# Dalton & Michael: The hard conversations founders don't want to have

**Author:** Dalton Caldwell, Michael Seibel
**Type:** Video
**URL:** https://www.ycombinator.com/library/IQ-dalton-michael-the-hard-conversations-founders-don-t-want-to-have
**YouTube ID:** hUbM-bURoJE

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In this video, Y Combinator partners Michael Seibel and Dalton Caldwell discuss the importance of having honest and
difficult conversations with startup founders.

While having hard conversations can be uncomfortable, Seibel and Caldwell argue that this transparency is essential for
founders to grow and ultimately, these experiences help founders have their own hard conversations that they've been
avoiding with the people around them.

## Transcript

I think so much about being a YC partner is like is is exactly that like I've made all these mistakes before I go and the only thing that I could say is I know the way out this is Michael Seibel with Dalton Caldwell at YC we often have to have challenging conversations with Founders when giving them advice

today we would like to talk through some of the hard conversations that Founders don't want to have Dalton why don't you uh set this up for us well look let's start by trying to define a hard conversation by definition if it's a conversation you're looking forward to having it is not a hard conversation a hard conversation sucks that's why it's called A Hard conversation you don't want to have them they're bad right

um they don't feel they don't feel good you dread the hard conversations and so you know a hard conversation is when the stakes are high like it could go bad it could go off the rails it could be you're saying something risky or you're making a point uh maybe you're doing something that's impolite or saying something that's impolite because again think about an easy conversation easy conversation is superficial and you used to agree with someone just like hey you're great way to go that's an easy conversation

right yes hard conversation is not that um a hard conversation is When You're vulnerable you're putting yourself out there you're saying something that someone in the conversation is in a is uncomfortable you know it's funny was as you set that up what's tricky being a startup advisor is that you know it's going to help someone to have hard conversations with them but you also know that they're not going to

enjoy it and I think as an as a YC partner in the early days I think I measured my Effectiveness based on how much fun Founders had talking to me and and and only after a couple batches that I realized that doesn't really do anything um and then when I started having honest conversations and talking about like my actual opinions about their product or about how hard they were working oof like the job changed did you

experience that yeah I mean if you just agree with someone it's easy to you know and you like mirror their body language like there's all these techniques you can do to be likable or you're like oh wow like you're so smart everything you say is correct your jokes are funny you know you can do this stuff and the problem is it's not that helpful um if it's just not that helpful like and again if you think about us

as Founders are thinking about friends think about friendships with people the people that you would consider your two true friends in life are the people that can say the things to you that no one else will yes and if you're surrounded by by crowds of people that um for whatever reason or unable or unwilling to tell you the truth about anything you're having a bad time one how are you going to learn right how are you going to learn when you're giving people inputs and their

output back to you is dishonest because they would just want to make sure that you feel good so let's talk about some of the hard conversations that we have um with Founders let's take an easy one I'll give you an easy first example the founder comes to office hours with us they have already made a decision it is obvious they've already made a decision and they want us to spend an hour validating that they've made the right

decision that's kind of a hard conversation because like Dalton what do like if we were being one thousand percent honest what would we actually just say like bluntly well here's I think there's two ways to handle this there's the dishonest way the easy conversation is to take them at face value and be like oh wow seems like you've thought about this really well I I see no errors in your logic you're a genius with no you did it again exactly yeah with like without the information to even verify that right

like with no actual fact wow like what amazing strategy I just I this is just a plus work um and then then there's the hard thing and what I think the hard thing is is not even disagreeing with it it's to say it's the question behind the question which is hey it seems like you've already made a decision cool why are we talking about this yes why are we here right now like what's the

question behind the question is it is it that someone else is it that your co-founder disagrees with you and what you're trying to do is bring my opinion into it to prove that you're right yes is it that someone else disagrees with like like there's always a real question hiding behind the scenes and man people it's always there when I when I when I bring this up it like they're like yeah there is there is you know there's a question behind the

question yes yes it's such a common theme like I think if you really want to understand office hours in a nutshell 60 to 80 of the time a Founder will go into office hours with one question and we won't even end up talking about that thing like that's not the actual question that's not the action this comes up a lot with like people talking about applying to YC like people are always like think it's really important Michael I have some really important questions I want to ask you about applying do I see and he talks to them and it's just like

should I apply to like like there's no there's no there there yeah it's a no-op there's nothing there's not my Revenue monthly or quarterly it's like what like who like just yeah and so again I get where they're coming from and what they what they're really the question behind the question I think is I feel insecure and I want to talk to you Dalton and Michael about this so that you give me validation that I should apply great but and so

