Steve Winnie of CampusDoor: How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Stay clear and focused. Communication is always a two-way dialogue. You have to be ready to empathize and listen, genuinely and openly. You need to come to the virtual table with a clear head.
That’s more difficult these days given COVID-19. As a leader, I’m naturally ruminating all the time. If I wake up thinking about a particular issue, I have to decide if this is something the team and I can address, or if it’s out of our collective control. As much as we work collaboratively, I set the tone — and I can’t come onto Zoom distracted by what is out of our hands. I need to be present to move real opportunities forward.
I start the day with optimism — open to new possibilities, and enjoying my family. By the time I’m sitting at my desk, I’m 100% focused on CampusDoor and the individual members of our team.

Weare living in a new world in which offices are becoming obsolete. How can teams effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Steve Winnie.

Steve Winnie is CEO of CampusDoor, one of the largest third-party loan origination shops in the country. He joined CampusDoor 13 years ago as Vice President and General Counsel, rising to COO, President and then Chief Executive Officer when the firm became an Incenter company in 2017. Steve has also been an attorney for 19 years and has deep experience in technology, intellectual property and information security. He earned his B.A. in Political Science from Mansfield University of Pennsylvania and his J.D. from Cornell Law School.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Leading CampusDoor, a technology company which has processed over $24 billion in student loan applications for 2.2 million unique borrowers, is a reflection of all I believe in.

I grew up in extremely humble beginnings and was the first person in my family to go to college, and then law school. If not for the generous financial aid I received, we wouldn’t be having this interview years later.

I am thrilled that my work helps others who grew up in a similar position.

After completing my J.D. at Cornell, I worked in the financial industry and also served as Associate Counsel with college lender Sallie Mae. I had been with CampusDoor earlier and returned in 2009 to reinvigorate the company. It was exciting to be in the trenches with a fabulous team — innovating a white-label technology platform that makes borrowing easy for students, and private lending easy for banks, credit unions and educational institutions.

In 2017, CampusDoor became an Incenter company, and we are an acknowledged leader in our space. I am thrilled to have come full circle with this wonderful business.

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

I mentioned that I had been with CampusDoor earlier — -having been hired as Vice President and General Counsel. On my second day there, I was given a pivotal assignment — negotiating the terms of its sale to Lehman Brothers. Five Lehman attorneys from all over the country came to our offices in Lincoln Town Cars to meet with me, as the sole lawyer who would be handling the transaction. It was both a challenging and exhilarating assignment and it made me realize how much I loved the business of business. When Lehman closed operations and CampusDoor made the decision to restart on its own, I was incredibly excited to lead the charge.

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

My college basketball coach said, “Always tell the truth and you’ll never have to remember what you said.” That is my North Star. Without a photographic memory, and with an extremely busy schedule, it’s the only way I can navigate business and life. I am a very transparent leader. I only know and share one version of the truth, whoever I encounter.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I owe my law school education to a former administrator at the Pennsylvania State House named Jean Schmedlen. I met her during my senior year in college, when I was interning for the Speaker of the House. We became friends and she asked me about my career plans. I told her that I was interested in becoming an attorney, but could not afford the law school applications. Outside of work, she took up a collection to pay for everything. She also detected my struggle with confidence, and pushed me to apply to Cornell despite my doubts that I would be accepted. When I was offered a place in Cornell’s class with generous financial aid, I called my father first and then immediately phoned Jean.

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

One important benefit is collaborative thinking. Our people specialize in software design and development. We are constantly drawing on a whiteboard as we envision new creations. Doing this online just doesn’t get us to the same place quite as fast.

It’s also much easier to build and maintain a distinctive culture in person. It’s all about how we treat each other. There are more opportunities to embody the little things that make us who we are — for instance, everyone holding the door, or senior management taking out the trash and washing the dishes.

True friendships are easier to build, too. I can walk around, see who is having a hard day, and draw people out. My colleagues can do the same.

I’m a believer in leading by example. My style is hands on, working side by side with the full team. When we are all together, it’s much easier for everyone to witness and believe in the culture that I’ve worked to build.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

Leadership and collaboration are both very challenging. I’ve had to develop and draw on my emotional intelligence as never before. I have to combine what I know about the people that I work with, and the signals that I’m reading on video, email or text, to draw them out in new ways.

Running a business requires candid and collegial conversations, quick and smart decision making, and confident action. When you’re not physically together, all this is harder to perfect.

