Today on The Startup Chat, Steli and Hiten talk about the dangers and the downsides of being overprepared.

Sometimes we tend to overprepare for a meeting that we screw it, meaning we research the other party a lot, and go into that meeting trying to impress them. This can be a bad thing, and can be as bad as being underprepared.

In today’s episode of the show, Steli and Hiten talk about how to overpreparing is a bad thing, why you need to chill out a little bit, they share some tips that can help you prepare for a meeting and much more.

Time Stamped Show Notes:

00:00 About today’s topic

00:34 Why this topic was chosen.

01:33 Why you need to chill out a little bit.

03:27 How we don’t like people that need to be liked.

04:21 An example of being over-prepared.

05:20 How VCs are good at evaluating people.

06:00 How you can be overprepared.

06:40 How most people are either over prepared or underprepared.

07:40 The cons of being underprepared.

3 Key Points:

  • You need to chill the fuck out a little bit!
  • We don’t like people that need to be liked.
  • Be honest about your flaws.



Steli Efti: Hey everybody. This is Steli Efti.



Hiten Shah: And this is Hiten Shah.



Steli Efti: And today on The Startup Chat, I want to talk about the dangers or the downsides of over prepared. Right? Yeah, here’s the reason why I want to talk to you about this. I had a friend recently who is applying for kind of a high level VP of sales position at some really amazing companies in the Bay Area. He has gone very far with one specific company that’s kind of the company that he’s now incredibly excited about. There’s so much alignment. There’s so much opportunity. It seems to be an amazing fit, so he’s super enthusiastic about the whole process. And he’s just about to take kind of the final step in the whole process, which is to meet with one of their board members, who’s a big, famous venture capitalist. Meet with him for coffee and have him kind of be the last person to evaluate the candidate before they say they’d make an offer, right? And so he called me to talk about that interview, that coffee meeting. And he wanted to get my feedback and advice and he was telling me about all the research he has done about that VC and his portfolio and his background and history and he’s watched videos and talks and really tried to like analyze and get a perfect sense for who this person is and how to win this person over. Right? How to make sure that basically the offer is not going to be taken back because this famous legendary venture capitalist doesn’t like him or doesn’t approve of him. And at some point listening to him and at some point I had to interrupt him and I just told him, “Listen dude, I love the research that you have done. I do think it’s a good idea to prepare well for these conversations, but you have to now get to a point where you relax, right? You do chill the fuck out a little bit.” And you need to be aware that this is not just a contest of you winning the other person over. This should be a mutual exchange, right? You are also trying to evaluate the company and you should see this as an opportunity to understand the company, the challenges, the founders, the investors. You should see this as an opportunity of learning for yourself as well and not just selling right? Not just trying to sell yourself to this person, but also try to learn, try to gain more insights. What are the things that this person could help you understand better about the company or understand a bit about how to do the job well and also don’t go in that conversation with an expectation to win this person over and make this person love you or like you. You’re setting yourself up for failure. One of the main things that we humans can spot from a mile away is when somebody is needy, needy of approval. When somebody comes around as like, I want to be liked by you people for whatever reason, we instantly go, fuck you, we don’t like you. Even before that person says anything else. It’s an instant emotional responsible. But we don’t like people that need to be liked. And so make sure that you go in there with, of course you know you’re prepared, you know things, but go in there with the expectation of just getting to know somebody, have coffee and talk about the business and talk about the challenges in the business and be honest about your flaws and get feedback if that board member how he or she evaluates this opportunity and who would be the right VP of sales and all of that. Just relax a little bit. And this made me think, and I’ve seen this in many, many other scenarios as well. Where in sales specifically or this could be in fundraising. This could be in big sales presentations with potential customers. This could be in many different areas where I’ve seen people over prepare and then they come into the conversation both with too hard of an expectation of how this meeting will go. Too hard an inflexible of an expectation or worldview of, I know who this company is or how this person thinks like you come into this with all these preconceived notions because you’ve done so much research and you then let the relaxation and the flexibility to be in the moment, right? And to have kind of a beginners mind and the way that you interact with people. And so I’ve seen this over and over again where people over prepare themselves to a point where they cannot perform well in the actual meeting or the conversation. And I wanted to bring this up because I thought it as always, you probably have something interesting or weird to say and you’ve talked to many founders and help them prepare for meetings with VCs and famous silicon valley people. So I’m just gonna stop here before I continue with some of the other stuff that I told him and just want to check in and get your reaction on this.



