The thing is - I'm not certain this is entirely a property of the person involved. Yes, there are certain skills that make it easier to find information on your own. But this is also a function of the problem domain and how well you know it. If you give me a credit card and a problem statement, chances are that I can come up with a working webapp that solves the problem. But if you give me the name of a VC and tell me to go raise money - where do I start? How do I approach him? What will burn bridges and what won't?
So my question to PG and any other resourceful folks out there is: how do you approach a problem domain in which you know nothing, and manage to gain enough of a map of the territory so that you listen to someone's one-word suggestions and instantly grasp the implications?
In my best job situations, I've generally been approachable and ready to change directions based on outside input. In my worst job situations, I can see that I've been less approachable and this has been a function of being overwhelmed by the situation.
Now, one way to avoid going into a new situation and not being overwhelmed by the situation is to take the situation bit-by-bit - don't immense yourself in all the details but instead deal calmly with one thing then another. In fact, most competent people know this. And so, a lot of the time when a reasonably competent person winds up still paralyzed by a situation, it is because they've been confronted with some kind of emotional trap - "I know this should take a week but this puppy will die if you don't finish it tomorrow!" etc.
My skeptical side says that as long as you have a product and traction that are both awesome enough for him to consider investing in, it doesn't really matter.
That's sort of where I take issue with this article: he may just be picking up on signs of confidence that are the result of really believing that you have a kickass product. That reality (as well as the attitude that it inspires) make it both a lot easier to successfully pitch your wares, as well as to talk about them to previous investors.
Similarly, in the Google example, a large part of what you see is probably that the people there really understand their domains of expertise exceptionally well. As a result, they're confident that they know what you're talking about, and eager to just get to the meat of it, without bothering you for details that they already know about.
I'd be hesitant to assume that emulating the confidence that comes along with expertise or good prospects necessarily works causally in the opposite direction, I've seen many examples to the contrary...
For example, hypothetically, if one has a weakness regarding chasing down money and one knows their career path is likely to involve raising money, then one could get a fairly rapid education in the subject for the price of a few cups of strategically ordered coffee. Don't know the character of a VC? Thirty seconds of Googleage should give you the names of five compulsively chatty people willing to give you their take.
I can sort of see why, if one were busy, one would quickly burn out on explaining How To Email People A Question to folks who did not immediately see that in the solution set when they had a plan of action which required a bit of discoverable organic knowledge.
And to add to that what one person is able to pull off given their skills is not always possible by another person even if they have been told what to do or how to do it.
Seat of the pants feel involves knowing how to react and adapt when the situation changes ever so slightly (a nuance). It's impossible to prepare someone for every possibility that might come up. That's something that comes, as you said, from "from previous successful experiences".
The best advice I can give is to learn concepts as opposed to a specifics and to understand exactly why something (say in a negotiation) should be handled a certain way. It's like the difference between learning what streets to turn on in NYC and learning the way the streets and avenues run so you can arrive at your destination even if you miss a turn.
Think of yourself as an actor playing a role.
If you tell people where to go, but not how to get there, you'll be amazed at the results.
As for working in domains outside your comfort zone... it's uncomfortable! If you are smart and willing to give it a shot then admit your ignorance, to yourself and others, and then begin learning what you need. Here's a personal anecdote...
Some time ago, the big boss here came to me with a problem of a malfunctioning instrument. The instrument is one of a kind, on a spacecraft, so we are limited to figuring this out from whatever telemetry is available and there is no option of replacement with a different unit. Now I'm a software guy with no prior training or experience in hardware, and certainly not with this kind of thing. This problem had been given to other people but nothing came of it, so he gave it to me. Knowing nothing, I learned whatever seemed like it could have a bearing on the problem. I thought about it. A lot. I asked questions. A lot. The problem was sporadic, so I tried to find correlations. For two solid weeks I had nothing to show for my time but I kept at it, and then I found a 100% correlation, leading to the instrument people finding the problem and correcting their firmware. I'm not one of those prodigy polymath people. I grasped nothing about this instantly. The only reasons I succeeded were that I kept an open mind, kept thinking and learning, asked for and used any help I could get, and determined to see this through until I had an answer.
I'm sure the process of getting money out of VCs is exactly the same, except all the details are different.
I think in this case "getting it done" also includes asking questions like this. So if someone says they'll into you to a VC but you're not sure what to do next, don't try to guess. Ask for advice.
My sense is that PG's frustration comes from people who don't act without him prodding them every step of the way.
If you're afraid or unwilling to admit your weaknesses and ask for advice, you're ipso facto closing off communication.
If I hand someone a task and they ask me follow up questions, go away, do some real work tracking down more information or carrying out tasks, then comes back to me and asks more questions about new things based on stuff they've learned since last time, and repeat the process, that is not handholding to me.
The difference is who is driving the process forwards and whether or not they are absorbing the information they are given and taking initiative.
On the hand-holding point, it's really just about taking action and trusting that you will figure out how to see it through to completion. You don't have to know much to set up a meeting with a VC, but you do have to follow-up and actually set up the meeting.
It's amazing how few people in the real world follow through on things this simple. I have a friend who complains about his job every time I talk to him. I've offered many, many times to put him in touch with companies he might want to work for and even an HR specialist friend at Google for some free career coaching. He always says "sure!" but never follows through. This has gone on for years. Years!
