Monday, October 6, 2025

The Time Trap

 


Your time estimates are wrong.  Don’t try to fix them.


Yeah, I said that.


I have been part of millions of planning meetings. I have seen thousands of project plans. The time estimates in them are all wrong.


All of them.


Instead of spending time coming up with a very precise estimate for how long it will take to build a feature, spend about five minutes working with engineering to figure out if the feature is "Large", "Medium" or "Small" (otherwise known as T-shirt sizing) Define those terms by talking about the number of sprints required to get them done.   You’re still wrong, but you didn’t waste days or weeks coming up with the wrong estimate. 


For example:


Small = 1-2 sprints

Medium = 3-9 sprints

Large = 10 or more sprints


Once you accept that the estimate is wrong, you can move on to planning with uncertainty.  When you stack rank, you know that "Small" things at the top of the stack will likely ship this quarter but not definitely. Similarly, "Large" items at the bottom of the stack aren't shipping any time soon. This drives your roadmap. Estimate by quarter how much work you will get in those chunks based on stack rank.  Of course, smaller chunks are better than larger chunks.  If possible, take a look at the large items and see if you can break them down further.  The smaller the chunk, the more accurate your estimate will be.


Is your estimate correct? No, it is not.


If you spend weeks developing a time estimate, will it be correct? No, it will not be correct.


Is it possible to be 100% correct in your estimate? No.


So, instead of investing a lot of time, take a quick stab at it, base your estimates on some objective reality and move on. It's wrong, but that's OK. The broad estimates can still give you an idea of how many things on the roadmap will be accomplished in a quarter.  The reality is that you are way better off just accepting this level of uncertainty than trying to get to a “correct” answer that you likely will never find.  For a PM, this discussion is usually driven by roadmap.  Your execs want to know when a certain feature will ship.  Don’t make the mistake of committing your product team to a specific ship date for a feature under development.  PM doesn’t commit to shipping deadlines.  Only engineering can ship a feature.  Let them answer the “when” question.


What you want to do is be very transparent about your stack rank and the size and complexity of features. Small features with low risk and high priority should show up soon. If they don't, there is something wrong. Focus on that.  This type of discussion can inform your leadership of what you’re working on and why and give them a view of where the effort and risk is. That’s what they really need to know.


What you should be presenting instead:


  1. A good stack rank. Is eng executing against the stack rank? If not, stop. Until you agree with eng on stack rank, nothing else matters.

  2. A good view of complexity. Are "easy" features really easy? If eng says "piece of cake" do you get the feature quickly? If not, stop. If you don't have a good view of complexity and risk, you cannot estimate with any accuracy.

  3. A VERY VERY rough idea of time. It's way more important to know that X comes before Y. If you say X is six weeks out and it ships in eight weeks, does it matter? Not really. If you tell sales that Y is "THE MOST IMPORTANT THING ON OUR ROADMAP" but you don't ship it? You have a problem.


If you have those three things, you can build a roadmap and get leadership buy-in. 


I’ve said this before, but it bears repeating.  There are really only two things that distinguish a good product team from a poor product team.  Those are quality and velocity.  If you are executing with a high degree of quality at a high velocity, your odds of success are much higher than if you are operating with low quality and/or low velocity.  As a product management leader, quality and velocity should be the two things you focus on the most.  What you should not do is try to manage velocity with deadlines.  Artificially setting dates simply lowers quality and doesn’t really address the underlying velocity problem you’re trying to solve.  



Do You Have a Solution in Search of a Problem?

 


Do You Have a Solution In Search of a Problem?


When working with product teams, I often find that they’re working in one of these modes:


They have a problem and are looking for a solution.


Or


They have a solution and are looking for a problem.


As product managers (PMs) we are supposed to be focused on customers and their problems.  However, it’s not uncommon to find product teams that start with a solution and then look for problems that their solution solves.


That’s not a great place to be.


