This article focuses on a simple technique that helps you prepare for situations where you don’t know how someone will respond — asking a friend for a loan, or asking your boss for a raise.
Asking “What if?” ahead of time helps you make better decisions and walk into a conversation prepared instead of just reacting.
This isn’t just a personal trick. A large analysis covering 642 independent studies found that thinking through “if this happens, then I’ll do this” plans in advance measurably improves how often people follow through and reach their goals, across a wide range of situations.
Let’s look at a couple of scenarios.
Scenario One:
You’ll just walk up to your boss and ask for a raise.
You: Can we talk for a moment?
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Your boss: What’s on your mind?
You: Well, I have been here for over a year, and I think I deserve a raise.
Your boss: Why do you think you deserve a raise?
You: Um, I think I am doing a good job.
Your boss: Give me an example.
You: Well, I am trying harder, and I am doing better.
Your Boss: I’m sorry; I don’t see much of a difference.
You: I think I have improved a lot since I started.
Your Boss: Give me an example.
You have a blank expression on your face for 10 seconds.
Your Boss: We can revisit this during the next review period, but I need to see something from you that merits a raise.
Scenario Two:
You will ask your boss for a raise and use the “What if” method.
What if my boss asks, “Why do you deserve a raise?”
I’ll say I have increased my workload by 28% since I started, and I’ll provide examples. Plus, I have never missed a day of work. I worked extra hard on the financial reports we talked about doing every month.
What if my boss asks how much I want?
I’ll say that 5% would be excellent, but I’m willing to negotiate, so it’s a win-win outcome.
What if my boss tells me there is no room in the budget?
I know the budget must be tight, but at the same time, I have financial responsibilities that are becoming tougher to handle. Isn’t there something you can do? It would help me focus more on my work than on my finances.
What if my boss tells me to wait for the next pay review then we will look at it?
I can say, “Okay. I will wait, but can we talk about how much of a raise I can expect? I don’t want to plan for a raise and not get one.”
What if my boss tells me that I’m underperforming and that doesn’t merit a raise?
I will prepare all the tasks I have been doing and ask my boss to help me by identifying the areas where I’m underperforming and how I can improve.
What if my boss tells me, “I can’t authorize that because of upper management”?
I’ll say, “What if I take on more duties? Will that justify a raise?”
Scenario two shows a real improvement. My chances of getting a raise go up because I prepared and thought through what my boss might say. I built a series of “what if” questions about what might happen, and I came up with a response for each one.
Researchers have tested this same kind of preparation in real negotiations, including under difficult conditions where concessions felt harder to make, and found it still helped people reach agreements.
Here are a few other examples of situations where you can use this technique:
- You’re about to negotiate a price for a car.
- You need to ask for a loan.
- You have a big meeting coming up to get approval for a project.
- You need to ask for an extended vacation.
- You need to ask one of your employees to take on extra work.
- You need to bring up a complaint to one of your employees.
- You need to tell your boss you have too much responsibility.
When you spend time asking “What if” before any meeting or important conversation, it gives you an advantage. Once it becomes a habit, you don’t need much time — a few minutes is usually enough.
For important, life-changing matters, you can extend the process over a few days, spending half-hour periods on brainstorming. When new ideas come to you, and they will, add them to your list.
Issues you didn’t think about may still come up. But being prepared this way puts you well ahead of not being prepared at all.
Key Points and Facts About the “What If” Method
- The “what if” method means listing the likely questions or objections you’ll face in a conversation, then preparing a calm response for each one before it happens.
- It’s a plain-language version of a psychology technique called “if-then planning.” A meta-analysis of 642 studies found it effective across a wide range of goals, not just workplace conversations.
- It works for both quick conversations (a few minutes of prep) and major decisions (spread prep over several days).
- It’s useful anywhere you’re unsure how the other person will respond: asking for a raise, requesting a loan, pitching a project, or asking an employee to take on more work.
Action Steps for the “What If” Method
Identify the conversation
- Pick the specific conversation or decision you’re preparing for.
- Write down what outcome you’re hoping for.
List the likely pushback
- Write out every question, objection, or reaction the other person might realistically raise.
- Include the uncomfortable ones, not just the easy ones.
Draft a response for each
- For every “what if,” write a short, calm answer.
- Keep answers specific — use real examples or numbers where you can.
Practice out loud
- Say your answers out loud once or twice before the conversation.
- This is what separates scenario one from scenario two above.
Give big decisions more time
- For major decisions, spread your prep over a few days in short sessions.
- Add new “what if” questions as they occur to you.
Checklist for the “What If” Method
- Know what you want
- List your short-term goal for this conversation.
- List what you’d accept as a reasonable outcome if you don’t get everything you want.
- Know your fallback
- Decide what you’ll do if the answer is no.
- Knowing your fallback ahead of time takes the pressure off the conversation itself.
- Think through their side
- List the constraints or concerns the other person likely has (budget, policy, timing).
- Note what they might need to hear to feel comfortable saying yes.
- Write your “what if” questions
- List every likely objection or curveball.
- Draft one calm, specific response for each.
- Confirm you’re ready
- Bring your written “what if” answers with you, not just what’s in your head.
- Double-check you know your fallback if the answer is no.
FAQ: The “What If” Method
Is this just overthinking things?
- No. Overthinking is circling the same worry without a plan. This method is the opposite — you write down specific “what if” questions and a specific answer for each, then you’re done preparing.
How long should I spend preparing?
- For a routine conversation, a few minutes is usually enough once you’re used to the method. For a major decision, spread your prep over a few days in short sessions.
Does this only work for asking for a raise?
- No. It applies to any conversation where you’re unsure how the other person will respond — pitching a project, asking for a loan, negotiating a price, or asking an employee to take on more work.
What if the other person asks something I didn’t prepare for?
- It will happen sometimes. Preparing for the questions you can predict still leaves you in a much stronger position than preparing for none of them.
Further Learning
Courses on LinkedIn Learning Related to Preparing for Difficult Conversations
Courses on Udemy.com Related to Predicting an Outcome
Books from Amazon Related to Predicting an Outcome
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