Breakthrough Sessions In Circles with Dan Hoffman and Engaging In Tough Conversation with Jessica Pettitt

Fostering deeper learning with deeper connections in learning environments and meeting spaces is Founder of, Dan Hoffman. is a video platform to make it easy for small groups to help each other work and grow. Dan shares what it is all about and how it can effectively create enduring connections. Used by schools like the Harvard Business Schools, he shows how it addresses a common problem with the learning experience, which is what happens after when the meeting is over. Dan shares the structures of that helps with this as well as the three things to have breakthrough sessions, how to get people to stay with their tasks, and how to get different kinds of participants involved in a meeting.


Many people flinch at the thought of having tough conversations, delving into controversial topics, and facing issues that they would never thought of otherwise. Jessica Pettitt is an expert at breaking through this dilemma. Referred to as the Margaret Cho of diversity trainers, she merges politics, humor, identity, and local flair with big city passionate energy through direct, individualized, and interactive conversations. Jessica dives deep into getting people engaged in tough conversations, weighing in on different points of view, and ridding yourself of self-doubt, self-limiting beliefs, and habitual excuses.

TTL 290 | Breakthrough Sessions


I’m glad you joined us because we have Dan Hoffman and Jessica Pettitt here. Dan is the Founder of It’s a website unlike anything you’ve ever seen to get teams and people to interact. Jessica is a diversity trainer but she’s part comedian because she’s been doing that for years. She goes around and helps people to have tough conversations so she’s entertaining.

Listen to the podcast here

Breakthrough Sessions In Circles with Dan Hoffman

I am here with Dan Hoffman who developed, a video platform to make it easy for small groups to help each other work and grow. Circles are used by schools like Harvard Business School, companies like Square and communities like Millennium schools and YPO. It’s nice to have you here, Dan.

Thanks, Diane. It’s great to be on the show.

How are you using Circles? What is Circles? It was fascinating about how this all came out from a Sabbatical that you took. I want to know more about your background and how this all came to be.

I’m an entrepreneur and I had some companies in the ‘90s as the internet started. In 2000, I started a cloud communications company called M5 and grew that for many years combined with the Silicon Valley public company. We got about 250 employees on our own, 1,000 together. I took a break and I got to think about what I loved growing a business? What didn’t feel great? Thinking about that, I concluded that I loved the moments when an employee or a fellow manager would light up and say, “I want to grow. I want to learn.” I felt that most of the solutions we were using around learning and development weren’t that effective. I started to research ways that we could help people grow and so Circles was the product of that research.

It’s What’s the .es and what was the meaning behind that?

España, that’s the Spanish domain and the sabbatical we went, we took the family to Barcelona for a year and stayed for a couple. That’s where I conceived Circles and started to do that research. I realized that in my own life the type of learning and development that helped me the most was done in circles, not in rows like a training room. I’ve been in peer groups like the Young Presidents Organization, Entrepreneurs Organization. At the time I was picked for one by the Aspen Institute, a fellowship. I started to ask the question, “Why doesn’t everyone in the world have the ability to learn this way? What could we do to make it easy to pull groups of peers together and get them to share challenges and help each other instead of sitting in a classroom in rows and listening to an expert?”

TTL 290 | Breakthrough Sessions
Breakthrough Sessions: Humans are advice-getting machines.


I taught online courses for years because I wasn’t a real fan of sitting through lectures. It leads to my research, which I wanted to find out what kept people from asking questions. Why they weren’t more curious to learn more things? You said lighting up, wanting to learn and that’s what I’m looking to do for people. With the being España, I understand that it’s tied to your learning that from your trip to Barcelona. Do people expect it to be a Spanish site?

We would have done if it were available, but it’s cute the way it looks. The world is moving to more different domain name structures so it’s funny that it spells the word circles.

I looked at your site and I know you worked with a variety of organizations. What does Harvard use it for? I’m interested in the school aspects. What did they do with it?

