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When I first launched my company, countless issues kept me up at night: financing, finding the right talent, developing my go-to-market strategy. The list seemed endless. I complained about my problems to a successful entrepreneur, who I believed had it all worked out. She patiently listened for a while before snapping me out of my delusion. I needed to enjoy the honeymoon phase of my company, she said, because by the time my startup reaches her stage of development, just ensuring you make payroll can cause sleepless nights.

Admittedly, the grass always seems greener in someone else's pasture, and many believe that success – most often measured in dollars – to be the stage when life gets easier. After perusing the most recent survey of top-paid U.S. CEOs, I started to wonder how well they sleep at night. Does Larry Ellison, chief executive officer of Oracle Corp., sleep soundly while drawing pay of $96.1-million (U.S.)? Does he rest better than John Brock, CEO and chairman of Coca-Cola Enterprises Inc., who earns only $10.2-million?

I reached out to several experts in the field and it appears that money doesn't buy peace of mind and a leader's biggest worry often comes down to variations on the same theme: managing people. And if that's not their top concern, it should be.

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"In my opinion, what should be nagging everyone in a leadership position is employee disengagement," said Nicole Lipkin, a Philadelphia-based organizational psychologist who works with executives around the world and is the author of What Keeps Leaders Up At Night.

"If your employees' level of engagement isn't a priority – a problem in and of itself – then consider the impact it has on your customers," she warned.

The alarming rate of employee disengagement, said Ms. Lipkin, can be linked to reduced productivity, poor performance, workplace safety, retention, loyalty and profit, to name a few.

Emotions are also contagious and negative ones can spread to every tier of a business. "It's just that powerful," she added.

Glain Roberts-McCabe, founder and president of the Executive Roundtable, a Toronto-based leadership organization for mid-career executives, concurs that one of the top concerns of leaders comes down to retaining key talent, specifically professionals looking for room to grow.

"I worry that organizations are becoming increasingly out of sync with the needs of this next-generation executive group and are losing their best and brightest because of apathy at senior levels," said Ms. Roberts-McGabe, who works primarily with leaders who are deemed "high potentials" in their organization.

For other leaders, retaining talent remains a concern, but it needs to include a better approach to gender diversity, which relies on an evolving corporate culture.

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"There are highly qualified women to hire and with their talent they bring added value to the various teams, as well as value added to the company's bottom line," said Susan Butler, CEO of the Susan Bulkeley Butler Institute for the Development of Women Leaders, based in Tuscon, Ariz.

"Given that most employers are assuming that women are 'short term' employees, they have not changed their cultures to grow them as 'long term' employees, moving up the career path," observed Ms. Butler, who before her retirement in 2002, was the managing partner for Accenture's office of the CEO.

"To really be successful, companies need to impact their current culture, which is based on a male work force," she added.

Competing demands can turn good bosses bad, according to Ms. Lipkin. She observed three flaws that can bring a leader down: being too busy to win, being too proud to see and being too afraid to lose.

As an example, she cites Antonio Horta-Osorio, group chief executive officer of Britain's Lloyds Banking Group PLC, who was forced to take an extended break in November, 2011, citing stress and overwork. Acute insomnia kept him awake for five straight days, forcing him to seek medical attention, which severely affected the company's share price, Ms. Lipkin said.

"You can't be a great boss when you are overwhelmed and way too busy," observed Ms. Lipkin. She explained that it's important for leaders to imagine that their brain is like a bookshelf. When you set it up, the instructions might warn that it can only accommodate 50 pounds, but many people will forget that fact and keep piling on more books, ignoring any sagging in the middle. When it snaps, they act surprised.

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"Leadership is hard. Being in charge or directing other people is rewarding but brutal, and if we're being completely honest, sometimes painfully annoying. However, our weapon, when it comes to evolving as a leader, is really a commitment to lifelong self-awareness. Self-awareness begins with admitting that you are a fallible human."

Leah Eichler is the founder of r/ally, a mobile collaboration platform for enterprises.

E-mail: Twitter: @femmeonomics

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