Sumit Gupta of Deploy Yourself: Giving Feedback; How To Be Honest Without Being Hurtful

I believe that leadership is standing for something bigger than yourselves. You show your team the way, give it what it needs to do the job, and then get out of the way. Your biggest job is to create an environment of respect and accountability, where people have fun and express themselves freely by continuously moving forward towards the team’s goals.

As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing Sumit Gupta.

Sumit runs a coaching program called “Deploy Yourself” to coach managers and individuals to express themselves and forge their own path. He started out as a software geek 15 years ago, but was soon thrown, unprepared, into management. After leading teams for 12 years and making numerous mistakes, he now feels as comfortable talking about feedback and emotional intelligence as about machine learning and distributed systems.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I started as a techie 15 years ago and fit the typical geek profile — good at computers and programming but introverted and quiet when it comes to communication. At that time, I had no idea what communication skills or emotional intelligence were, leave alone their importance.

As it happens with most people who are good at their job, I was soon leading a team of 14 people. I was 24 years at that time, and I had no idea what management was all about. To make it worse, I wasn’t even aware that people management and other so-called soft skills can be learned.

Needless to say, I made a lot of mistakes managing that team. Yet I did a few things which came naturally to me and which worked well, though I had no idea why. Fortunately, in 2010, someone pushed me to do a few leadership programs and it was then that I was exposed to the world of coaching.

I had a dedicated coach from 2010–2012 and those were my most productive years. After moving to Amsterdam in 2014, I started exploring the concept of coaching further. Since then, I have read more than 200 books on neuroscience, psychology, leadership, and philosophy to understand how human beings operate and what good leadership looks like.

These years of research led me to Deploy Yourself, which started just as a series of blog posts, and is now a coaching philosophy which I am developing while working with clients. I believe my journey as a coach has just started, and Deploy Yourself is an idea which will keep me busy for the rest of my years.

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

“Deploy Yourself” is about understanding ourselves, nurturing and developing our strengths and acting in a way that allows our own unique light to shine upon the world, instead of following the path others have decided for us.

For example — Recently a former colleague reached out to me thanking me for his recent promotion. He said, “It would not have been possible without the deep coaching sessions we had a few years ago.”

A message like this is more valuable to me than any other financial reward can be. My most satisfying moments of leading teams over the last decade have been those when I know I have made an impact in someone’s life. I believe leadership is helping people to be their own best selves, and Deploy Yourself is my attempt to do that.

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

This story is not interesting but sad. But I want to share it as it has great importance. In 2012, when I was working on my own startup, I had a friend who was helping me with some graphic design work remotely.

We used to communicate over the phone, and one day she told me that she wanted to take a break for a while to deal with something. I could sense some emotions in her voice that day, but I let it go and felt it too trivial an issue to ask her more about it. She was a strong woman, and I left her alone as I “knew” she could deal with whatever was going on in her life.

A few days later, I found out that she had committed suicide. I never knew that was the last time I would speak with her, and if given another chance, I would always ask — “I notice some tension/anxiety in your voice? What is going on? “

You never know what difference you might make in someone’s life if you know how to deal with emotions. After this incident, I learned how to help other people navigate their emotions better. Today I believe that our emotions can tell us what we care about, but only if we listen. Emotions can be an asset, but if we don’t know how to handle them, they can also become a liability.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

By promoting the good performers to be managers and leaders, people have assumed for centuries that the skills that made you successful as an individual contributor would also make you successful as a manager. If you have led people for any considerable amount of time, you would know how false this assumption is. Yet in the business world, this continues to be the norm.

I was first promoted to a manager because I was good at my job. And my funniest mistake would be the same. Even when I knew something was off in my leadership despite me being good at my job, I pushed for the best people in my team to be made managers, even when they themselves didn’t want to.

The lesson I learned from that was that just like any other job, being a manager requires you to master a unique set of skills. Most people promoted to managers are not even aware of these skills, let alone be good at.

What advice would you give to other CEOs and business leaders to help their employees to thrive and avoid burnout?

My advice would be to get to know the people behind your employees. Spend time with them, be curious and listen to what is going on in their lives. Nobody likes being treated like tools or resources. We are all someone’s children, siblings, parents, spouses, employees, and friends — and a small outreach by leaders can go a big way.