One of the problems they had was after the learning experience, then what? What happens when you have that intense week and your mind is on fire and you’re hugging it out at the bar with your best new friends and then it’s over? We know that you should do something to sustain the work that you did but all too often it’s hard to do. What happens when you go to Harvard’s legendary OPM program for a few weeks on campus is afterward you are placed in a Circle. That’s 68 peers you meet using our software in a video which makes it super easy to run a powerful session. That’s what that software is about. We recommend every other month but most have chosen to meet monthly and over time you form a real board of directors for each other. Sometimes people have emergency meetings and they share real challenges. It’s a bit connected to the work that they did on campus but more importantly, they’re connected to the people from campus. That keeps the work going, reinforces the changes and the epiphanies and what happens when you meet the office. It’s Harvard’s way of burning in the experience and making it last. Stopping the forgetting and getting more out of the investment on all sides.

It’s not necessarily a team activity where they’re creating an end product. It’s more of a social type of meeting.

One of the things we’ve learned is that you need three things to have breakthrough sessions. One is a leader. The other is a structure that forces you to go deeper and the third thing is a high level of trust. What these sessions do is there is a structure. We enter the room. There’s some quick warm-up, maybe this is an hour and a half. We think, “What’s the biggest challenge right now?” and that practice of thinking for a minute, go around and share equally what your big challenge is and then use a process to workshop one of those challenges. Maybe it’s something that everybody’s facing or there’s a common theme or something urgent. That process helps people to be curious.

[bctt tweet=”Great conversations are where the real learning can happen.” via=”no”]

Humans are advice-getting machines. If I share you a problem at a networking event or my problem, the next thing my conversation partner will say is, “You should talk to my friend or I read this great book or this is what you should do.” A structure in our case forces people to stop, ask questions for ten or fifteen minutes, practice being curious and get better at being curious. That skill of asking questions get to the heart of it then think and share stories of their own experiences that might help them. It’s a formal structure. The features of the room and the design of that conversation help build that high level of trust so people open and share and then learn to count on each other month in, month out. There’s a little bit of science and madness to it. It’s mostly processed and some technology to support it and people get a lot out of those sessions.

Is it always video where they see each other?

It’s always video. We have a lot of teams and we run some workshops that train what I’m talking about. Leaders can use this in their regular team meetings. It’s always better in person if you can be but we’re stuck and working with people from all over the globe. We’ve tried to make a video experience that’s as close as you can get to being in person. I didn’t think we’d be building a video room. I thought we’d be using all the off-the-shelf great technology but the problem is most of those tools start from a presentation metaphor. One person is big and everyone is off the screen doing their email. The features are in service of a great conversation. How often our meetings or learning sessions are great conversations and that’s where the real learning can happen at dialogue. We can flip it. We can watch the presentation. We can read the presentation. We should use our time together to have a great conversation. That’s what the design is all about.

What did you think of ideas like Google Hangouts and other ways of people trying to connect? What did you gain from seeing what others have tried to do to help you with this?

We stand on the shoulders of all of that great technology and videos become reliable and ubiquitous. Some people don’t like to be on camera but mostly we value the connection. Most of those video platforms are fixed Hollywood Squares and they haven’t gotten to the point of taking advantage of the technology to not only have meetings but have great meetings. Our system is not focused on every meeting the way some of those platforms are, it’s just small groups. We’re only good at one thing. Call it three to ten people. As Bezos says, “The two-pizza rule.” The features are in support of trying to reach a great conversation and we have a library of different meeting structures for different purposes. There’s some content that you can pull into the room to look at short videos or share documents or applications in a structured way. It’s a little bit of the next level of what we’re going to be able to do in video experiences.

There are issues sometimes with technology when you get a lot of people in a team or a group thing. Is there a maximum number you recommend for one of these groups of Circles? You were talking about different purposes that they serve?

TTL 290 | Breakthrough Sessions
Breakthrough Sessions: Setting the mood is an underutilized leadership skill.


It’s important that the participants are heard, that you have some airtime in our style meeting.
Interestingly, when Google researched what makes their team successful, that’s what they found to be the number one factor. Their research is called Project Aristotle. It’s interesting how important it is for people to be heard, to feel part of a team and for a team to take advantage of the diversity of viewpoints or making decisions or learning. That’s the rule and most people get this. Most teams are that two-pizza rule. If you’re hungry, maybe four people if not eight or ten. You can’t sit in the video all day. If somebody comes in with a team of thirteen or fourteen, it’s not a technical limit, it’s that your team is too big. It’s hard to have that real teamwork, that deep session over video. You can push it to ten or twelve but think about five minutes a person. An hour and a half, do you want to be in the video for more than two hours? You go crazy. That’s the real limit. This is a world of teams and let’s get good at that, whether it’s for learning or for work that’s the right size for a true team.

