Welcome to another Going. Ahead. With Gage interview! I had the privilege of interviewing our CTO, John Cunningham, who shared insight on being a leader and how his team operates. I hope you all gain some valuable insights and enjoy the read!
What are you doing to ensure that W2O Group is at the cutting edge?
I suppose that’s my purpose here, right? The funny thing is that the cutting edge is not always the right place to be. It’s fun and exciting, but it can also be dangerous. What we really do is to experiment and learn from the cutting edge, then come back to the pragmatic side of what is the right thing for our clients. If cutting edge is the right place to be, we back it up with tried and true tech; delivery is what’s most important.
In a few words, describe what your team does for the company.
At the highest level, we are building the tools that empower our people and our clients in every part of the PESO model.
There is a massive amount of clutter out there, especially within earned and shared media. It’s about getting through that clutter and understanding the parts of the conversation that really matter, which W2O is known for – our tools take it a step further. Now, it’s not just a matter of finding those people, it’s the matter of tracking everything they say, everything that they do, and knowing how you can utilize this information to get your message out and understand the conversation before it affects your company. We build the tools to make that possible.
The other thing we do well is injecting great process into all things done at W2O. You cannot build software with an unorganized process. We’ve brought in agile methodologies in order to test ideas, validate assumptions, and build out what we are doing. I’m seeing it affecting the rest of the company and it’s awesome!
Thinking of your most successful current employees, what characteristics do they share?
It sounds cheesy, but teamwork. From the day I came in I’ve been working very hard to push transparency and openness throughout the group, which is not something that comes naturally for everyone. People are often surprised to see how transparent I can be and then when they get used to it there’s a natural tendency to adopt it. For me, that’s probably the most important thing you can do in building a business because when you’re not transparent, you’re always looking back on past problems instead of working as a team to build for the future. Strong teams aren’t built with closed doors.
All the leaders in my group share this openness, transparency, and a drive to put the company first. I push Jim Collins’ idea of the level 5 leader: the company comes first and individual accomplishments comes last.
How do you empower your employees to do their best possible work?
I am the world’s worst micromanager and I tell my folks that from the get-go. Therefore, empowerment is at the core of my management philosophy. One of the best compliments I’ve received was, “If I can’t find you I know exactly who to go to for any need that I have.”
I hand big parts of the business over to the leaders, and then I work with them. I drive the overall strategy of what we are doing, I dive deep into projects to make sure that things are on track, and I spend time with clients to understand their needs and how we can solve their problems. When it comes to how we handle Client Services, Solutions Architecture, Devops, Product Management, and Engineering, I expect my team to function well.
How do you encourage creative/innovative thinking within your organization?
You always need to strive to do better at that. The challenge is to keep people on track while exercising creativity. There is always a new technology that’s coming out and I encourage my team to experiment, which is one of the fun parts of this job, but to do so after they deliver. We don’t have 20% time here; we’re still building the software business up. No one on my team works 40 hour weeks; everybody works 50, 60, 70 hours because everyone on my team is passionate about what they do. They put in the time needed to build new tools for our clients. Footprint is a great example of this – John Steinmetz saw a need and built out a proof of concept then we ran with it, and it’s become a leading product.
What is the most difficult leadership decision you’ve had to make in the recent past?
Firing people is always the toughest thing to do and I think that’s the case for every entrepreneur. It’s really tough to affect someone’s life in that way. I had to let a roommate go in the early days of my first company – that made for some awkward evenings.
In the recent past the most difficult thing for me has been deciding and designing the organizational structure. My preference is to first get the right people on the bus and then put them in the right place. There have been some challenges where I’ve brought some amazing people in, but I didn’t necessarily have them in the right seat when they first came in. Even now we’re close, but it’s still not perfect. Trying to find the exact right place where a great person fits is a lot more challenging than just looking at the structure and creating a role you think you need. The recent challenge is more along the lines of getting the structure organized in exactly the right way. I strive to allow the structure to form naturally and then pave the talent path, but it’s not a perfect system.
What did you learn from that experience?
Organizational structures are tough; there is a lot of personal identity wrapped up in someone’s title and role in the company. Great leadership is vital to manage great talent, and leaders must be capable of keeping their feet on the ground while watching the horizon. This capability is so rare that it’s not possible to build the perfect structure without knowing everyone’s strengths and weaknesses, so you have to let it develop. In contrast, however, it’s difficult for an organization to thrive when there are constant changes happening to the structure, so I’ve learned to “pave the cow paths”. I build good people up and give them opportunities to shine. Once a leader has proven themselves, I will commit them to the position. This takes longer, but it builds a great team with minimal course correction.