Keep their responsibilities in mind — when the full-scale Russian invasion began, I couldn’t afford to panic — I had so many people depending on me and the decisions I was going to make were crucial for them. At that time, that and the safety of my family was all I could think about. Keeping my responsibilities in mind helped me ground and sustain myself until everything came back to at least some kind of norm.
As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Daria Leshchenko.
Daria Leshchenko is the CEO and Managing Partner at SupportYourApp — Support-as-a-Service company that has been providing secure technical, customer support and CX services to growing companies around the globe since 2010. Taking charge of the company at the age of 21, Daria turned it into a multinational business and one of the TOP customer support providers in the world. Today, SupportYourApp has 5 offices and 7 international hubs around the globe with over 1400 people on a team and over 250 clients from over 30 countries.
Daria graduated from MIM Business School and Aspen Institute in Kyiv. She is also a Harvard Kennedy School alumna.
Daria was included in the 200 Female Founders 2023 list by Inc. She received the Accomplished Leader Award by CCA and was also recognized as Customer Service and Success Woman of the Year by the Globee Business Awards and Woman of the Year in Customer Service & Sales by the Stevie Awards.
Thank you so much for your time! I know that you are a very busy person. 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?
It seems odd to say this today, but I can’t say I grew up wanting to be a CEO of any company. I actually wanted to be a teacher, so this is what I started to study. While I was studying, I got a job as a customer support consultant. I saw the potential in the industry and decided to take a leap — I suggested I be promoted to the position of the support department’s manager. With time, that department grew to be the SupportYourApp Group that includes three companies — SupportYourApp, Label Your Data, and Outstaff Your Team. We grew from a 1-person team to over 1400 people from 80 countries and speak 60 languages. We are still growing and developing new ideas to perfect and innovate our services.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
There’s a bunch of people that made our current achievements possible. The first one is my business partner, and the first person to believe in the idea of creating an outsourcing company that became SupportYourApp. It was his precious advice, friendly support, and unstoppable motivation that took me through a lot of challenging moments and helped me grow into the leader I am today.
I was quite picky about my team members — I wanted people around me to share the passion for customer service and to be determined to achieve the best results. With time, we managed to form an outstanding team, a group of talented people that made everything we have today possible. And I am grateful to every member of the SupportYourApp team. Without them, none of our achievements and successes would be possible.
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
One of our international hubs, with a big part of our team, is located in Ukraine. In February 2022, Russia launched an unprovoked and unjustified full-scale war against Ukraine, and, along with all Ukrainians and the entire world, we were forced to adapt to the new reality. Immediately, we started to take actions to ensure our team’s safety, assure our clients that we would continue to provide services for their customers, build plans, and continue working in constantly changing circumstances.
For me as a leader one of the biggest points was to keep our communication constant and consistent. My team and I were constantly connected and could make decisions fast and together. We also made sure our entire team was informed about the changes that might have been coming, and we did everything to ensure our team’s safety and continuous processes. As challenging as it was for all of us, that was the lesson I learned — communication is truly everything. The more effective and instant it is, the better teams can overcome any challenge, even the most difficult ones.
Diversification was also vital for SupportYourApp’s success in the last half a decade. When COVID hit, we lost about 25% of our client base. Then, after the beginning of the full-scale invasion, we stopped cooperating with all our Russian and Belorussian clients and those who were affiliated with or conducted their business in Russia and Belarus. In both cases, diversification of our client base, our team, and services helped us survive. The company continued to work, transferred tasks and projects to supporters in other countries for a short period of time, and could maintain our processes almost without skipping a beat.
Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?
For me, giving up was not an option. I know that many people are counting on me and my decisions can affect not only their professional, but their personal lives as well. This feeling of responsibility is what gives me motivation to pull myself together and continue working, no matter the obstacles.
I also thrive on the knowledge that overcoming obstacles is what makes me wiser and more experienced. It helps me be a better leader and a better human. I try to use every challenge as a lesson and an opportunity to learn and gain something new. Not giving up IS what sustains me.
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?
As I first became in charge of a customer support team, I couldn’t picture clearly what a real leader should be, and first tried to be everyone’s friend. That didn’t work out well — my team didn’t see me as a manager, and just wouldn’t listen to me. Finally, I had to make a tough decision, fire everyone, and spend nights in the office, responding to the customers all by myself. I had to sleep on the floor (sometimes I even joke that the mattress I slept on back then was my best friend), study while I was riding the subway, and eat without ever leaving the office. That story taught me that sometimes tough choices just have to be made if you need to ensure success, and helped me shape my leadership style more effectively. I am so grateful to myself for not giving up and pushing on. Without those tough decisions and harsh conditions I would probably not end up where I am today. And I am fairly certain — this is where I was meant to be.
What process or toolset can a leader use to make a choice between two difficult paths?
When making a decision — spin both or all choices. Think through all possible outcomes and make plans for every one of them. This is a good approach for those who like and want to take a safe route. It takes more time, but it makes taking a tough decision simpler. After all, you almost know what to expect and how to deal with the consequences.
On the other end of the spectrum is just risking. This is something I used to do when I was younger. I wanted to see what would work and what wouldn’t. I remember a time when I thought our company would be better off developing in the United States. So I sold everything I had here in Ukraine, gave up my title as a CEO, and moved to Boston. I was in the first half of my twenties and I felt like risking. Of course, in 6 months I saw it wasn’t working out, so I came back, and I haven’t looked back since.
So I would say that meticulous planning and risk management is the best approach when making a tough business choice or decision.
Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?
