Sep 30, 2026 · 7 min · 4 segments
Why do Sales, Customer Success, and Engineering keep hitting the same friction? In this hot take, Meg Bear and Amy Wilson break down Conway's Law — the idea that your org structure shows up in how…
Meg BearHostAmy WilsonHost
We started to recognize that customer retention was different than support and that we needed to think about making sure customers were using all of the products as opposed to just buying all of the products.
And so we started to see a tension between is an upsell something that the sales team is responsible for? Or is that something that there's a customer success team that's responsible for it? While there were lots of ways you could solve this problem, the organization structure really became a bottleneck of its own.
And understanding where those dividing lines were is important for understanding the kind of places where you can predict human challenges emerging in this.
And so on one hand, you can think of this as coordination costs, right? But I think that there's an emotional element over and above coordination cost, and that gets to the sense of autonomy and agency that most leaders want to be able to deliver their goals.
I've used a lot of different tactics over my career, and I've seen others use a lot of different tactics.
people like to use are directly responsible individuals, naming a person that has responsibility and really clarifying roles and responsibilities.
People really, really like this because it creates clarity when there's a place of friction or conflict.
And so most of the time when you're in a leadership position and you have some of these cross-functional pressure points, somebody is going to come to you and say, I need clarity of roles and responsibilities.
To me, this is always an indicator that we have human friction, not just organizational friction, but it's always positioned or brought up as an organizational friction.
And so back to your point, I believe the solution is aligned incentives and not just clarity of roles and responsibilities.
Because if you just clarify roles and responsibilities, what you've done is you've solved the problem by taking the responsibility yourself as the owner for defining the structure, as opposed to solving the systems problem of the leadership team to care about that shared goal.
It's allowing people to define success as their function in a silo versus forcing them to define their success as a shared success.
While I'm all for agency and autonomy, I think that high functioning organizations require leadership teams to have shared goals that are aligned by design not just aligned by boxes of organization responsibility let's
We started to recognize that customer retention was different than support and that we needed to think about making sure customers were using all of the products as opposed to just buying all of the products.
And so we started to see a tension between is an upsell something that the sales team is responsible for? Or is that something that there's a customer success team that's responsible for it? While there were lots of ways you could solve this problem, the organization structure really became a bottleneck of its own.
And understanding where those dividing lines were is important for understanding the kind of places where you can predict human challenges emerging in this.
And so on one hand, you can think of this as coordination costs, right? But I think that there's an emotional element over and above coordination cost, and that gets to the sense of autonomy and agency that most leaders want to be able to deliver their goals.
I've used a lot of different tactics over my career, and I've seen others use a lot of different tactics.
people like to use are directly responsible individuals, naming a person that has responsibility and really clarifying roles and responsibilities.
People really, really like this because it creates clarity when there's a place of friction or conflict.
And so most of the time when you're in a leadership position and you have some of these cross-functional pressure points, somebody is going to come to you and say, I need clarity of roles and responsibilities.
To me, this is always an indicator that we have human friction, not just organizational friction, but it's always positioned or brought up as an organizational friction.
And so back to your point, I believe the solution is aligned incentives and not just clarity of roles and responsibilities.
Because if you just clarify roles and responsibilities, what you've done is you've solved the problem by taking the responsibility yourself as the owner for defining the structure, as opposed to solving the systems problem of the leadership team to care about that shared goal.
It's allowing people to define success as their function in a silo versus forcing them to define their success as a shared success.
While I'm all for agency and autonomy, I think that high functioning organizations require leadership teams to have shared goals that are aligned by design not just aligned by boxes of organization responsibility let's
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