I chose people who asked uncomfortable questions, challenged briefs, and could sit with ambiguity — long before I scaled teams or departments.
In the world of business and within every industry, there are forward-thinking leaders who go against the status quo and find success. Their courage to take risks, embrace innovation, and inspire collaboration separates them from the competition. Until 2002, Apple’s famous slogan was “Think Different”. This attitude likely helped them become one of the most successful organizations in history. This interview series aims to showcase visionary leaders and their “status quo-breaking” approach to doing business.
As part of this series, we had the pleasure to interview Dr. Ankoor Dasguupta.
Dr. Ankoor Dasguupta, a Marketing Practitioner, with over 25 years of work experience, is an ICF accredited Professional Certified Coach (PCC) with niche in transformational leadership & business communication. He uses frameworks and tools to do root cause analysis enabling deeper levels of self-awareness practice, acting as a catalyst to helping leaders become their next best version. Dr. Ankoor is a deep listener, warm and helps people challenge the status quo. He coaches senior leaders and people who are on their growth path in leadership by unlocking their limiting beliefs.
Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?
Thanks to you Chad. I grew up in New Delhi, travelled quite extensively, worked primarily in advertising, marketing, media. I have been an average student in school and learnt and practiced to get better at getting better every year. I love connecting with people of different cultures. For me success means deeply to have the innate ability and intent to help people become better version of themselves and today, apart from being a marketing & business leader, I am also a leadership and communication coach. I am grateful to have a wonderful life partner and a daughter without who are my lifeline.
Can you give us a glimpse into your journey into this industry and share a story about one of the most significant challenges you faced when you first started out? How did you end up resolving that challenge?
My first job was actually as a Tabla (a musical percussion instrument) teacher in my alma mater and then GE happened. That was my first corporate workplace and I am grateful to have spent my 3 initial years with them. Post that it has been advertising industry and one of the significant challenges was when I took the plunge from moving from print (India Today Group) to Digital (Yahoo!). Navigating an industry driven my paper and fax machines to a completely paperless workplace was a challenge which took me few months to navigate as everything was driven my technology and robust processes. However, my prior experience with GE helped me overcome this challenge faster.
Who has been the most significant influence in your business journey, and what is the most significant lesson or insight you have learned from them?
My strength and my influence has been my wife Arpita, who has always supported me through thick and thin. I keep learning a lot of things from her, one of which is the art of multitasking impeccably with focus. And my mew influence is my 6-year-old daughter Kiyaana, who keeps me on my toes by asking the simplest of questions that make me think deeper and keeps the child in me alive. I am grateful.
Can you share a story about something specific that happened early on that you would consider a failure but ended up being a blessing in disguise or ended up being one of the most valuable lessons you had to learn on your own?
Indeed, many such situations, however, one such was the time when I was handed over event sales and production off the hook because of shortage of staff. That was around 2013 and I did not consider myself a good sales person and anything related to events was taking me out of my comfort zone. I sold 90% of our event inventory 30 days before the event date, handled multiple aspects of production and came out with flying colours! Then I formed this mindset that what we focus on deeply can be accomplished. Of course, there were catalysts like a wonderful boss and much freedom given to me to operate in my style.
Leading anything is hard, especially when grappling with a difficult situation where it seems that no matter what you decide, it will have a negative impact on those around you. Can you share a story about a situation you faced that required making a “hard call” or a tough decision between two paths?
Few years back in one of my past workplaces, I had to ask someone to leave due to certain reasons that I and my management had a debate on as I wanted to allow some more time to that person. That person had only completed 15 days in the system, however, my peer leaders disagreed and requested me to do that ‘talk’ (probably because I am excellent in any kind of communication and in ways certain sensitive things must me put across. That was a hard call which I took against my own wish as other stakeholders voted to let go of that person. I’d say that my gut and inner voice was right as we did lose a good employee as stakeholders judged too soon. This is one area where I request leaders to take a step back and not judge people too soon.
Let’s shift our focus to the core of this interview about ‘Successful Rule Breakers’. Why did you decide to “break the rules”? Early on, did you identify a particular problem or issue in how businesses in your industry generally operated? What specifically compelled you to address this and want to do things differently? Please share how you went about implementing those changes and the impact they had.
A pivotal point at present is our shift from conventional business operations to bringing in more tech expertise while also building on trust as a unique currency. I see business problems more as business opportunities with respect to the upcoming 5 years where almost every industry is going to see multifold change. With AI seeping in deep in our lives, grabbing the bull by the horns is the way we choose. That involves already building on a machine learning team, investing in deep discussions to make ourselves future relevant while bringing on the table a solution driven approach each time for our clients. Implementing becomes easy when you have the right people with a shared vision and that is what we are doing.
In the ever-changing business landscape, how exactly do you decide when to adhere to industry norms versus “breaking the rules” and forging your own way? Can you share an example?
