YC
The Hard Conversations Founders Don't Want to Have
@ Y Combinator
02/24/23
Takeaways
DC
Dalton Caldwell
02/24/23
@ Y Combinator
A hard conversation is one that you dread and involves high stakes, where the outcome could go badly or involve uncomfortable truths.
MS
Michael Seibel
02/24/23
@ Y Combinator
As a startup advisor, I realized that having hard conversations is essential for helping founders, even if they don't enjoy it.
DC
Dalton Caldwell
02/24/23
@ Y Combinator
True friends are those who can tell you uncomfortable truths, which is crucial for personal and professional growth.
MS
Michael Seibel
02/24/23
@ Y Combinator
In office hours, founders often come with a question that isn't the real issue; the actual question is often about their insecurities and seeking validation.
DC
Dalton Caldwell
02/24/23
@ Y Combinator
When advising early-stage companies, it's challenging to tell them they won't raise the funds they expect or execute their unrealistic spending plans for achieving product-market fit.
MS
Michael Seibel
02/24/23
@ Y Combinator
It's important to set your expectations low and prepare for the worst, so if you get surprised, it's on the upside, not the downside.
MS
Michael Seibel
02/24/23
@ Y Combinator
Having hard conversations is uncomfortable, but it's essential for growth and helps founders address issues they've been avoiding.
MS
Michael Seibel
02/24/23
@ Y Combinator
When someone asks for a deep dive, it often indicates they have underlying concerns about your understanding of the business.
MS
Michael Seibel
02/24/23
@ Y Combinator
Founders often mistakenly believe that advisors have complete knowledge of every user base and problem, but they should be talking to their customers instead.
MS
Michael Seibel
02/24/23
@ Y Combinator
If you want to succeed, you need to organize your thoughts and be productive in meetings rather than expecting others to accommodate your lack of preparation.
MS
Michael Seibel
02/24/23
@ Y Combinator
Co-founders who have never had hard conversations may face explosive disagreements when they finally do, highlighting the importance of prior relationship building.
MS
Michael Seibel
02/24/23
@ Y Combinator
Learning how to disagree constructively is a skill that prevents irreparable harm to relationships during conflicts.
MS
Michael Seibel
02/24/23
@ Y Combinator
It's crucial to release pressure in a relationship through honest conversations, rather than letting it build up until it explodes. I have to understand who I'm talking to and realize that sometimes I need to take a step back, even if I'm unsatisfied, because pushing forward can create more problems.
MS
Michael Seibel
02/24/23
@ Y Combinator
If you're only having easy, superficial conversations with your employees, it might seem fine until it isn't. It's crucial to find the right way to have hard conversations.
MS
Michael Seibel
02/24/23
@ Y Combinator
Avoiding hard conversations means no one wins, especially the employee, who likely knows something is wrong and expects you to address it.
MS
Michael Seibel
02/24/23
@ Y Combinator
As a startup founder, allow yourself to consider that you might have picked the wrong person for a role. Sometimes, the right fit for an employee might be elsewhere, and acknowledging this can benefit both parties.
MS
Michael Seibel
02/24/23
@ Y Combinator
Good startup employees want honesty and transparency about the company's situation. They understand the challenges and want to know how they can contribute to improving outcomes.
MS
Michael Seibel
02/24/23
@ Y Combinator
Sharing bad news, like having only two months of runway, can actually motivate great startup employees to engage and find solutions together.
MS
Michael Seibel
02/24/23
@ Y Combinator
It's important to continuously ask ourselves if we're lying to ourselves and to dig deeper into the questions we ask, rather than assuming our initial inquiries are complete.
MS
Michael Seibel
02/24/23
@ Y Combinator
No one is perfect, and it's important not to put anyone on a pedestal. Recognizing this can be freeing and empowering.
MS
Michael Seibel
02/24/23
@ Y Combinator
Being a Y Combinator partner means having made many mistakes before and knowing the way out, rather than claiming to play error-free.