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What kind of talents are we looking for?



Fortunately or unfortunately, I am recruiting again. This time for a Chief of Staff.

I am very fortunate to have received 100+ applications from many extremely qualified candidates within hours. While browsing through these resumes and interviewing the front runners, I often get asked: "What are you looking for?"


For specific roles within the company, such as engineering or sales, experience often triumphs everything else. But for a role such as Chief of Staff, the criteria are a bit more complex. Granted, as a legal AI company, a person with legal experience would go a long way. But that’s not exactly what I am looking for. So what am I looking for?


Intellectual capacity

I think there are two dimensions to this: the curiosity and ability to learn. Note that I am not looking for pure IQ. Raw intelligence, as often reflected by education and pedigree, is of course important. But that’s not all. For example, I would not hire a very intelligent law student who is only interested in learning more about the law.


What I am really looking for is that intellectual thirst to learn new things, often things the person had no prior exposure to, and the ability to learn it quickly.


I remember my first manager at a large consumer tech company frowned upon my lack of electrical engineering background and questioned whether I could effectively source software for system on a chip (“SoC" ) design. I didn’t blink. However, when he started explaining to me the key metrics for SoC (speed, footprint, and power consumption), I found it fascinating. Not only did I learn it quickly, but I also immediately started using the knowledge I gained to negotiate better deals with IP providers.


That’s the kind of intellectual capacity we are looking for. As the CEO, or the Chief of Staff, who is the eyes and arms of the CEO, anything is fair game. To balance a balance sheet? Sure. HR contracts? No problem. A new security compliance standard? We’ll figure it out.


Velocity for execution

I have had team members in the past who needed "to-do lists" or detailed instructions about what to do. But we don’t have that kind of luxury at a small startup. What I want is some high-level guidance about the objectives and then the person needs to just push forward and get it done, very quickly.


Some have compared the operation of a startup to fighting a war. Or at least a football game. You have a group of highly skilled soldiers, or players. You have a general plan and some strategy about how to attack. But because things are changing so fast and everything happens on the fly, you cannot give pilot-style instructions. The general, or the quarterback, just needs to start an attack and the team just needs to go with it. Extremely agile, often precise, but without instructions.


More importantly, note that we are talking about velocity, which is by definition, a vector quantity. Doing a lot or doing many things fast is not sufficient. Knowing why we are doing something fast, and achieving results is what matters. That’s why I often tell my team, I really don’t want to hear “what” you are doing. I am more interested in seeing what results you have achieved, instead of just spinning your wheels.


Can-do attitude

In the past, I have worked with very talented folks who often seemed beaten down.


To be fair, the startup life is like a boxing match. You take more hits than you hit. You feel okay until they hit you in the nose. You get the idea. I often tell my team and my family, it’s all about taking the hits.




Kind of like in “Raging Bull”, when La Motta said to Robinson, “You didn’t get me down, Ray.” Still standing after being hit that hard is what matters.

But I still encourage myself and my team to carry on with optimism and confidence despite the setbacks. We must hold our heads high, smile, and carry on. So the team should have a spirit and attitude accordingly.


There is the attitude and then there is the how. Don’t tell me why you cannot. Show me how you can. Too much trouble, too little time, not enough money? Say no more, but let’s figure it out.


The startup game is not for the faint-hearted. You are doing something that the odds are against you and it's guaranteed to be difficult. However, if you have the right people and do it, the reward in terms of impact and freedom is also tremendous. For that, I am continuing to hustle every day. For that, I am hiring a rock star to help me on this journey. Could that be you? You just need to let me know.


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