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Ankoor Dasguupta Of Shisham Digital: 5 Ways Empathy Will Affect Your Leadership

An Interview With Cynthia Corsetti

Better decision making

From my above three points, I myself realized during the past years of practice that decision making cant be taught. It needs to go through a process where there is no fear of failing and we fail fast and understand why a particular decision did not span out well. So, if we start these practices early in any organization, better decision making and ownership at all levels start happening, which actually is a good sign for the top management.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Ankoor Dasguupta.

Trained from Dale Carnegie in Mentoring, a CMO Council Member, Ankoor is a marketing practitioner, a knowledge manager, a thought-leader, an avid writer with more than 50 published articles and has multiple guest columns, one of which is Reputation Today .Ankoor is an established speaker and jury member for multiple esteemed forums including reputed B-Schools in India. Ankoor is also on the Advisory Board -Marketing Department at ISBR Business School. Recognized by DMA Asia as a marketing Ace, Ankoor is an advocate of social impact, driven by kaizen, he believes in the power of Energy and Energize while bringing to the table a pedigree of 23 years with a rare combination experience across the spectrum of media — print, digital, mobile, event productions & successful pilot projects. Worked across functions — ad operations, business operations & strategy, content, brand strategy, sales, events, media planning & buying and spearheading P&Ls. Ankoor has been part of six Sigma projects and worked in cross functional roles with — MNCs, media conglomerates and start-ups. A process expert, Ankoor has been part of the core pilot team of launching and scaling International IPs such as ad:tech, iMedia Summits, Modern Marketing Summit and TechCrunch events in India. Ankoor has directed and enabled the winning of multiple pitches while actively involved in overall and tactical strategy. Ankoor is also on the Screening Council for MMA APAC and MMA Global for Smarties Awards. Ankoor is POSH Certified and has been selected to be part of core Committee for POSH at two organizations during his work tenure till now. Ankoor is your non-status quo leader.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

First of all, thank you for having me for this interview. I was an average student and from my high school days I was aware of some of my strengths but not all. One of my strengths was writing. I believe in the magic of the universe that if we want something from our heart and mind in focus, it will happen. I knew that I wanted to be working with media world and I wanted to study it. So, after my specialized Diploma in Advertising & Marketing, the first three years of my career was with GE which prepared me a lot for the world. I am grateful to have quite a few path breaking breaks and the opportunity to work with tough bosses. I got through the leading media conglomerate Bennet Colemen that publishes Times of India, the leading daily newspaper. Post that thigs started rolling with moving from newspaper to India Today which is into magazines and those times the focus was print as Digital has just started gaining traction. I realized quite later in my career what it is that drives me, and it is curiosity and the hunger to learn and work with different teams and cultures. So, when I got an opportunity to get into Yahoo!, I jumped in and from there I believe more magic started happening as I faced and overcame multiple challenges, one of which was ofcourse moving from an industry run on paper and fax machines to a paperless and software enabled environment.

Can you share the most interesting story that happened to you since you started your career?

During my first job and second year appraisal, my manager told me during the one-on-one session that ‘Ankoor, your work hard, however, you are not visible’. It took me almost the next 5 years to understand the depth and connotation of this word ‘visibility’, Although he gave me one or two examples, but I don’t think I had the mindset during my initial days to comprehend and I was more interested in ‘am I getting promoted?’ Well, I didn’t get the promotion, but it kept me thinking till the time I actually figured the nuance. I thank him for nudging me to find my answer. If I see my 22 old self today, I’d say to him “Ankoor- reflect deeper on your goals and aspiration, specifically on the ‘why’ aspect. The ‘how will follow”. Not sure if this is interesting enough, but I do hope the readers find value in this, being one of my interesting stories when I started my career.

What do you think makes your company stand out? Can you share a story?

