Care Deeply and Challenge Directly


One of my goals in 2018 was to learn more about management as I transition from being  an individual contributor to a manager. I have started attending management training at work, but have also been looking for books, podcasts, articles to learn more. Radical Candor was the one of the most recommeded books on this topic. The author Kim Scott traces her journey from a startup where she was CEO to Apple and Google where she effectively managed people and even ran management bootcamps.

As CEO, Kim was afraid of giving hard feedback as she did not want to be seen as a jerk. However this meant that her employees were not aware of their flaws and did not correct them which led to even more uncomfortable conversations down the line.

radical-candor-2x2.pngShe set out to investigate how to “be a kick ass boss without losing your humanity”. The answer which is in the top right of the quadrant is the title of the book and it consists of the following two steps.

Care Deeply – The first step to understand the employee’s goals (both personal and professional) deeply. This can be done through a series of 1-1 meetings with the employee. It is then the manager’s job to put the employee in a position where they can make progress towards those goals. Too often, managers assume that all employees want to be star performers – there are many who derive satisfaction from working 8 hours a day and spending their free time with family and friends.

Challenge Directly – The next step is to challenge the employee whenever they fall short of the goals that they have set for themselves. If the manager has established a good rapport (step 1), then the employee will see these challenges as an attempt by the manager to guide them rather than attack on their performance. Feedback should happen quickly and be not reserved for 1-1 meetings or annual reviews. The “directly” in “Challenge directly” advices that feedback cannot be diluted lest it be ignored.

One thing that the book does not detail is how personality type may influence the efficacy of the book’s advice. Most managers are familiar with Myers-Briggs or similar personality tests which specify that employees should be motivated or challenged differently depending on their personality. For e.g. certain employees may not take too kindly to being challenged, even if the manager has a good rapport with them.

Overall, the book is a great read and full of useful advice. It goes into great detail on how to establish a culture of radical cantor in the workplace. I highly recommend it to managers especially new ones like me.


2017: Year in Review

It’s the start of a new year, so once again, it’s time to reflect a bit on 2017 and look at what went well and identify my goals for 2018.

Reading: My target in 2017 was to read 12 books and to write about the ones that I found interesting. I had also wanted to get outside my comfort zone of self-improvement books and explore biographies, history, and non fiction. Sadly, I did not achieve this goad as only two books were outside the work related and self improvement categories. I managed to read a total of nine books (and write about six).

  • The Ascent of Money by Niall Ferguson
  • INSPIRED: How to Create Products Customers Love by Marty Cagan
  • Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain
  • What Every Body is Saying by Joe Navarro
  • Emotional Design by Don Norman
  • The Everything Store by Brad Stone
  • The Goal by Eliyahu Goldratt
  • Product Leadership by Richard Banfield, Martin Eriksson, and Nate Walkingshaw
  • Radical Candor by Kim Scott

This year, I am going to try harder to move outside my comfort zone and explore other categories. I think the problem is that every year, there are at least 5-10 books in the core categories that I find interesting. Hence, in 2018, I plan to raise my target to 15 books and cover these categories.

Writing: I had set a target of 18 blog posts in 2017 and managed to do exactly half. The main issue was that I was unable to branch out from my main category of book summaries. I had a few ideas for a product management topics but kept procrastinating until I lost interest in the topics.

The blog received a total of 330+ visitors this year which was about a 35% drop from last year. Most visitors still visit the blog for the MBA related posts. I am not really worried about visitor numbers at this point as the main goal is to churn out good content.

In 2018, I am targeting 15 blog posts. I hope to get at least 5 posts that are not book summaries. In addition, I want to learn how to use an illustration tool to create simple drawings and graphs to make the content easier to read.

Career: 2017 was the year in which I became comfortable as a product manager. The added experience meant that I was largely unfazed even though the domain that I am working in (APIs, platform) is largely technical. Last year I noted that I had not yet decided if I wanted to be a technical PM but this year I realised that I am good at it and it is a niche skill and I quite enjoy it.

The company that I work for underwent an agile transformation and my team was one of the more successful adopters of the new process. We plan to continue being champion for the agile way and set an example for other teams. Having fixed the execution problem, in 2018 I want to move away from 6 month roadmaps and focus on goals/metrics based roadmaps.

In 2017, after two years on the job, I was promoted to senior product manager.  Therefore one area that I want to focus more this year on is my managerial/leadership skills. I have started reading a few books on this topic and have enrolled in management training that is being offered by my company.