Hiten Shah: I really like this topic. I think that there’s a couple of things here, the people on the other side, the VC, the investor is a professional people evaluator. That’s their job, they’re good at it. I got to say, especially if you’re talking about a top tier investor, I will say that if you’re not a top tier investor and you’re kind of like, it’s a little bit of a different story, but top tier investors their job is to evaluate people. Their job is to make decisions with money based on the people they meet. That’s really like a simple way to think about it because they need to predict what’s going to happen with this person and their business regardless of what size the business is today, they’re making a bet on the person and the person’s ability to create some kind of future outcome. And so that’s what they’re going to do when they talk to you. You might not notice it either. That’s where it gets interesting. So I think that you can be over prepared, usually they say you can’t over prepare no, you can be over prepared. And it sounds like that’s what your friend was kind of heading into. Be yourself and don’t put on that sales hat during that meeting, just talk to the person honestly, like you said, talk about the business, talk about those things. So to me, I think you’re giving good advice and it’s super critical when you’re dealing with people on the other side that have more experience than you in terms of not like work experience or anything like that, but doing what what they’re doing with you right there.



Steli Efti: Right. I think that people to be in a skew, in one area of the spectrum, and I’ll share kind of as a final tip, the way that I approach these things. I think most people are either over prepared or under prepared, right? They either come into the conversation and you quickly realize that it doesn’t matter who the evaluator is or what the evaluation is, it could be a potential buyer, it could be a potential future boss. Whatever it is, right? A partner. If you come into the conversation and it’s clear you know nothing about the person you’re talking to or nothing about the context of company around them, you have not thought about what the important questions here are, and what the goal and structure of the conversation should be. I’m going to be, that’s not gonna go well, right? Because you’re lacking clarity. You’re probably asking questions that are not that thoughtful and are wasting time. Asking questions that you could have easily figured out anywhere else on the planet and on the web versus having to ask me directly. And so when you’re under prepared you’re making the impression that you’re clueless, right? That’s not awesome and you’re wasting people’s time. The exact opposite is what we just described, where you over prepare you come into the conversation and obviously humans has the need. If I’ve spent 10 days reading everything about your life and all your books, most humans will have the need to now do something with that knowledge, right? Or to impress the other person with their knowledge and research. And so they’re going to talk too much. They’re gonna say things like, “Oh, I read all your books and I know this about you and I know that about you.” Or, “I have done all the research on this market and I know your company has done this, that and …” Don’t try to impress me about knowledge about me and my company. Right? It’s gonna be very difficult. In most cases, especially if it’s generic knowledge. Now it’s different if you tell me I signed up, I visited one of your current customers and I spend the day with the users that are using your product and I did some research and here’s what I learned from them, or I used your product in these three scenarios and here’s how I broke down and here’s what my personal experience was with it. That’s interesting, unique knowledge. But if you just go on my blog and read my blogs and now you tell me about all the techniques you learn from me, that’s not really engaging or interesting to me. I already know this stuff. Right? So you’re not really impressing me with that. I think the ideal is the golden middle, which is kind of the model that I’ve always tried, which is I don’t know how to prepare to do a little bit of research, right? So I also tends to do very in depth research about people and things in general. And I’ll read everything and anything I can, I’ll do as much research as possible, I’ll do background references, I’ll talk to people who know that person. I’ll try to really cover all my bases and know everything. And then for whatever reason I’ve learned to let all of that go, right? Just like detach, like I’ll do a ton of research and then a few days before that meeting I’ll just detach, and just let go of it. And when I come into the meeting I pretend this is the first time I’m meeting this person and I’m coming into the conversation with an open mind. Hopefully I’m asking better questions. Hopefully I’m giving better answers, but I’m trying to figure it out in the moment. Like who this person is, what the buyer needs, what the right questions are, what the challenges are? I’m trying to figure that out in the moment, using all my research to help me make better evaluations or interpretations of the information given to me in the moment, but I’m not coming to the conversation with A, a need to show my prep or a very strict framework of thinking I already know what’s going to happen or I know this company well or I know this person well because I don’t, right? So I feel like, and that has worked incredibly well for me in terms of the real result I’ve been able to generate and so that’s kind of the model I’ve always been teaching and coaching people prepare a lot, but then take a few days to let go of that prep, relax, and then come into the conversation with a beginner’s mind again, as if it’s the first time you hear about them, the first time you hear about the person you’re trying to be in the moment, learning, exchanging from person to person. Don’t try to use your preparation. Don’t try to impress with research. Don’t try to come into the conversation with a preconceived notion of what’s going to happen, who these people are, and what the situation is, because you really don’t. You can’t just based on research, you have to talk to people in the moment and pay attention and truly listen to get the results that you want. And you need to relax. Right? It should always be a two way evaluation, and no scenario I can think of. It’s a purely one way street. It should always be a two way street, right? When people talk. So, yeah, that’s it. I think we’ll wrap the episode up with this little bit of hopefully actionable advice. Don’t over prepare it’s not going to really help you be your best self and get the results that you want. That’s it from us, we’ll hear you very soon.



Hiten Shah: Take care.