Plan Critique Assistant
Budget: $3 – $4 USD
I am looking for a Google Meet-based personal assistant to assist with my plan writing on most days. Plans usually fail because their details are not fully thought through, not enough questions are asked, not enough negative scenarios are considered, and priorities are not clearly defined. A good plan should address all possible scenarios, set clear priorities, and verify every detail against actual documents, for example, confirming deadlines and proof.
The assistant should raise as many comments and doubts as possible on every part of the document. Hence, the goal is to play devil's advocate here. The goal is "not" to confirm me or say "such a great plan!" The goal is almost the reverse! looking for flaws everywhere and being as critical as possible (while remaining polite). It is 100% okay to say, "I don't think the plan works." With that said, the main goal is not to reach any conclusion; that is mostly my job. The main goal is to ensure the plan is well thought out and that all details are considered. Hence, as far as I can tell, the goal is rarely to ask you whether you think it is a "good" or "bad" plan. Your goal is to make sure I'm looking at everything objectively and accurately. The simplest things are: If I'm saying a deadline is, for example, April 30th, where is the proof? Or if I'm saying I'll get my card by a certain date, you should help me explain why that is the case (for example, how long it takes to produce the card, and how long it takes to deliver it). With that said, the goal is not always to present evidence for "everything". I might say it takes 1 to 2 weeks for the card to arrive. You may ask, "How do you know that?" I might say, "I've read it somewhere, " and for now, we will assume this is correct, and at some point, we will get back to proving. In this example, you helped pinpoint the source of the claim, which in that case was my own memory rather than a document. Also, an initial document might be preliminary, and there might be many placeholders (i.e., []) for us to come back to later. For example, we might have a plan on what to do depending on when my work permit arrives. One possibility is that the work permit might arrive with a 3-year delay! Instead of thinking initially about what to do in that case, we might say: "This is so improbable, we will think about it later," or just write "plan TBD (To be discussed later)." Generally, the best tone is a neutral or welcoming/kind tone, but detail-oriented and not-afraid-to-ask type at the same time.
As said, I am looking for a Google Meet-based personal assistant to assist with my plan writing on most days. We have to figure out the exact time and days, but for now, 10:45-11:45 AM CST (8:45 PM-9:45 PM Pakistan time) should be good. Generally, the timing will be somewhere between 9:30 AM and later CST (US Central Time). Any changes should be coordinated, and there will be no penalty or expectation for cancelling or declining a meeting time. If your schedule is different, just let me know which days do not work for you and propose alternative times. Each meeting will be on Google Meet with a fixed meeting ID. You should be able to join with your video on at all times. Also, either party can cancel a meeting in advance without penalty due to travel, sickness, or any other reason, though it is not ideal to cancel meetings frequently. The frequency of meetings might change over time, depending on my work situation and the number of plans. If a schedule change is needed, both parties can discuss possible options. Either party may end the contract at any time without penalty. During the meeting, AI mode must be off. For part of the meeting, I will share my screen, and in other parts, I will unshare. We will both work on the same Google Docs in the same meeting, so you should be comfortable with Google Docs and have a laptop to edit the documents and keep your video on. At any time in the meeting, I may ask you to check or write something, or just give comments. You should be proactive in asking questions and figuring out flaws in a plan. You can do it either by asking (preferred) or by leaving comments. I may also send a PDF or a document related to the plan for review (a contract I'm signing or anything else). You should have a working email address to receive PDFs or links, though many will be shared via Google Meet. When doing tasks, you should never use AI to write. Using a spelling software like Grammarly is okay. Using AI for grammar edits might also be acceptable only if it is used solely for grammar checking, not for rewriting; AI that rewrites is prohibited. Because almost everything will be very personal and sensitive, it is very important to take privacy seriously. You should not share any personal information about me, including my name, with anyone, including but not limited to your partner, siblings, children, friends, or parents. Either party can cancel the contract at any time without penalty. You should log the time manually. You will be paid only for sessions that actually take place (i.e., realized), not for those that are scheduled but later canceled. That said, if the Client is late, the missed time should be logged. For example, if the scheduled session is 9:30 AM-10:30 AM and the Client joins at 9:40, 1 hour should still be logged. Generally, the time logged should run from when the worker joins until the end of the meeting (if the worker joins earlier than planned, it should not log that time). If, for example, a worker joins at 9:35 and the meeting ends at 10:55, then 1 hour and 20 minutes should be logged. Upwork allows 10-minute intervals; use the higher amount. Hence, if the meeting was 1 hour and 7 minutes, just log 1 hour and 10 minutes. The only exception is when one minute has passed. In that case, just save the extra minute for later and add it to the next session. For anything above 1 minute, log it as 10 minutes.