Product Leadership by Richard Banfield, Martin Eriksson, and Nate Walkingshaw


Product Leadership is a book that distills the best practices of Product Management into one source. Mark Ericsson is the founder of Product Tank and Mind the Product and  has a wealth of experience in Product Management. The book covers topics such as leadership, vision, strategy, prioritising, user research, and many more.

I skimmed through this book very quickly since I found that it covered a lot of material that I was already familiar with and there was very little that was new. I’m probably going to skip reading Product Management books for a while. However, if you are a new  or aspiring PM, reading books such as this one or Inspired are a quick way to get up to speed.

The Everything Store by Brad Stone


A lot has been written recently about the big five technology giants (Microsoft, Google, Amazon, Apple, and Facebook) that dominate the technology sector. There are fears about the power and influence that they will wield and that they will crush all competitors and stifle innovation. One of my goals for 2017 was to understand these five giants better. I started off last year with Apple by reading the Walter Isaacson biography of Steve Jobs.

The Everything Store tells the story of Jeff Bezos and Amazon. Jeff Bezos possessed an extremely high IQ and attended a school for gifted children. His first job out of college was with DE Shaw a hedge fund that used algorithms to identify opportunities. As the internet started to become big in the early 90’s, Shaw had Bezos investigate a number of potential internet enabled businesses including an “everything store”. Realising that it would never truly be his if he stayed at DE Shaw, Bezos made the decision to quit and start up by himself. He made the decision using what he called the “regret minimisation framework” i.e. what would he regret more at the age of 80, giving up a big bonus or not starting a business that he was excited about?

Steve Jobs loved music and this passion surely had an impact on Apple’s decision to make music a big part of the company’s offerings. Jeff Bezos on the other hand loved books and it’s probably why it entered consideration as the item that Amazon launched with. However, there was a solid business reason as well – a book is a commodity that is the same in every store, the SKUs are large, no physical store would have them all and the number of distributors was low. Even when Amazon started to expand, the products were chosen the same way i.e. CDs, DVDs etc.

The big book stores at the time Borders, Barnes and Nobles did not take the internet seriously. Eventually, they realised the threat and began building out e-commerce departments. Analysts thought that Amazon was toast but the large companies had trouble competing as their distribution centres were optimised for their large physical stores. Secondly, in big companies, it is hard to move your best people away from the cash cow and onto emerging areas as demonstrated by Clayton Christensen (whose work had a big influence on Jeff Bezos.

Amazon is a very interesting company to study for a variety of reasons. Some of the things that struck me are as follows:

  1. Intense customer focus: Many companies say this, but few actually mean it. An example of this is the Amazon Marketplace. Facing a threat from Ebay, Amazon was under pressure to respond. The problem was that the Amazon website and the marketplace were two different sites and the marketplace had very very low traffic. Bezos’s genius was to allow third party sellers to be listed alongside the Amazon listing on one site. In most companies, internal politics would have prevented this move and even in Amazon there was strident opposition, but Bezos prevailed.
  2. Work Culture: Treatment of workers is in stark contrast to the rest of Silicon Valley where employers compete to offer perks. Work culture at Amazon is intense, with people burning out frequently. The behaviour of some of the managers at Amazon would not be accepted in most other places, yet they clearly seem to attract talented  workers who are highly driven and ambitious (like Wall Street??).
  3. Continuous Innovation: Most companies innovate when they are small, but become more risk averse as they grow larger. Amazon has a very interesting organisational structure. Teams are highly autonomous and can choose their own technology stack. Multiple teams can work on the same problems. Bezos also formed secret teams whose mandate was to disrupt existing businesses. Amazon’s many innovations came from diverse sources.
    1. Kindle – Observing Apple’s disruption of the music industry and fearing the same would happen to books, Amazon had a secret team work on the Kindle.
    2. Prime Membership – An internal tool where employees can submit ideas was the source of this idea.
  4. Amazon Web Services: How did a e-commerce store become the largest seller of technology infrastructure? Bezos had always harboured ambition of being a technological innovator. The motivation was the increasingly hard process for teams to get access to resources at Amazon. Bezos was also influenced by a book called Creation that describes a video game where players guide intelligent creations rather than control them. He mandated that the primitive building blocks (storage, computation) be available for developers to use as they saw fit.
    1. Since the book was published Amazon has expanded its AWS offerings and released Alexa a voice activated speaker that uses AI.