As leaders, we often get so busy in meetings that the people we lead don’t get the attention they deserve. Do you know what your employees “care” about, what they value or not value in life, and why? Do you know what motivates or drives them? Do you know what frustrates them?

As a leader you can help people figure out what they “care” about. If we explore this simple yet powerful concept of “care” with our teams, it can open up a new world for them as individuals, and for us as a leader. This builds engagement and avoids stress and anxiety, as people find belonging and community.

How do you define “Leadership”? Can you explain what you mean or give an example?

I believe that leadership is a privilege and an opportunity to serve. Leadership is not about power or authority, nor is it about popularity.

Leadership is about character — which you will need to express yourself authentically, compassion — which you will need to grow and develop your people, and integrity — which you will need to serve your people with the respect and transparency they deserve.

I believe that leadership is standing for something bigger than yourselves. You show your team the way, give it what it needs to do the job, and then get out of the way. Your biggest job is to create an environment of respect and accountability, where people have fun and express themselves freely by continuously moving forward towards the team’s goals.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

Stress is nothing but emotions which we don’t know how to express. So the first step is to be proactive and learn how to listen to and express our emotions. The more attention we pay to our emotions, the more aware we can be of what they are trying to tell us.

Before a high stakes meeting, I make sure that I am well prepared. Also, just before the meeting, I spend a few minutes in silence just listening to my breath to ground myself in the present moment. This helps me to act in a way which is consistent with my values and long term objectives. And when I can do that, there is no stress.

Ok, let’s jump to the core of our interview. Can you briefly tell our readers about your experience with managing a team and giving feedback?

I have been managing teams since 2008. In the early days of my career I saw feedback as a distraction which keeps me away from “real” work. I wanted to get done with feedback as soon as possible as it would make me anxious and nervous. After all, nobody ever told me the purpose of feedback, how to do it well and how to make it a tool in my development.

It was only through my own mistakes receiving and giving feedback that I realised that feedback is work itself and not something external to it. Feedback is as much a part of my (and everyone else’s) work duties as any other task I consider essential. Over time I came to see feedback as a tool to improve not just my own performance, but also of the people around me, and of my team/organisation as a whole.

This might seem intuitive but it will be constructive to spell it out. Can you share with us a few reasons why giving honest and direct feedback is essential to being an effective leader?

The most important and obvious benefit of feedback is that it shines a light on and reveals our blind spots. We all need feedback to reflect, learn and grow. It helps us become aware of our strengths and weaknesses, and identify any actions required to address them and improve performance. Timely feedback is essential to create a loop where we are constantly reflecting upon what we did in the past and how we can do better in the future.

In addition to the above, regular feedback helps us build better relationships with people, have clear expectations, and create a culture where feedback feels normal and not like the dreaded world FEEDBACK can be.

One of the trickiest parts of managing a team is giving honest feedback, in a way that doesn’t come across as too harsh. Can you please share with us five suggestions about how to best give constructive criticism to a remote employee? Kindly share a story or example for each.

The first step to giving good feedback is to realise the importance and reason behind doing so. I believe that the only reason to provide feedback is to improve performance. The purpose of giving feedback is never to measure performance, blame, to prove yourself right, to make others wrong or to put someone in his/her place.

I believe this is the most important aspect of feedback which we often miss. I see feedback as a ‘gift’ given from one person to another, with the only purpose of improving how they work together. When we see feedback as a ‘gift’, the feedback conversations tend to be more natural and less awkward.

  1. Start by stating why you are providing feedback, which is always to improve performance (of the person, team, organisation). You demonstrate that by stressing on the impact of the person’s actions (on the team and their performance) and not on the person themselves. For example — Instead of saying “you are a weak communicator”, say “your communication style can be refined to make a better impact in team meetings”.
  2. It is very important to have an open mind going into the conversation. We must be willing to investigate / apologise if things turn out otherwise. For example — If the person you are sharing the feedback with brings up new facts or information you weren’t aware of, make sure to acknowledge them and take a time out to investigate rather than thrusting your feedback upon the person.
  3. Be specific in your feedback. Give examples. Do not be vague in your statements. For example — Say “I think your presentation would make a better impact with fewer words and more visuals” rather than “Your presentation needs improvements. You have a long way to go.”
  4. Be aware of the other person’s body language. Be prepared for an emotional reaction. If that happens, give space for emotional release. Listen.
  5. Don’t Push — When you push people, they will push back. Present your thoughts without trying to push them through. Use non-conflicting language. Use “I” instead of “you”. For example — Say “I felt disappointed when you did that.” rather than “You disappointed me by doing that.”
  6. Thank them for listening to your feedback. End the conversation on a positive note, with the other person thinking about the next steps. He/she should see the feedback as a stepping stone, not as a stumbling block.

