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Simon von Hertzberg of Holidu: “Embrace Transparency In Order to Create a Fantastic Work Environment”

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Simon von Hertzberg. Simon is the COO of Holidu, a leading travel tech start-up with worldwide presence and headquarters in Munich, Germany. Holidu operates a search engine for vacation rentals, allowing its more than 10 […]


As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Simon von Hertzberg. Simon is the COO of Holidu, a leading travel tech start-up with worldwide presence and headquarters in Munich, Germany. Holidu operates a search engine for vacation rentals, allowing its more than 10 million monthly users to find their perfect rental for the lowest price. The company also offers a software and service solution under the brand Bookiply, which enables vacation rental owners to multiply their bookings with less work. Holidu is one of the fastest growing companies in Europe and was recognized to have one of the highest employee satisfaction ratings among German start-ups.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

Ihave always been fascinated by entrepreneurship and the idea of growing a business. After studying International Business Administration, I started my career at Procter & Gamble. It was a great place to learn leadership skills and I had the opportunity to take on roles within multiple functions, ranging from Brand Management over Finance to Digital Media. In 2015, Johannes and Michael Siebers, the founders of Holidu, asked me to build Holidu together with them as Chief Operating Officer. I joined as one of the first team members and helped to scale the company to more than 250 employees from 40 countries today. As COO, I’m responsible for the functions Human Resources, Inbound Marketing, and Customer Service as well as for coordinating company-wide processes like OKRs (Objectives and Key Results).

Can you share the most interesting story that happened to you since you began leading your company?

I’d like to share a story that relates to the topic of this article. To build broad personal connections in spite of our fast growth, I schedule lunch dates with many of our new team members. During one of these lunches, a new joiner told me that she had been asking around about my role and was told that it was to take care of the company culture. This was an “aha moment” for me. I spend most of my time on tangible operational projects, but for many colleagues the subtle contributions to shaping our culture seem to be among the most important things that I do. This shows the high relevance that company culture has for our team and that we should consciously nurture it every day.

What is your company working on right now? How do you think that will help people?

The vacation rental market is very fragmented, providing bad experiences for both travelers and rental owners. Travelers need to spend hours browsing through many websites in order to find all available rentals in a region and to choose the perfect one. Rental owners, in turn, need to dedicate substantial time to listing and maintaining their properties on multiple websites in order to get sufficient bookings.

Because each website has its distinct fee structure, the same rental is offered for different prices across the web. Travelers therefore have to compare offers carefully or they risk paying too much. As availability calendars between different websites lack synchronization, vacation rentals are often falsely shown as available although they were already booked on another website. This leads to double bookings, resulting in cancellation rates of up to 30% in the industry and major frustrations for both travelers and rental owners.

Holidu’s mission is to make the search and booking of vacation rentals finally easy. We help travelers browse through all 15 million properties of our more than 1.000 partner sites with only one click. Our proprietary image recognition technology identifies the same property across different websites and always shows the best price offer, so that users can save up to 55% on their booking.

With Bookiply, we help vacation rental owners market their property effectively on multiple websites with a one-stop solution. We automatically synchronize the availability calendars, increase listing attractiveness through optimized photos as well as multilingual description texts and professionally handle the customer service towards the traveler.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

A simplified concept for happiness is that it results from the difference between expectations and reality. The high degree of unhappiness cited in the study indicates to me that there is an opportunity to work on both factors.

Expectations towards work have risen significantly over the last years. For many, work is no longer a means to earn money in order to satisfy basic needs, but rather a vehicle for self-actualization. I think this is a great development! However, we’re now so used to instant gratification as consumers that we may have become too impatient in the way we think about our careers. Also, as we see our jobs primarily as a source of fulfilment, we may have become too weary of the less exciting tasks, which are an unavoidable component of every job. In this sense, checking in with our own expectations and discussing them transparently can be a first step towards more happiness at work.

At the same time, employers can do so many things to increase happiness in our work reality. It starts by articulating the company’s purpose and vision and enabling everyone to recognize how their work contributes to it. It includes granting freedom regarding how to reach objectives, providing the resources required to succeed, enabling development opportunities, as well as ensuring transparent and fair company processes, etc. In my opinion, however, the most important factor for happiness at work are positive personal relationships. Companies can foster them, for example, by training their people managers to build a trustful rapport and by creating informal opportunities for growing friendships among colleagues.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

In my experience, both happiness and unhappiness are contagious. We’re very fortunate that employee happiness at Holidu is high. This becomes visible in our quarterly internal surveys as well as on employer rating portals like Glassdoor or Kununu. We see that new joiners are equally happy as long-term team members, so happiness seems to spread quickly. This positively impacts our company performance in multiple ways; it facilitates productive teamwork, for example, attracts high calibre talent and leads to a low absence rate.