Also, if the Client just doesn't show up (without cancelling in advance), the one hour should be logged as well.
There should be no use of AI due to privacy concerns and, most importantly, because AI responses tend to be long, generic, and may miss details specific to my case. No sentence in your comments should be written by AI. Typos are fine as long as the meaning is clear. You should also be familiar with the comment feature in Google Docs.
Example:
Plan for continuation of health insurance
-Deadline for them to receive: March
-Usual mail delays
-What should be filled out?
-Is it electronic or by mail?
These will be written in a shared Google Doc. The assistant’s role is to be very critical, questioning, and curious. Comments should challenge the plan, for example, “How do you know the deadline is in March? Do you have proof?” “What if the mail delay is longer?” “How do you know only one form is needed? Can you share it?”
A challenge of this job is commenting based on partial information and limited knowledge of specific topics, such as specialized talks. You should still be comfortable and good at giving comments and generating ideas. The goal is not to enforce deadlines or act on plans, but to help build strong plan documents. All responses or proposals should be brief, no more than two paragraphs, and not AI-written. Typos are acceptable.
Privacy and Confidentiality
All documents, Google Docs, and personal information are highly sensitive and confidential. You may not discuss any content with anyone, including partner, spouse, family, friends, counselor, or anyone else. The contents are extremely personal, and you will be responsible for any damages caused by a confidentiality breach.
Ending the Contract
Either party may end the contract at any time without penalties or fees.
The assistant should raise as many comments and doubts as possible on every part of the document. Hence, the goal is to play devil's advocate here. The goal is "not" to confirm me or say "such a great plan!" The goal is almost the reverse! looking for flaws everywhere and being as critical as possible (while remaining polite). It is 100% okay to say, "I don't think the plan works." With that said, the main goal is not to reach any conclusion; that is mostly my job. The main goal is to ensure the plan is well thought out and that all details are considered. Hence, as far as I can tell, the goal is rarely to ask you whether you think it is a "good" or "bad" plan. Your goal is to make sure I'm looking at everything objectively and accurately. The simplest things are: If I'm saying a deadline is, for example, April 30th, where is the proof? Or if I'm saying I'll get my card by a certain date, you should help me explain why that is the case (for example, how long it takes to produce the card, and how long it takes to deliver it). With that said, the goal is not always to present evidence for "everything". I might say it takes 1 to 2 weeks for the card to arrive. You may ask, "How do you know that?" I might say, "I've read it somewhere, " and for now, we will assume this is correct, and at some point, we will get back to proving. In this example, you helped pinpoint the source of the claim, which in that case was my own memory rather than a document. Also, an initial document might be preliminary, and there might be many placeholders (i.e., []) for us to come back to later. For example, we might have a plan on what to do depending on when my work permit arrives. One possibility is that the work permit might arrive with a 3-year delay! Instead of thinking initially about what to do in that case, we might say: "This is so improbable, we will think about it later," or just write "plan TBD (To be discussed later)." Generally, the best tone is a neutral or welcoming/kind tone, but detail-oriented and not-afraid-to-ask type at the same time.
