, the pioneer in IT Orchestration software, which sold to BMC in 2007 in a highly successful exit. After BMC Software acquired RealOps in July 2007, Sean continued on at BMC as the VP of Service Automation Solutions where he was responsible for their $200M Service Automation portfolio.

Sean also has extensive experience raising venture capital, advising VCs on investments, and participating on boards, and brought interesting perspective to the class.

Betsy Lewis, an organizing board member for MindShare and partner in the Employment and Labor practice group at Cooley, LLP, hosted the programming.


MindShare speaker Sean McDermott, with Betsy Lewis, partner for Cooley, LLP, who hosted.

Some highlights from his remarks (including some great sound bites that I captured…he was full of them!):

– Sean graduated from Villanova University with a degree in electrical engineering, despite wanting to be an art major originally. Perhaps that’s why he believes communication is so critical in leadership–he applied some of his liberal arts learning to his business today. He believes that no matter what, success in business is all about the relationships, and even though they provide technical solutions, it’s always a relationship business, not just a services business. For example, he never sold to a customer he didn’t meet…

– He believes you need to surround yourself as a CEO with people who really buy into your vision, and then communicate, communicate, communicate. Encourage your team to ask questions…”people believe they know what I want, but then they guess wrong…it is incumbent upon me to make sure people don’t feel like they get ‘points off’ for coming to ask questions.”

– “There are too many people who will tell you what you are doing wrong…people ask too few questions then come to conclusions too easily.

– Sean believes in face-to-face conversations whenever possible. Email, even phone or conference calls, diminish the conversation. He spoke about one of his investors at RealOps who was from the west coast, and it was hard for him to make board meetings regularly in person, so Sean decided to hold them in Santa Monica after realizing they were losing some of the value he could provide by not being able to sit face-to-face, have dinners, build a relationship. It changed their relationship immensely, and he became one of their biggest champions throughout the run at RealOps.

– One of Sean’s initiatives is from time-to-time, hold a “skip-level meeting” where he takes a dozen people at random to come into a meeting and talk. No management, no filters. Open communications. It helps him to engage, understand, and better communicate.

– Sean is also a big believer in consistent management and all hands meetings. He actually commits four hours per week to his management team in a meeting held every Friday, to discuss the sales pipeline, consulting projects and their status, finances and staffing. It’s mandatory, and then on top of those, he holds an offsite once a month for eight hours where they can really get into strategic thinking about company direction, vision, execution, etc.

– If you want to get Sean fired up, talk to him about email! Or texting!  He adamently believes one cannot have a relationship over text, and one cannot have it over email.

– A second hot button is one’s ability to write when it really matters, or even in any business communications. He believes too many people write too casually, and it’s becoming more and more accepted, which is wrong. He is so passionate he sits on a board in the College of Engineering at Villanova to ensure writing is a core part of the curriculum. He believs that in business communications, one’s writing style is indicative of who you are. He talked about how shocked he has been over some emails that came to him–as CEO–from (now former) members of his team–that were barely comprehensible. And if emails to him were that way, what was the customer seeing?

– When you can’t meet with someone in person, use a video conferencing tool, even if it’s klunky or awkward. He’s used Google Hangouts, Facetime for 1on1s, Skype. At least it helps to read body language!

– In response to a question from the class about the hardest thing he’s experienced, Sean replied that when things aren’t going well, that’s when it can get really hard. He quoted Phil Merrick, another MindShare alum, who said, “The name of the game is to stay in the game…you can’t win a home run if you don’t get to the plate.” Then Sean added, “things are funny when you’re making money…” but when the chips are down, that’s when it can get really, really hard.

–Elizabeth Shea @eliz2shea

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