In today’s episode of The Startup Chat, Steli and Hiten talk about how to hire people that are much more senior than you are.

Sometimes when it’s time to hire new staff for your startup, you may be in a situation where you’re hiring people who are much more senior than you, both in terms of age and experience. It can feel intimidating when this happens, but it really shouldn’t be.

Tune in to this week’s episode to hear Steli and Hiten thought on how to hire people that are much more senior than you are, how to manage this situation, how this could be an opportunity for learning and much more.

Time Stamped Show Notes:

00:00 About today’s topic.

00:30 Why this topic was chosen.

01:44 Hiten’s first response to the question.

02:43 How being a founder is management.

04:00 Why a big part of this struggle is a mindset thing.

06:01 Why hiring is no different than any other function of a business.

06:50 Why you shouldn’t put unnecessary pressure when it comes to managing this situation.

07:21 How unnecessary pressure can lead to bad outcomes.

08:01 How you can learn from senior people.

08:50 Why you consider every time you work with senior people as a learning opportunity.

3 Key Points:

  • One thing to realize is that this is part of learning.
  • Being a founder is management.
  • A big part of the struggle is a mindset thing.



Steli Efti: Hey everybody, this is Steli Efti.



Hiten Shah: And this is Hiten Shah.



Steli Efti: And today on the startup chat we’re going to talk about how to hire people that are much more senior than you are. Right. So the reason why I wanted to talk about this is that a listener has emailed me a few days ago and asked this exact question. He was basically describing that he has never worked in a large company. He has never been an executive in a larger startup. He had a bit of solid experience as an intern and then he worked there as an individual contributor and now he’s started his own startup. They raised some money. They have I think a five to 10 person team. And he is not out there trying to hire and recruit some senior people. And he was saying that it was really hard for him to talk to people that had 10, 20 years of experience. That had been VPs and CXOs and in bigger teams than he is built himself. And he’s like, “How do you hire somebody that’s a lot older than you? That’s a lot more experienced than you. How do you A, deal with the intimidation and also the self doubt.” It sounded to me like he was doubting his own abilities to judge these people. So I thought that will be a perfect topic to unpack on the startup chat. And so thank you for the question for the listener and now throwing the ball to you Hiten. What’s your first response to this question?



Hiten Shah: Yeah. Wow. Well, yeah, thank you to that person, thank you. I mean this is a topic that you don’t really see a talked about much in this way with a lot of honesty. And so I think this is a huge opportunity for us to share our thoughts on it. I’ve had to do this over and over again. And it’s not challenging. I think that I would first want to tell this person and whoever’s listening about hiring people more senior than you. So more experienced, older, and have done things you haven’t done yet. Oftentimes the one thing you’ve done, they haven’t done which is start a company. Oftentimes not all the time. So that’s something to remember and to realize. Another thing is this is part of the learning. So one thing I would say that has actually been in my mind a little bit is being a founder is management and management period. Manage Yourself, manage your family, you know, with your partner, manage your team and that means everybody on your team. And so that’s your responsibility. Even if you’re like, let’s say like a co-founder and not the CEO, it’s still your responsibility. You started the thing. I mean there’s a lot of weight there and you can contribute. And so I feel like hiring and hiring senior people is literally, it’s one simple statement which is like we’re all human. And we all have our own experiences and being intimidated by somebody else because they’re more senior than you represents I would say a situation like you’re an employee, but you’re not, you’re now a manager. And a manager of managers if you make it out of the 10 person company situation, which it looks like this person will. So you’re a manager. Managing means hiring. It doesn’t matter who they are that you’re hiring.



Steli Efti: I love that. I love the first thing you said, which is why we like each other so much, which is like, it’s not that hard. Right. And this actually points to … This is a big part of his struggle is like a mindset thing, right? It’s like you-.



Hiten Shah: Right. That’s why I said that.



