How to Improve your Estimation Skills.

Allen has joined a new product team that is building a digital product for a medium sized company. Allen is a junior software engineer who's still learning the ropes when it comes to building production quality software. His problem solving skills are strong yet his task estimations have been a stressful source of concern.

Kate, A junior designer, shares Allen's feelings toward her own task estimations; "How can someone estimate creative tasks with accuracy?" After all, both Kate and Allen are working in fields that require creativity in design and engineering to push the envelope and address business challenges. There are design patterns, usability studies, and guidelines that are set to give them a guard rail, yet neither Allen nor Kate are satisfied with them when they evaluated the effectiveness of their own estimations.

Kate & Allen's struggle is not atypical. Their struggles have been magnified by the shift towards remote work. Indeed, numerous companies have voiced concerns regarding company culture, domain knowledge transfer, and employee productivity. The lack of a clear change adoption strategy to address the changing team dynamics, and the vilification of change, in itself, have exasperated the challenge for the junior workforce. But, What should Kate & Allen do to navigate these "remote" rough seas when it comes to estimating their work?

The "Crowd Within"

In chapter seven of the book "Noise: A Flaw in Human Judgment", Daniel Kahneman, Olivier Sibony, and Cass R. Sunstein, discuss the research of Edward Vul and Harold Pashler, who wanted to know whether a person can get closer to the truth by joining one's own guesses. Vul and Pashler stated that a person could "gain about 1/10th as much from asking yourself the same question twice as you can from getting a second opinion from someone else."? They have also tried to space out the time between the first and second opinion by a period of 3 weeks. After the three weeks have passed, the gain rose to 1/3 the value of a second opinion. They named this technique, the "crowd within."

Two other researchers, Stefan Herzog and Ralph Hertwig, conducted a, similar but slightly different, research in which participants where to produce 2 estimates, but they had to do it according to the following rules:

1. Assume that the original estimate is inaccurate.
2. Identify few reasons and assumptions that could cause your first estimate to be inaccurate.
3. What are the implications of your findings so far?
4. Come up with an alternative estimate.

Herzog and Hertwig named this technique, dialectical bootstrapping. Kahneman and his coauthors wrote:

" Because the participants forced themselves to consider the question in a new light, they sampled another, more different version of themselves -- two "members" of the "crowd within" who were further apart. As a result, their average produced a more accurate estimate of the truth. The gain in accuracy with two immediately consecutive "dialectical" estimates was about half the value of a second opinion.

The upshot decision makers, as summarized by Herzog and Hertwig, is a simple choice between procedures: if you can get independent opinions from others, do it -- this real wisdom of crowds is highly likely to improve your judgement. If you cannot, make the same judgement yourself a second time to create an inner crowd."?

The "Enemy Within"

As I kept on mulling over the "crowd within" and "dialectical bootstrapping", I began reviewing the retrospection notes, employee 1:1 feedback notes, and other recordings to identify what was missing in all the agile training material discussing poker card estimations, sprint planning, among other courses that we adopted as a department.

A specific pattern emerged in the majority of the feedback that I had. Most of the estimations that were off were not estimated by the whole team but rather by the task assignee directly. I asked the team, on a previous occasion, why did some of them decide to estimate tasks independently? The answers varied from: doubts over the efficacy of an estimate when its given by a team member who does not have the domain expertise as an engineer or as a designer, or the fear that other members are more optimistic or more pessimistic when estimating.

What is clear from my findings is that each one of us has an "enemy within". This enemy within:

1. Assigns one's own estimates a higher weight during estimations.
2. Values one's past experiences and professional opinion more than the group's.
3. Minimizes one's own bias and inaccuracy.

There is a plethora of books, articles, and videos that go into the minutia of estimation techniques, yet the failure that I have witnessed is in the psychological preparedness of team members to trust each other as a collective and acknowledge the internal struggle to let go of the fear that drives them to distrust the estimates of their peers while over valuing their own.

Conclusion

To improve your estimation skills, you need to acknowledge the existence of both bias and noise in your estimations, regardless of your background or skill level. If you are part of a team, always engage your team in estimating your work and vise versa; the "wisdom-of-the-crowd" effect is a proven practice. If you have to make decisions on your own, engage in "dialectical bootstrapping".

Once you acknowledge the existence of the "enemy within" and lean towards the "crowd within" or, better off, the crowd outside, you will be ready to tackle future estimation challenges with more confidence and more success.

References

? Kahneman, Daniel; Sibony, Olivier; Sunstein, Cass R.. Noise: A Flaw in Human Judgment.