In today’s episode of The Startup Chat, we talk about being a people-pleaser, the problems it can create within a start-up, and whether being one can a strength or a weakness when you are hiring team members.

When it comes to hiring staff, especially customer-facing roles, you may be tempted to hire someone who loves to please other people. This can be a great thing, as people-pleasers are usually awesome people and can make great team members.

However,  there’s a risk that a people-pleaser’s inclination to please others may be abused or taken advantage of by other team members, and this can lead to that person becoming very unproductive and ultimately this can hurt the company.

Tune into this week’s episode to hear more about Steli and Hiten’s personal experience of working with people-pleasers, their distinction between being selfless and being a people-pleaser, what you can do to stop being a people-pleaser and much more.

Time Stamped Show Notes:

00:04 About today’s topic: Being a people pleaser.

00:26 Why being a people pleaser may or may not be good for you.

00:38 Context of a people pleaser.

03:08 Hiten’s definition of whom a people-pleaser is.

05:04 Pleasing the company and the team vs pleasing the customers or the users.

06:26 The big distinction between being selfless and a people-pleaser.

07:27 What does a people-pleaser mean to Steli?

08:16 The act of people-pleasing.

09:14 The downside of saying “yes” all the time.

10:40 The risks of being a people-pleaser at work.

12:17 Steli’s recommendations of what to do if you’re a people-pleaser.

14:05 Are you a people pleaser?

3 Key Points:

  1. The most selfless people I know are people pleasers.
  2. If you have the ability to be a people pleaser, it’s a skill, it’s a talent. But you can use it in a way that is not beneficial to you or your endeavour.
  3. The risk of being a people pleaser is that you’re not dealing with truth and conflict in the most effective way possible.


Steli Efti: Hey everybody, this is Steli Efti.



Hiten Shah: And this is Hiten Shah.



Steli Efti: In today’s episode we want to talk about being a people pleaser.



Hiten Shah: Here we like to talk about more than just sales and marketing.



Steli Efti: We just want to bullshit and chat about business and life, and hopefully while we’re doing that provide a lot of value to people.



Hiten Shah: The world’s best business podcast, shit.



Steli Efti: Shit, we’ve got it.



Hiten Shah: For people trying to get shit done.



Steli Efti: Done, yeah. We don’t want to give you feedback that’s bullshit.



Hiten Shah: We want you to do your best.



Steli Efti: Why that may or may not be good for you in life in general but also specifically for you when you work in startups, either as a founder or somebody often times that is working with any other person. Here’s the context why I want to talk about people pleaser specifically. We’ve had this case a few times, where people on our team, especially people on our team that are very customer facing, that a few of them at some point identify themselves as, “You know what, I am somebody that, I am a people pleaser, I’m somebody that likes to say yes to others, that likes to help, that likes to be liked, and that avoids often times any kind of thing that would get in the way of that.” Which means usually avoiding conflict, avoiding rejecting people or saying no to people, avoiding being critical to others or avoiding anything else that can create … Anything that stops other people from really, really liking you. People pleaser are really awesome people, and often times in customer facing roles you would assume that that’s the type of person that you’d want hire in support or in success or in many other roles where it’s about taking care of the customer. You would want to have somebody that loves to please other people. But it’s also a big problem, and we can talk about this, in a startup how you need to be mindful of that yourself if you’re a people pleaser, but also if you’re managing a team how to think about that. Because I’ve seen this, we have an engineer that’s a people pleaser and we’ve seen how that created problems for him and the engineering team an others. I’ve seen this in sales. I’ve seen this in so many roles. Yesterday I was talking to a candidate for a position with our company. One game that I like to play is always the game of weakness at the end. Where I’m like, “I’m going to tell you something that sucks about our company, you tell me something that sucks about you. We’ll go back and forth and if we can discourage each other from wanting to work together, awesome, then we’ve accomplished something useful. And if can’t that’s awesome too, maybe that we should work together.” One of the weaknesses that that person shared with me, that was one that nobody had picked up on in the interviewing process prior. It was that she identified herself as somebody that’s been a people pleaser and it’s been something that’s a weakness of hers and something she’s working on. I love that she identified that as a weakness instead of a strength in her position. I wanted to talk about this a little bit and share some of mu thoughts and get your input on this, because I’m curious. But in general, does any of what I just described resonate with you? Have seen this in yourself or with other people? What is your definition of people pleaser? Do they struggle or do they thrive in environments?



