One of the most interesting parts of my job at 1871, a Chicago-based entrepreneurial hub for digital startups, is listening to our member companies. For most entrepreneurs, effective and patient listening is a fairly foreign concept. They think that the opposite of talking isn't listening, it's waiting to talk. Partially this is because they think they have to always be selling, so they're always trying to fill any dead air--and end up sucking all the oxygen out of the room. But sometimes you just need to catch your breath and let the other guy have his say. As it happens, when you listen you are often rewarded with bits of actual wisdom.

Listening is a rare and highly undervalued skill, one that every one of us could stand to improve. Good listening skills can make a world of difference for your business and in your leadership. Listening carefully is the highest form of courtesy and professionalism.  As my mother used to say, “This is why God gave us two ears and only one mouth.”  (If I had only listened back then, there's no telling where I’d be today.)

Want Advice? Then Be Prepared To Take It

Every day I listen to as many of the trials and tribulations of hundreds of entrepreneurs as I can stand. I try to be patient and objective, as long as they have taken the time to (1) do their homework and get prepared; (2) organize their thoughts and their questions; and (3) specifically identify the areas where they think I can help or at least advise them. Folks who just drop by to shoot the breeze quickly find themselves shooting it somewhere else with someone else.

If they're not prepared and if they have such little respect for my time it's hard to imagine that they would really care about my thoughts and opinions, or that I should waste my relatively scarce time sharing my reactions with them. I think this is a very fair expectation on both sides--whether you're the "oldie" or the "newbie" in any conversation you need to bring it or don't bother coming.

Whether I'm asked or not, I'm not especially shy (and rarely polite) about giving my impressions and the (alleged) benefit of my years of experience, which may occasionally keep someone from making the same mistake I made in similar circumstances. Sometimes I discover that the entrepreneur is trying to create solutions before they've spent enough time listening to their customers' problems, which is a lot like working in the dark.  Other times I find that just the act of having someone seriously listen to them (who doesn't have an attitude, a vested interest, or an agenda) does wonders for their mental health and their anxiety levels. But that's not to say that I think that these skull sessions should be warm and fuzzy chats.

I like to save the "strokes" for their co-workers, friends, and families. Honestly, I'd rather be fair and frank than spend my time beating around the bush and worrying more about their feelings than their future. My process is aggressive and unapologetic-;I'm trying to make them and their businesses better, that's all there is to it. It's never about me. But it does have a lot to do with argument and challenge--pressing and pushing them to think about the tough issues and the non-obvious answers--rather than supplying standard responses. I want to make sure that they have the courage of their convictions and the willingness to stick to their guns. We often describe this posture as "sometimes wrong, but never in doubt."

That's because you need a thick skin to succeed in this crazy startup business, and the internal and external calluses that will ultimately protect you are developed and grow strong in the crucible of confrontation (and hard questions), not in courteous conversations steeped in superficial compliments. Some babies are just ugly, and some ideas just suck. It always helps to tell it like it is; the truth only hurts when it should.

Having said all that, I'd still certainly rather have them not just listen to my advice but take it as well. I do vehemently believe that great serial entrepreneurs are masters of pattern recognition, and in the startup space there are very, very few problems that represent truly new issues or, as the courts say, cases of first impression. In almost every case I've seen this "movie" before. Everyone I know who has made it their life's work to consistently light up new businesses will tell you that while you're always gonna make new mistakes the real key to success is to avoid making the same mistakes over and over again.

I can't speak for the many people who've been successful once as an entrepreneur. I'm sure that even they aren't sure whether they were terribly smart or terrifically lucky or, most likely, a bunch of both. Not that there's anything wrong with succeeding thanks to a confluence of events. But, as I like to say, “Just because you've done it once doesn't make you Jesus.”

I’ve written before about marginal mentors and about how little having made or accumulated a lot of money has to do with having the mental horsepower and the chops to help someone drag his business out of a ditch. Money doesn't really care who makes it, and having a lot of money--as we all know from experience--clearly doesn’t make you wise.

But for those of us who have lived through the very prolonged and painful process of successfully birthing businesses over and over again, it all comes down to listening and paying attention. And to one other thing: the winners are those who learn to listen patiently without losing either their self-confidence or their temper.