Peter Dudley: How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Create intentional team time on a reliable cadence. Everyone hates staff meetings, but that’s because when you’re all in the same space all the time, staff meetings feel redundant and wasteful. When you’re remote, however, most interaction is project or task based; our only real connection to feeling part of a whole team might be through the staff meeting. It’s important that these times be team oriented; don’t give updates and reports that can be emails. Use this time in ways that make the people in the team feel like they belong.


We are 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 interviewingPeter Dudley.

Peter Dudley’s career has taken him from aerospace to the dot-com boom (and bust) to corporate social responsibility to nonprofit leadership. Along the way, he worked on the first stealth aircraft (B-2 Spirit), the first PDA (Casio Z-PDA), and the first smart phone (Nokia 9000), in roles as diverse as tech writing, web development, marketing, and community management. For the last two decades he has been a nationally recognized leader in workplace giving, volunteerism, and corporate responsibility. Peter currently serves on the national boards of directors of CHC: Creating Healthier Communities and Artists United. A writer at heart, Peter has published four novels, and as the father of a transgender woman, he is a vocal ally and advocate for equality in all its dimensions.


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?

Ifeel like my career has been in a constant state of “getting started.” Like many people, I’ve morphed my career as opportunities have presented themselves. As a kid, I was sure I wanted to program computers, so I got a software degree. But after college I realized I had an equal love of writing and communications, so I found myself building a tech writing team for a startup. Through the 90s, I got a taste of leading teams in marketing, software development, operations, communications, even training and support. In 2001, an opportunity I never expected presented itself: corporate responsibility at a big bank. It was a complete change, at a time when CSR was a growing concept. I knew nothing about workplace campaigns or employee volunteer programs, but by the time I left, the team I led had built a set of programs that were among the largest and most comprehensive in the country, and I was chairing a global industry council of my peers at top companies.

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

The one that comes to mind right away was in 2009. I had just been promoted from project staff to a manager position, in charge of Wells Fargo’s workplace giving and volunteer programs. This was during the subprime mortgage crisis, which Wells Fargo had largely stayed out of. In the thick of that, Wells Fargo bought Wachovia, and suddenly my little 130,000 person company became a nationwide behemoth of 270,000. With the economic recession and a lot of employees uncertain about their future, some in management thought we should skip the workplace giving campaign that year. But with the help of the CMO, I convinced them we should do it. This meant rolling out an application to a newly merged enormous enterprise, new branding and materials, and managing a huge cultural change for 140,000 employees. I had to quickly befriend all the new community relations managers around the country, so I went on a getting-to-know-Peter tour of the key markets. Although there were a lot of risks and challenges, I was sure it was the right cultural move. The results proved that to be true. It was complex, and a tremendous amount of work, but the team was motivated, skilled, and dedicated to the end goal, and that year helped vault my campaign to the #1 ranking for the first time. (A distinction we held on to the nine years I led it.)

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

When I was nine years old, my 15-year-old brother was trying to teach me how to ski. He got frustrated because I was being too cautious. Finally, he said, “If you don’t fall down, you’re not having enough fun.” Of course, we’ve all heard “if you don’t fall down, you’re not trying hard enough,” but I’ve always thought of that as pretty cynical — you should be working so hard that you risk hurting yourself. I like my brother’s version better.

Although I’ve been innovative at times and love new ideas and challenges, by nature I’m more deliberate and cautious. I let ideas simmer rather than blurt them out. This quote reminds me that life is short, and the risk of falling down is nothing compared to the risk of missing out on the joy that can come from trying new things. We’re all going to fall down sometimes. We’re humans, and we’re all stumbling through life the best we can. When faced with a choice between two seeming equals, or two unknowns, I try to pick the one that will be more fun. I’d rather have a super motivated team get an 80% result, than get a 100% result but burn people out or destroy their morale along the way. I’ve had both kinds of leaders in my career, and I know which one I’ll keep working hard for.

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?

There are a lot of those people, but Tim Hanlon comes to mind first. He ran the Wells Fargo Foundation for years and years, and I don’t think I’ve ever worked for someone more fiercely loyal to their employees than Tim was. Tim was kind, and funny, and understood that his role as manager was to empower and enable and support the teams that reported to him. He shielded us from higher level politics while focusing on us not only as leaders and employees, but as people. He genuinely cared about everyone on his team, no matter how you came to be there or what your history or your role was. If you were part of his team, he had your back.