Hiten Shah: Yeah, such a good question, such a good topic. I think a lot of this has to do with psychology in a lot of ways, and someone’s own personal psychology around it. I’ll say some things, I don’t mean to judge anybody in any way. I would say there are people out there that don’t have this affliction basically, of wanting to please other people. They are just going about life looking to please themselves. Again, no judgment. This is like something that you either learned when you were growing up or something you’re dealing with as a human based on your personality or whatever, whatever you want to believe in about why you are the way you are. Then there’s people who have actually a more balanced approach to it. I call it balanced because they have a tendency to be able to think about others in certain situations, while are really good at thinking about themselves in other situations. Then we have people that are on the other end. So this is almost a spectrum I would say and you could almost peg somebody on the spectrum. The last side of it would they’re completely selfless and that’s their mental model. I use the word selfless very specifically, because to me the most selfless people I’ve met are actually people pleasers. They are looking to give themselves to the other and provide whatever they can to the other person in every single scenario that they see, just because they want to make other people happy. In a way, it is a selfish act in itself to do, because that’s what gives you joy. Making other people happy gives you joy. So this person that you’re talking about, she might be somebody who gets pure joy out of making someone else happy and pleasing them so to speak. Honestly, some of the folks that I’ve met in certain disciplines tend to be more like that or less like that. For example, I found a lot of the designers I’ve worked with to be really excited about pleasing other people. They can go wrong on this, and this is where my point is I guess. They can go wrong on this by pleasing the company and the team, versus pleasing the customer or the user. It’s a tool you have. It’s a skill. It’s a talent if you have the ability to actually be a people pleaser. The thing is, you can use it in a way that’s not beneficial to you or whatever organization you’re doing. So yeah, I’ve seen this. I have this tendency. I kind of have this tendency both ways to be honest. I don’t think I’m balanced at all in this, I’m working through a lot of this type of stuff personally around, do I please other people a lot? Am I actually thinking about myself in those scenarios? What’s going on here? For me it’s more existential, which is more like, I’ll say it like this but like, what does want? I went there, but yeah, that’s kind of like for other folks I know, like my co-founder Neil, he doesn’t have a problem with what does Neil want? What does Neil want is on his mind and he’s doing it right now. Like literally, right now I can guarantee you, whatever he’s doing it’s thoughts, right? I’ve learned a lot from it, because I am, for the majority of my life I’ve been a lot more about what does the other person want, not what do I want. That’s lead me to please other people even when I probably shouldn’t be.



