I once spoke with a founder that said they didn’t know if they were cut out to be a CEO. 

When I unraveled the conversation more, this individual gave me an anecdote, “I was recently sitting in a meeting with my team. We were discussing things that may need to be done in the future, and I was feeling grossly inadequate.” 

The team was asking questions related to things like:

The founder told me, “As I was sitting in that meeting, I thought I should be doing something more than I am.”

The founder’s countenance had a look of desperation, and the body language was pleading with me for help. As they spoke, it was as if the founder had imagined a vision of themself as a CEO executing at a higher level - a higher level that they weren’t hitting. 

Worse still, they didn’t know how to become the CEO in ther vision nor hit this imagined standard of execution.

The person said, “I’ve never been a CEO before. And yet, here I am.”

This conversation took me back to when I was a founder.

I didn’t plan on founding a startup, I just fell into the opportunity when my father, my co-founders, presented the opportunity to me. I didn’t know anything about running a business, let alone building a tech product, getting to market, etc. 

Transparently, if you could read from my journal or read my mind in those early years, the constant question that I had was, “Am I doing the right thing?” 

As a founder, I remember feeling inadequate and insecure as a CEO, so so often. 

Looking back, I believed that two things existed:

It took me years to learn that the “right” answer and the “right” execution two false beliefs. 

At the time, I believed that being a CEO meant that I had to know the “right” answer for nearly everything. Product building, getting to market, etc. And that successful startup execution involved staying on the “right” path and avoiding the “wrong” path. 

And I continually measured myself according to those two false standards. 

It was incredibly discouraging. Can you relate at all?

It’s taken me years to realize this, and I wanted to share it here:  

✅ Every question in a startup has a timeframe and a context tied to it. ✅

The relevance of any question a founder asks is inherently tied to the startup's specific timeline and current context. 

Simply put, there are questions that are relevant at different stages of the business - at differing levels of product maturity, size of the customer base, capital raised/in the bank, etc. 

In practice, this could relate to anything:

When the startup is at the pre-seed, a question “Which investors could we raise our Series B round from,” is completely irrelevant. 

But to determine the relevance of a given question, there are three categories that I think about: 

You can imagine that with any question, the potential relevance of that question could be plotted on an XY axis of time. 

I see it as three categories of relevance for questions:

✅ 1) Questions that need to be answered right now. 

2) Questions that will need to be answered at some point in the future. 

3) Questions that you don’t know if you will need to answer. ✅

Questions that need to be answered right now - you need clarity on this immediately because there is an external force or need that is causing you to answer this question. 

Questions that will need to be answered at some point in the future - this category is for questions that you are almost sure that you will need to answer at some point, but don’t know when. It could be a month from now or it could be three years from now.

Questions that you don’t know if you will need to answer - for questions in this category, you don’t have a clear light of sight that you will need to answer it. So, you can park it. Future execution will determine whether or not you will have to answer this in the future.

Category 1 tends to be very clear. Often, it is very hard to distinguish which questions are in which are in category 2 and 3. 

Here is the insight: 

✅ Current execution often helps us clarify the relevance of question over time. ✅

As a startup executes, their context changes and their timeline changes. They are presented with additional questions that they were not asking six months ago. That is a very good thing. Our minds guide us to the questions to ask that are relevant.

My suggestion is this: 

✅ Understand the most mission critical questions to answer right now.

Everything else belongs in the future - a future that will likely happen (Category 2) or one that we do not know if it will happen at all (Category 3). ✅

Execution drift often happens when a founder takes a question and miscategorizes the relevance, thinking it needs to be answered and acted on now. Instead of considering that it is a question that needs to be answered in the future, or maybe not at all.

When I was a founder, our FinTech startup graduated from the FIS Startup Accelerator in July 2018. One of the key figures in the accelerator program told us that FIS sometimes makes follow-on investments in the accelerator companies. But, he said, “FIS typically needs to see that you have D&O insurance on your startup before they invest.” We didn’t have D&O insurance, so this illuminated a gap and potential need in our minds.

This person’s statement presented us with a question, “Do we need D&O insurance?” 

We had never thought about the need for D&O insurance. Frankly, we didn’t need it at that moment.

As I mentioned about that each question in startup is tied to a timeframe and context, the D&O insurance was tied to context. We needed D&O insurance in the context of an investment from FIS.

Yet, FIS had never mentioned that they were interested or planning to do a follow on investing in us. We never, ever heard anything more about it. And, they never did.

But, I miscategorized the relevance category of the question. this is a question that only needed to be answered in the context of an investment for FIS, category 3. But, in hopes of getting a follow-on investment from FIS, we moved it to Category 1. We spent weeks of time getting quotes from insurance firms about D&O insurance for our startup. 

This was horrific for my execution. Across the board as a founder, my continual miscategorization of the relevance category of questions lead to a zig zag pattern in my execution. 

Here is one practical thing to do about this - create a a question/timeline board.

Have the Category 1 Questions. Then have a spot for Category 2 Questions - ones that you anticipate you will need to answer in the future. Then, have another spot for Category 3 questions - ones that you do not know if you will need to answer.

The idea is that with this question and timeline board, you have done two things. You have:

1) Notated the question down, so that you can refer to it in the future, and

2) Assigned a potential time frame to it

The questions you ask and try to answer determines your execution. Having a question board helps guide that execution in the proper way.

Let me ask a direct question to you - are you the insecure CEO?

Let me remind you that..

✅ As CEO, you will never have all the answers to the questions you face.

But you can always categorize the relevance of which ones to answer, now. ✅

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