Overall, I found the book quite interesting and I recommend it. I think it’s a must read for anyone who wants to understand the current technology landscape.


Agile Transformation

Last year, Freshdesk underwent an Agile transformation. Some of the changes that we adopted were as follows:

  • Cross functional teams – A team must contain all skills required to take a feature from ideation to deployment. This avoids the need for handoffs to other teams and communication overhead.
  • Iterative development – Develop features in bite sized chunks and aim to deploy every sprint (A sprint is a timeframe between 1-4 weeks)
  • Transparency – Break silos by brainstorming ideas and planning for Sprints together as a squad
  • Limit WIP – Productivity improvement due to decreased multitasking and opportunity to spot improvements


Agile borrows heavily from the lean methodology in manufacturing and aims to avoid waste. Waste could be due to picking up features that not required, inefficient processes, communication overhead, quality issues etc. During the initial training, I recognised several similarities to concepts that I has learned during the Operations Management MBA course.

My squad (teams in Agile are called squads) has made several improvements over the last year which have increased our development velocity. While some of the changes (avoiding handoffs, iterative development) came part of the process, others (continous integration, test automation) were a a result of the squad embracing the need for continous improvement. Here’s how we went about it.

MAKE WORK VISIBLE – When I began my first job, I was confused about how little I was saving. I was earning a decent amount and not making any large purchases, yet I was saving very little. I took the advice of a personal finance site and started using budgeting software to keep track of my spending. Once I did this, I was able to see exactly where my money was being spent and I was able to make the necessary changes and start saving.

Agile does something similar to drive improvements. It makes work visible by ensuring that large features are broken down into bite sized user stories and tracked using a too such as JIRA. The sprint ceremonies also a vital role in in improving transparency.

  1. Sprint planning – At the start of the sprint, the squad estimates which features will be deployed at the end of the sprint. This is entered into JIRA and it is visible to everyone throughout the sprint.
  2. Daily stand ups – Update the squad on what we are currently working on. We use the Kanban board to track the current status of user stories and be reminded of the sprint goals.
  3. Backlog grooming – Gain visibility into what is coming up in the next few sprints and collectively brainstorm.

INSPECT AND ADAPT – The agile principle “Inspect and Adapt calls for squads to come together at regular intervals to reflect on how to be more effective and adjust their behaviour accordingly. This is achieved through the sprint retrospective.

Sprint Retrospective – During the retrospective the squad identifies what prevented them from achieving the goals. This feedback is then prioritised and we figure out the best way to address it. It was feedback that led us to embrace continious integration, mock testing, and increased test automation.

One important point here is to keep the number of features taken up each sprint down to a minimum. Only features that you think will be shipped should be taken up. Why? First, it reduces multitasking which is a known productivity killer. Secondly, “Inventory is Evil”. Having buffer, prevents you from identifying bottlenecks in the process. In lean manufacturing, inventory is compared to a lake that hides sharp rocks underneath it.

Imagine that your code reviewer falls sick. If you maintain a buffer of code reviewed features, then the QA engineer would never waste time waiting for a new feature to test. This seems good in the short term, but may hurt you at a critical time. In Agile you face the delay and then introspect on how to prevent this. For example, you could set up a process to ensure that there are multiple engineers who can code review a feature.

The retrospective is critical as transparency by itself will not drive change just as keeping track of you expenses by itself will not make you save more. You need to act on the information and make changes i.e. Adapt.

Emotional Design by Don Norman


I’m a big fan of “The Design of Everyday Things” by Don Norman so I picked up the sequel. When the author wrote DOET, he was was frustrated about the lack of importance given to behavioural or functional aspects of design. Therefore, that book is entirely composed of functional design critiques and advice. However, he received criticisms that he ignored the other aspects of design that he then addressed in this book.

There are three aspects of design – visceral, behavioural, and reflective. Visceral is how a product looks, behavioural is about usability, and reflective is how it makes you feel.


Take the teapot above for example. The author notes that he loves it, even though it’s hard to use. The unique look (visceral) and satisfaction (reflective) that it gives him more than make up for its behavioural deficiencies.

Reflective: It’s the third component of design that the book spends most of its time on. Norman uses the example of souvenirs to highlight the role that emotions play in our attitude towards products. For e.g. souvenirs that look cheap and have little utility value are loved as they are usually associated with fond memories.