At a personal capacity I don’t overthink, if I need to take a decision, I just take a step back and then lean forward to make that decision. Industry norms are good to follow in specific situations to be in tandem, however, whenever I need to do something path breaking, I take the plunge. For instance, having been in advertising and marketing most of my journey, couple of years back when I was thinking about ‘what next’ for me, is it another executive education that I should do or something else; the answer I got was from what I am naturally good at, which is speaking in front of any kind of audiences while also helping people & organizations become better version of themselves, starting with having that defined clearly. So, I took the plunge and I became an ICF accredited coach in leadership, business & communication.
What guidance or insight can you offer to new entrepreneurs trying to follow existing and accepted industry norms while at the same time trying to differentiate themselves in the marketplace?
I’d say don’t just launch something for the sake of it. Launch something keeping in mind how the dynamics may change in the next 10 years. Having a long-term vision is something I recommend and don’t change it once fixed. For example, 6 sigma methodology has DMAIC framework where D stands for Define and which is of utmost important. Defining what are you solving for. Are you solving for the next 1 year or more is something you need to decide? Also, read relevant books, and have this habit as a constant in your daily calendar.
Here is the main question of our interview. To make an impact, you have to champion change, get creative, and take risks. Please think back about the decisions you’ve made that have helped your business get to where it is today, and share your top 5 strategies or decisions that helped you succeed by doing things differently. If you can, please share a story or example for each.
1. Recognizing weaknesses but playing on strengths.
So, I recognize what I am good at and what I am extremely good at. In every task I do while accentuating on that strength in tandem with focus on what is the job to be done. This has helped me compliment how I approach any decision. For instance, I know I am not good with sales, however, I formed my own style of selling by not selling but attracting attention on what can I solve for someone and how optimally I can do that differently which adds distinguished value.
2. Taking the plunge
— in my professional journey, whenever I have been in vulnerable moments induced with some sort of fear, I have just gone ahead and done it either way. That way, my learning was faster and I did not overthink. Even today, If I need to take a decision (however small or big), I just take a step back, evaluate few things and take the plunge. Even if I feel 70% right about something instinctively, I do it. And yes, I do trust my instinct.
3. I chose people who asked uncomfortable questions, challenged briefs, and could sit with ambiguity.
Long before I scaled teams or departments. For instance. In my early years, I once rejected a highly profitable campaign because the strategic foundation felt wrong. My team supported the decision, even though it meant missing quarterly targets. Six months later, that same client returned with a far larger, long-term engagement because they realized we weren’t just service providers, we were strategic partners. Also, I chose to build a culture of reflection, not performance theatre. Most modern organizations are obsessed with visibility: dashboards, KPIs, town halls, recognition systems, productivity tools. Very few invest in structured reflection. In pursuit of making reflection a design principle. Like normalizing slow and quality thinking, post-mortems without blame, and conversations about what didn’t work not just what performed well.
4. I deliberately blurred the line between business and intellectual capital.
Leaders may separate ‘work from ‘thought leadership’. I took the leap and fused them. For instance, I treated research, writing, frameworks, keynote speaking, and academic exploration as core business assets and not personal branding side projects. For, what began as internal thinking models around leadership, presence, and communication eventually became published articles, keynote topics, and training programs. Today, those intellectual assets generate clients who already trust our thinking before the first conversation.
5. One of the most counter intuitive decisions I made was to stop making myself indispensable.
In the early years, everything flowed through me strategy, clients, hiring, creative, even conflict resolution. It felt powerful, but it was also fragile. The business was only as strong as my availability and energy. So I consciously started removing myself from operational gravity. That is one of the boldest moves I have taken; however, I always keep myself ready for rolling up sleeves and getting my hands dirty where absolutely required, else I believe in empowering
As a leader, how do you rally others to align with your vision? Also, how do you identify those who may not be fully committed or even silently sabotaging or undermining your efforts? What steps do you take to address these situations?
Great question. My practice has been starting to being patient and avoiding to judge a person or a situation, Rather, evaluate what all needs to be done to accomplish a goal within a stipulated time. When I interview candidates, I try and understand how they think, their values rather than only skills. Rest is giving it some time to observe how people carry themselves at work. For me it is not about work-life balance. It is more with daily patterns that we create and it is a top down approach. So I identify the top performers over a period of time and have them set examples for next in line. That way, the second line of leadership keeps getting ready within teams. Another thing I promote is cross functional interaction between teams. That is not easy but if gradually worked on, it brings in more trust and work also becomes fun and engaging.
Imagine we’re sitting down together two years from now, looking back at your company’s last 24 months. What specific accomplishments would have to happen for you to be happy with your progress?
Our company sees substantial growth and more success leveraging deeper aspects of technology while nurturing business relationships. At a personal level I would be grown spiritually even deeper with more Keynotes to inspire people globally.
You are a person of enormous influence. If you could inspire 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. 🙂
That is a wonderful question! I would want to have a movement for building more for the underprivileged and to support this cause in action and not only in words.
How can our readers continue to follow you or your company online?
Please follow https://www.linkedin.com/in/ankoordasguupta/ and https://www.garagecollective.agency/
Thank you so much for sharing all of these insights. We wish you continued success and good health!
Grateful to you for making time for all the wonderful questions and bringing out the best of this interview.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Successful Rule Breakers: Dr. Ankoor Dasguupta On How To Succeed By Doing Things Differently was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.