When my co-founder Jared and I started HotelTonight, we wanted to build something lasting, from our product to our company culture. We had a ton of ideas – we knew we wanted to be wildly different than the large corporations we’d both spent a bit of time at, and create a place where people could do the best work of their lives, learn more than at any other job on both a personal and professional level, and build relationships that would last far beyond their time at HotelTonight. Jared and I boiled down the elements of our culture into three words – build, question, and respect – and we knew the specific tactics we would use to establish this type of workplace would change and evolve as the company grew.
Today we proudly have more than 200 employees, including six offices internationally and 55 customer support rockstars who work remotely. And like any rapidly-growing company, we've experienced some growing pains, such as communication between offices and teams, and going from a flat team to having more reporting structure.
"Not providing feedback is doing you both a disservice – and it sets someone up to continue to disappoint you."
One particular piece of feedback we heard as we’ve grown is that people weren’t giving or receiving enough feedback (note the irony!). Our team had great things to say about the overall office culture – that these were the smartest, coolest people they’d ever worked with – but expressed that they didn’t always feel they had the ability or resources to give honest, direct feedback both to their peers and to leadership.
To improve communication and foster a spirit of collaboration and openness – a core aspect of a respectful, questioning culture – we realized it was time to invest in leadership and feedback coaching. This was something Jared and I had resisted for a long time. We saw the potential value in coaching, but worried it would be too “corporate” or cheesy, or boring and a waste of time – all things that are contrary to HotelTonight’s values. And things that we as employees of the company would have hated to endure as well.
So it was really important to do it right. After a lot of searching, Jared found an amazing, down-to-earth coach, Anamaria. She and her business partner Michael really got what HotelTonight is all about, and designed a custom, action-oriented coaching program that was perfect for us. We kicked off the program with team leaders, many of whom were managing others for the first time in their careers. The feedback about these sessions was so overwhelmingly positive that we decided to roll out a program for the entire company.
"To improve communication and foster a spirit of collaboration and openness – a core aspect of a respectful, questioning culture – we realized it was time to invest in leadership and feedback coaching."
We broke up into small groups, each of which went through several sessions, focusing on specific language to use when giving and receiving feedback, how to avoid being defensive when getting feedback, and overcoming fears and other barriers to providing feedback. The coaches guided us through role-playing sessions, and we gave and received feedback on our feedback (yes, there was feedback overload at times!). We flew in senior leaders from our international offices to make sure they and their teams would reap the benefits, too. Each session was a safe, confidential space where team members felt comfortable expressing their frustrations, their successes, and their progress.
During the final of each group's three sessions, either Jared or I sat in and received feedback directly from the group on things we’d done that were both motivating and demotivating. While this was done to allow the team to practice their ability to give real feedback, it was also invaluable to me as a leader. Some of the feedback I received I was hearing for the first time, which meant I’d never been able to address it previously. To paraphrase Anamaria: “not providing feedback is doing you both a disservice – and it sets someone up to continue to disappoint you.”
For example, while I am very detail-oriented, I’d often felt apologetic when providing highly detailed notes or feedback on my team’s work. During these sessions I heard how much the team really does value my input and perspective — and that they were actually hungry for more. I also heard that I can sometimes seem distracted in meetings and that putting my phone away would go a long way in communicating my interest and engagement. Now, we all stack phones at the beginning of meetings (mine on the bottom). One other really valuable piece of feedback I received was that when meetings are running long, I sometimes quickly propose a course of action that appears arbitrary to the team, or like something I’d already decided beforehand. This had the unintentional result of making people feel like the meeting was a waste of time. I’d never explained the context – that I have a bias for action, and that my intention was to create a path of decision. Hearing this feedback from the team and sharing my perspective with them in return was genuinely helpful for all of us.
"At HotelTonight, the impact has been absolutely transformative."
It can be easy to overlook the importance of training and coaching, as I’d done earlier, but it’s something that will be part of every organization I lead from now on. At HotelTonight, the impact has been absolutely transformative. I’ve seen firsthand the incredibly positive impact – we are working more collaboratively, communicating more, and shipping improvements and innovations at a faster pace than at any point in our company’s history. As a leader, it’s essential to invest in the development of your team – and when you do, everybody wins.
More from the executive spotlight series:
URX on Re-Aggregating the Web – John Milinovich, CEO, URX
From rags to riches: What one CEO learned from his biggest mistake – Ryan Smith, CEO, Qualtrics
Creating Culture: An Imperfect Recipe – Andy Dunn, CEO, Bonobos