You know the drill. The CEO shares a new idea, something they just heard from a customer, an investor, or maybe it came to them in the shower. It’s vague, but they’re excited. They tell you it’s important and then ask for a detailed plan or delivery estimate by the end of the day. You haven’t even had time to understand what they’re asking for, let alone think it through. But the expectation is clear: move fast and make it smart.

It’s an unfair ask. But it’s also part of the job.

As a product leader, your role is to bring clarity to messy situations. But that’s hard to do when you’re being pressured for answers before you even know what problem you’re solving. The challenge isn’t just the time pressure. It’s how quickly urgency can push you into the details and leave the bigger picture untackled. You want to be helpful. You don’t want to come off as resistant. You want to deliver results. So you start typing. 

You might be making assumptions, but most likely, you don’t even allow yourself to do that. Most people go directly into the tangible outcomes. A plan, a screen, feature design. And just like that, you’re no longer thinking strategically.

This dynamic is common, especially in fast-moving startups or when trust is still being built between you and the CEO. But obviously, you would be doing both yourself and the company a bad service this way. If you want to be seen as a strategic partner, you can’t just react. You need a way to hold onto your product thinking, even when you’re being put on the spot.

Here’s a five-step approach I’ve found helpful for staying strategic under pressure. It’s designed for those moments when you don’t have time for a perfect process but still need to give a good answer.

1. Understand What They Need Exactly, by When and Why

A great way to learn what is truly needed is to ask for additional context. It is very different if they heard this idea somewhere and want you to add it to your backlog, vs. if they need to commit on a plan to the board or to a customer.

Let them know that you are on it before you start asking questions.

This puts your follow-up questions in the right context and reduces (however does not completely eliminate) the chances that the CEO will see your questions as push back.

2. Ask Clarifying Questions

Help them take their thoughts to the next level of detail.

You can say things like, “I want to make sure we are aligned, and I fully understand where you are coming from .  I’m assuming our goal with it is X, is that right?”

Another example is, “So you are assuming that if we do X, Y will happen, right?”

It does require you to think quickly about the bigger picture ,  which is a skill that develops with practice. Don’t give yourself a hard time if it’s not perfect on the first attempt. But don’t give up, either.

Make sure you leave the room (or the written conversation) with a general understanding of where they want to take it and what the logic is behind their idea.

Note: not all CEOs like to share their logic, and not everyone’s logic is intact. But they all do have a reason for asking you to do things, one that makes sense to them. It’s your job to figure it out.

3. Set Expectations and Provide an ETA for a Plan

You should already know from step #1 what they need and generally when. If you feel you can do it, say it (“I’ll have a draft ready in 2 days”).

If there’s a gap, it is even more important that you raise it at this point. It is much better to say, “I need about a week to put together a decent plan,” and negotiate the timeline or scope of work than to avoid conflict and miss the deadline (real or not).

Explain what you are going to do with the time you are taking, or they might assume you are just not making it a priority. You and I know you have some real work to do in order to come up with what they need from you. Assume they don’t know  and  help them understand it.

If they insist on having something before you can be ready (which typically means there is an external constraint they need to adhere to), say what you CAN do in this timeline. Try to help them get what they need while explaining what they can and cannot expect from such a plan.

This discussion is very important and oftentimes yields good enough solutions which can both satisfy what the CEO needs right away and give you the time to do good product work afterward.

For example, you might learn that for the decision they need to make, what they really need to know is the order-of-magnitude of the feature  –  is it a 1-month effort or 1-year? You need much less information to give them this kind of answer than an actual plan.

4. Build to Yourself a Very Rough Product Strategy Quickly

It can be a few paragraphs outlining your thoughts and organizing everything you have learned so far (you can find key elements to be included in a product strategy here).

As part of this draft, keep a list of open questions. You’ll probably have many at this point, some more fundamental than others.

You will not be able to close all the details in this one-pager, let alone align everyone on it quickly, but it is important that it makes sense to you, at least at a high level.

Ask yourself if it sounds plausible. You will undoubtedly have gaps in the story at this point, but you should distinguish between first and second-order gaps –  ones that tear the whole story apart vs. ones that are more likely to be resolved one way or the other later.

If you have first-order questions at this point, go back to step #2. For second-order questions, it’s enough to only list them in the doc for now.

This is a good place to practice making decisions under uncertainty. If this skill doesn’t come naturally to you, and you prefer deciding only with complete knowledge, it only means  you need to make yourself comfortable in deciding without perfect knowledge.

If this skill comes too naturally to you, and you feel very comfortable making decisions without fully considering the implications, force yourself to create some clarity in this highly uncertain world and dive just a little deeper than you tend to before making the decision.

5. Provide an Initial Plan

Based on the very rough product strategy, create a draft plan and explain that you are diving deeper into it, so the plan might change when you learn new things.

It is imperative that the CEO gets a plan in a timely manner, and understands which assumptions you made when building it. Otherwise, they feel (unfortunately) that nothing is happening, despite the hard work you are putting into it.

Try this approach and let me know how it works for you, and don’t forget to keep sending the questions you want me to answer!