Steli Efti: Yeah. I actually think that there’s a big distinction between being selfless and being a people pleaser, in that I think they do overlap but I do think they’re distinct in that I think somebody that’s selfless is interested in helping others in the best way they can. Which might mean being not liked, which might mean telling them something very inconvenient, or something very harsh. Or which might mean doing something that is in the best interest of the other person, although it might not be making them the most popular person. A good example of this is a good parent, right? Good parents, you don’t want to just please your children all day, because if that’s your goal you’re probably feeding them chocolate and letting them watch television all day long. If you just go by whatever is going to make the happiest the next moment, you’re going to do a lot of things that will make you momentarily popular but long term are not in the best interest of the child. To me that’s not a selfless act, that’s a pretty selfish act. So people pleasers to me can be selfless, but also can be very, very selfish in that their number one priority is not helping others or doing what’s in the best interest of others. But their number one priority is being popular or being liked, and that is very selfish in my mind. There’s a distinction. As I said, those things can overlap, and people pleasers can be amazing human beings that really care about others, that are very selfless at times. So it’s not really black and white, it’s very, very all kinds of shades of gray here. But when you are people pleasing, when you are doing the activity, not even to say, to tack somebody as a people pleaser. If it’s like you’re a man or woman, or you’re this tall or that tall. It’s like of thing that can’t be changed. But when you are people pleasing, when you’re doing the activity of people pleasing, I think that that’s oftentimes not a great activity. I think that the reason for that is because you’re probably changing your own tune, your needs, and changing your version of what’s happening or what reality is or what needs to happen next, based on what you think the person wants to hear. I don’t think that that’s a great way to operate in the world. But I do think that people that have done the activity of people pleasing for a really long time, they have very valuable skill sets. They have typically a very high level of empathy. They have a very high emotional compass and they pick up on how people feel and they pick up on communication clues. They are much more in tune socially with how other people feel and what’s going on around them than other people, and I think that that can be a very, very valuable skill but you have to use it wisely. I brought up an example with an engineer that we have that used to be people pleasing a lot. What that did was that everybody in the company knew that if you had a request to engineering, you just went around the head of the engineering team and you went straight to that guy. You asked him, “Hey, could you do me a favor and help me with this little project?” And he would say yes, and then another person would come and would say, “Hey, we need help. Can you run this queries and give us that?” He would say yes. He would just say yes to too many people and then struggle with his core work. He couldn’t do the stuff that he was responsible for because he was trying to help everybody else with the stuff that they needed a little help in. These people would gravitate towards him, they would not go anybody else in engineering because most engineers were not people pleasers, were not concerned about saying yes and being liked and everything. It’s funny because that very engineer the other day was showing me his current reading list, and one of the books was No More Mr Nice Guy, which was funny to see. But you have that example, like when you try to say too much within the team. It can be abused in a way that makes you very unproductive and ultimately harms the company. It could be abused in a way that, as you said, trying to please what other people in the company want to do, versus focusing on the customers. But to me the worst thing about being a people pleaser, or the biggest risk of it, is that you’re dealing with truth and with conflict in the best way possible because you usually try to avoid conflict and you usually try to adopt your truth to match the other persons around you. I think that that’s probably the least productive part of that. It’s something that I think, in myself, in other people on the team, but also as hiring, is something we’re looking at. It’s not a reason not hire somebody, but it’s something to be aware of and something that I think most society looks upon positively. “Oh, this person’s an amazing person. She’s so liked and she’s a people person and everybody loves them.” But I think that when you look under the hood you can see also the risks of that behavior. You need to look at it holistically, versus just the, “Oh, this person should be in customer success or sales because everybody loves that person.” Everybody loves is not the only criteria that really matters oftentimes.



Hiten Shah: Yeah. I think you nailed it in terms of description. So, what does a people pleaser do?



Steli Efti: What does a people pleaser do? I think first you realize that you are one, that you’re involved in that activity. It’s funny you identified yourself in that bracket because I would do myself as well. I think that for most of my life, especially as a kid, I was growing up, I was absolutely a people pleaser. Somebody always concerned about being loved and liked by everybody and adopting the way I was communicating with people that way. I think that when I told this to one of my colleagues in the team, she was shocked that I said, “I think I was a people pleaser for most of my life.” I think identifying yourself is step one. I think step two, realizing that’s it’s not just a positive trait and that it has cost associated with it. Meaning maybe not being fully truthful, maybe not helping people the long term, just in the short term, maybe avoiding difficult conversations and making them worse. Focus a little bit on the negatives because I think people, especially superficial relationships might have encouraged the positive sides of the people pleasing too much. You might have gotten so much positive feedback of how awesome of a person you are and how much people thank you because you say yes to them all the time, that you are not seeing the downside of it enough and looked at that enough. So making a list maybe of what are the things that I failed at, or the cost that I’ve paid in my life, because I’ve been people pleasing or because I’ve been a people pleaser, might be the second step. Then, I don’t know if it’s buying a book, No More Mr Nice Person, or whatever it’s called. Or maybe finding a coach or a mentor or a friend, that you’re telling, “Hey, you know I want to get better at this. I want to be liked but I also want to be better at times, not having that be my number one concern.” Find somebody that is maybe good at this, that’s not a people pleaser at all, and have them either officially or unofficially as your coach and somebody you ask for advice and somebody you get feedback from. I think once you realize the downside, I think that’s the thing that’s missing for most people that involve themselves in that activity a lot. But once you realize the downside, I think it’s finding somebody that has learned how to deal with this, so that is really good at this type of stuff. And then just talking to them, checking in with them, giving them updates, asking them for help. Find a coach that will help you to get better at this, would be my advice.



Hiten Shah: I really like that. I’ll give one more, which is try to figure out why you’re a people pleaser. Where does it come from? I think that can really help you come to terms with it and realize that you’re doing, and why you’re doing it.



Steli Efti: Awesome. I think that’s it from us for this episode.



Hiten Shah: Happy people pleasing.



Steli Efti: Or not people pleasing.



Hiten Shah: Bye.