Okay but, before I say, I’d like to clarify that I don’t think I’d be perfect at this, which is one reason I’m not leading weird things. But I think if you are gonna make requests like that of employees you live or travel with, you basically have to be. (because it gets so much harder then, and this type of communication that makes weirdness safe is the leader’s responsibility not the employee’s).
Okay, at risk of sounding cringe, it’s things like:
Hi Chloe, some of us were talking about going to St. Barths for the day, would you like to come? As a separate question, would you be willing to help get things ready so we can make it happen before the ferry leaves at X, and possibly be available for some ops tasks throughout the day trip too? Before you answer: I realize it is your day off today, so I wonder if there is a good solution for that? My thought was maybe you can take your day off tomorrow and I pay you overtime to make up for the surprise? I don’t know, does this appeal to you or what do you think?
Hey Chloe, the group of us would really appreciate an Ops lead for today’s trip. But before I ask, I want to clarify that there’s no pressure at all. It’s completely up to you as I bet I can wrangle people to turntake as things come up instead. If you want to take it on though, we can discuss how to make up for your day off or what overtime pay makes sense. Feeling keen or no?
Hi Chloe, asking as a friend, not your boss.. We were thinking of going to St. Barths and we wonder what might be your happy price for helping today? Or do you not even want to be engaged with in this way and want your days off to be sacrosanct? I understand that navigating the social stuff while also being employed by me is probably awkward and I’d like to give you the chance to take the lead and clarify on what feels beneficial, not just passably appropriate, for me to ask you about bonus tasks like this. [hopefully this conversation happened early on but it could happen then if not]
[After any reflective but nonconclusive response] Okay, that makes sense. Hm. I am noticing that I want you to have time to think about it, but then feel conflicted that I am on a deadline to make this St. Barth’s trip happen. So let’s get some quick takes, and if you still aren’t sure, hang back and just enjoy your day to yourself as you planned and as I’ve noticed you like to do :) Sound good? [Okay] Ok, what’s your gut take on what minimizes your expected regret? … And, gut take, what maximizes your expected joy and wellbeing?
[As a friend, relies on a jovial environ Chloe is already included in] Okay everyone, let’s put our heads together to make this St. Barths trip work! Raise your hand if you’re coming and I’ll delegate something to you, you can trade your tasks if you want. Chloe could you chime in if you think I’m missing anything? [Everyone, before they head out: Thanks Chloe, enjoy your day :) ]
[If Chloe helps, with or without bonus pay, give lots of check-ins and thanks throughout the day]
I mean, it would depend on how everybody is/the feel of the group, and how much Chloe was needed Sunday, and how much this is considered personal (make offer out of my pocket/crowdfund out of group’s personal pockets, eg “guys before I ask Chloe to work on her day off is anyone willing to put some money forward for her overtime pay? Let’s get some revealed preferences out in the open as to how much we really want this trip and need help with it) vs professional (okay it can be considered a teambuilding exercise but it forces you the leader to think how important it is compared to next week’s work because she will need more time off).
But I feel pretty confident that people can patchwork something together to make this type of thing feel happy and good. Rationalists get weird looks for speaking in this way and coming up with frank, novel solutions, but honestly it can make all the difference. Of course, you have to sort people out in interviews to make sure there is a cultural fit for this level of flexibility and frankness.
I’m curious what others would think of being approached in such a way. Especially Alice or Chloe but I can understand them not responding
(Edited to try to escape the cringe but probably failed)
Okay but, before I say, I’d like to clarify that I don’t think I’d be perfect at this, which is one reason I’m not leading weird things. But I think if you are gonna make requests like that of employees you live or travel with, you basically have to be. (because it gets so much harder then, and this type of communication that makes weirdness safe is the leader’s responsibility not the employee’s).
Okay, at risk of sounding cringe, it’s things like:
Hi Chloe, some of us were talking about going to St. Barths for the day, would you like to come? As a separate question, would you be willing to help get things ready so we can make it happen before the ferry leaves at X, and possibly be available for some ops tasks throughout the day trip too? Before you answer: I realize it is your day off today, so I wonder if there is a good solution for that? My thought was maybe you can take your day off tomorrow and I pay you overtime to make up for the surprise? I don’t know, does this appeal to you or what do you think?
Hey Chloe, the group of us would really appreciate an Ops lead for today’s trip. But before I ask, I want to clarify that there’s no pressure at all. It’s completely up to you as I bet I can wrangle people to turntake as things come up instead. If you want to take it on though, we can discuss how to make up for your day off or what overtime pay makes sense. Feeling keen or no?
Hi Chloe, asking as a friend, not your boss.. We were thinking of going to St. Barths and we wonder what might be your happy price for helping today? Or do you not even want to be engaged with in this way and want your days off to be sacrosanct? I understand that navigating the social stuff while also being employed by me is probably awkward and I’d like to give you the chance to take the lead and clarify on what feels beneficial, not just passably appropriate, for me to ask you about bonus tasks like this. [hopefully this conversation happened early on but it could happen then if not]
[After any reflective but nonconclusive response] Okay, that makes sense. Hm. I am noticing that I want you to have time to think about it, but then feel conflicted that I am on a deadline to make this St. Barth’s trip happen. So let’s get some quick takes, and if you still aren’t sure, hang back and just enjoy your day to yourself as you planned and as I’ve noticed you like to do :) Sound good? [Okay] Ok, what’s your gut take on what minimizes your expected regret? … And, gut take, what maximizes your expected joy and wellbeing?
[As a friend, relies on a jovial environ Chloe is already included in] Okay everyone, let’s put our heads together to make this St. Barths trip work! Raise your hand if you’re coming and I’ll delegate something to you, you can trade your tasks if you want. Chloe could you chime in if you think I’m missing anything? [Everyone, before they head out: Thanks Chloe, enjoy your day :) ]
[If Chloe helps, with or without bonus pay, give lots of check-ins and thanks throughout the day]
I mean, it would depend on how everybody is/the feel of the group, and how much Chloe was needed Sunday, and how much this is considered personal (make offer out of my pocket/crowdfund out of group’s personal pockets, eg “guys before I ask Chloe to work on her day off is anyone willing to put some money forward for her overtime pay? Let’s get some revealed preferences out in the open as to how much we really want this trip and need help with it) vs professional (okay it can be considered a teambuilding exercise but it forces you the leader to think how important it is compared to next week’s work because she will need more time off).
But I feel pretty confident that people can patchwork something together to make this type of thing feel happy and good. Rationalists get weird looks for speaking in this way and coming up with frank, novel solutions, but honestly it can make all the difference. Of course, you have to sort people out in interviews to make sure there is a cultural fit for this level of flexibility and frankness.
I’m curious what others would think of being approached in such a way. Especially Alice or Chloe but I can understand them not responding
(Edited to try to escape the cringe but probably failed)
Wow that’s pretty darn good nice job