Steli Efti: He’s overthinking. He is making this a bigger deal than it is, right. Instead of looking at it matter of factly, he’s making this some kind of a big thing that intimidates and overwhelms him. And that intimidation overwhelment will play a much bigger role in potentially making mistakes then this situation or the lack of experience of it. Right? And so yeah, I think you said it brilliantly, the first thing that I thought when I read the email was like, “Well, you did all kinds of things for the first time and it seems to be going all right.” This is the first startup he ever started. Seemed that it worked. First people that he hired, he has a team that’s close to 10 people. That seems to have been working so far. Raised money. He didn’t say his first time he ever raised money, that worked out. So there’s a lot of things that he’s done for the very first time and funny enough, maybe for whatever reason he didn’t seem as intimidated. We all have our different reasons of what intimidates us or where we have insecurities. So he was able to do all these things for the very first time and accomplish them successfully. So why does this need to be different? Right? This is something he’s doing for the first time. It’s still like he can succeed. If you just goes back to what are the core things like hiring somebody inexperienced or somebody super experienced. There’s a lot of overlap in terms of looking for cultural fit. In terms of looking for is there somebody I’d like to work with? There’s a lot of more benefits because with experienced people you should have a lot more evidence of their capabilities. You should be able to look at a ton of past work that they’ve done to see if you think their work is great. You should be able to get a ton of references of people that can tell you how it is to work with him. So hiring senior people, yeah, there’s some differences, but there’s also a ton of overlap for hiring that is going to be true for no matter who you hire. And in hiring in general, you always have to be okay with potentially making mistakes. We all try our hardest, but it’s an impossibly hard task to expect to talk to somebody for a few times, look at a few emails and then know everything about them and have a guarantee that it’s going to be a relationship that will work out. That’s just an unrealistic expectation. You can do your best, you can optimize for avoiding some obvious mistakes. But if he has this, if you have the expectation that you need to get it right and I’ve never done this, and if I get it wrong, something terrible will happen. Then you’re now going to put yourself in the worst possible position to do this job right. Your job is to hire somebody senior or not, doesn’t matter. And if it’s senior then you should look at this as like, “Oh, this should be easier.” There should be a lot more evidence. This person should be somebody that I’m not going to have to do as much betting on their potential, but I can do a lot more. I could look a lot more at their past performance and their already realized potential to make a decision if they are who we need right now. So I think a lot of this is just mindset and fears and this creating unnecessary pressure. And that then oftentimes leads to bad outcomes. Much more so than you doing something for the very first time and potentially getting it wrong. If you’re not emotional about it, you’re probably going to, even if you make a mistake, realize that quicker correct, that quicker move forward quicker than if you’re trying to do this perfect.



Hiten Shah: Yeah. I want to add one thing before we go and I would just say it, maybe it’s my tip on this. And it’s like those senior people, those are the people you can learn from. Those are the people that will tell you how to do something you might not understand how to do yet. Whether it’s managing a 100 people or learning the more, what an expert’s opinion is or how they think about a certain area, right? If they have some expertise, so to speak. So to me, I would consider every interview, every meeting, even every time you work with those people every day as a learning opportunity for you. And that can be one of the most powerful ways to think about it because we should be learning from everyone around us. If you’re intimidated by somebody, then start asking them questions about what they would do in the situation your company’s in. In fact, a lot of times that they’re like that because they want to understand the situation you’re in and you kind of want to almost treat them as if they’re on the job. And what you would do if they’re on the job is you’d figure out how to support them. And a lot of that has to do with learning about what they’re trying to accomplish and how they recommend doing the job.



Steli Efti: I love that tip. And just to double click on that. Yeah, if you talk to these people and you just use a framework of maybe this is a consultation session, and you just share with them your hardest problems, and see how they would respond. How they would approach these problems. If they’ve seen this before. If they’d had to solve that type of problem before. That’s going to be a much more both enlightening and educational conversation, but also a much more productive for both sides. And that will give you a lot better data oftentimes if, “Yeah, this is somebody I want to work with on our hardest problems.” Versus “No, I don’t. I don’t think that this is the right person for this.” Versus just talking high level, what have you done in the past? And then they just run through all their accomplishments and all the jobs they had. Just talk about and not just talk about future potential of your startup and all the amazing things you’re going to do. But talk about the heart problems you have right now, you don’t know how to solve and see how productive of a brainstorm you can have with them about those problems. So I love that. I’ll end with one more tip before we wrap this episode up on my end. Which is a simple one that we’ve given many times, but it’s so important. I will probably never stop giving this tip for the rest of my life. Which is if you have a bad feeling about a person, if you dislike a person, if you have doubt, and I’m talking about especially like gut doubt. Your mind thinks you should like this person and this person is the perfect person for the role, but something inside of you doesn’t like the idea of hiring this person. Just don’t hire them. It doesn’t matter how impressive their resume is. It doesn’t matter how impressive their references are. It is so tempting to hire somebody with a shiny resume. Especially really senior people. They come from really prestigious places with the idea that that’s going to impress investors. That’s going to impress your teammates. That person might just solve all your problems, but if you have a bad feeling about somebody. If you feel like somebody isn’t a culture fit, no skill in the world ever will make up for that. It’s going to be a problem and more likely than not, it’s going to lead to you having to part ways with them and in the meanwhile them destroying a lot of value. So never hire somebody no matter how senior they are or how impressive they look on paper if you don’t think they are a culture fit. If you don’t believe them or don’t feel good around them or don’t want to spend time with them, right? The famous quote, “You don’t want to spend the rest of your life with somebody you shouldn’t.” Or if you don’t want to work for the rest of your life with somebody, you shouldn’t work with them for a single day. So keep that in mind, especially when you hire super senior people.



Hiten Shah: Absolutely. Sure.



Steli Efti: That’s it for us for this episode. We’ll hit you very soon later.



Hiten Shah: Later.