First of all, if you already have a solution in mind, that drives the discussion.  There is a reason why “if all you have is a hammer, the whole world looks like a nail” is such a common phrase.  It’s just human nature to try and make what you have work.  In product management circles, we tend to use the term confirmation bias but it’s the same idea.  If I go into a customer meeting with something specific to sell, I can usually find reasons why the customer needs that thing.  Which is fine, if you’re in sales.


However, if you’re trying to decide what to build, that’s the worst thing possible.  All you’re doing is selling the thing you already have.  That may or may not mean that you have the thing the customer really needs.


On the other hand, if you walk into the meeting looking for problems, you are now open to whatever the customer has to tell you.  I have spent the majority of my career working on enterprise-class software, so other areas may be different, but I can tell you that enterprise customers are more than happy to tell you their problems.  However, most enterprise software companies are not really listening.  What you see all the time is product teams trying to sell what they have on the truck instead of trying to figure out what the customer really needs.


And that’s a shame.


Here are some symptoms of solutions looking for problems:


  1. Engineering builds a prototype that you didn’t ask for.  It’s pretty common for high-performing engineering teams to come to you with great ideas.  Sometimes those ideas are truly amazing and you learn things.  However, most times, these solutions aren’t actually aligned to customer requirements.  Now you have an amazing idea and you go around trying to figure out how to use it.

  2. Leadership “vision” is divorced from customer reality.  If senior leadership is driving the roadmap, it’s common for the roadmap to  become divorced from customer requirements.  Good leadership will listen to the field and adjust based on what they hear.  Yes, you need to have a strong product vision. No, you should not ignore what customers are telling you.

  3. New ideas for customer problems to be solved are automatically quashed.  Yes, I admit I have done this.  If you are leading a product team with very tough goals, you have to remain focused.  Sometimes that means quashing or ignoring customer requirements.  All I can say is, know you’re doing this and do it on purpose if you need to do it.  You can get away with this for a while, but there are limits.

  4. PMs are not meeting directly with customers.  Several times in my career I’ve been told by sales that I don’t need to talk to the customer—that sales will tell me what the customer wants.  With all due respect, that’s not acceptable.  PM needs to speak to customers DIRECTLY and regularly.  Without direct contact, PM will make poor decisions.


So, what is a PM leader to do about all this?  How can you shift gears and move away from solutions and towards problems?


  1. Prioritize quality customer time.  I cannot emphasize enough how vital this is.  Unless you are talking directly to customers in relatively unstructured settings, you simply do not know what they want.  Spend the time.  Focus on their needs.  Ask questions.

  2. Put customers first.  When meeting with customers, always make time to discuss their issues and ask about their problems..  I have been in hundreds of customer meetings where I am expected to go over the roadmap in detail in just thirty minutes.  That just isn’t enough time.  I need at least fifteen minutes to ask questions.  Therefore, my minimum customer meeting is an hour.  More is better.  

  3. Focus on why.  When sales (or anyone else) says that customers want X, always ask “why do they want X?”  You need to dig down into the underlying customer needs to really understand the requirements and develop a solution to the actual problem.

  4. Have strong opinions, loosely held.  This phrase always stands out in my mind as the definition of PM.  As a PM I have to be very firm in my opinion.  I have to have a reason for it.  I must be able to defend it.  On the other hand, I have to be willing to abandon my position given evidence that it’s wrong.  I can’t fall in love with my own plan.


As usual, when we get off track it’s because we forget why we are here.  As a PM team, our only job is to make the product better by serving the customer.  We don’t do that through surface interaction.  When I joined Splunk many years ago, I adopted a huge (1000+ user stories) backlog of “customer requirements” that the team had been working on.   The first thing I did is insist that I meet directly with customers who had these problems.  Every time I talked to one of these customers, I learned something.  The product got better as a result.  The PM is not a feature vending machine where you put requirements in and get features out.  The only true measure of a successful product is customer adoption.  If the customer likes and uses the feature, it’s a good feature, full stop.