Humans have an intrinsic need to create a sense of identity. They often purchase products that reflect their identity. This is reflected in the demand for branded goods that are often similar to cheaper generic versions. Brands exploit this by attaching emotions to their brands through advertising. Hence a brand such as Rolex will associate itself with top athletes to signal high class and success.


Prior to reading this book, I had been puzzled by some of the design decisions made by Apple. For example, the mouse pictured above is usually panned for the fact that the side buttons are in fact not buttons but for design alone. After reading this book, I understood that the designers made a conscious decision to sacrifice functionality to appeal to the visceral and reflective aspects of the buyers. They went too far in my opinion, but I now understand why.

Overall, the first few chapters were interesting, but the second half of the book that goes deep into the role of emotion bored me and I skimmed over most of it. It’s not a must read in my opinion.


What Every Body is Saying by Joe Navarro


Joe Navarro is an ex FBI agent who was a founding member of the FBI’s Behavioural Analysis Program. He was a body language expert who he used his ability to successfully identify suspects who were lying or attempting to conceal their involvement in any wrongdoing.

In this book he draws from his years of experience to list the various ‘tells’ that different part of the human body exhibit and why they do so. I enjoyed the ‘why’ much more than the ‘what’ and therefore my summary is all about the ‘why’ but I think it’s worth a quick read if you are interested in understanding non verbal behaviour.

Why ‘Tells’ Exist: When our ancestors encountered danger they were typically a few standard responses. Most of us are familiar with the first two – flight or fight. The third response – freeze is unfamiliar but actually the most common response to perceived danger. The modern incarnations of these responses and ‘pacifying’ behaviours that accompany them are the reason that these tells exist.

Freezing is a mechanism that our ancestors deployed to make themselves less visible to perceived predators. Today we use it when we make ourselves small or perhaps unnoticed when we feel uncomfortable or threatened. The reverse is true, we make ourselves large to show dominance.

Flight is another way to escape danger. While today, we cannot run away when uncomfortable, we try to cope by blocking behaviours such as looking away, closing our eyes, placing barriers between ourselves or leaning away from people. The feet are excellent indicators here – feet pointed towards exits or preparing to leave are clear signs that the person wants to end a conversation.

Fight is the final option when facing a threat. Thankfully, it’s becoming quite rare and people tend to restrain or limit themselves.

Pacifying behaviours are those that people deploy to calm themselves when they are agitated. Common pacifying behaviours include massaging the neck or touching their face. Since these behaviours are employed when a person is agitated, they provide valuable clues about their state of mind.

Quiet: The Power of Introverts in a World That Can’t Stop Talking


Yet another book that I had wanting to read for a long time. This book entered my radar after I watched Susan Cain‘s TED talk on the power of introverts. The talk was viewed nearly four million times in its first year alone.

As an introvert, I found the book really interesting. In particular the first part of the book was a real eye opener and resonated strongly with me. I had not realised how biased everyday life is towards the ‘extrovert ideal’ and how I should respond. Therefore, this book is a must read for all introverts.

The Extrovert Ideal
As adults, many of us work for organizations that insist we work in teams, in offices without walls, for supervisors who value “people skills” above all. To advance our careers, we’re expected to promote ourselves unabashedly.

Surprisingly, it wasn’t always like this. In the early 1900s, there was a shift from the culture of character to a culture of personality. This coincided with a migration to urban centres where you had to interact with people that you didn’t know and extroverts gained an advantage in this new reality.

The Myth of the Charismatic Leader
“Among the most effective leaders I have encountered and worked with in half a century,” the management guru Peter Drucker has written, “some locked themselves into their office and others were ultra-gregarious. Some were quick and impulsive, while others studied the situation and took forever to come to a decision.… The one and only personality trait the effective ones I have encountered did have in common was something they did not have: they had little or no ‘charisma’ and little use either for the term or what it signifies.”

Nature vs Nuture
There is a strong biological aspect but it can be altered by upbringing (like a rubber band, you cannot stretch too far from your default state). The intricate interaction between the two that makes us who we are.

Impact of Culture
Migrant cultures are considered more extroverted as they had to move around while others were introverted. Hence, Asian cultures are not as extroverted as American ones. Yet, they too are following the American example of the ideal worker.

Introverts in the Workplace 
Research suggests that extroverted leaders enhance group performance when employees are passive, but that introverted leaders are more effective with proactive employees. This makes sense as introverts tend to listen more and are therefore more likely to be open to new ideas. The most effective teams are composed of a healthy mix of introverts and extroverts, studies show, and so are many leadership structures.