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Thanks for posting this. One question I have is this: When, as the CTO, you approach an engineer with the intent on coding together or otherwise building some s

by JakeSc 12y ago

Thanks for posting this. One question I have is this: When, as the CTO, you approach an engineer with the intent on coding together or otherwise building some system, are there not organizational challenges with an executive working with a subordinate? I realize that this has been tremendously beneficial to you, but I wonder how this works mechanically--do you just say, "Hey Jeff, let's build this together."? I have to imagine that if you're ever wrong technically, an individual contributor-level engineer might hesitate to tell you.

richardlblair 12y ago
I would suspect that their culture has evolved in a way that allows people to point out the CTO that they are wrong. If he has always been involved and close to his team then pointing errors would feel more like giving feedback to a peer rather than giving feedback to a superior.
- gdb 12y ago
  Yep, this is right.
- lifeisstillgood 12y ago
  Yes, but it is a very difficult line to walk. The difference between "have you considered using X?" and "I tell you to use X", the difference between "can we hit date Y?" And "we must hit date Y so start cutting corners" Authority as a position is a difficult stick to carry - if you are telling people "my way or the highway more than once of twice a year" you are over doing it. "I feel uncomfortable with this architecture" or "this will take longer than you hope" are all indicators you are doing it right. Stop hearing those and you should worry.
  - gdb 12y ago
    I think a lot of these cultural questions require you to say over and over what's important, and demonstrate that you really mean it. I always ask people what they think, and when I sense hesitance I work to draw them out. In the end a lot depends on your relationship with the individual; I make sure to spend time getting to know every engineer who joins. More broadly, one point Marc often makes is, if someone does something you don't like/disagree with, let them know directly. (There are some exceptions to this, and sometimes it's helpful to role-play with a manager to get some practice before doing so, but we work hard to make direct feedback a core part of Stripe.)
  - richardlblair 12y ago
    I spent a few days in the Stripe office with my team (Hey guys!) and I can tell you with certainty that they have a very strong collaborative team. They actually have a really great culture that they actively try to build (thanks for including us while we were in town!). Fridays are particularly awesome. Anyway, my point is that I never got the feeling like people say "it's going to be this way, no questions", but also got the feeling that if a superior did say "look, I know you guys feel this way, but we are going in this direction and the deadline is X" that the team would rally behind their leader and support their decision. Stripe, from what I saw you have done a great job building out your team. Congrats, it's nice to see companies doing it right!
spydum 12y ago
I think it's precisely because he is known directly to the engineers that this works. No idea how well it will scale for them -- I wish them well. In most "big" organisations, the C-levels are practically celebrities, everyone wants to be "connected" some how to them, but hardly anybody works "with" them. Everybody works "for" them (and even those direct reports/workers are imbued with some special celebrity powers by just saying the name). The hierarchical relationship of everybody working "for" you causes plenty of insulation -- communication grinds to a halt besides the cordial banter.

by JakeSc 12y ago

richardlblair 12y ago

I would suspect that their culture has evolved in a way that allows people to point out the CTO that they are wrong. If he has always been involved and close to his team then pointing errors would feel more like giving feedback to a peer rather than giving feedback to a superior.

gdb 12y ago
Yep, this is right.
lifeisstillgood 12y ago
Yes, but it is a very difficult line to walk. The difference between "have you considered using X?" and "I tell you to use X", the difference between "can we hit date Y?" And "we must hit date Y so start cutting corners" Authority as a position is a difficult stick to carry - if you are telling people "my way or the highway more than once of twice a year" you are over doing it. "I feel uncomfortable with this architecture" or "this will take longer than you hope" are all indicators you are doing it right. Stop hearing those and you should worry.
- gdb 12y ago
  I think a lot of these cultural questions require you to say over and over what's important, and demonstrate that you really mean it. I always ask people what they think, and when I sense hesitance I work to draw them out. In the end a lot depends on your relationship with the individual; I make sure to spend time getting to know every engineer who joins. More broadly, one point Marc often makes is, if someone does something you don't like/disagree with, let them know directly. (There are some exceptions to this, and sometimes it's helpful to role-play with a manager to get some practice before doing so, but we work hard to make direct feedback a core part of Stripe.)
- richardlblair 12y ago
  I spent a few days in the Stripe office with my team (Hey guys!) and I can tell you with certainty that they have a very strong collaborative team. They actually have a really great culture that they actively try to build (thanks for including us while we were in town!). Fridays are particularly awesome. Anyway, my point is that I never got the feeling like people say "it's going to be this way, no questions", but also got the feeling that if a superior did say "look, I know you guys feel this way, but we are going in this direction and the deadline is X" that the team would rally behind their leader and support their decision. Stripe, from what I saw you have done a great job building out your team. Congrats, it's nice to see companies doing it right!

spydum 12y ago

I think it's precisely because he is known directly to the engineers that this works. No idea how well it will scale for them -- I wish them well. In most "big" organisations, the C-levels are practically celebrities, everyone wants to be "connected" some how to them, but hardly anybody works "with" them. Everybody works "for" them (and even those direct reports/workers are imbued with some special celebrity powers by just saying the name). The hierarchical relationship of everybody working "for" you causes plenty of insulation -- communication grinds to a halt besides the cordial banter.