I also want to mention the manager who hired me into Wells Fargo, Joan McDade. Joan was similarly an incredible mentor and colleague, a truly driven person whose primary goal was to make the world a better place. She was diagnosed with stage four lung cancer while I worked for her. I’ll never forget our last conversation. She actually apologized to me for not giving me a “proper performance review” … that’s how much she cared about her team members. She died a few weeks later. That was ten years ago, and she was exactly the age I am now.

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?

There are obviously many benefits to being together, but I’ll focus for now on these three: building trust, the organic flow of information, and what I’ll call “contact in the darkness.”

First, building trust. Being physically together allows us as humans to experience the totality of the other humans we work with. We see their movements, their body language, and all the other things that don’t come through in even the best video conferences. There’s also something about sharing a physical space — a cold office, an unreliable coffee maker — that builds empathy and trust between people.

Second, the organic flow of information. I shorthand this as “hall talk.” I don’t like it when people “just pop in” because it’s “easier than sending an email,” but when people bump into each other in the halls or the elevator or the break room, information flows organically; it’s like organizational lubrication. When people are remote, they don’t bump into each other — one has to intentionally make contact. For example, when I’m in my office I bump into the CFO all the time. When we’re remote, we can go a long time without connecting outside a staff meeting.

Third, the idea of “contact in the darkness.” Especially this year, with COVID-19 keeping most of us home all the time, isolation can wear us down. It’s like being alone in the dark, and for many people that isolation breeds negativity. Some people get that awful feeling of having been intentionally excluded from the party. When you’re physically together, you know where everyone else is and what they’re doing, so you can’t get this workplace version of FOMO.

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?

Fundamentally, the biggest difficulties come down to three things: Information flow, trust, and fatigue. Remote teams struggle constantly with trying to find a balance between information overload and information starvation. A quick “hey did you hear X” in the hall becomes yet another email. Before you open and read everything, there’s no way to separate the irrelevant or uninteresting from the urgent and important, especially if the subject line is “quick update,” “following up,” or “checking in.”

Trust is hard to build but easy to lose. We think of broken trust as coming from betrayal, but in truth trust is something that has to be nurtured and refreshed constantly. Without constant effort, trust can erode in nearly imperceptible ways. All the little miscommunications and disconnects are like termites eating away at the structure of trust. People are good at saying everything is fine when it’s not… when you’re together, you’ve got more opportunities to notice the erosion and shore things up. When you’re remote, it takes constant attention and a willingness for all the team members to speak up, even when it feels uncomfortable.

And all this overcoming inefficiency and fighting isolation leads to fatigue. Even introverts get tired, trying to reassure the extroverts that everything is fine. It’s harder for everyone, and it’s a difficult cycle where nurturing trust takes energy, and depleted energy makes it harder to keep up the effort.

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.)

As a manager, here are the five things I’ve found, over more than 20 years managing remote teams.

  1. Adapt to the communication style of your direct reports.

Some of your team need scheduled, structured one-on-one time, and some need frequent micro check-ins. Become aware of your own communication biases and adapt to your team rather than force them to adapt to you. In one role I had three remote employees: one wanted to encapsulate all our communication into a single 90-minute meeting each week, one did best with several quick connections every day, and the third just wanted to talk when talking was necessary.

2. Create intentional team time on a reliable cadence.

Everyone hates staff meetings, but that’s because when you’re all in the same space all the time, staff meetings feel redundant and wasteful. When you’re remote, however, most interaction is project or task based; our only real connection to feeling part of a whole team might be through the staff meeting. It’s important that these times be team oriented; don’t give updates and reports that can be emails. Use this time in ways that make the people in the team feel like they belong.

3. Tend to the team’s balance.

Don’t let a few voices dominate every conversation. I am a quiet participant in a bimonthly videoconference where three or four people always dominate the conversation because they’ve known each other for years. As someone who was raised not to interrupt and who is new to this group, I feel irrelevant and unvalued. This can be incredibly destructive to team and individual engagement, and it’s up to the leader to be aware of and fix this.