that's the actual question behind the question not hey I have this really complicated question about the application that's I don't know all right let's stick with hard ones um we're talking to an early stage company and it's becoming obvious that they're not going to be able to raise the amount of money that they want to raise and they're not going to be able to execute this magical explosion of spending that they want to execute that they've convinced themselves is what's required to get product Market fit

what do you do in those situations you know that's a that's a really tough one because you want people to be optimistic as we've spoken about before and it's hard to you never want to be short on someone's startup and so what I would usually say on this one is think about what a great life of philosophy it is to set your expectations low and prepare for the worst and then if you get surprised you get surprised on the upside not the downside and so the key in this hard hard

conversation is not to debate someone that their plan is bad keep the optimism you know but isn't it better to sort of have a plan for the worst and not be surprised on the downside and if you're surprised on the upside fantastic right you're winning man people don't want to hear this this is a hard conversation to have it's like going up in the airplane do you want to bring the parachute with you or not like I'm not trying to be Grim by saying

bring a parachute but wouldn't you want to bring the parachute yeah if you had the choice what's the downside of bringing the parachute you don't use it it's fine all right so here's another one that comes up a lot um Dalton I'd like to spend two hours really going deep on this problem um but our office hours um don't go that long how do you how do you deal with the I

want to do a deep dive yes this is another one of those question behind the questions and again it can be different things depending on the people I think sometimes what's going on is you're an idiot and I don't have confidence you can give me advice unless I spend two hours showing you a slide deck so I can explain everything to you sometimes it's it's not really about the meeting I just want a lot of face time so we can build a relationship or

whatever and so this is yes yeah okay that's fine but you see what I'm saying there's usually when someone asks that there's something else going on and again my It's usually the first one for me where they think we don't understand yeah maybe we don't I don't know but like they're instead of them directly saying I am concerned that you do not sufficiently understand our business and so I want to make sure you do X Y and Z okay that's a hard conversation but then I'm like okay I know where you're coming from all right I hear you yes but some weird like can we meet for

three hours yeah I'm always like why I want another question behind the question you know yes well and what's so funny is if they just said I don't think you're smart about this particular thing we would get to the we would get to them yeah okay I think there's a couple others that I see one is this assumption that we are like god-like advisors with complete understandings of every user base and every problem in the world and like

they can kind of like shortcut talking to users if they just spend enough time talking to us and so that one is just like folks like so often in this one I'm just like you're having a conversation with me that you should have with your customers like talk to them like I don't use your product talk to the people who do I think the other one which um I really try to push back on is I'm lazy and I didn't come up with the agenda I want to like roam my random

thoughts and over the course of two hours we will have 20 minutes of productivity but I don't want to organize my thoughts and I want you to accommodate that and for that one I'm always just like that's like you're not training yourself for Success here like you expect more from yourself like if your competitors can get 20 minutes of input 20 minutes of output they will do way better than two hours of input 20 minutes of output

um and just you know that seems to kick people into gear um what's another one that that you're excited by I I think we can shift gears to a couple other contracts for hard conversations let's talk about hard conversations not with us but with co-founders and so the thing I want to set up here is the classic thing is people become co-founders yes they've never once had a disagreement or hard conversation it's all been superficial we're best friends we worked you know it's all wonderful and then the first time they have a hard

conversation that's it explosion tell you've seen this man like what what's going on here like well first things first right this is why we like teams who've known each other for at least a little bit and have some kind of work or personal relationship because I always say that like when you have some kind of non you know if you have some kind of Base relationship that you might want to maintain even if this startup doesn't work you won't say that thing

or you'll think really hard before saying that thing that will like shatter the relationship but when you're like oh the only reason why I'm even talking to you is because of the startup and now I'm convinced that our startups [ __ ] which by the way you'll be convinced your startups [ __ ] just continuously that's like a normal feeling and then you're like well [ __ ] it man like you can't you know there are things you can't unsay and um wow sometimes the original sin was like

you shouldn't have started the company with this person but like let's say you are doing a company with your co-founder and it's just really frustrating let's see if I skip the founders on how to kind of process them I think like you have to learn how to fight and maybe fight the wrong word how to disagree it's like um you have to learn how to pull your punches and have a disagreement that's a real disagreement and actually release the pressure

of the disagreement in a way that doesn't cross the line so that the relationship is irreparably harmed and it's a skill you have to learn and if you don't if you've never been through a major disagreement with someone or had the skills for both of you to have a fundamental disagreement and talk it through yet not blow the relationship up yeah and again this is a skill like any other skill man let's go you know it's funny because

