One of the biggest adjustments I had to make when I started working with startups was learning to make decisions before I felt completely ready. I had spent years working in a much larger technology environment, where there were established processes, historical information, and more people available to weigh in. There were certainly times when things moved quickly, but there was usually a structure around how decisions were made.
Working with startups felt different. There were situations where we had maybe 60 or 70 percent of the information we wanted, but we still had to make a decision. At first, that was uncomfortable for me. My instinct was often to gather more information because I thought more information would lead to a better decision. Sometimes it did. Other times, I learned that waiting simply meant making the same decision a week later.
That experience changed the way I think about uncertainty.
Waiting Is Still a Decision
I used to think of waiting as the cautious option. If you were unsure about something, taking more time seemed responsible. After working with startups, I no longer think it is that simple.
There are absolutely situations where waiting makes sense. If the consequences of getting something wrong are significant, taking additional time to understand the risks is worthwhile. However, there are also situations where another week of discussion is unlikely to tell you much more than you already know.
I have been in meetings where everyone agreed that we needed more information, but when I stopped to think about it, I wasn’t always sure what information we were actually waiting for. Sometimes the missing information was important. Other times, we were waiting because making the decision felt uncomfortable.
That led me to start asking a simple question: What are we expecting to know later that we do not know today?
If there is a good answer, waiting may be worthwhile. If there isn’t, the delay itself deserves to be questioned.
Startups Make the Cost of Time Easier to See
Time matters in every business, but startups make its value much more obvious. Teams tend to be smaller, resources are limited, and the market does not stop moving while you decide what to do.
That does not mean I believe every startup should move as quickly as possible. I have seen the downside of that mentality too. Speed can become an excuse for poor planning, and urgency can make a team feel productive even when it is moving in the wrong direction.
The real challenge is deciding how much time a particular decision deserves.
I have seen teams spend hours debating something that could easily be changed later while much larger questions remained unresolved. I have probably participated in those conversations myself. Smaller decisions can be easier to discuss because they feel manageable. Meanwhile, the difficult decision that actually matters keeps getting pushed to another meeting.
Over time, I started looking at both sides of the equation. I want to understand the risk of making the wrong decision, but I also want to understand the cost of doing nothing.
I Have Learned to Ask Whether a Decision Is Reversible
One of the most useful lessons I have taken from working with startups is learning to separate decisions that can be reversed from those that cannot.
A surprising number of business decisions can be changed. A team can test new messaging, adjust a sales process, try a different approach with customers, or reposition part of a product. If the approach does not work, the team can evaluate what happened and make another change.
I have become much more comfortable making those decisions without perfect information. In many cases, actually trying something will teach you more than another round of internal discussion.
Other decisions deserve much more caution. A major financial commitment, an important hire, a security decision, or something that could affect customer trust is harder to undo. Those are situations where I want to slow down, ask more questions, and make sure we understand what could happen if our assumptions are wrong.
Even then, the distinction isn’t always clear. Something that looks easy to reverse can have consequences you did not expect. Experience helps you recognize more of those situations, but I don’t think anyone gets them all right.
Customers Often Answer Questions That Meetings Cannot
My years working in go-to-market roles have reinforced this idea more than anything else.
A company can spend a remarkable amount of time debating what customers want. Sales may have one opinion, product may have another, and leadership may see the market differently. Everyone can have reasonable evidence for their position, which can make the conversation even harder.
At some point, I usually want to know what happens when we put the idea in front of an actual customer.
I have had customer conversations that changed my understanding of a situation very quickly. A feature we thought would generate excitement might barely come up, while something we considered secondary becomes the focus of the conversation. Customers may describe their problem differently than we describe it internally. They may also reveal concerns we had never considered.
One conversation is not enough to define an entire market, but it can expose assumptions that deserve more testing. Sometimes you need to move forward a little before you can collect the information required for the next decision.
Moving Quickly and Moving Well Are Not the Same Thing
There is a danger in taking this philosophy too far. Startups often celebrate speed, but movement should not be confused with progress.
I have seen situations where teams changed direction so frequently that they never stayed with an idea long enough to learn whether it worked. If you launch something on Monday, change the strategy on Wednesday, and replace it the following week, you may be moving quickly, but you are not necessarily learning anything.
That has made me more interested in deliberate experimentation. If we are going to try something, I want to understand why we are trying it and what we hope to learn. If it does not work, I want to know whether the idea was wrong or whether we simply did not give it enough time.
That involves judgment, and there is no perfect formula.
I Have Become More Comfortable Saying That We Do Not Know Yet
One unexpected thing I have learned from working with startups is that I am more comfortable admitting when I don’t have an answer.
Earlier in my career, I probably felt more pressure to arrive at a meeting knowing exactly what I thought should happen. Experience has made me realize that there are plenty of situations where the most accurate answer is that we do not know yet.
The important part is deciding what we are going to do about that uncertainty.
Sometimes we need to talk to more customers. Sometimes we need to run a small test. Sometimes we need another piece of information before making a larger commitment. Sometimes we simply have to make the best decision we can with what we know today and remain willing to reconsider it later.
Working with startups has taught me that you don’t eventually eliminate uncertainty. It is part of the work.
I still like having good information before making a decision. I still question whether we are moving too quickly sometimes. The difference is that I no longer assume waiting will automatically clarify the answer.
Sometimes the information you need only becomes available after you make the first move.
