Leadership Lessons From the Trenches of Silicon Valley

Real world lessons in leadership behavior from America's high-tech startup mecca and beyond.

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By Steve Tobak

Opinions expressed by Entrepreneur contributors are their own.

There's nothing more worthless than a perfunctory board or executive meeting where everyone just goes through the motions and no strategic decisions are made. Over the years, I swear there were times when I thought my head would explode from sheer boredom.

But every so often when the conditions were just right, an emotionally charged brawl would erupt between warring factions. The pressure would build up like an earthquake fault line until someone dropped a one-liner that breaks the tension and cracks up the room.

I'll never forget one board-strategy offsite. After a day of executive presentations and heated debate, we went around the room so our directors could vote on a major change in strategic direction. When it got to this one VC, he said, "I don't know," in his trademark deadpan Louisiana drawl, "but this whole idea just makes my butt pucker."

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Every company may have a different leadership culture, but some patterns of behavior inspire people to perform and make a huge difference in the outcome. Here are some real-world lessons from deep in the trenches of high-tech America, Silicon Valley, and beyond.

Never lose your sense of humor, especially in a crisis. There's a world of difference between serious business decisions that affect thousands of stakeholders and taking yourself too seriously. If you lighten the mood, people will be more candid, your team will be more effective, and you'll make better decisions.

The best inspiration is perspiration. I think we can all agree that work just for work's sake really sucks the life out of you. That said, nothing inspires the entrepreneurial spirit more than working hard, getting the job done, beating the competition and winning the business. Absolutely nothing.

Authority and authoritarian are too different things. If you manage to get to the top of the corporate ladder, then by definition, you have the authority. Congratulations. But if you want your handpicked leadership team to hold themselves accountable, speak their minds, and perform at their best, then respect and treat them as peers.

Challenge your people to excel, but stand firmly behind them. The best and most successful CEOs I've known over the years expect their people to be the best at what they do and push them hard in private, but back their decisions and support their efforts 100 percent in public.

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Engagement starts at the top. We talk a lot about delegation and employee engagement these days, but nothing destroys morale and productivity more than a disengaged leader. Delegation is key, but when things are going wrong, CEOs have to be hands-on.

Do what needs to be done. I've known too many leaders who put their own comfort ahead of the needs of their company. That doesn't fly in the startup world. If you want to beat the odds and win big, you've got to be the first one in and the last one out. You've got to hop on a red-eye to meet with a customer on a minute's notice. That will inspire folks more than anything will.

Be straight with your people. Most CEOs and business leaders are as uncomfortable being honest with managers about their weaknesses as they are reluctant to shower them with public praise. That's unfortunate because everyone needs both.

Do the right thing. Every corporate culture has an ethics statement and every set of corporate values has a bullet about integrity. It's become so boilerplate nobody even notices anymore. If you want people to do the right thing no matter what -- especially when everything's on the line -- then demonstrate that quality in your actions.

Probably the most dysfunctional and damaging thing that business leaders do is let their position, their authority, their success go to their heads. If you spend time with a top executive and it feels like you're hanging out with a regular guy, that's a good sign. That's how it should be.

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Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at stevetobak.com, where you can contact him and learn more.

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