Leadership Skills: 7 Books For Aspiring Leaders

Leadership Skills: 7 Books For Aspiring Leaders

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Are you really a leader or just the person sitting on top of the heap right now? I always think it’s fascinating when I hear talk about “self-proclaimed” leaders. I feel the same way about the word “visionary”. But I also feel there are qualities and habits you can…

Are you really a leader or just the person sitting on top of the heap right now? I always think it’s fascinating when I hear talk about “self-proclaimed” leaders. I feel the same way about the word “visionary”. But I also feel there are qualities and habits you can learn to become a good leader. Here are my top seven thoughts on leadership, along with books that have influenced me.


When first developing a business idea, most people don’t think about inspiring others because they don’t have anyone to inspire yet. This is the best time to start working on this skill. I listen to Simon Sinek’s talk at least once a month on “knowing your why”. When you know your ‘why’, you’ll be able to inspire others to join your revolution. Inspiration through your ‘why’ creates clarity – and that’s a part of what fires people up.

“Offer someone the opportunity to rebuild a company or reinvent an industry as the primary incentive, and it will attract those drawn to the challenge first and the money second.”

Simon Sinek

Book: “Start with Why”, by Simon Sinek


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Honesty is one of the best forms of integrity. if you’re honest with your team, you’ll naturally earn respect. Transparency is another form of integrity that helps build trust throughout your organization. Buffer, a San Francisco startup, took transparency to another level a couple years ago when after they decided to post a transparency salary formula. it went viral. You can read more about it on their blog.

“Poem by Howard A. Walter (Character)

I would be true, for there are those who trust me;

I would be pure, for there are those who care;

I would be strong, for there are those who suffer;

I would be brave, for there is much to dare.

I would be friend of all – the foe, the friendless;

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I would be giving, and forget the gift;

I would be humble, for I know my weakness;

I would look up, and laugh, and love, and lift.”

John C. Maxwell, Developing the Leader Within You

Book: “Developing the Leader Within You”, by John Maxwell


I believe that listening is one of the most powerful skills ever, not only for leaders but in every facet of life. Really listening and being present(no glancing at the phone, texting) improves connection, it will drown out the unnecessary noise and allow you to get to the bottom of an issue or get to the top of a huge success.

One of the most under-utilized communication skills is asking good questions. What is a good question? “What could we do differently? How could that make a difference? Tell me more about your idea

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“We have two ears and one mouth so that we can listen twice as much as we speak.”


Book: “Selling 101”, by Zig Ziglar


I believe that learning the art of listening turns you into a good communicator.

Creating a great system for communication within your business and life will make or break you. There is a difference between tools and systems. “Slack” is a fantastic tool for communication, but it’s not a system. You add systems in your life to maintain focus. Part of my system is that I try not to respond to emails between 7pm and 7am. As a startup founder, I found that habit to be rare. I allow a few exceptions – like if something is on fire, my wife is working nights, or I’m in a different time zone. I know several entrepreneurs who implement different systems to improve communication, like meditating in the middle of the day, taking standing meetings, and implementing open-floor seating.

“Be sure your communication goes beyond words. How can you do that? By connecting on four levels: visually, intellectually, emotionally, and verbally.”

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Book: “Everyone Communicates: Few Connect”, by John Maxwell

Book: “Crucial Conversations”, by Kerry Patterson


During a recent trip to NYC, my friend Micha and I were talking about startup founders. Micha is a mentor for several well-known startup accelerators. I asked him what he likes to see in founders. He said, “I like a founder who’s paranoid that someone else will get there before them.” When you’re a leader, it’s okay to be paranoid. It makes you focus on the most important parts of your business.

“Expect the unexpected. Focus on what you can control and acknowledge what’s out of your control.”

Jack Canfield

“Only the paranoid survive.“

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Andy Grove

Book: “Power of Focus”, by Jack Canfield

Human Engineer

Great leaders build more leaders. I know that becoming a human engineer might sound strange, but I’m a big believer in building leaders internally.

“You can have everything in life you want, if you will just help enough other people get what they want.”

I was reading an article an article on Mark Zuckerburg and said, “You need a bunch of people working on an adaptive concept together for a long period of time. You don’t need to be a prodigy to start your own cool company — you just need to be passionate and focused.”

Book: “How to Win Friends and Influence People”, by Dale Carnegie


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When you lead, you eventually have to build other leaders around you that you’ll be able to mastermind with. I have a few different groups – one internal, one for entrepreneurs, and one for mentoring.

The benefits of having these groups are endless. It’s always easier to talk through challenges when the people around you are experiencing the same challenges.

“More gold has been mined from the minds of men than the earth itself”

Napoleon Hill

Book: “Think and Grow Rich”, by Napoleon Hill

I blog and speak on topics that help entrepreneurs. You can find me on the social webs if you want to get in touch. I'm @richwinley.

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