Navigating Midlife career shifts — My experience as a Technical Assistant to Dr. Anand
Part I – Introduction to the Wonderland
Whether it is the evil stepmother of Cinderella, the little old woman who baked the gingerbread or Jack who traded the family cow for magic beans, fairy tales hold leadership lessons for today’s executives. Although executives with seemingly busy schedules are an unlikely audience for a fantasy trip, the truth is everyone likes a story. Like fairy tales help children to answer a few essential life questions right from an early age, they hold immense rich lessons for all of us to introspect. In this series of blogs, I intend to uncover the details of my learnings as a Technical Assistant to Dr. Anand Deshpande by taking you through the Wonderland of Alice.
The motivation for writing My Story
I recently completed a year of playing the role of a Technical Assistant (TA) to Dr. Anand Deshpande. Anand is the former CEO and current Chairman and MD of the reputed Software development company Persistent Systems Ltd. My journey so far in this role has been super exciting. When I began playing this role, I had several questions in my mind, right from understanding what the role and responsibilities would be to the apprehensions of being able to deliver to my best.
While it has been a year full of learning, I thought of documenting my experiences, insights, and some tips for aspiring candidates. The first important thing I learned or realized is that the role is very fluid. The learnings will depend on how open-minded you are to absorb as much as you can, each day. Many companies offer similar roles, typically called “Chief of Staff” to support company executives like the Chairman, CEO, Presidents, COO, CTO, etc. The role naming convention and responsibilities vary depending on which executive you are assisting and the type of organization. However, the main objective remains the same. It is to allow the executive to scale and help him find the most precious resource, which is “time”.
I thought of writing this blog to align my thoughts in order and understand for myself what and how much have I learned in the past year. At the same time, it is meant for individuals who aspire to play similar roles or make a shift in career from a linear growth path. I would also like this to be a guide for my peers in the mid-life who are on the fence of making similar career shifts. As a woman, I wish that it will make a domino effect so that more senior women raise their hands for taking similar roles. There is a sincere hope that representing more women in similar leadership roles will one day even out the gender disparity in boardrooms.
The writeup is primarily based on my personal experiences in this role and may vary based on which enterprise you are working with as well as which executive you are serving. Many learnings can be relatable, however, please treat this as a guideline to understand the intricacies and day to day expectations – which can help be better equipped to make the career decisions.
I have tried to use the analogy from the classic fable by Lewis Caroll, “Alice in Wonderland”. I am sure most of you must have read this book or watched the Walt Disney movie of Alice during your childhood. This will make it easy for me to explain the key steps in my journey as a TA.
Let’s see how some of the learnings from this story and its casts, can be applied to understand this leadership role.
How did I land in the wonderland - Why this role and how to begin?
Let us begin by asking a few questions to know how and why I landed on this path.
Are you often confronted with this question as Alice did?
Which road to take?
Persistent was a dream company for many of us back in the 2000’s and for me, it was a dream come true. After having served Persistent, for a good fifteen years and playing different roles, it was time to shift the gears. Software programming, project management, managing customer accounts taught me a lot that one does not learn in schools. The job not just gave me a livelihood for the past so many years but has pumped life each day. My urge to learn and contribute never ceased to date. Well, the answer to why this role is simple. Who wouldn’t like to work with the best mentor you could have, given an opportunity? Wouldn’t you like to test the waters to find where you stand? Anand has been offering this key role to the mid-level grades at Persistent since many years. He intends this role to groom future leaders and means this to be a mentoring exercise as well.
Do you feel as if you are falling down the rabbit hole?
Traditional career structures are usually single-threaded. They make one accustomed to think and grow linearly. We are accustomed to defining a person based on the most recent title that they carry – e.g. She is a good Project Manager or a good Program Manager. Can the career paths instead be multi-threaded, and give one enough exposure to varied experiences and opportunities?
When one does not get such experiences, it feels as if you are falling down the rabbit hole. It’s getting harder for everyone to decide what to do, especially during midlife. My encounter with this role was on a similar juncture which changed my perspective of looking at options available and made me confident about my capabilities, likes, and dislikes.
What does it mean by being in the wonderland - Nature of role and its beginning?
First thirty days in this land
The first thirty to ninety days in any new role are very crucial. The first impressions and the first deliverables count. One should start building your network with the new team, learn, deliver, observe, and repeat. While I reflect on my first thirty days, I think that this was the time when I learned the most about the nature of this role, the differences, and key people to work with. In such roles, do not expect to always get any formal orientation. Everyone brings in different skills on the table and deals and works differently in similar situations.
More often, at the start, expect to encounter questions like the below. While I was myself trying to figure out the answers to these, I understood that they immensely helped me dig-in and understand the role better for myself.
• Why did you choose this role? Why did you move away from the software delivery team?
• Do you think you can contribute and apply your past learnings to this role?
• What do you do?
• How busy are you these days?
• Is this the way you contribute to a meeting – by being a listener alone?
• Oh! Do you just take notes in a meeting – what happens after that? Is it a kind of project management?
• How technical is your role?
• Some even go ahead and ask - how busy is your boss and what’s he doing these days?
As I progressed through my journey, I realized that my colleagues meant is to understand something more about this role as interpreted below.
• Why did you choose this role? Why did you move away from the software delivery team?
o Risks on shifting roles horizontally, fear of losing what is already acquired.
• Do you think you can contribute and apply your past learnings to this role?
o Skills required and what one will gain/lose from the new role.
• What do you do?
o The work pattern of this role
• How busy are you these days?
o Schedule and hours to be clocked
• Is this the way you contribute to a meeting – by being a listener alone?
o Day to day responsibilities and challenges
• Oh! Do you just take notes in a meeting – what happens after that? Is it a kind of project management?
o Skills required to fulfill this role or apply for similar
• How technical is your role?
o Technical depth required
• Some even go ahead and ask - how busy is your boss and what’s he doing these days?
o Strategy and Company growth and how it would impact them
At the core, I understood that each question was meant to understand the role better. Each one wanted to validate how easy or difficult it is to opt for this role.
As we move forward, you can expect to get answers to most of these questions. However, there can still be a few that either doesn’t have a straightforward answer and/or are not required to be answered and/or may need a longer answer.
If you sail through these days successfully, you can very well survive and succeed in the coming months.
Nature of role and frameworks
Many theories and explanations already exist on the internet for this role. To name a few:
Richard Hytner is his book Consiglieri, explains it as follows
McKinsey Research points out similar characteristics
Tyler Parris, in his book “Chief Of Staff: The Strategic Partner Who Will Revolutionize Your Organization”, defines the role as “chief of staff is a catch-all role, filled by someone with exceptional organizational and people skills, who handles all manner of tasks not covered by an existing member of an executive’s leadership team or administrative staff”.
We also have some good reference frameworks to understand this better:
One Mission: How Leaders Build a Team of Teams, Chris Fussell
To those who are interested, I recommend reading these theories to understand them further. In my next story of this series, I will try to take you all through the day in the life of Alice in the wonderland to explain what she must deal with on a typical workday based on my learnings.
This article was first published on my LinkedIn account here.