analogy that I'm thinking in my head is that like you know it's a pressure release valve and you don't want to just rip it open yeah you but if you don't release any pressure you also have it it builds up and blows up yeah either way it blows up either way it blows up if you let the pressure just build build by only having super official conversations for years one day someone will snap boom and on the flip side if you just like leave it open all the time and you fight constantly that ain't gonna work either

no it's sort of like the happy medium thing I think the biggest thing that I had to learn and and um Amy our former batch director used to talk about this a lot is this concept that like people will deal with conflict differently I love to engage and like lean in and talk through conflict but it's just as likely the person I'm working with um wants to avoid conflict or wants to take

time to process conflict or doesn't process conflict through conversation and like I have to look at those cues I have to understand who I'm talking to and realize that when I have to kind of take a step back even though I'm unsatisfied because I'm creating more of a problem by like continuing to push forward um and I think that this is one of those situations where you can't blame the other person for like not acting correctly like you have to take responsibility because you can

both blame each other into an explosion all day long right like that's easy so next what about what about employees what do you think there I think it's I think it's the same sort of situation and the the dynamic might be a little bit different but if you're only ever having easy superficial conversations with people it's cool until it's not and sometimes the best way to work with Folks at your company or whether colleagues employee whatever we want to call them

is to find the right way to have some of these hard conversations and you know what they are you know you're probably I'm sure someone watching this is like yeah I can think of a few more I can think of some things I would say if I weren't you're afraid of the consequences uh you know like there's a right way and a wrong way to do it we're not saying go blow people up but if you're just avoiding hard conversations no one wins no and the most importantly the employee doesn't win because like

the employee probably knows something's wrong and if you're the boss they probably expect you to be the one kind of addressing it you know one thing that I say about employees a lot and I want to limit this to like startups and startup employees like first like allow the idea in your head that you might have picked the wrong person that the person isn't the right fit like like it's like even if you did your best in interviewing and they were

really good and did it like allowing you had the idea they're like that might not be the right fit and like this person might be able to do 10x better work somewhere else um and like that would make their life better just as much it was make your life better like allow for that because sometimes people feel like they have to solve unsolvable problems um and then the second thing I think about with like good startup employees is they want honesty like they good startup employees kind of understand this is a really hard task

and that like the likelihood of being successful is really low and they want to be in the know they want transparency they want to know how the company's doing and they want to know how they can do 10x better to impact the outcome of the company that's why you join a startup because you want an early stage job because you want to impact the outcome of the company I've been often surprised at like sharing bad news like oh we only have two months of Runway right I would think would be demotivating but for great startup

employees they're like all right how the [ __ ] are we gonna fix this and then you can get juice from them you're like well all right I mean if we're on the trenches together maybe we can make something happen um but like it's really bad when like you know your startups in the trenches and you're like employees are like clueless well well I thought everything was going fine we raised a bunch of money you never told me anything was wrong and you're like uh I think that to our credit you and I say this a lot if we were doing office hours

with ourselves what would what would we say and yeah man I think sometimes we Dodge hard conversations like sure like we're not saying uh to be vulnerable here we're not saying we always get this right 100 of the time in fact I might argue many times the first conversations we have are wrong I think the only thing that we do well is we continuously ask ourselves are we lying to ourselves or is there uh like what did you say what's the deeper question

what's the question behind the question what's the question behind the question I think we are good at asking that and sometimes we assume that the initial Salvo of questions are complete [ __ ] ourselves like within within YC itself and I think that's life man I guess what I'm trying to say is no one's perfect don't put anyone on a pedestal it doesn't matter who they are they have their own [ __ ] and that should be freeing and empowering and make you feel optimistic and not bad

right isn't that the right takeaway here that's the right takeaway you know to close out this reminds me of this like um scene in The West Wing where one of the characters has a drug problem it's that's pretty bad another character is going through PTSD and is really struggling but doesn't want anyone to know and this character is like a drug addict that like cleaned up and so and so forth and is noticing the first character is struggling you know the way the kind of story goes is that other people who don't understand

how much pain the person's in will like say oh you should go see a psychiatrist or you should go get a prescription like they'll do these superficial things but this character knows and so like he actually you know the analogy is like he jumps down to the bottom of the well with him it's like I'm at the bottom of the well struggling and then my friend jumps down with me and you know the thing that they say at the end is that like well I'm jumping down with you because I've climbed out of this well before and I know the way out

and I think so much about being a YC partner is like is is exactly that like I've made all these mistakes before and the only thing that I could say is I know the way out as opposed to like oh we play error-free ball which is obviously all right man great chat thanks [Music]

[Music]
