InfraLoka AcademyPathwayAI
PathwayAI

Module 3 · Ask clearly

AI as a fast new colleague

3 min read6 min readReviewed 26 October 2026

In short

Treat AI like a fast, well-read new colleague: explain clearly, check the result, and stay responsible yourself. It tends to agree with you, so ask for weaknesses outright.

After this lesson you can

  • Use the picture of a fast new colleague to decide how to work with AI
  • Recognise a model's tendency to follow the direction of your question
  • Ask AI to show the weaknesses in your plan, not just agree with it

Terms in this lesson

Understand

Imagine you have a new colleague. They are very fast: in a minute they can draft a letter, summarise ten pages of minutes or come up with five title options. They have read a great deal, so formal letters, reports and tables are familiar to them. But it is their first day. They do not know your office, your manager, the unwritten rules, or what the team tried last month. They also do not remember yesterday's conversation, unless the app keeps a memory or you paste the notes in again.

This is the most useful picture for working with a large language model, the kind of AI that writes text like the chat assistant you use. The picture answers three everyday questions straight away.

First, how much do you need to explain? As much as you would explain to a new colleague on their first day. If you only write "please make a report", a new colleague guesses, and the guess is reasonable but not necessarily what you need. A prompt, the request you write for the AI, needs the goal, who will read the result and the material to use. The next lesson gives the checklist.

Second, how far can you trust the result? The same as a new colleague's work: read it before it goes out. They are fast, but fast is not the same as right. You still answer for the result.

Third, what work is fair to hand over? Work whose result you can check quickly: a first draft, a summary of material you supply, a list of options, another version of something already written. Decisions about money, people or the law stay in your hands.

There is one trait of this new colleague to know from the start: it wants to please. If you ask "this plan is good, right?", it tends to answer "yes, it is good" and add praise. That is not a sign your plan is good. The direction of your question shapes the answer. A colleague who always agrees feels comfortable, but does not help you find the holes before someone else does. In this lesson you learn to spot leading questions, then use the same trait to ask for honest criticism.

Why does a model follow the direction of a question so easily? Models are trained in two big stages. The first makes it good at continuing text. The second, post-training, shapes it into a helpful, polite assistant, partly by rewarding answers people prefer. A side effect is that agreeing answers often feel preferred, so the model leans that way. The full explanation is in the lesson Training and the knowledge cutoff.

In everyday work the tendency shows up in a few ways. A question that already holds its answer, such as "wouldn't it be better to move to the new supplier?", is usually answered in the same direction. If you dispute an answer that was actually right, the model sometimes gives way and apologises. If you write up a plan proudly, the review comes back warm.

The good news is that you can steer the same trait. If you ask the model to act as a reviewer looking for weaknesses, it will look for weaknesses in earnest. There are three keys: ask neutrally, ask for weaknesses and risks explicitly, and rule out praise or an "overall it is good" verdict at the end. Then judge for yourself which criticism makes sense. Not every criticism from the model fits your situation.

Worked example

Before

The prompt

I want to propose replacing our weekly team meeting with a written report through a form every Friday. I think this will save a lot of time. Good idea, right?

What came back

Good idea! Replacing the weekly meeting with a written report can save the team real time. Written reports also leave a tidy record anyone can read at any time. Some other benefits: 1. Team members can fill it in when it suits them. 2. Your manager gets a structured overview. 3. Discussion becomes more focused. This proposal is worth putting forward.

After

The prompt

I will propose to my manager that our weekly team meeting (8 people, 60 minutes every Monday) be replaced by a written report through a form every Friday. My goal: find the weaknesses of this proposal before my manager asks about them. Act as a sceptical colleague. Write the 5 biggest weaknesses or risks, most serious first, one or two sentences each. Then write 3 questions my manager is likely to ask. Do not praise the proposal and do not conclude whether it is good.

What came back

Weaknesses and risks, most serious first: 1. Issues that need a group discussion can wait a week, because a form leaves no room for back-and-forth. 2. Written reports are easy to fill in carelessly. Without someone reading and replying, they soon become an empty routine. 3. New or quiet members lose their only regular chance to be heard. 4. The time saved may move to messages and ad hoc meetings that are more scattered. 5. It is not yet clear who summarises the reports and follows them up. Questions your manager may ask: 1. How will we know when work is stuck? 2. Who reads all the reports, and when? 3. Can we try it for a month first and compare?

What changed

  • "Good idea, right?" steers the answer. The new version asks for weaknesses outright.
  • Real figures (8 people, 60 minutes) make the criticism specific rather than generic.
  • Ruling out praise and a verdict stops the model drifting back to agreement at the end.
  • You still judge the result: weakness 4 may not apply to your team.

Common mistake

Mistake
Writing a question that already contains the answer you hope for, such as "Isn't option A cheaper?"
Why it hurts
The model tends to follow that direction and supply convincing supporting reasons. You feel sure because "the AI agrees too", when you steered the answer yourself. A decision that looks tested has not been tested at all.
Do this instead
Ask neutrally, for example "Compare options A and B on cost and risk", or ask the model to argue for the option you do not favour first, then compare both sides.

Try

You want AI to draft an announcement about new service hours for customers. If you treat the AI as a new colleague on their first day, what matters most?

Sorting card

Sort these questions: leading, or neutral?

  1. What are the three strongest reasons to reject this proposal?

  2. I am sure this schedule is realistic. Can you confirm?

  3. Which part of this report is most likely to confuse the board?

  4. This report is clear enough for the board, isn't it?

  5. Compare the old and new supplier on cost, delivery time and risk.

  6. Wouldn't it be cheaper to move to the new supplier?

6 cards left

Ask AI to test your plan

Works with any AI assistant.

Fill in your parts
For example: moving the paper archive to a shared folder in three months, done by two people
For example: the head of finance

Your prompt

I am preparing the following plan: ‹rencana›. It will be read by ‹pembaca›. My goal is to find its weaknesses before I put it forward. Act as a sceptical reviewer. Write the 5 biggest weaknesses or risks, most serious first, one or two sentences each. Then write 3 hard questions ‹pembaca› might ask. Do not praise the plan and do not conclude whether it is good.

Take home

Working with a fast new colleague

  • I explain the task as I would to a colleague on their first day: goal, reader and material.
  • I ask neutrally, without planting the answer I hope for.
  • For an important plan, I ask for weaknesses and hard questions, not a verdict.
  • I judge the AI's criticism myself, because not all of it fits.
  • I read the result before it goes out, because the responsibility stays with me.

What went wrong for us

How we work

Plans are also judged by an attacker

Context
When planning a feature, we ask AI to judge it from several viewpoints: engineering, strategy, revenue, and an attacker.
What tends to go wrong
A plan judged only by people who want the feature to work tends to miss how it can be abused, such as an agent allowed to run any action.
What it costs if ignored
A dangerous design can reach the build stage and then be costly to undo.
Root cause
We judge ideas from the viewpoint we like.
How we do it
The attacker persona tries to use the feature to delete data, send mass messages or bypass permissions. Its findings become design limits, such as a list of allowed actions and user confirmation.
The rule we keep
Every plan that touches data or automated actions is also judged by an attacker persona before approval.

The lessonAsk AI to attack your plan before someone else does.

What it means for your workBefore you put forward an important plan, ask someone, or the AI, to look for its weaknesses on purpose. People who want a plan to succeed rarely see its holes.