We are a client services business, and in-person meetings with our customers are very important. They offer a chance to read the room and watch nonverbal cues. The same goes for internal mentorship and training. Being in person is more effective.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space? (Please share a story or example for each.)

1) Stay clear and focused

Communication is always a two-way dialogue. You have to be ready to empathize and listen, genuinely and openly. You need to come to the virtual table with a clear head.

That’s more difficult these days given COVID-19. As a leader, I’m naturally ruminating all the time. If I wake up thinking about a particular issue, I have to decide if this is something the team and I can address, or if it’s out of our collective control. As much as we work collaboratively, I set the tone — and I can’t come onto Zoom distracted by what is out of our hands. I need to be present to move real opportunities forward.

I start the day with optimism — open to new possibilities, and enjoying my family. By the time I’m sitting at my desk, I’m 100% focused on CampusDoor and the individual members of our team.

2) Reinforce your people-first culture by listening

CampusDoor has a genuine people-first culture. When we’re together all day, people can feel my sincere interest in them as individuals. When we’re not, I have to work harder to reinforce it.

I avoid bland questions like “How was your weekend?” which is really meaningless. Instead, I might ask, “You mentioned you were getting a puppy. How is he doing?” It’s important to maintain the strong and authentic connections that make us an effective team.

3) Harness your emotional intelligence (EQ)

I can’t manage by walking around right now, so I’ve had to dip into my EQ skillset to draw people out.

I have to “ask to listen” — understanding that there are different pathways to eliciting the suggestions, feedback and information that may be affecting our group’s performance.

For example, by asking a team member recovering from illness what she needed most from CampusDoor, I found out that she wanted to accelerate her return to work. She needed a special desk to put over her bed for that to happen. We ordered it and she was delighted.

4) Go from monotone to multi-tonal

The technology that facilitates our communications, such as texts or emails, is flat and monotonal.

We as leaders have the opportunity to use those as conduits for engaging, multi-tonal dialogue. At the same time, we have to be careful that we harness them constructively. There are many ways to do this:

I choose one “regular” mode of communication for each individual. Some people seem to prefer and be more responsive to texts and others to email or phone.

I also think about how others will perceive my communications. I avoid early Monday morning calls because people will think that I’m either checking on them or about to share bad news. For the same reason, I stay away from texts or calls after 3 pm on Fridays. I never mark a message as urgent unless it truly is time sensitive.

People who are used to working in person are always wondering how their managers perceive them. They’re waiting for that “catch” when you contact them. I like to just check in on everyone periodically. I keep calls brief so that everyone is reassured that they are valued, and there is no other agenda.

I might bookend phone conversations about potential business challenges with personal chatter — so colleagues understand that I sincerely want to collaborate with them to tackle whatever is going on, and there is no “blame game.”

There’s an art to walking that fine line between compassion and intrusiveness. When you can engender trust, people are also more likely to open up about the reason behind behaviors that you might otherwise question. Someone might never turn on his/her camera for a Zoom meeting because of self-consciousness over humble surroundings, for example.

5) The end game is still productivity and profitability

Whether we’re using Zoom or texts, we want to offer safe and productive spaces for brainstorming and innovation.

If we are having Zoom team meetings, my only ground rule is that no-one complains without offering a solution. COVID-19 has given everyone a new way to step up and solve unexpected challenges, and I want to foster this.

I also use Zoom and other technologies for polls/surveys — constantly trying to measure progress against goals.

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

Yes, we’ve had some challenges due to our Central Pennsylvania location.

We have a largely rural workforce and some people have spotty phone and Internet connections. We have had to supplement these connections with hot spots or new devices, or reallocate some of their duties temporarily.

Some of our people are currently using their own cell phones, and we give them gift cards to help with the costs.

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

Video is clearly best, though not perfect because some people just aren’t comfortable with it. For that reason, we can’t fully measure its effectiveness.

I happen to like Microsoft Teams because of its multimedia approach. Not only can we share files and videos through it, we can express our emotions. I used to have an aversion to emoji’s, but now I favor them, as long as they’re not overused. They make collaboration more fun and natural, and less sterile.

If you could design the perfect communication feature or system to help your business, what would it be?

I’d love a system that gets us as close as possible to teleportation — e.g., moving into someone else’s workspace.

