Wow, my previous post must have hit a nerve. I got so many responses, questions and requests for deep dive — it’s definitely a topic you care about, so I am going to dedicate a few posts for Q&A on this topic. Feel free to send additional questions my way.

One common question I got was:

Product strategy is great, but it takes time to complete. What should I do when my CEO wants the features and timeline shortly after making the request?

That’s a real challenge I’m sure many of you are facing.

5-Step Approach to Remaining Strategic Under Time Pressure

1. Understand what they need exactly, by when and why

A great way to learn it 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

that 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.

Do make sure you leave the room (or the written conversation) with a general understanding of where they want to take it and what their logic is behind the 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, which 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 the 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 — 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 to 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 order-of-magnitude of the feature — is it a 1-month delivery 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 to yourself everything you have learned so far (a deeper dive into what needs to be included in a product strategy in a future post).

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 — 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, 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!