Asking for advices is not bad as long as you process it and act on it accordingly. Pretending you know something that you don't, OTOH, is another form of arrogance. I've never heard anyone say "that guy's not arrogant enough."
One of the best feelings when handing a task to someone is when you know that once you've handed it off, it will either get done quickly, or it will spawn a rich bramble of e-mail conversations that only ends when someone in the network has figured out what needs to be done, and then the person will do it. And if nobody knows, they'll be on the phone with you telling it straight the moment they realize that fact.
That's a very difficult quality to discern in the context of interviews, unfortunately. One thing that's useful is to try to push all of your candidates beyond what they can reasonably handle, and see how they react - people that are quick to look for help when it's needed tend to deal with these situations honestly and quickly, admitting the limits of their knowledge. The worst will just wubble about endlessly, never realizing that something is beyond their reach.
Once I realized how attractive that "quick to admit ignorance" quality was in job candidates, I stopped feeling so nervous about being interviewed, and started just being rigorously honest about what I can't do and don't know. It's better for everyone that way, and most interviewers I've met with seem to appreciate it. The only downside is that I've lost some work that I genuinely wasn't qualified to do, which is not such a great loss anyways...
Well, before answers were available online here is how it was done by an example just today.
Although it has nothing to do with my current business, I decided to explore the possibility of renting out luxury cars (high end performance cars).
The first thing I wanted to know about was the insurance.
But if you google "car rental company auto insurance" all you get are links to auto rental insurance (the type you get when you rent a car). I want companies that sell rental insurance to rental companies.
So the old fashion way to do this is to start to make phone calls to hone in on the brokers who handle this type of insurance (I did turn up AON as a vendor because they offer it in the UK but so far w/o a phone call I can't see if they offer it in the US).
So if I decide to pursue this idea I will make some calls and ask questions.
But the other thing I will do is visit a local small car rental agency (they rent beat up trucks) and I will do some form of either social engineering or play the "doing some research" angle after gaining their trust.
Or maybe I will make a deal with the owner to guide me in the business by making him a partner (edit: or paying him for consulting)
So this is something I know nothing about. But in the course of an afternoon so far this is what I came up with to start to vet the idea. If the initial metrics work I will take the idea further.
In other words be curious, ask questions and do some research. This has worked for me in starting three businesses in which I knew nothing about the business.
Through trial-and-error, intuition, and a bit of luck. :)
I think the most important first step is to not get scared. You have to feel comfortable with the fact that you don't know anything, and so you have to be a beginner. That is a great thing to be though, as beginners tend to be very open and enthusiastic about learning.
From there, it's just like studying any other art or endeavor. You start with enthusiasm, build up your skills, and eventually you feel confident enough that you can take more advanced instruction.
It's at that point that the one-word instruction can give you tremendous insight. That's been my experience, anyway.
Of course there are many ways to handle this but one way would simply be to practice on another VC or four in order to get comfortable.
In the 90's I was able to get two different VC's to show up at my office. They wanted me to meet them at their office. I told them I was ready to make a decision and didn't have time. That I had met someone else and had an offer on the table. That only got them more interested.
It probably goes without saying, but this tactic should be employed only if it's true. One should never gamble his long-term reputation on a short-term bluff.
But in the end a gamble is a gamble and much of business is made up of chances where you bet correctly. Of course there is a risk. On the other side you can be totally honest and that has it's own problems, right?
Telling someone that "I had met someone else and had an offer on the table" isn't really concrete enough to be called a liar. Deals fall through all the time for many reasons.
You don't necessarily need to instantly grasp the implications. You need to listen, and if you don't grasp everything, you need to ask probing questions and learn. And you need to make sure you chase down any implications afterwards.
The first thing is to figure out what you don't know.
Note the part about glassed over eyes? If you listen actively, inject comments and questions and think about questions, most people can get a rough idea of quite complex areas they previously knew nothing about relatively quickly, and you won't be that guy with glassed over eyes.
The problem is not taking time to process something. The problem is when people are listening to the words but not the meaning, and then trying to find a way to force the words to mean something that fits into your existing world without changing it.
If someone gives you advice and you realize you don't understand it or it bores you or you don't agree with what's being said, and so you zone out, then you lose out. If you realize you don't understand something, or you disagree, and you use that as a signal to pay more attention and make an effort to understand or to figure out the cause of your disagreement, then you win.
But let's take a group of people who have the same experience in a domain. Then I would define resourcefulness as the component of outcome that depends on the person, specifically how much self-drive the person has, and how much the person can leverage the tools in his or her situation.
Resourcefulness, as define this way, I think is some part skill. You have to be intelligent enough to put the match and sandpaper together to start a fire. Part of it is tolerance for being burned -- it's much harder to cold call a VC if to you it's personally painful to be told to shove off. And as pg mentioned in previous essays, the last part is determination. Resourcefulness is inherently related to schlepp and you won't schlepp unless you really, really, care about the problem.
Basically, I think you're right in that some situations really benefit those who've seen it before. But at the same time, to dismiss the effort and self-ambition of the person isn't quite right either.
Just so I interpret correctly, are you basically saying that if someone cut you a blank check, you can solve any problem? Or that with a blank check, you can take a stab at a problem?
Either way, I could give you my credit card and tell you of my personal problems, and I doubt you'd be able to solve them. I'm also not rich, so I can't pay for the possibility of getting a solution to my problem, I only want to pay for results.
Perhaps you could be more specific.