Estimating Features: options, context and God

“We need to support registration in the application. Here are some details, how many days to develop?” — Where should you start from? Should you simply throw a number? Maybe read it first and use your gut feeling, your experience? Is there a trap here? Although there are no recipes for estimating successfully™, I want to elaborate on the options in front of us, before we dig into the details.

Guesstimate everything months in advance by 20 seconds of thought

If you are able to read a Feature specification and give estimation based on “whatever works for you”, you win! For small features this should probably be as simple as pie, but what about the big ones? Still easy?

“We have someone who can do it with some sort of dark magic ball !”

I call him (or her) God. If you have God in your company, you win!

(1) Estimate by detailed breakdown

Giving proper estimation without feeling bad about it 10 seconds later is not cheap. I don’t care how much experience you have. So, are you ready to invest? You should not only consider coding effort, but also organization time – testing, deployment, monitoring, bug fixing etc. After you have this in mind, did you consider risks? What about 3rd party integration? What about inexperienced developer who might work on this feature?

One way to provide detailed estimation is by actually doing the Design (of the solution) and bring one to the table; This means doing a Design Review with your peers, break the feature into tasks, estimate hours needed per task and give very solid numbers. You can do it by yourself, you can do it with others; the price is not 20 seconds, but this is highly useful for solid estimation.

Wait, Context is king!

Before you start throwing numbers into the air or diving into an expensive design to come up with estimation, what is expected of you?

1. Purpose – how your estimation is going to be used? To determine roadmap? To understand feasibility? For prioritization between 2 Features? Each might require different “estimation plan”

2. Size – is it good enough to say “it’s a big feature” or maybe “it’s around 20-40 days” or maybe “it’s 24 hours”?

Back to your options list

Well, you could estimate by detailed breakdown, if you really need low granularity. Sometimes, rough estimations might be enough. What now?

(2) Estimate by personal hunch

You can obviously estimate based on your personal hunch, taking into consideration organization time, risks and what not. In many cases, assuming you’ve got enough “gut feeling” built by your sheer experience, this should suffice to build roadmap or understand feasibility. If this is the expectation, it’s probably the cheapest way to provide numbers.

(3) Estimate by collective hunch

You can improve (or at least feel more confident) granularity by adding one or more experienced teammates into the mix, double-checking your hunches and forming a collective hunch.

(4) Estimate by team hunch

Again, more people involved might mean better estimation, due to larger feedback. There is the obvious risk of “2 people, 3 opinions”, but at least you’ll have some other, non imaginary, voices of sense.

What does it all mean?

Each method offers some advantages and suffers from some inner faults. Understand the context and pick wisely. Accept the fact that things change and features might be thrown away – do not waste time on estimation more than is really required. More about features estimation to follow…


Planning your Sprint

With a given time window and people, how much can you pull off?

Many managers are requested to offer a plan. Knowing how much you can actually deliver is one of the toughest question managers need to face with. It’s too elusive to measure it correctly, and there are many moving parts. You need to please your customers and your teammates, creating a plan to deliver external and internal value, picking wisely what is really feasible.

I tried to come up with a few tips to make this process a bit more structured, making it less elusive, less daunting and less “we’ll see as we go”:

1. Pick by External Priority – what will make your customers happy? Make sure you have the right priority from product / business teams and give it high consideration in your planning. At the end of the day, you are here to provide value to your customers.

2. Pick by Internal Priority – making sure you are building confidence as part of your Sprint. You want to excel over time, you must devote the time to allow it.

3. Pick by Features Size – try to see how many features of each size you can deliver in a Sprint. For example, after 2-3 Sprints, you might notice that you’re usually able to do X big features, Y medium features and Z small features. Usually there is a connection between feature size and QA effort or deployment effort, thus making this size estimation very useful.

4. Pick by Velocity – if you know you’re able to complete X Story Points (or Ideal Days) every sprint, based on your last 2-3 Sprints, use this information to pick Features to fit this number give or take. I always believe that you should aim for ~120%, to allow positive pressure which encourages self-improvement ideas, but don’t aim for failure or naïve success. There is nothing to gain there.

5. Pick by Personal Growth – you might pick some features to allow inner growth in your team. For example, you might notice a need to strengthen one of your teammate’s leadership skills by allowing her/him to lead bigger features. It doesn’t mean you should act naively; organization needs is more important than personal whims, but the organization will never actively push toward personal growth as a goal. It’s up to you to make time for it.



You probably meant to write mail but the keyboard fooled you; but hey! you can read about leadership, development and coding instead of reading your emails! What a win!

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Visibility over Progress

After talking quite a bit about how to break a Feature into tasks and avoiding leftovers, I would like to address the natural habit of what I call “blindly moving forward”. How often do you find yourself after 3 days of coding, still unclear of how many days are left or whether or not you’re closer to the end? How often you tend to forget what exactly you originally meant by “the end”? How often you find yourself feeling too invested to stop and figure out what the hack is going on?

We are, naturally, very outcome oriented. “I need this Feature done until tomorrow” or “I need to see your plans for next Sprint until end of day” keep pushing us during our daily effort. We are driven to supply outcomes, losing the ability to track the big picture because of vast, ever growing demand for results. Just like multi-threading coding, it’s not enough to throw some languages, tools or IDE with cool debugging options to the mix; we need to change the way we think and act, to supply visibility rather than mere progress.

When breaking a Feature, ask yourself these questions:

  1. Do you fully understand the Feature business value?
  2. Do you have Risks mapping (what can go wrong and what to do on such case)?
  3. Do you have the right people in-sync? (QA, Operations or other relevant team members)
  4. Do you break the Features by layers or by verticals? Are you OK with that?
  5. Do you have low granularity of tasks (up to 3-4 hours)? Enough to make you feel good about “no surprises”? Enough to allow others to join you?
  6. Do you know when you’ll be code-ready? Can you commit to a date?

As a Team leader, you should ask for visibility from your teammates. They should earn your confidence by offering a complete plan, knowing what the expected outcome is and communicate their status during the development time. If you ask me, I will always prefer better understanding of current status over naïve “I managed to progress today”.

As a developer, you should aspire for complete visibility to make sure you’re moving in the right path. This will allow others to give you honest feedback, join you if you’re a bit behind schedule and practice leadership in a way that is building confidence in your organization: people will feel that you know what you’re doing and will trust your good judgment and commitments. They will feel more confident when you’re behind the wheel.

If you feel that this is an overhead, you probably in a misconception of the time it will take you versus the time it will save you. Answering the above shouldn’t take 5 days; it should take couple of hours. This will ease your mind regarding “did I miss something?”, saving you hours of juggling between building confidence with your manager(“Can you update your progress?”, “Where are you standing?”) and actually building the software.