We as a team believe in not only building but nurturing relationships with our customers. It is actually a simple story that we play on repeat mode which makes us better as getting better. We often go out to eat together, we play cricket on Fridays (we book at playground close to our office), we brainstorm for free-flowing ideas, and we are extremely good with ‘how’ we solve for our clients. So, we usually tend to find stories within stories during our conversations. That helps in keeping your team inspired and this reflects very well externally as well. When our clients see and hear about our camaraderie it induces deeper trust in us. Our DNA is non-prescriptive and educative and it is the freedom that our team has that helps them unwind and think better.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

If I’d pick three-character traits, –

  1. Being in the moment — the simple art of listening well and being in the moment with that person. Be it team member, boss, clients, or networking at an event. If I have one minute to just say hello to someone, I will say it meaningfully, by looking in the eye and using that moment effectively. While doing feedback or appraisal sessions with my team members, what they found trust inducing is that I let them finish, listen and then respond. For me, this communication skill has worked wonders as when people know that someone has a listening ear and shares authentic feedback or guidance, people would want to work with you or connect with you. This character trait has been one of my core strengths as this trait has always helped me with my storytelling while sharing my thoughts or observations.
  2. Discipline — This is something that was imbibed from my grandfather. It all started with starting my day early. I realized from early childhood that there is no shortcut to discipline and this trait till date helps me to perform optimally daily and helps me achieve my goals with clarity of thought. Infact while doing my thinking, I always ask the ‘why’ to myself.
  3. Organized — this stems from my being disciplined. I start my day with making my bed, having a tall glass of water, making myself tea, reflecting on the previous day, making a to-do list bifurcated into priority 1 and priority 2 and then reading few chapters from my mini library. Also, I love keeping everything at my desk both office and home organized. It helps me to find my things easily. Being in senior leadership it is important that I start with an inside out approach and start with myself.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

I’d love to share an anecdote. In one of my previous companies, there was a visible rift between 2 team leaders that was not conducive to the functioning of their respective teams as both the functions needed to work together to achieve the goals that we had in our SoW with client. It was seeming next to impossible initially as I could not have even taken a hard call because of two reasons — (a) they were good at their work and managing their respective teams and (b) the client will not let go of them easily as we had outsourced the business with a dedicated team on our payroll. I had 3 months to rectify this conflict to avoid a worse situation of teams working in silos. The two of them wont even come for lunch together as they avoided even talking to each other. For next 3 months, I closely worked with both of them and showed them the larger picture, did not tell them right or wrong, just coached them to see the power of one team.

My take is people challenges are the most complex and most important ones than business challenges. As leaders we need to invest time guiding people. Business happens towards customer delight one teams work together towards goals. Similar thing applies to CXOs working together as stakeholders. Only then a decision will yield towards long term sustainable benefits.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

For me, empathy is making a genuine attempt to provide a non-distracting listening ear to anyone in team, with the intent of understanding the root cause. It could be with my peer, my team, any colleagues. The intent of — ‘hey, I hear you and I am involved in listening to you and will try and make your moment or day easier’ is empathy in leadership.

I believe it must be in the DNA of top management leaders that must get imbibed into the people with a top down approach. It is the responsibility of senior leaders to set good examples and have regular training sessions hosted for their teams so that Empathy is not only a word to talk about but gets fit in by default into maximum people in that organization.

The beautiful thing about empathy is that it has a great rub off effect and in essence it is ‘giving’. Giving my listening ear, ensuring I understand the concern. Empathy can be reflected in small conversations as well as deeper long conversations. That challenge is more in short conversations as the listener gets less time to absorb, understand and then respond in such a conversation. But yes, that is why experience counts. Having been in multiple challenging situations with complex conversations, leaders are perceived (rightly) to have the best navigation skills, being the captain of a ship.

It starts with a listening ear and not putting the person in front but visualizing the ‘situation’ my colleague is going through.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

It may seem like just another regular example, but it happens a lot and hence once I thought about bringing this more to the forefront of conversations at work. At one of my previous workplaces, my group heads were facing difficulty in managing how team members used to take unscheduled leaves. Also, while working, efficiency was somehow on a downward curve as unscheduled leaves impact a bigger objective with defined timelines.

What I did was to invest time in having conversation with all my group heads. I split that into two parts. First meeting in office and the next meeting was scheduled over lunch outside office. My thought behind doing this was to allow team to come up with the initial thoughts in office meeting and since these topics need to be give some time to reflect deeper, the lunch meeting next day was extremely helpful. This is because they themselves thought about the root cause of team taking unscheduled leaves and themselves came up with solutions as they got time to sleep over our first discussion. The root cause was lack of motivation which had creeped in gradually. So, we identified the root reasons ans he team came up with a solution conducive to making certain interesting and exciting practices at work.

