HR Talks with IT Leaders ep. 7: Dimitar Karaivanov on authentic leadership, radical transparency, and successful project management

HR Talks with IT leaders is a campaign organized by Bica and our goal is to give more visibility to the knowledge of how great tech teams are built. Every week, we will meet with accomplished entrepreneurs and managers who will share their personal experience and what’s their approach to leadership, communication, hiring, talent development and much more.

In our next conversation, we talk to Dimitar Karaivanov, co-founder and CEO of Businessmap (former Kanbanize)— Sofia-based IT product scaleup and a global leader in the kanban software space. At this point, about 1000 clients, both startups and Fortune 500 enterprises, use the company’s solutions to “get better visibility across projects, connect planning with execution, and help teams deliver results faster.” In the next couple of years, Kanbanize will likely pursue scale of its operations outside Bulgaria and open offices in other locations across the world.

What’s the number one lesson about leadership you learned over the years with Kanbanize?

You have to be authentic and make no compromises with your true self. Because if you make too many compromises, in the end, you will feel miserable and this will reflect on the whole organization.

What are actually the components of authentic leadership?

You start with a very honest look in the mirror in order to get a clear view of what you’re good at and what you are bad at. If you’re good at conceptualization and not so good at execution like I am, you should not be afraid to admit that. Another component is that you need a balanced process about other people’s opinions — you have to be genuinely curious about what they have to say — yet, this doesn’t mean you have to take them into account every time. It means that simply you’re curious about what others have to offer and not living in your own box thinking you’re the best in everything.

Then, there is this moral perspective good leaders usually have and which makes them charismatic. If you’re trying to motivate people with how much money or what monetary success they will get, this only works in a fraction of the cases — there has to be something of a higher moral stance for everybody. And again, you have to be truly honest about your feelings and your actions. In his book Principles, Ray Dalio talks about radical transparency. The more of that you have, the more of an authentic leader you can be. This is what I try to teach people I work with and improve myself towards as well.

How do you encourage such a kind of transparency in Kanbanize?

It’s all embedded and starts with the hiring process. First of all, we’re very picky about the people we work with. There must be a very strong cultural fit. It’s not rare for us to take between 6 and 12 months to find the right person for the spot. Why does it take so long? Before there are a bunch of interviews and once we like someone, there are a bunch of actions to make the person quit the process. It’s a bit counterintuitive but we tell them all the ‘bad’ things about the company.

Not that there are that many but we do expect them to work very hard, to be very honest and transparent, and to accept constructive criticism very well and act on it. We expect them to give constructive criticism to others — be it the CEO or the new trainee that just started.

We tell them everything they can expect from us even before accepting the job offer. We ask them to consider whether Kanbanize is their place or not. If they say yes, we send them a job offer with a document that’s about 3-pages long and it goes over everything we’ve talked about, making clear what all the expectations are — what’s acceptable, what’s not acceptable, what we won’t tolerate. So, there are many opportunities for people to get out of the process but if they have stayed, it’s extremely rare for us not to have found the right person.

Talking about values and expectations, how did your culture at Kanbanize change since the start of the company? Did it evolve in any way?

I think if a company doesn’t evolve it will go extinct at some point. We’ve evolved mainly around the workload of everyone at the company. At the very beginning, we were extreme fanatics; we used to work crazy hours. Then, at some point, we realized that nobody would love this company and its work if we continue this way. So, we stopped expecting heroics from people but it’s interesting that then it started happening more and more.

On the other side, our values and beliefs have not moved even a millimeter. We’re still extremely dedicated to being there for our customers; honesty and directness as well going beyond the borders of what’s lean and kanban and putting that into our products.

Your LinkedIn profile says you’re passionate about achieving extreme performance at scale. Can you break it down into smaller chunks — what are the prerequisites for achieving extreme performance at scale?

It certainly starts with a sense of unity and sense of purpose — why are we doing what we’re doing? It certainly touches on who we are as a company and who we are as people. A few years ago, I participated in this reality show ‘The Farm’. I was detached from civilization, friends, and family for 3 months. When this happens, you gain some sort of higher consciousness, at least for a while you get so much clarity in your mind. We used to hear Simon Sinek with his Start with the Why but who is by your side is equally important. To me, extreme performance has two different components. Besides purpose, you need to have the right type of relationships in your organization. People who achieve extreme performance at scale — they have to really like if not love each other. There’s a lot of empathy; a lot of helping each other out. And unless these relationships exist, it just doesn’t work. Of course, there’s also a mechanical component to it — what we do as a company as a process.

No matter whether you’re a CEO, HR specialist, or product person, nowadays project management is one of the skills you’d need if you want to be successful in these roles. So, what’s the best approach to managing projects and kanban boards, even if you’re not a project manager per profession?

The thing that attracted me to the Kanban method it’s actually one of its principles — Start with what you are doing now and then evolve. Respect the current processes, don’t go into a company and break its operations just because this or that framework says so. In that regard, I don’t think there’s one best method, one best approach, or one best framework for management. It has to be guided by principles. People have to face the fact that if they want to improve something, sometimes it doesn’t work in the best possible way.

So, let’s start with realizing what we’re actually doing now. Let’s make it visible. We use these kanban boards not because it’s fancy but because in knowledge work, the work is invisible. In order to manage it, you have to make it visible to the human eye. We use the boards because it’s equivalent to what’s happening in our heads and we can have sensible discussions on what should be done next; what we should not do. Start with what you do now, realize what’s really going on through visualization, and start improving the delivery of work, and only start new projects when you have free capacity. And when it’s all visualized it’s very clear whether you have free capacity or not.

It’s amazing how most large organizations don’t know how much work their company can deliver. Yet, they plan billions of dollars for new developments. Once you have a true idea of what you can do as a company, you can experiment and see how to scale it, add more budgets here and there but first you need to lay the foundation.

How would you measure your success as a leader moving forward?

It may not sound very humble but I think I am already very successful, and I will tell you why. At the end of 2020, when we had one of the biggest Covid-19 waves in Bulgaria, my father got the virus and pneumonia. He wasn’t feeling good at all and had to be treated in a hospital. At that exact time, we were actually closing an enterprise deal with one of the companies producing Covid-19 vaccines. So, on the one hand I am driving my father to the hospital and on the other selling software to companies who use our software to improve their processes and actually deliver new medicines faster. This is the moment I understood we actually make a difference as a company. Because we help companies to literally save lives. And, that’s when I felt accomplished for the first time in my life. I thought to myself that even if our company would disappear tomorrow, I’ve already made a difference. Whatever happens in the future, it could only be of benefit to that but I don’t think I will ever feel more accomplished as a human being.