Everything I have learned came from people that had already done what I wanted or needed to do...or via shear stubbornness and entrepreneurial and intestinal fortitude. Leadership and management books have helped too, and I'm a big fan of many of the top authors in the field, but sometimes a real conversation with a real person is what is needed to crystalize an idea or catalyze a change you and your team may have been contemplating.

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Coaching can be, and should be as simple as listening and asking good questions. The questions and sequence are what is important and the answers typically find a way of presenting themselves. Real clarity comes from thoughtful discussion and is truly useful when the answers are not forced.

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Most entrepreneurs find themselves with titles that are not always indicative of their previous skillset or current abilities. We are creatures of necessity that "figure it out" and we always "find a way" to get it done. That may be fine early on, but as you and your business grow and change, what worked in the beginning will ultimately not work at scale. This isn't "bad", or something anyone has "done wrong", but it it is a real phenomenon that can make or break a business, a deal, or possibly a career. It takes guts to identify your strengths and admit where you may want or need some help. Finding your way through a difficult situation may help you grow, but it may be at the cost of another employee, customer, or the business in general.

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Help isn't far away. Sometimes taking a step back to evaluate your surroundings and slow things down is a great way to regain perspective and clear your head. A great next move is to seek out a discussion with a trusted advisor or colleague who may have "been there" and can offer their experience and ears as a sounding board.

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In the last 15 years, Chicago has become home to some of the world's largest and most successful technology start-ups and incubators. Many of us have worked with, founded, invested, or helped start and grow some of Chicago's fastest growing SaaS companies.

 

We've made all the mistake entrepreneurs make. We've seen the best and the worst days from the inside some of Chicago's top companies and learned tough lessons from our first-hand successes and failures. Talking with an experienced entrepreneur can provide perspective and help you navigate the decisions that are critical to the success of your business. The answers are usually there, it is just difficult to see them clearly when you are neck deep in the day-to-day detail.

 

Sometimes, all it takes is a conversation over coffee (or a beer) to spark a fresh idea, get a process "un-stuck", or make that tough hiring decision.

 

Connect with us today and tell us your start-up story! We're here to listen, make useful introductions, and offer helpful suggestions...and we never charge for an introductory discovery conversation.