Technically, I did nothing. I brought the group heads together, listened and gave them time to reflect and yes, I told them that this is priority one for us to solve and that it will be great to solve this together, considering the sensitive nature of this situation. Seeing it from outside-in perspective, empathy is the glue.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

My point of view is not to aim striking a balance because focusing on balancing will make us lose our balance in this case. The aim must be to first consistently build trust so that any such feelings that need attention can come to the forefront in some way, because if I as a leader is not cognizant of the problem, I can not solve it in the first place. In tandem, have a 360-degree anonymous feedback done atleast once every year to know the root causes. You’d be surprised in not such a pleasant way. Anonymous feedback takes lot of courage for the management and HR leaders to implement and follow through on deeper issues. Next step is to invest structured time on calendar to do one-on-ones only on the emotional quotient. Where we can improve is taking out time for non-performance conversations and talk about the person and how do they actually feel? ‘d ask myself ‘before taking a hard call, have I evaluated the situation from a non-judgmental perspective and am I sure that there is no other way but to take the tough decision?

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

It is definitely important for leaders to distinguish as the emotion, tone changes accordingly. They are different side of the same coin, but we need to flip it wisely. Leaders must undergo classroom training sessions on this to avoid any grey areas. What has worked for me as not to over-think the difference each time I am required in such a situation that needs this emotion. It must start coming naturally to be in the moment. Since I have been trained in this aspect as also been on the committee of PoSH (Prevention of Sexual Harassment) committees, I recognize sensitive aspects of a discussion easily, while listening effectively helps.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

Investing in specialized training sessions and following through those training courses to understand if the trainee leaders have understood in totality. The training sessions must be done module wise with mock sessions. Most of the companies I know either do this training once in 2 years or once a year just to showcase their culture on social media. This does not help at all. What helps is having a defined budget for trainings like these that happens atleast 3 times a year so that professional trainers can help measure the progress of understanding. Empathy may be easy to read and understand, but its application in real situations needs training sessions, more than once.

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

My point of view is Empathy is also empowering. Once we understand and respect perspectives and thoughts that others have, diverse teams start believing more in the leader and this only happens with the intent of applying, imbibing within teams while also having candid conversation sessions without judging. The fear a team member will have is mostly grounded in ‘how will my boss judge me/ what if I am judged’’. Empathy must not be an act, it must be present within the self to utilize as and when needed. Leaders who are not empathetic but tend to apply it, it wont work in its natural essence and that is dangerous as the people get to know that empathy is being faked and they may never open up to you again.

What’s your approach to ensuring that succession planning is a holistic process, and not just confined to the top layers of management? How do you communicate this philosophy through the organization?

Very relevant and good question. This has always been one of my KRAs in past few years of work Succession planning must happen at all levels and must be present in the KRA discussion least till the team leader level. What I have observed is that teams find it both — challenging and empowering as a part of their appraisal. Reason being, if I got to plan a succession, I need to take care of broadly these six things –

  • I am an expert in my present role
  • I have at least one hour during my day that I can use constructively and creatively for self enhancement
  • People love to work with me
  • Clients are happy with me
  • I have nothing more to learn in my present role
  • Having a plan already ready as to what all I will do once I am promoted, even before my manager tells me

Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

It is my pleasure sharing these 5 points from my experiences till now and you will also see the connection between each of these points as none of the points are siloed. Essential it happens as a snowball effect if point number one is done well and with patience.

  1. Building Trust as the Unique Currency

An example of whenever I have joined a new organization. I have always spent the first 45 days doing both structured and unstructured conversations with not only my direct reports with till the level of interns. This takes a lot of effort but is worth it. One such story is my boss in one of my earliest stint observed that I was spending the first month of my joining, spending time with my direct reports and their teams together at lunch, having combined brain storming sessions, understanding each other’s aspirations, telling them about my experiences and so on. He walked up to me one day and told me ‘Ankoor, you can save a lot of time by only speaking with your direct reports as you don’t need to be talking to their teams and juniors.’ My reply was something around ‘the results that you need me to deliver within the first year, will be delivered, just that I need you to allow me to work in my style and approach’. He understood that moment and also after few months as he now was aware of my tactic. I was attacking the root cause of any issue and for that understanding your direct reports and at least one level down (I did 2 levels down in a way that no one felt bad) was worth my effort for the larger cause and checking all boxes on client delight as well. This whole initiative is nurtured by empathy.

