Good Judgement Comes From Experience Essay Samples

Good Judgment Comes with Experience, But Experience Comes from Bad Judgment

This is part of my Startup Advice series of posts.

I heard Bruce Dunlevie of Benchmark Capital say these words at a conference in London nearly 10 years ago. I jotted the words down (I normally pay little attention to anything said at conferences. Most of it is BS) and thought about them much over the years. I later learned that the quote was taken from somewhere else (perhaps as early as the 13th century!) but whoever is responsible I just want to help spread it.

There is a folklore in Silicon Valley that you should fund first-time entrepreneurs. When you see the successes of Mark Zuckerberg, Bill Gates, Steve Jobs, Larry & Sergey, Marc Andreessen and Marc Benioff it is easy to see the allure (either that or invest in people named Mark ;-)

But it’s not my strategy. I definitely don’t rule out first timers — I just invested in one to be announced soon who I am really excited about — but I greatly prefer experience. It’s easy to say you’d back a great team that has previously been successful -

that’s a no brainer. Fred Wilson outlines why in his piece “Swinging For the Fences.” He outlines that Union Square has overwhelmingly had success with either first-timers or serial succeeders.

I can’t argue with Fred. He has a great track record and I’m a newbie. But I was asked recently whether I would prefer to back a first-time team or a team that had failed once before. Obviously it depends on the team and the idea but holding all else constant I would personally back the team that had previously failed.

I’m fond of saying that I F’d up everything as a first time entrepreneur. Actually, we got much right, too. We corrected mid flight. I believe great entrepreneurs do that. They do what VC’s like to call “pivot.” Boy did I pivot. I went from 92 staff members + 30 contractors (e.g. 122 in total) to 38 people in one day and then down to 33 immediately after that. I went from managing a team to “flipping burgers.”

So in my case, I believe that I acquired good judgment from my previous bad judgment. We eventually got a successful exit but I can’t say it was a Google like exit! I believe that it helped me succeed in my second company.

Seeing how entrepreneurs handled adversity and difficult decisions tells me a lot about who I’m going to be working with if I invest. I learn much from hearing whether they have humility, understanding what they learned from their failure (or success), gauging the speed of decision-making and willingness to admit when they were wrong. I also look to see whether they can make the really difficult decisions (like firing all of your friends — this is no fun.)

The way I like to make my point about the quote is with something that all of us know innately. When your parents told you at 15 not to feel so heart-broken when your girlfriend or boyfriend broke up with you because you’d meet many more people in life you probably remember feeling like the only special person you’d ever meet just got away. They couldn’t tell you this — you had to learn it.

For many of us we had warnings about not drinking too much and yet we still found ourselves “praying to the porcelin G-d” on prom night or at a frat party. Instructing people can’t create wisdon, experience will.

Which is why I recently wrote a post called, “Is it Time to Earn or to Learn” asking people to think about what they hope to attain from their current job or from the job for which they’re currently interviewing. I wasn’t trying to encourage everybody to become a CEO tomorrow — I was encouraging them to learn.

Every day I talk with entrepreneurs in my office. I’ve been a VC for 2.5 years now (an entrepreneur for nearly a decade before that) and as a result I’ve gotten to see many first-timers progress over time. It amazes me the pattern spotting you can pick up from all these meetings. I had so many discussions with people when they launched their companies about what each of us thought would happen and now it’s enlightening to have those conversations 18 months later.

Some of these people are people I wasn’t ready to back but I said, “I’d love to find a way to work with you on your next company.” I think this quote would resonate with most of them.

I prefer second time (or more) entrepreneurs. Sure, I would love to work with people who have had multiple successes. But I’m not afraid of entrepreneurs that didn’t succeed the first time. I want to work with talented people with good judgment. And so I’m out to spread the word, “Good Judgment Comes from Experience, but Experience Comes from Bad Judgment.” Go out and learn.

Behavioral interview questions often throw people for a loop when they first encounter them- because their goals and methods are not as clear and easy to comprehend as those of traditional interview questions. This is because they are not seeking specific information that can be relayed easily; they are looking at a snapshot of your problem solving process- both to evaluate the process and to find out what its outcomes tend to be. This gives the interviewer insight into how people are likely to function on the job- but it also means that the interviewee needs a little more preparation to be successful.

When interviewers give you prompts like- ‘Give me a specific example of a time when you used good judgment and logic in solving a problem-‘ they are looking for more than just your command of the procedures and protocols of the job. They are also evaluating exactly what you consider good judgment to be- and what your priorities and assumptions are when you apply logic to a situation. Acknowledging that this is their goal and crafting an answer that uses the STAR method to ensure clear communication and identifiable results is the key to giving a memorable response that helps you clinch the job offer down the road.

How to Answer the ‘Give Me a Specific Example of a Time When You Used Good Judgment and Logic in Solving a Problem’ Behavioral Interview Question

Set Up Around the STAR Method: The easiest way to make sure you are getting the most out of the STAR method for organizing responses to behavioral interview questions is to begin there. That way- you know that each aspect of your answer relates to one phase of the method or another- and it becomes easier to keep things concise without leaving out important details. The STAR method is this:

  • • ST: The situation or task you were put into. This should be a single- specific event or project.
  • • A: The actions you took. Specifically describe what you were responsible for and how it fit into the overall situation.
  • • R: The results you obtained. These results should be clearly tied to your actions- so the listener is able to understand the cause/effect relationship between them.

Values-Match Your Answer: Your answer needs to do more than just be specific. It also needs to demonstrate clear critical thinking and good judgment. What constitutes good judgment is partially in the eye of the beholder- though- and that means understanding the corporate mission and values of the company you are interviewing with. This ensures that your answer provides them with the kind of judgment they hope to see in a candidate that they want to hire.

Maintain a Positive Approach: The goal with these questions is to demonstrate how deftly you are able to manage difficult situations and resolve them. This means that whatever the situation was that led to your use of good judgment or logic- the emphasis should be on your actions and their favorable results. You need to explain the problem in a way that clearly shows why it is a problem- but staying mired in its negative effects and outcomes will not advance your explanation- so you need to keep the outline of the problem as value-neutral as possible while you highlight the details the listener needs to know.

Keep Things Concise: Behavioral interview questions have a tendency to invite longer answers than traditional interview questions do- but it is important to keep them to a manageable length to avoid rambling. The longer you take to answer- the more likely it is that the listener will miss a detail or misunderstand the point. The best answers will last about as long as an elevator speech—long enough to tell a clear- brief story and make a point- but that is all.

Sample ‘Give Me a Specific Example of a Time When You Used Good Judgment and Logic in Solving a Problem’ STAR Interview Answer

After my last promotion- when I was left in charge of running the loading dock for the entire second shift- we had a problem with our label printer giving us UPCs that did not match the orders going out. No matter what we did- the software said that things would scan correctly- but the actual hand scanners were giving us different inputs. I organized a cross-shift problem solving team that spent the next day going back through our product codes and orders to find the discrepancy- so that we had the shortest possible delay on properly packing and shipping out orders- and I helped to keep our packing department moving forward during the delay by designing and implementing a short-term hand-tracking system that sidestepped the computer until the crisis was over. That way- our longest delay shipping out an order was 48 hours.

Your own answers to behavioral interview questions should be about this specific- and they should also reflect the same kinds of stages of description and explanation. To get to your best response- keep practicing throughout your interview preparation period.


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