How I helped the CEO of one of my first investments (From C player to A player)

Summary

A few years ago I co-invested in a super-smart founder that soon started to have performance problems that compromised his business. In this video, I discuss how I helped him transform from being a C player to an A player with a simple tool.

Transcript

A simple digital tool saved one of my first startup investments

Hello everyone, Leon Castillo here. And today I want to discuss how the tools we use shape the behavior we have. And this can make or break the success of your startup. But before we continue, consider subscribing, we release a few juicy videos every week to help entrepreneurs master the personal performance in their businesses, so they can scale much faster.

So, the story today is about one of the first entrepreneurs that I invested a few years back and picture him: he was incredibly smart, incredible work ethic very quick on his feet, his thinking skills were top notch, and he was extremely good, and be like very, very good at operations.

And he came to us as being myself and my partners at a moment that he wanted to create his own business he'd been hired, by one of the top unicorns in the world that I'm sure you've heard about, in a heavily operational-focused role for quite a few years in the MENA region. And when he came to us, he was ready to be his own boss, he was ready to be the founder and CEO of his own startup.

So of course, he had a very good idea, sensible business plan, good understand of the market, and I thought it was a safe bet - there are not safe bets in early stage investment but you get my point, he was probably one of the safest bet that I thought I would ever do.

But, a few months in, I started to see that the reports that we were getting were not too good. I could see the results were actually lackluster. And I reached out to the CEO to see what was going on.

Why was he not able to take his business, his startup up off the ground. As soon as I realized that this gentleman was operating at very low performance level, he was in fact constantly overwhelmed, unable to focus for more than 10 minutes unable to take swift and fast decisions that he could actually honor.

In fact, he was known for backtracking on some of the things that he had previously agreed with his team. So performance was nowhere to be seen.

Results were lackluster, and I was very worried because he was very talented, very smart, very
able to execute. But he was not able to execute in his business. Why was that?

So I didn't want to waste my capital. And I really wanted him to win - because he's an incredibly talented person - I started mentoring him one on one to see what the problem might be. And to my surprise, I soon realized that the biggest problem he had was that he was using the wrong tools. He was operating from a TO-DO list, which was is one of the surefire ways of engaging in suboptimal decision making and end up overwhelmed and burned out.

The previously incredibly smart, very good operation person that this unicorn had hired was now a low performer CEO of his own startup, something that he has built for himself. Imagine the pernicious effect that choosing wrong tools can have for your performance. And he had four main problems that all stem from using a TO-DO list, he had no historical context of the task he needed to do at any given moment. In a TO-DO list, all the tasks are the same size, and they look the same.

So you do not have contextual information about why does it matter is toric Lee, why are you doing this? What workflow does it belong to? What project is it part of? And that's why a TO-DO list is not good for tasks. But not only that, using a to do list also implies a lack of priority context.

So how do you know something is urgent or important? If it does not fit within an established workflow? You don't know. How do you know for instance, if you should be working on A task or B task, if it's due tomorrow? Well, you don't know because you cannot link that deadline to the task and to the project and to the objective and key results that you are working on.

But also the third reason why to do lists don't work is that you do not have a good understanding of the complexity of the task. You can have two tasks per together that have totally different complexity profiles. One can be a 25-min tasks that can easily be done by anybody on your team, and the other can be a 10,000 dollars an hour tasks that requires three hours of solid focus, and you are the only one in your startup that has the ability to pull it off.

If you're operating from a TO-DO list, you are prone to do the low level things that provide quick dopamine rewards, instead of focusing on what actually moves the needle, that was one of the main problems my friend and investee had. And finally, you need to understand each task within the context it belongs to.

So why you're doing what you're doing, who is working alongside with you, when is it due, when's the deadline? All those kinds of considerations need to be taken into account when conducting your operations. And this is what was happening to my investee to my friend: as a CEO, he needed to be the one taking decisions about how to set priorities, set level of complexity, assign different tasks to different people, but he did not have a tool that allow him to have that information.

And as a result, he was having terrible focus problems, terrible leadership problems, because he was backtracking on decisions taken before, he just could not manage his stress levels. In fact, his personal performance protocols were not good enough to help him sustain the damage this business venture was inflicting on his health.

So everything was a mess. And it was a mess, because he didn't have the right tools to make it work for him. Buckminster Fuller, one of the most important architect in the 20th century American, an incredible systems thinker said that "If you want a person to think differently, give him a different tool". And I strongly believe that operating with the right tools can really make the difference.

In any case, remember, tools always come at the end of a process, you need to choose the tools based on the problems you have, not on the tools you have available. That's another problem that some entrepreneurs face, that they believe that just by solving the or using the best SAS software for whatever for project management, they are going to do a good project management.

And maybe that's not the answer, because that's not the problem. So as a recap, you need to be using the proper tools, you need to have an intimate understanding of the problems that you're trying to solve. And then choose tools that allow you to have context, context on the difficulty on the complexity of the task context, on the priority importance context on the history of the task.

Why does that matter and context on the collaboration framework that task belong to. So I hope this was useful. This is a very simple but super important lesson. Because if a highly skilled, extremely capable overachiever in operations at one of the largest unicorns in the world, became an extremely ineffective CEO in a matter of five months, you can bet that the right tools have a massive impact.

So I strongly suggest you stop using a TO-DO list because it's probably the worst tool in your arsenal to help you manage yourself and start using a dashboard.

A dashboard will provide that storica perspective, that sense of importance will illuminate which tasks belong to each project. And you will soon understand what's the best way of collaborating with your team based on that dashboard.

I strongly suggest you build your own self management dashboard. And if you want, of course, to have ours more to happy to onboard in our community and help you grow your company using a proven systematic framework for peak performance.

Please let me know in the comments if this was useful if you tend to use a dashboard or you use a TO-DO list or what else do you use, maybe there's something else that we haven't considered. And please subscribe, like, comment and do everything you know you have to do so that we are able to help you the most and of course, if you want a deeper understanding of what a Dashboard is, we have a video called "TO-DO Lists Don't Work 5 reasons & 1 solution" that I believe will help you get more knowledge on the topic. Thank you very much.