It would be a platform like Zoom that empowered our teams to a) be mobile b) easily drop files in and have several people working on them at once (similar to Google Docs) and c) replicate all the nuances and quirks of sitting in a room together, like watching people’s hand motions. It would also make everyone more locked in by automatically shutting off their other devices. Of course, it would need to incorporate different levels of security, depending on the topics of discussion.

Basically, it would offer the catalytic energy of a meeting room. We’re getting close to that but we’re not there yet.

My particular expertise and interest is in Unified Communications. Has the pandemic changed the need or appeal for unified communications technology requirements? Can you explain?

It has absolutely amplified that need, especially when you’re communicating with prospects or clients.

There has to be a better way to create, manipulate, edit, and share documents in real time, conveying context and emotion, and read the room.

It’s really a challenge of using technology to be more high touch. We’re a technology company, and yet we use a giant whiteboard to foster both innovation and camaraderie. If we’re creating a new solution, we often have people throw out ideas on sheets of paper attached to the board, and then discuss them. It’s super popular and we also use it for polls about what to have for lunch!

Speaking of lunch: We integrate email and Yammer to keep the social aspects of our work front and center. We might poll people, for instance, on what music they enjoy on a Sunday morning. The more relaxed we can be with one another, the more effective any unified communications that we implement will be.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

Yes; there are many advantages to VR. We would love to offer an environment where people can interact almost like they are in a video game.

We want to make sure that if we adopt such a technology, it fits with our culture of support and inclusion. It needs to be comfortable, accepted by and engaging for everyone, and meet our security needs.

Is there a part of this future vision that concerns you? Can you explain?

Yes — We need to make sure that future technologies will be embraced by everyone, regardless of their skills and experience; don’t present huge bandwidth constraints; meet stringent security requirements; and are easily affordable. The goal of the Internet and digital communications is to advance global collaboration. In that spirit, whatever becomes standard will need to be inclusive rather than exclusionary.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

I’m much less formal now. I find my clients appreciate the chance to talk about life outside of work, and so do I. Those more relaxed relationships are more satisfying and good business too.

This has definitely changed the tools I use. I used to rely on email. Now I’m much more likely to pick up the phone, get onto video or do a chat.

I also had an opportunity recently to meet safely with a client in person. Because fewer people are doing this now, the meeting was especially impactful, and got me excited about the “new normal” ahead.

In my experience, one of the trickiest parts of working with a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote team member?

First, form a strong relationship beforehand, if possible. You need a foundation to build on. It’s so much easier to provide feedback when you know and trust one another.

Second, structure the conversation like a sandwich. The first piece of bread will be a compliment of some kind. The filling will be a discussion of what needs improvement, and the top piece of bread will consist of more positive reinforcement.

Third, all feedback about improvement opportunities should be done by video, versus email, so each of you can see the other’s reaction. Don’t record the conversations, either. You don’t want to seem as if you’re building a case. Good managers regularly offer constructive recommendations to help their teams advance. Video is the best channel for that.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

We set up open tabs at favorite local restaurants (no chains). This definitely builds camaraderie. People feel good about going someplace of their choosing during a certain night or weekend, and helping businesses in their communities. It’s even better when they pass each other in the parking lot picking up takeout and get to talk.

We also set up Zoom gatherings, with some curated topics of discussion before and after the formal meetings. These can be done in breakout rooms. Or we’ll set up Zoom surprise parties with an open tab if someone is retiring or celebrating a birth.

We leverage snail mail, too — sending gifts for special occasions, and also mailing extra assistance when someone’s family member is experiencing a health crisis or job loss. This is done very privately; only the few work friends who initiate it, and the recipients, know. It’s heartfelt and definitely keeps us all together.

Ok wonderful. We are nearly done. Here is our last “meaty” question. 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. 🙂

I’d like to inspire a movement of more empathetic and diverse leadership — based on the principle that every team member has something special and unique to offer. Leadership is a privilege and too often, CEOs think of people as one-size-fits-all, disposable commodities. I am so grateful to the CampusDoor team who are each pulling us forward in their own ways. Embrace your colleagues like family, and never take them for granted.

How can our readers further follow your work online?

I look forward to hearing from and connecting with your readers at:

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.

About The Interviewer: David Liu is the founder and CEO of Deltapath, an award-winning unified communications company that liberates organizations from the barriers of effective communication. Liu is known for his visionary leadership, organic growth strategies, and future-forward technology. Liu is highly committed to achieving a greater purpose with technology. Liu’s business insights are regularly featured in Forbes, Entrepreneur Magazine, Tech Crunch, and more.


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