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Dmytro Gryn, CEO, Jooble


Dmytro Gryn is CEO of Jooble, a Job Aggregator, has gained valuable insights on effective leadership. He recognizes the advantages of non-violent communication and understands the significance of proper delegation in fostering the growth of his team members.


Firstly, can you give us a little bit of background about your business journey?

I joined Jooble more than 16 years ago as a Software Engineer and was the first person hired by the founders. My main goal back then was to create great software, and I quickly understood that it takes more than just code to achieve that. So I started to change roles within the company. At some point, I was a project manager, leading Jooble’s international scaling. At some point – I became a Scrum Master, implementing agile transformation. And in the exact same moment – Chief Technical Officer. That sounds extremely weird, playing two so different roles simultaneously, but it worked for me and brought the most valuable insight. You can be a good manager and a Servant Leader at the same time.

What role has self-belief played in your journey as a business leader? How has it influenced your decision-making and overall success?

Every manager is paid to make the best judgments in a volatile and uncertain environment and to make decisions based on them. The less self-belief you have, the more time you will spend doubting yourself and avoiding decision-making. And time is often crucial. I prefer to make decisions in hours or days rather than weeks. Validate them with data and colleagues, but trust myself.

I am not always right, but the pace helps to build an adaptive organization, and it pays off.


Can you share a specific moment or challenge in your journey where your self-belief was tested? How did you overcome it and what did you learn from that experience?

February 24th, 2022, Kyiv, Ukraine.

A full-scale russian invasion of Ukraine breaks out. Here I am and other 350 colleagues all over Ukraine scrolling news feeds, completely devastated. Our usual life is shattered, and the future is uncertain. It felt like you couldn’t do anything, just sit and wait for your destiny. But seeing how the Ukrainian Armed Forces fiercely fought the overwhelming enemy brought me back to reality. I had a business to run and a large team to care for. So, disregarding uncertainty, I started doing my best to make management decisions. And I believe it helped the company not to fall apart.

How do you cultivate and maintain a mindset of self-belief amidst the inevitable ups and downs of life?

I practice Acceptance. You can learn from the past when something bad happens. But it has already happened, and you don’t want it to slow you down in the future.


Are there any specific strategies or practices you follow to boost your self-confidence when facing uncertainties or setbacks in your business?

In moments of weakness and despair, I just need to remind myself that almost every setback is temporary and there is a way to change things in your favor. Of course, chances are high that your actions can’t change the situation instantaneously.

To accept that, I will sit and reminisce my successful decision, which took a year or two to reach maximum impact. That helps a lot.


How do you handle self-doubt or negative self-talk that may arise as a business leader? Do you have any specific techniques for reframing negative thoughts?

My two favorite techniques to deal with self-doubt are “Socratic Conversation” with myself and “Hallway Testing” with colleagues.

“Socratic Conversation” is a technique of asking questions to see the situation from different perspectives and make a better judgment as a result.

For example, I need to make a business decision, and suddenly, I am struck by the thought, “This is extremely risky, and you will fail.”

From there, I start asking myself: “Why do I think that’s true?” “Is it the only way?” “What is the worst that could happen?”

And the last one is the best question ever. I can’t imagine how many bad decisions were made because of a sense of abstract fear. And business leaders should transform “fear” into a “risk” and mitigate it. “Hallway testing” is a product management practice. When you are building something new, just create a simple prototype, and show it to five colleagues in your office hallway or near a water cooler to get fast feedback on whether your product may make sense. I use this practice with new concepts and ideas, allowing my colleagues to assure me that I am not totally insane :)

What advice would you give to aspiring entrepreneurs who struggle with self-belief? How can they start building a stronger sense of confidence and belief in themselves?

The ultimate self-belief booster is the first incoming payment and the first positive feedback on your business. Try to find early adopters for your product, spend some time with them, gather the feedback, and get your first “five starts” review. It will support you through the “valley of death.”


Have you ever encountered external skepticism or negativity regarding your business ideas or decisions? How do you stay grounded in your self-belief despite external influences?

Who didn’t? :)

I believe people always try to do their best acting with positive intent. That’s why I appreciate skepticism, mainly grounded on fears, risks, and immunity to change.

It can highlight important aspects of decisions that I overlooked and help to become better. Or just convince me that the idea is not good enough. There is no problem with being wrong sometimes, and it wouldn’t hurt my self-belief in general.

Are there any books, podcasts, or people you'd recommend checking out for anyone who wants to change to a more self-confident and belief-rich mindset?

Nothing helps to be more self-confident than understanding how people think and feel and why they act as they act. So I would recommend some books:

“Immunity to Change” to be more confident facing external skepticism “Nonviolent Communication” and “I Hear You: The Surprisingly Simple Skill Behind Extraordinary Relationships” to better deal with your emotions and understand your colleagues. And, maybe, “The subtle art of not giving a f” to be more chill 🙂

Finally, what are some practical tips or exercises you can recommend for entrepreneurs to strengthen their self-belief and mindset on a regular basis?

Conduct retrospectives on your business at least once a quarter. Celebrate your previous decisions' positive impact, even small ones. Talk to your customers at least once a month to build a strong grip on reality 🙂

Thanks so much for sharing your knowledge with us here! Where should people follow you to find out more about your work?




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