Note: this is a non-religious post.

This weekend was Yom Kippur, holiest of the Jewish holidays and the day of atonement. It's also the day when most Jewish minds are least focused since one needs to fast for 24 hours.

I sat in schul listening to the rabbi's sermon and given my mind is prone to ADD anyways I must admit that my consciousness often floats around the room but even more so on Yom Kippur. But our rabbi captivated me this year and reminded me of one of the most important lessons I learned myself 15 years ago.

She started with a story--a parable--as Jewish people are wont to do. She told of the teaching of the Talmud--a book which scholars use to debate doctrine and from which Jewish people are reminded to always learn and to debate.

"A rabbi is teaching a young Jewish scholar and he says, 'Two men go down a chimney, one is dirty and the other is clean. Which one takes a shower?'

'The dirty one takes a shower says the young scholar.'

'Are you sure? What if the dirty one saw the clean one perhaps he would assume that he himself was clean. And if the clean one looked at the dirty one perhaps he assumed he was also dirty and thus took a shower.'

'I see. I guess maybe the clean one took the shower thinking he was dirty.'

'No. How can you say that? Perhaps there was a mirror in the room and each could see whether he was clean or dirty.'

'Oh, you're right. Of course the dirty one took the shower.'


'Rabbi. I don't understand? You first told me the clean boy may have taken the shower. You then told me the dirty boy took the shower. I'm confused. Which one took the shower, Rabbi?'

'That is the wrong question to even ask. You should be asking yourself ... how could two boys go down the chimney and one end up dirty and the other end up clean?!'

The correct answer is 'I don't know.'"

And that was the lesson from the rabbi to us. She reminded us that in the world we live in, we are often expected to be experts. We are expected to know everything and many people rush to conclusions given a limited set of information.

The Talmud, like much of Judiasm, encourages debate and discussion and we are taught to always question our assumptions.

Learning comes from starting with a point-of-view that says, "I don't know." I said I learned this 15 years ago because that is when I stopped being a consultant. I enjoyed the first half of my time at Andersen Consulting (now Accenture) because I was a computer programmer and had to build stuff that actually worked. But as I rose in my career (and post MBA) I moved into a role in which I was to advise board-level executives on topics where I was expected to rapidly become an expert.

Some areas were easy because they were technical and the answer was knowable or estimate-able. I did a study for a large European mobile operator on whether they should bid for 3G spectrum and if so how much was it worth. That was an awesome project and the answer was quantifiable.

But much of the work was unknowable. What is the right organizational strategy for a large UK conglomerate to operate more effectively? How should a large European telco deal with a rival "free Internet access" startup? What would the right technology strategy for Telecom Italia be in five years. The problem with consulting is that they hire very smart, young people out of top colleges who come in to evaluate data and advise large organizations but the people doing the work are often only book smart.

As a consultant you're not paid to say "I don't know." You're paid to come up with an answer. And the problem is that you know that you're being paid a lot of money to seemingly know the answer and to almost know it even before the work has been done. Consultants spend all of their time pretending to know these answers. In the end my guess is that many internally feel conflicted because it never feels nice to pretend to have all the answers when you really don't.

If you started every project assuming you really didn't know the answers, and if you were in search of experts who probably had more experience than you, the chances are you would expand your consideration set when you chose how to tackle each problem.

In my experience many VCs fall into this "I'm expected to know all the answers" trap. For me, after nearly a decade in the trenches of being an entrepreneur I felt I was un-brainwashed from trying to pretend I had all the answers.

I remind my colleagues this all the time. I believe that our job can be stripped away to its core: We have to be really good at identifying talent and we have to be competent enough in startup operations and finance that they want to work with us and figure out the answers together. We are their sparring partners, their sounding boards. We are not to lead them into some vision in our head of how their markets should work. It is unknowable. Any true disruption will change all the rules.

The more self-assured the VC is and the more impressionable the entrepreneur is, the worse the outcome. You have on one side somebody really smart pretending to know the answers and on the other side somebody who is staring at the problem, the facts and the data every day but trusting the judgment of somebody who is faking as though they know what to do. Every situation is different.

I don't know.

I sometimes see VC's come up with "thesis-based investing" and I get this at 20,000 feet because we can be smart enough to know the general fields where we believe innovation will have attractive properties. That's part of the value we provide. But then we must go in search of teams who are passionate about solving these problems and going to battle every day in their respective fields. It's OK for us not to be the experts.

I often hear pitches and think to myself, "that sounds plausible," but I nearly always start with the position that I'm not sure. I love the intellectual challenge of trying to figure out what hypothesis I think holds for each opportunity. And often the better question for me than whether this solution will work is, "Will this entrepreneur be able to figure out which solution will work over time given that more than 95 percent of the time I won't even be there to debate with him or her?"

I've already blogged about how I work through this process: I triangulate. And I encourage entrepreneurs to triangulate as well.

It helps as a founder or CEO to start with a position that you don't know. To quickly assemble experts and ask them 50 questions until you have a point-of-view. Don't start by thinking you know all the answers. Don't feel that you need to. I find that most people respect others who are willing to learn rather than preach.

Sometimes in your own small organizations you feel like you're expected by your staff to have the answers. To the extent that your organization feels this way you could form networks of your peers, hold lunches and share knowledge. The funny thing about peer groups is that the more you open up about the issues you're struggling through the more you'll find your peers will open up, too.

In fact, I would go as far as to say that when I encounter entrepreneurs who I can see pretending to know everything I tend to be more skeptical. I am never put off by somebody who answers one of my questions with, "That's a great question. I'm not totally sure. I would think a, b, c. But let me spend more time thinking about that and get back to you."

Willingness not to pretend you know all the answers lightens your burdens. Opening your mind to the fact you may not always be right will force you to seek others opinions more readily. As a leader you have to make tough decisions with incomplete information but that is different from pretending you know the right answer.

The right answer often is, "I don't know."

This article was originally published on Mark Suster's blog, Both Sides of the Table.

Published on: Oct 6, 2014