I am lucky to have a whole team of people I can turn to when I need their professional opinion. For some people, getting help and recognizing that knowing everything is impossible is tough. I am not one of them. I understand we all have strong sides and different sets of knowledge and skills. So I turn to my team and I encourage them to turn to me if I can help them with anything,
As far as a mentor not being helpful goes… it usually does not work for professionals who want to be self-sufficient and want to make most of their decisions themselves.
What would you say is the most critical role of a leader when faced with a difficult decision?
The most essential thing for a leader to do in rough times is to be there for their team. When facing a crisis situation, teams need someone who will take charge, make necessary and hard decisions, and take responsibility for. It gives people a comforting feeling of certainty.
The next most important thing is to fulfill your obligations. If people know that even in uncertain times they still have their job, familiar responsibilities, and will receive their compensation regularly — they will do their best.
Last, but not least — it is paramount to be in contact with a team. People may require guidance, professional advice, or just reassuring, and a leader needs to provide them. Events like regular meetings or online team buildings may seem minor in challenging times, but it is a great way to lift the team’s spirit and give people an opportunity to share their thoughts and emotions.
Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?
I don’t think there is a person on this Earth who doesn’t every once in a while think “I wish I had done it differently”. Of course, I would like to have been more organized and calm at the very beginning of my career. I wish I had done certain things earlier and some things later. But what’s done is done. I do not have a habit of pining after the past and instead I am making plans for the future. The important thing to remember is — everybody makes mistakes. Leaders do too. The easier we will look at them and the faster we will let them go, the more time we will have for learning something new and for becoming better. For me, that is the main lesson.
What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertain times?
The best thing to do for a leader in turbulent times is to keep on going. Nothing that can be said will be as inspiring as a personal example. Even in the most challenging and disturbing moments, for me, it is crucial to be in touch with my team and let them know that I’m here, and I am doing what I’m supposed to.
I would also like to mention social responsibility. Supporting and helping others, especially those who are in need, is a must for modern businesses and leaders. It brings an additional value and satisfaction to the team’s everyday job. Our team has been actively participating in charity activities, raising donations, and doing brilliant work to support those who need it. It unites us and helps us make the world a bit better.
Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?
The first and most common thing I see is panic. Some people just can’t help it — this is their nature. Their initial reaction to any crisis is to panic, which is completely normal. But it prevents them from thinking rationally and making important decisions in those first moments. And I know first-hand how crucial those first minutes and hours are. Making a hard decision is not easy (no pun intended) and sometimes just thinking about them may send a leader spiraling down, but panic is hardly the answer. It is best for everyone involved to avoid it. I know, I know — easier said than done.
Second is shutting down. When trying to make a difficult decision, some tend to completely shut down. They spend hours if not days brewing in their thoughts and plans. They clam up and nothing and no one can get through to them. Once again, I know how important it is to communicate during rough times and while making difficult decisions. It is okay to take some time to think and gather your thoughts, but completely shutting down is not a good option.
Third is making rash decisions — a complete opposite of the previous point, when a leader or a manager takes no time to think and just goes with the first solution that pops in their head. I understand this train of thought completely. It’s like medicine — if it is bitter and unpleasant, we want to take it and forget about it as fast as possible. But when it comes to business, things tend to get complicated and rushing through the decision-making process can’t do any good. The key here is to strike a balance between taking one’s time and speeding through the process.
Based on your experience and success, what are the five most important things a leader should do when making difficult decisions?
- Keep their responsibilities in mind — when the full-scale Russian invasion began, I couldn’t afford to panic — I had so many people depending on me and the decisions I was going to make were crucial for them. At that time, that and the safety of my family was all I could think about. Keeping my responsibilities in mind helped me ground and sustain myself until everything came back to at least some kind of norm.
- Understand the possible implications of their decisions — this is part of that risk management approach I talked about earlier. I am thinking ahead and processing all possible scenarios. This professional habit has also made its way into the way my mind works outside the office.
- Take the course of time into consideration — the world is moving fast and the decisions we make today may not look as good tomorrow. To avoid this, my team and I are future-proofing my decision to make sure they stay relevant for some time. One of the best examples of this would be AI. We started implementing it into our in-house developed software long ago. We knew — this was the future. The process demanded a lot of resources and a lot of time, which forced us to expand our tech team. This decision did not come easy, but I knew — this was something we needed to do. Today, when AI is a must, we are fully prepared to embrace it and have already built our support processes around it, which makes everything a bit easier.
- Make sure there are resources — and now more about the resources. In business, whatever decision is made, it will demand some kind of resources — time, investments, additional teammates, and so on. When we decided to expand our operation back in 2020, we also made a risky decision to start hiring abroad. Our team had to rebuild a lot of processes such as sourcing and onboarding, and we needed to consider how to maintain the same level of productivity and team work with team members working not only remotely, but from different countries too. We needed to make sure there were resources for us to take such a leap. We expanded our HR and Onboarding departments, and simply started trying the process out. Today, we have teammates from 80 countries, so I would say the decision was a success.
- Understand there are going to be mistakes along the way — it is impossible to be right all the time or not to make mistakes along the way, especially if you are a leader and a manager and have a lot on your mind. I could go on and on telling you about the mistakes I have either made myself or witnessed others make, but instead I want to give young managers a piece of advice: do not be afraid to make mistakes. They are unavoidable. Instead, make them your teachers and use them as an opportunity to learn.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Howard D. Schultz once said, “Success is best when it’s shared”. One should not forget about people who helped them reach their goals, appreciate their input and share the delight from the achievements.
How can our readers further follow your work?
They can follow me on LinkedIn or X (Twitter). I actively share our updates and achievements there, insights from important industry events, and post articles on leadership, business, trends, and my own experience.
Thank you so much for sharing these important insights. We wish you continued success and good health!
Daria Leshchenko Of SupportYourApp On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.