Can you address how to give constructive feedback over email? If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. How do you prevent the email from sounding too critical or harsh?

If possible, I would avoid giving feedback over email as emotions get left out in written communication. Expressing ourselves via email is a challenging task as we have limited means to express our ideas. So if possible, set up a phone or video call with the person. You will thank yourself later.

Having said that, I realise that sometimes it is unavoidable to share feedback via email. In those situations, it would be prudent to consider the below guidelines to avoid misinterpretation :-

  1. Write messages in simple and short sentences. By adopting a simple style of writing, we become more effective since there is less room for misinterpretation.
  2. Ask others if they understand the message you’re expressing. The most effective way to ensure that no miscommunication happens is by confirming the message with others.
  3. Be careful in being funny or sarcastic. It’s alright to add some humor to messages, but be sensitive to others ‘ emotions.
  4. Avoid emotionally-charged messages. Written communication is not meant for emotional release. Ask yourself if you would have the courage to say the same thing face to face. If not, don’t express it as an email either.
  5. Ask for acknowledgement if you expect something back. Or follow up if you don’t hear back or hear an unsatisfactory response to make things clear.

In your experience, is there a best time to give feedback or critique? Should it be immediately after an incident? Should it be at a different time? Should it be at set intervals? Can you explain what you mean?

Feedback works best if it is given immediately after an incident, so that the person can recall the incident easily. However, it is best to wait a few hours or a day if the person is emotionally overwhelmed for some reason. In that situation you want to wait a while while they feel more settled, but don’t wait too long either.

You should try to avoid giving feedback at set intervals like 1-on-1 meetings as there are more important things to talk about in a 1-on-1. Regular meetings are when you have deep and meaningful conversations keeping the long term in mind. These conversations are to understand your people deeply (fears, insecurities, biggest ambitions) and empower them, rather than share feedback.

How would you define what it is to “be a great boss”? Can you share a story?

When I was living in Bangalore, there was a mango tree in the front of our house. During the fruit season, children from the neighborhood would throw stones at the mangoes so that they can eat them. Seeing them, my mom used to tell me — “People only throw stones at trees which bear fruit. But the tree keeps growing mangoes every season. Be like the tree, not like the stone throwers”.

I hate the word boss as it implies hierarchy, but I feel the above story highlights good leadership for me. Which is to do what you are capable of doing, to give your best despite the critics and the naysayers. If we can do this at work — to be fair with our people, to be ambitious with our dreams, and to be creative and innovative with our ideas — I think that is the definition of a good leader.

You are a person of great 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. 🙂

If I could inspire a movement, it would be to “Love and Empower People” and that is the idea behind Deploy Yourself. It is so easy to hate and belittle people, and there is so much of that going around our world today. I would love for people to see their inner genius, and that comes out by loving and empowering people for who they are, both at work and in life in general. When you love people you don’t shout at them, you don’t shoot them, and you don’t treat them in a way you yourself wouldn’t want to be treated.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Young people need models, not critics.” — John Wooden

I love this quote, and this is also related to feedback. This is relevant to me because today I realise that the example I set with my behaviour and leadership is more important than my feedback. As a leader, people see you as a role model, and if they don’t trust you or believe that you have their best interest in mind — no feedback will work.

Another of my favorite quotes is

“It’s the action, not the fruit of the action, that’s important. You have to do the right thing. It may not be in your power, may not be in your time, that there’ll be any fruit. But that doesn’t mean you stop doing the right thing. You may never know what results come from your action. But if you do nothing, there will be no result. ~ Mahatma Gandhi

This quote from Gandhi is also the core message of the Bhagavad Gita, and I have seen my parents act this way, which brings home its relevance to me. It’s the journey, not the destination. It’s the action, not the fruit of the action.

How can our readers further follow your work online?

They can visit where they can read my articles on topics ranging from feedback, emotional intelligence, and conflict resolution. I also run a bi-monthly coaching newsletter. On signup, you also get a Free Workbook containing 164 Powerful Questions that can transform your life, work and relationships.

Thank you for these great insights! We really appreciate the time you spent with this.

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