I want to make sure I get some of the other purposes out there.

It was all about learning and development but what we found was there’s a lot of pain out there in teams and team meetings, standing work teams. We’ve moved more and more to that to helping leaders run great team meetings and great conversations. While we work with HR departments, learning and development professionals and exec ed programs like Harvard who want to have those deep learning sessions. I’m the leader of a software development team, a sales team and I want my team to learn from each other. We have a leader at who uses the process to do deal reviews so that when they come back from the field, they hop into a meeting. Someone goes to the center. The other people ask lots of questions, “What’s happening with this deal?” and the team helps the team. The structure helps share the wisdom and unlock the experiences around the team in a super-efficient way. Those are also skills that help in the field asking questions, listening, being curious and sharing stories. There are lots of uses. We have people doing Bible study on our platform. We have people with all kinds of different small group book clubs. What we’re focused on are workplace applications.

Have you thought about shuffling them to avoid silos? The team has to work random shuffles to look at what they’re not talking about that this team is talking about. Has anybody ever wanted to do that?

By design our work with Square, a Silicon Valley company with a few thousand employees. Globally they’ve grown very fast and they have a problem with silos between departments and offices. We deliberately placed leaders from Singapore, with leaders from St. Louis and San Francisco. Sales and engineering, different disciplines and people that don’t get to share the diversity of their experience and they come together and build those connections across the workplace. You go pretty deep and build a high level of trust and it has ripple effects in the culture. Deliberately designing the group, shuffling them is a great best practice in our financial services industry with life insurance companies like Bankers Life. We do that specifically.

I’m thinking at some of the meetings we’ve had from my experience and sometimes they have meetings just to have meetings. We have a meeting and then you go around and you talk. You tell us what has happened to you this week. Sometimes you’re planning meetings for the next meeting and all you do in the meeting is planning the next meeting. How do you get people to stay on task and what they need to do?

[bctt tweet=”Conversations are transactions with other human beings.” via=”no”]

There are some best practices and we’ve baked them into the software to make it easier to do. Is there a purpose for this meeting? Is there an agenda that’s thoughtful? It takes a few minutes and it’s nice to have your agenda saved in the room, so when you beam in you can quickly build an agenda. The mood is important. You talked about that great video with all the people having trouble connecting. We measure wheels up, we call it and go to great lengths to make sure you start strong. In fact, we let the leaders play music at the beginning of meetings. We have this YouTube integration. Setting the mood is an underutilized leadership skill. If you start that meeting in a place of a little laughter, some smiles, some feelings of teams. In our team meeting, we rotate running the meeting. One of my colleagues put up a picture as we were starting the meeting of us at the offsite. It was this hilarious shot and it immediately brought people back to that place where we were having fun. There are some practices that make all the difference between our usually longer lists of tasks. “How are you on the project? Where are the metrics?” Move quickly beyond that drudgery to the important conversations and give space to the important conversations. That we find helps teams not only face their big challenges, their real challenges and the breakthrough opportunities but also feel more connected.

As you’re talking about challenges, it makes me think of some of the issues that people have in some of these group meetings that I’ve been in. You get introverts, for example, who sometimes don’t feel comfortable participating or they need more time to consider what they would like to say. You also get groupthink when you get a bunch of people that all have an idea. How do you address any of that with your software? Is that something that people have to deal with on their own?

It’s probably the thing that people say makes the biggest difference and if you do one thing in your meetings, I recommend equal airtime. It’s not for everything but let’s say we’re going to do a structure that we recommend. A structured meeting we call challenge exploration. For people that are in EO or YPO and know the practice of forum, this is familiar. You ask the question, “What’s your biggest challenge?” Give people a minute to think. We automatically generate a random order. We’re going to each share for one minute. It forces people to be concise. The introverts are called on automatically and for introverts, they will sit there with the best ideas in the world. We had a leader that said, “There were two people on my team that was never speaking up and I was getting ready to drop them. I tried this process and I realized that I was the one that should be dropped.”