4. The “slow 8 count”

I wish I could recall where I heard about this, years ago. On conference calls when you ask for questions or comments, do a slow, silent count to eight before moving on to the next topic. You’ll be shocked how many people are sitting on good questions or ideas and will raise them just before you get to eight. The silence will be uncomfortable, but it’ll be worth it.

5. Be vulnerable and authentic.

This one may not apply in all situations, or for all managers. Some people are commanders at heart or are in roles that demand a strong hierarchy; I’m more a player-coach. I lead with my own vulnerability, which creates space for trust to be built. I work hard to make myself approachable, and I see the returns in the way people trust me, and in the way team members trust each other.

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?

We were fortunate that, as a small nonprofit where everyone worked in the office, our infrastructure was set up so we could all work remotely from day one. We already had a shared file system, email and calendars set up for group access, and most of our other tools were accessible over the web. Most of us switched to our own cell phones right away, and although at first some of the staff had trouble learning Zoom, everyone got it pretty quickly. Our phone system sent voice mails to our email inboxes. The two most tricky parts of the pandemic were making sure someone could pick up the mail (we still receive a lot of donations by check), and printing our mailings (some employees don’t have printers at home, and our office printers are more cost effective). The biggest challenge, though, was that our former CEO retired in May, so our new CEO had to be interviewed, hired, and onboarded during the pandemic. We accommodated this by having the small executive team (four of us) come in to the office two days a week. We observed strict COVID protocols and distancing, but being able to meet in person even infrequently meant so much.

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?

To be quite frank, we have not explored too many new tools. We already had some tools for collaborative file editing and file sharing, and we were all used to using email and shared calendars. We just had to get better at using those, and I think we’re still learning. For meetings and most personal interaction, we turned to Zoom. But I think videoconferencing is good at giving the illusion of connection in the same way cubicles are good at giving the illusion of privacy. They work up to a point, and we collectively agree to believe that is good enough. I personally don’t believe people need to be in the same space all the time to be efficient and effective, but I do believe some direct human connection is necessary from time to time. I think most videoconferencing is effective for this, when it works smoothly.

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

The perfect communication system would know how and when I need to be delivered a particular piece of information. So much of our time is spent sorting out the urgent and important from everything else, and another huge chunk of time is spent going back to find the things we set aside to deal with later. A lot of systems try to reduce the friction in information flow, but sometimes more friction is better. The trick is in knowing the difference. One of the things that would be really useful, I think, is an easy way to manage the huge Venn diagram of all my contacts — personal, clients, coworkers, management, project teams, vendors, etc. I am in so many circles in real life, but they are all in different platforms. My writer friends are mostly on Facebook. My coworkers are in email, text, phone, zoom, and calendar. My family are in email and text and some social media. It’s a mess, and I’m managing it all in my head. The perfect platform lets me glide in and out of the circles in my Venn diagram seamlessly, while also protecting the integrity of those circles.

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?

I think as with a lot of things, the pandemic has mostly accelerated the recognition of the need for these tools. A funny meme early in the pandemic captured it. It asked the question, “What drove your migration to a digital workforce?” and gave the possible answers of the CEO, the CFO, your clients, or COVID-19. In my workplace, we’re getting better at using shared documents rather than emailing different versions all over the place. We’re getting more sophisticated at shared calendaring. But certainly, being in person can hide a lot of communication inefficiencies that start to become obvious when everyone is remote.

In my organization, we work with a diverse population of clients. Many of our older clients have difficulty understanding technology well enough to attend our videoconference programs. Some of our lower income clients don’t have technology capable of connecting. For others, the internet connection can be unreliable or can get overloaded (imagine trying to work when you have three kids in distance-learning on three different computers all sharing the same wi-fi).

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?

All of those technologies are exciting, in part because I can’t wait to see how they’re put to use when they’re accessible and out in the wild. I worked on some of the first PDAs and smart phones, and I’m always eager to see new innovations. Some of my colleagues and I have talked about using VR for taking donors on a virtual tour of a project we’re planning. I can imagine VR allowing collaborative art projects, and mixed reality being incredibly useful for our support groups; when people can’t get out of their house (or hospital bed) is when they most need the connection of their support group, and the more we can imitate the human experience of being together, the more effective we can be in helping people.