Unfortunately, unhappiness spreads equally quickly from one person to another. We’ve had the case of a highly valued team member being unhappy with an organizational change. We were aware of the situation, but we failed to properly address the concerns, explain the reasons in a way to get a buy-in or find a different role for this team member. Over time the unhappiness caught on to the entire team, dragging down productivity and leading to high employee turnover. We were able to rebuild the team and have a great spirit again, but it required a lot of effort. This was definitely a big lesson for us to be fast and proactive about unhappiness.

Can you share 5 things that managers and executives should be doing to improve their company work culture?

  1. Recruit for cultural fit the right way. Recruiting for cultural fit is a double-edged sword, because it opens the door for all kinds of biases to influence the hiring decision. However, if done the right way, it builds a strong foundation for a great work culture and high-performing teams. We use behavioral interview questions to learn more about situations in which candidates have acted in line with our company values in the past. This is a good indicator that they will thrive in our company in the future.
  2. Discuss expectations regularly. If we don’t know each other’s expectations, it’s almost certain that we fall short of them or end up dissatisfied. However, talking about expectations can sometimes feel uncomfortable, so we tend to avoid it. Therefore, we make it a habit through our standard processes to regularly discuss mutual expectations. It starts during recruiting, it’s emphasized during the onboarding phase and continues in our regular feedback sessions.
  3. Promote from within. Even though our organization grows rapidly, around 75% of our people managers were promoted into this position vs. hired externally. This underlines our dedication towards personal development of our team. Promotions are one of the greatest forms of recognition and they are also one of the strongest culture-building signals for the organization about desired behaviors and results. When role models are promoted to leaders, their influence grows, and the company culture is positively reinforced.
  4. Foster strong relationships. Personal relationships are a major driver of happiness and in work life they also positively influence productivity. Therefore, we take selecting and training our people managers very seriously in order to facilitate trustful relationships that combine achieving ambitious goals with caring on a personal level. Equally important are the relationships among colleagues, so we invest in many social activities like quarterly team events, company parties and informal get-togethers like foosball tournaments or movie nights. Also, we are committed to treating everyone with respect and therefore have a “no-gossip policy” and avoid criticizing someone who is not in the room.
  5. Embrace transparency. We create value for our customers by bringing transparency into the vacation rental market and we also believe that internal transparency builds our culture and business. For example, in our bi-weekly all-hands meetings we transparently share the most relevant business figures and give timely updates on good news and bad news. We believe that if everyone is aware of the objectives and challenges, we can source the creativity and knowledge of the entire company to get ahead. Another example is that all new job openings are posted internally and are open for everyone to apply. This way we want to make sure that the process is fair and that we identify the best candidate for each role.

How would you describe your leadership or management style?

I like the concept of “situational leadership”, meaning adapting the leadership style depending on the situation, the individual and what needs to be achieved. A recent college graduate may require more guidance and needs to be motivated differently than a team leader with many years of experience. Even individuals with similar qualifications might react differently to certain styles, so in my opinion good leadership is about dialogue and empathy rather than a one-size-fits-all approach.

Having said that, management by objectives has proven to generate high output in many situations. I like to give a lot of freedom and trust to each individual in accomplishing their objectives. As a company, we systematically apply a form of management by objectives through the use of OKRs and it works very well for us.

Even while managing by objectives, I try not to be detached from the work of my team members and I periodically dive deep into the hands-on challenges. This way I can give relevant feedback and offer meaningful support, which in turn enables me to coach towards even more ambitious targets. During all of this, I try to act as a sparring partner on eye-level and to show that I also care for the person and not only for the results.

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

One “Life Lesson Quote” that I use as a guiding principle is “always choose the harder right”. It is helpful for me in small and big decisions both in private and professional life. For example, it gives me the needed push when wrestling with myself on whether to watch a show on Netflix or go to the gym. In professional life, I apply it for instance in recruiting when we urgently try to fill an open position. I know it is the harder but right thing to leave the position vacant until we find a great candidate. We do not want to give in to short-term pressures to hire someone that is not a good fit.

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. 🙂

One of the trainings I give at Holidu is about feedback. I think many people are actually quite good at giving constructive feedback, but most of us can get much better at giving positive feedback. At the end of each training, I challenge the attendants to give at least one honest and specific positive feedback every day. If this inspires a movement, we can significantly boost happiness, confidence and ultimately productivity.

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