When you go around random order, everybody speaks. The person that’s hogging the mic in all the meetings get to shut up and people love that too. Listen to each other. That thinking time practice also makes us much more present listening because we’ve had a minute to think about what we’re going to say in advance. That’s good for introverts too. Getting past the small talk is another thing that gives introverts energy. We’re getting to the real stuff. That equal airtime practice, everybody goes around shares equally. It’s possible to do in person, to do it on any technology. Ours makes it a little easier.

How is this structured if you wanted to use it outside of work or is it not?

We’re allowing people with interesting use cases to beta all kinds of approaches like that. There’s one group of leaders, all who have Parkinson’s disease. We have groups of college roommates have used it. At the moment, we’re putting it in people’s hands and saying, “You’re welcome to try and we’re going to figure out commercial models for that stuff later.” In the meantime, the workplace sees the direct value and some of the exec ed programs are direct value. A real theme here for us is that if the internet called Facebook deliberately on a mission to connect the world and they’ve done that. The problem is the connections are shallow. That’s driving all of us nuts. We’re connected to more people. There are more tasks. There is more information. We crave depths. What we’re doing in Circles is baking in ways to get deeper with people quickly. That applies to a lot of places. That’s our mission is to figure out how to help people connect more deeply so they can help each other work and learn and grow. That’s the big mad experiment.

TTL 290 | Breakthrough Sessions
Breakthrough Sessions: Listen before you speak. Think about what it is you want to say and what you want the meaning of what you want to say is.


Do you see that you would get to a point where you’d offer larger group-type things like how you can get into big groups that aren’t necessarily this intimate? Can you see other ways to use this software like that in the future?

We think a lot about communities and the structure of some of the best communities that I’ve been able to participate in Entrepreneurs Organization, Young Presidents Organization and the fellowships at the Aspen Institute. They have small groups at the heart. I’ve been in a YPO forum of seven CEOs. We’ve met for many years every month for four hours. We get deep. I am much more likely to go to the big community event because my friends are going. I’m much more connected to that wider group and I can use the network in any city. Through the smaller group, there are these molecules of real connection and then the bigger is shallower but a useful network. The LinkedIn Marketing community has a million people in it. What if we use that connection to create small focused deep groups and you can shuffle them? They’d get to know each other from that community. Sheryl Sandberg has done this with her Lean In community. They have over 30,000 Circles. It’s a broader community but there is a process and a structure for going deep around a common set of values and issues that they care about.

I’m looking forward to seeing what you’re going to do with this. It’s a great concept and I could see masterminds and different things tying into this. A lot of people are going to want to know how they can find out more about Circles. Can you share a website or links or anything you’d want to share? is our website. I’m People can feel free to reach out that way. We’re interested in working people that want to develop different use cases. We see ourselves as a platform and part of a big movement. We’re open with what we’re learning, what we’re sharing. There are more and more masterminds, more and more members of YPO doing forum. There are more and more small groups coming together for conversations about leadership or spirituality. It’s important that we learn to listen to each other deeply and to support each other across the world and in the workplace. I’d love to hear from folks. We’ll try and keep putting up what we’re learning on that website to share with everybody.

Thank you, Dan. I appreciate having you on the show.

Thanks for having me, Diane. It’s great talking to you.

You’re welcome.

Engaging In Tough Conversation with Jessica Pettitt

I am here with Jessica Pettitt who has been referred to as the Margaret Cho of diversity trainers. She blends politics, humor, identity and local flair with big city passionate energy through direct, individualized and interactive conversations. It’s nice to have you here.

[bctt tweet=”You don’t know what you don’t know until somebody points it out to you.” via=”no”]

Thank you for having me.

Our friend, Phil M. Jones, recommended you and he’s an amazing talent. I loved having him on the show. He’s got a way with words for sure. I put him on the spot with some sales ideas, “How would you say this? How would you say that?” He’s smooth. What you do is fascinating to me too because you have a way with words. You blend different things, humor and sense of history and different things. You have tough conversations. How did you get into this and give me a little background on you?