2. Encouraging Innovation

Cohesiveness has its own importance. When the first point of building trust is a gradual success, the cohesiveness automatically improves and once this improves, people in the team start having an innovation mindset. It could even to the effect of how we can reduce the turnaround time of a particular process. There are multiple examples, however, one such example I recall is that the team understood that a process that we were following, was broken, so they quickly discussed together with their group head, came up with a better and easy solution to streamline and also ensure adherence.

3. Building camaraderie & healthy competition

I have observed that with point one and two in place, colleagues become driven by stimulating conversations rather than unnecessary useless talk and politics. I have actually observed our water cooler (actually coffee machine) conversations also are towards a goal and solution. So if one team sees another team doing innovative work while also getting recognized, this creates a ripple effect and there is exciting competitiveness among teams which promotes best practice sharing as well as cross team positivity. Again, the spinal cord here is empathy.

4. Better decision making

From my above three points, I myself realized during the past years of practice that decision making cant be taught. It needs to go through a process where there is no fear of failing and we fail fast and understand why a particular decision did not span out well. So, if we start these practices early in any organization, better decision making and ownership at all levels start happening, which actually is a good sign for the top management.

5. Better talent and retention

This, however, is the most difficult of all challenges and more to do with how we have interview discussions and how HR onboards and inducts. People who know my approach to interviews, I do not go by resume. It comes handy just to take a glimpse of certain technical aspects. I would rather have a conversation to know all-possible sides of the individual and to get a deeper understanding of the human behind the resume. This works well when built as a standardized process across the organization. Yes, there could be a separate technical round, but that needs to be only checking the technical application of knowledge rather than just knowledge. One good example that I’d like to share is in one interview that I appeared sometime back, they let me know that they need to get to know me more as a leader in terms of my thinking, how I would be approaching various situations. It was a objective questionnaire format. The best part is what came to my mind first, and it was how deeply that organization thinks of people and how deeply they want to know that person. That is an immediate exchange of empathetic energies that builds from day zero.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

Well, empathy at times may be perceived as being vulnerable. My take is vulnerable is okay. It’s high time leaders shout out that it is okay to be vulnerable at times. People identify with basic aspects of working in a tribe, vulnerability, ownership, strength and more such. My goal as a leader is to have a sustainable purpose that my team will feel belonged to as a cause and we keep having structured discussions from time to time and recognize people for even small wins, achievements. Any leader must listen well before speaking well.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

This is a wonderful question, and I am glad you asked this. I believe that at a pilot position, I need to have a clear mind, at least as clear as possible. Like I eat every day, shower every day, brush every day, I need to ensure that I do something about cleansing my mind daily. With conscious practice, I have been able to steer clear of over-thinking. So, I have replaced the word ‘concerns’ in my mind with the word ‘solutions’. Even if it is an extremely complex conflict management situation, I do now allow myself to be judgmental, I listen deeply and if I need to take a step back to decide on something, I do that. What helps me think better is asking deeper questions that detach the conversation/ situation from the superficial cause (which may be at the first go most of the times) and look at the ‘why’, it becomes easier.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

My movement will be to inspire both — our teams and our customers to take action which translates to a purpose weaved by sustainability at its core. We as leaders and companies may be talking a lot about sustainability in our purpose and I see some action as well taken by various companies, but those companies are only a handful. We need to not only celebrate World Environment Day when it comes once a year, but it must be a part of our daily routine.

How can our readers further follow you online?

Ankoor Dasguupta | LinkedIn

Thank you for the time you spent sharing these fantastic insights. We wish you continued success in your great work!

Gratitude for this opportunity. I do hope I earned the privilege of your time.

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.


Ankoor Dasguupta Of Shisham Digital: 5 Ways Empathy Will Affect Your Leadership was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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