John Obelenus

Go And See

Every year when the calendar starts getting to the end, and life starts to slow down a bit, I get an opportunity to step back a bit and think a bit more broadly.

My mind wandered towards how many articles I've read and how much content is getting churned out. Our industry is constantly asking good questions. Yet, over the last couple of years many of the questions are the same, and the articles are repetitive. That isn't a bad thing, it just means people are focused and coalescing into the same spaces.

I'm in a large professional slack group, and over the years you can see strong themes in the kinds of questions people ask. And as more folks enter the group, the themes are even clearer. The same kind of phenomenon is happening within a select group of people.

Through some conversations in that slack, I was reminded of a little project I started for myself a few years ago.

In order for myself to get a handle on my views as a leader, I came up with over 30 questions & situations where I wrote a paragraph or three to try and explain my views and defend it just a little bit. I ended up writing ten pages! But it lacked a throughline that held everything together. I realize that I was just supporting specific tactics that I have seen succeed repeatedly.

I felt like I was making a directory, so when folks asked questions, whether in Slack, or an interview, or just having a conversation about work with a friend, I had responses that I had thought through, rather than trying to formulate a comprehensive approach in the moment. That approach has limited explanatory power and utility.

2025 was an amazing experience at System Initiative. We made lots of product changes, adding features, removing other approaches, rebuilding product experiences left and right, and aggressively going to market where we learned a ton.

Reflecting on the decisions we've made, I realized there was no way that I could point at my prepared tactics as having a forceful influence on my thinking. I still believe them, and see where they would have fit, but I was retrofitting it backwards onto a decision, rather than in the moment realizing I was leaning on something I built up mentally beforehand.

It finally dawned on me. I needed to express the strategy behind it all. The throughline that I observed was missing. The "why" behind. The tactics are useful, but tactics always fall out of a strategy. So I'm going to do that!

I identify four specific principles I can point to that turn into a concrete coherent strategy. Let's get to the first one: Go And See

This principle sits on top of foundational understandings of reality:

All models are wrong, some are useful. - George Box

The map is not the territory. - Alfred Korzybski

The philosopher Alfred North Whitehead named this error: "the fallacy of misplaced concreteness”

Or, to reference Adam McKay's opening in The Big Short:

It ain't what you don't know that gets you into trouble. It's what you know for sure that just ain't so.

What I really want to get across is: you are wrong. Often. About something. It could be a real small thing, or it could be big. Please entertain the idea that you are wrong.

When folks on your team come to you with problems, technology problems, people problems, product problems, marketing problems, sales problems, personal problems—whatever your first take on the situation, you are probably missing something.

One of the more frustrating moments in working with teams throughout my career is when someone asks a question, and people immediately try and answer it. Even the person who asked the question does this! No one asked clarifying questions, follow up questions. And no one brought any new information to the table.

When you're wondering "Why isn't X shipped yet?", "What is holding back Team A?", "I really thought we were going to close that deal" the answer is to go and see. There is data you are missing. Everything you think you already know does not contain the answer to the question.

One of the phrases that I will repeat in these moments is: "The answer is not in this room. If it was, we would have solved the problem already. The answer is out there somewhere".

Go And See. All leaders are tremendously busy. You are not always on the front line. There are some front lines you likely have not seen in a few years. It happens. You have to get back to the front line in those moments. And you need to advise the folks that report to you to go back to the front lines themselves. Get out of your comfort zone. Get out of the rooms you normally live in. If the answers to your problems were there you would have already solved the problems.

Now the act of “Go and See” that you perform should be timely and aggressive. A problem showed up on your doorstep. You can’t solve it without information you don’t have. You shouldn’t schedule a meeting for three days from now. Or ask someone to follow up with you without a constraint. If the data is outside your org and out in the market where the potential customers are, I hope reaching out is a motion you have practiced and have some repetitions under your belt.