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

Definitely. I am concerned that the pace of innovation is widening the technology divide. As a small nonprofit, we’re still struggling with document version control, so I’m not paying too much attention to VR or AR. And I think my organization has a strong staff compared to many that are providing truly critical services to those most in need. The costs of these technologies, and the learning curve to implement them, may concentrate all the innovation in the richest companies. How long will it take to trickle down? How much investment will be needed to make effective use of them? I personally am torn because on the one hand, I truly am excited by the impact these technologies can have on society, industry, and humanity. On the other hand, they still feel like cool toys for the rich while so many people and organizations continue to struggle with basic needs.

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?

The day the Bay Area was locked down (March 16, 2020), Cancer Support Community San Francisco Bay Area had our critical programs set up for delivery by videoconference that same night. The rest of our programs were online in the next two weeks. It was a challenge for a lot of our clients to make the switch, so our support staff worked extra hard helping them. The experience is lacking, though, because part of the whole experience of attending a support group, exercise class, or workshop is arriving at our center, socializing in the lobby, getting a cup of tea in our kitchen. We haven’t gone to chatbots or other AI, and I doubt we will anytime soon. But we do a lot of phone and video calls with our clients, and more and more we are recording video and holding video-based events.

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?

The answer is twofold: First, you need to have an underlying base of trust. This means you can’t just rely on a weekly status update or a few emails, or project communications. You need to make a constant effort to make sure that your team members know you care about them as people, not just as a function. Our executive team has made a constant effort to make sure the team know that we have their back, that we are loyal to them, that we appreciate the difficulties they’re facing. We talk about how we are facing those same difficulties, too. Having that base of trust gives you a platform for honest communications. The second part is, as with any feedback, it should not be a surprise. Don’t let something build up and build up until you need to have “a conversation” with the team member. Third, I might suggest actually giving difficult feedback on a phone call rather than video call. Sometimes the sensory void removes a lot of the background noise from the conversation, and the words become more important and immediate.

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

We are constantly struggling with that at my organization, but we are constantly trying. I would suggest keeping three things in mind:

  1. Always return to the mission. Connect everyone and every task to the mission of the organization. The more people feel the purpose in their work, and the more they feel everyone on the team is pulling for the same purpose, the more they’ll feel connected.
  2. Do tangible things to show you care. Periodically, our executive team has sent the entire team a DoorDash gift card or a branded blanket or some other trinket. We’ve even included our Board members in some of these. Giving people a flexible mental health day off also can go a long way to showing that you care about the people working for you.
  3. Create fun whenever possible. I’ve been in some pretty cynical organizations (not the one I’m in now), and still everyone mostly appreciated the cheerful naivete of the one who was always trying to insert some fun into the workplace. Have a “zoom happy hour” with a goofy ice breaker… but do it wholeheartedly if you do it. People may roll their eyes, but mostly they appreciate that someone is trying to inject levity. Also, if you can turn a project sideways to make it fun for the team, that will be refreshing. Last summer when fundraising was lagging and we had to do an additional outreach, I made a very off-brand suggestion for our campaign, and the team loved the idea. It suddenly turned from being just another chore in a difficult time, into a fun, creative project. We ended up with about the same result financially, but that project has become kind of a team touchstone that always makes us smile.

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 think the world suffers from a deficit of empathy. The pandemic has shut us all into our own houses, but it’s also opened up the world to us like never before, with so many more opportunities for virtual connection. I’ve attended and read poetry at a virtual open mic that I never would have even discovered before the lockdowns, and I’ve made friends I never could have met otherwise. We have an opportunity to connect with other communities and cultures that we would not encounter in our physical spaces. The movement I would inspire is one where people feel invited to attend events they never would consider going to physically, or simply couldn’t get to. Eliminate geographic and cultural boundaries for a short time, and build empathy and connection.

How can our readers further follow your work online?

My personal website is www.peterdudley.com, and I’m on Twitter as @dudleypj and LinkedIn at https://www.linkedin.com/in/peterdudley/. If people want to help cancer patients and their families (or if they are facing cancer themselves), they can go to www.cancersupport.net for a wide range of free services.

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