As said, I am looking for a Google Meet-based personal assistant to assist with my plan writing on most days. We have to figure out the exact time and days, but for now, 10:45-11:45 AM CST (8:45 PM-9:45 PM Pakistan time) should be good. Generally, the timing will be somewhere between 9:30 AM and later CST (US Central Time). Any changes should be coordinated, and there will be no penalty or expectation for cancelling or declining a meeting time. If your schedule is different, just let me know which days do not work for you and propose alternative times. Each meeting will be on Google Meet with a fixed meeting ID. You should be able to join with your video on at all times. Also, either party can cancel a meeting in advance without penalty due to travel, sickness, or any other reason, though it is not ideal to cancel meetings frequently. The frequency of meetings might change over time, depending on my work situation and the number of plans. If a schedule change is needed, both parties can discuss possible options. Either party may end the contract at any time without penalty. During the meeting, AI mode must be off. For part of the meeting, I will share my screen, and in other parts, I will unshare. We will both work on the same Google Docs in the same meeting, so you should be comfortable with Google Docs and have a laptop to edit the documents and keep your video on. At any time in the meeting, I may ask you to check or write something, or just give comments. You should be proactive in asking questions and figuring out flaws in a plan. You can do it either by asking (preferred) or by leaving comments. I may also send a PDF or a document related to the plan for review (a contract I'm signing or anything else). You should have a working email address to receive PDFs or links, though many will be shared via Google Meet. When doing tasks, you should never use AI to write. Using a spelling software like Grammarly is okay. Using AI for grammar edits might also be acceptable only if it is used solely for grammar checking, not for rewriting; AI that rewrites is prohibited. Because almost everything will be very personal and sensitive, it is very important to take privacy seriously. You should not share any personal information about me, including my name, with anyone, including but not limited to your partner, siblings, children, friends, or parents. Either party can cancel the contract at any time without penalty. You should log the time manually. You will be paid only for sessions that actually take place (i.e., realized), not for those that are scheduled but later canceled. That said, if the Client is late, the missed time should be logged. For example, if the scheduled session is 9:30 AM-10:30 AM and the Client joins at 9:40, 1 hour should still be logged. Generally, the time logged should run from when the worker joins until the end of the meeting (if the worker joins earlier than planned, it should not log that time). If, for example, a worker joins at 9:35 and the meeting ends at 10:55, then 1 hour and 20 minutes should be logged. Upwork allows 10-minute intervals; use the higher amount. Hence, if the meeting was 1 hour and 7 minutes, just log 1 hour and 10 minutes. The only exception is when one minute has passed. In that case, just save the extra minute for later and add it to the next session. For anything above 1 minute, log it as 10 minutes.
Also, if the Client just doesn't show up (without cancelling in advance), the one hour should be logged as well.
There should be no use of AI due to privacy concerns and, most importantly, because AI responses tend to be long, generic, and may miss details specific to my case. No sentence in your comments should be written by AI. Typos are fine as long as the meaning is clear. You should also be familiar with the comment feature in Google Docs.
Example:
Plan for continuation of health insurance
-Deadline for them to receive: March
-Usual mail delays
-What should be filled out?
-Is it electronic or by mail?
These will be written in a shared Google Doc. The assistant’s role is to be very critical, questioning, and curious. Comments should challenge the plan, for example, “How do you know the deadline is in March? Do you have proof?” “What if the mail delay is longer?” “How do you know only one form is needed? Can you share it?”
A challenge of this job is commenting based on partial information and limited knowledge of specific topics, such as specialized talks. You should still be comfortable and good at giving comments and generating ideas. The goal is not to enforce deadlines or act on plans, but to help build strong plan documents. All responses or proposals should be brief, no more than two paragraphs, and not AI-written. Typos are acceptable.
Privacy and Confidentiality
All documents, Google Docs, and personal information are highly sensitive and confidential. You may not discuss any content with anyone, including partner, spouse, family, friends, counselor, or anyone else. The contents are extremely personal, and you will be responsible for any damages caused by a confidentiality breach.
Ending the Contract
Either party may end the contract at any time without penalties or fees.