Since I have become the Lead Developer at Kidiyo, estimating has become an exciting and critical challenge. It’s no longer about getting the right number but about getting the best out of everyone and get it done as efficiently and predictably as possible.

Estimating a piece of work is tough. Various factors taint our ability to provide an honest and thought-through estimation.

Peer pressure
If you give the highest estimation, you are not good, fast or experienced enough. If, on the other hand, you estimate less than the others, it’s because you have no idea of how complex that piece of work, i.e, you are the optimistic ignorant. Or you are just the ultimate speed ninja that puts everyone to shame.

Ego
Our natural need to be important triggers in us the will to defy the impossible. We want to be that guy who finished before time and who got that hairy bug fixed in a blink of an eye.

Intimidation
Having a high figure demanding a feature in half of the reasonable time it would take to get it (well) done, never made room for better estimations. Despite it being your responsibility to negotiate that deadline at the light of your perspective and experience, it still affects you.

The (bad) habit of working extra time
Getting things done after hours is, unfortunately, a common practice. Not only does it exhaust you and makes you less productive when you are most expected to, working extra time taints how you see the actual difference between your original estimation and the true effort and time spent.

Why it matters

Identifying and realising the factors that affect our ability to estimate well is great, but understanding why estimating matters in the first place is fundamental.

Trust
As pointed out above, estimating involves personal matters. Growing in such a way where you can provide a professional estimation, despite all it takes, will make you earn the trust and respect from your peers, your followers, and your leaders.

Self-improvement
Have you ever had a colleague that said “oh, that takes 3 hours, at most”, that ended up spending a few days on it? Judgments apart, no one wants to be that guy. You want to be able to say “alright, I see this taking 7 hours” and see that occurring. You want to be aware of the reality of the work you have at hand, as well as your shortcomings. By doing so, you can start learning how to overcome them.

Planning
We work in teams, and teams need to plan. To plan, you need to trust one another to know how much you can handle and complete. The better the estimations, the less unnecessary stress and quality loss you will experience.

How I do it

The way I estimate work and make sure I deliver it, depends on what is the scale I am dealing with. Whether we are talking about a single issue, a day, a sprint or a quarter, this is how I go about getting a better estimation.

For a day

To better perceive the effort some piece of work takes, I allocate every single unit of work in my calendar. It turns out to be the simplest and quickest way to get a more realistic view of the feasibility of my estimations. Treating time as a resource is the key here, and we often forgot to do that.

For a sprint

When estimating how much you or your team can get done in a sprint, as a rule of thumb, experiment with doubling each original estimation. If it’s way off the available hours the whole team can put up with, you know it’s time to decrease the workload. Doubling or even tripling an estimation has proven to be precise, so if you’ve got to start there, you know it’s an excellent place to start.

For a quarter

For more extended periods of time, a technic I use to avoid underestimating is to only consider 4 to 5 hours of work available to work a day. It is far from being sensible. Meetings, tiredness, casual talking, coffee breaks, etc., all take a considerable amount of our time every day. Spending around 4 hours a day in deep work mode is a luxury for most of us.

In sum

Serve your team before yourself. Putting the business in jeopardy to try to look like a champion is nonsense. Embrace introspection and improve on what keeps you from living out to the thoughtful estimations you give. At last, keep in mind that over/early delivering is better than under/late delivering.