I’ve been having tough conversations forever because I was that kid. I didn’t have the language at the time but I noticed hypocrisy or when things were unfair either in the news or with my parent’s adult friends or at school myself. As I could have gotten more into my professional work of doing diversity training, etc. I noticed that even amongst diversity educators there are still topics that make it nervous to talk about or like, “How do we bring up politics?” or something like that. That’s exactly what I want to talk about. Everything that your grandmother warned you about is all I talk about. I hope people figure out how to have the most frustrating conversations like that uncle over the holidays so that you can then have important conversations with more confidence.

TTL 290 | Breakthrough Sessions
Good Enough Now: How Doing the Best We Can With What We Have is Better Than Nothing

There are a lot of problem conversations. I teach ethics where you’ve got to have some pretty tough conversations with people because it’s subjective and people get passionate and get people upset. People don’t always agree with everything and I guess we’ve got a split climate with politics and everybody seems to be one side or the other. How do you have these tough conversations? What advice do you give people?

The main thing that I give is to listen before you speak and people are like, “I remember that. We learned that in kindergarten,” but we don’t do that. By listening I mean the person you’re going to engage with. Make some observations about them. How do they look like they’re feeling? Maybe ask some questions about them. Feel out who you’re about to talk to. If that’s not hard enough then the next thing is don’t talk yet but think about what it is you want to say and what you want the meaning of what you want to say is. It’s a transaction with a human being. What are your intentions there? You’re much more prepared for any intended or unintended impact. Take responsibility for that. See if you need to make any changes because it’s about a connection with a human, not just a good conversation.

My book on curiosity is about to come out and I love that you’re asking questions. A lot of people don’t do enough of that. That’s why we’re having many interpersonal problems and the soft skills issues in the workplace. You also brought up empathy which is a big part of emotional intelligence, which I’ve done a lot of research in. A lot of people think that they’re asking questions or right questions or they think that they’re listening. It’s hard sometimes to know if you’re doing the right things. Do you offer people feedback? What do you tell them? You don’t know what you don’t know until somebody points it out to you sometimes.

Curiosity is one of the four pillars that I talk about. You have to be genuinely curious about someone else but that sometimes is too much and exhausting and you just want your Starbucks. You need to be genuinely curious about yourself. What patterns do you show up with? What are the positive assumptions that you’re making about a given situation? I use a lot of humor. Things are hysterical so I’m trying to make people laugh, but that doesn’t mean that I’m not offensive or not making bad choices with my humor. Being genuinely curious is the first piece paired with a genuine sense of generosity. When you’re making a connection with someone versus talking at someone, you have to have a sense of generosity that this is an even connection. We get hard which is about being vulnerable, allowing someone else to be vulnerable and that is an authentic exchange. The feedback piece, a lot of times diversity work and specifically my old types of diversity work focused on the other person. One of the flip sides is how do you get feedback to yourself? How do you receive feedback? How can you reclaim responsibility for whom and how you are with other people? Giving feedback to someone else is way easier than not getting self-defensive about your own inner voices. They go in tandem.

Part of my research was to create that instrument to determine the things that keep people from being curious. You have to know who and what you are in terms of what has impacted your curiosity and how you see yourself. Many people are impacted by their environment and growing up with teachers, family, friends, workers, co-workers, leaders and all those things impact what you feel comfortable asking or saying. It’s hard. Maybe somebody shut you down in the past for saying something or asking a question or pointing out something that could be better. You were saying how you can be offensive, maybe not intentionally, but if you use humor you could offend people. Do you find that you have to pull back your sense of humor a lot or do you just go with it?

It parallels what you’re talking about. I typically go with it and that is also how I become offensive. Instead of worrying about not being offensive, I’m prepared for that because that’s the risk of using a sense of humor. A lot of times, specifically when we’re talking about challenging topics or conversations, we think that it’s like a safe. If you have the right combination code, then it’s open free communication with no blunders. I don’t believe that exists. What can you do to be prepared for like, “This isn’t going well,” because you’re observing and paying attention? I created a model as well for you to be able to take responsibility for how you respond. The tighter or more critical things get so then you do pull back because your life has taught you, “Don’t go there. That’s how you feel safe and prepared.” You pull back and you’re like, “I’m not going to ask that question. That’s rude because my aunt didn’t like it in third grade.” Our lived experience informs all of our judgments and assumptions and that doesn’t make it wrong.

It makes it safe and prepared but the person you’re talking to that’s super frustrating to you and you have no interest in engaging them until they change. The important thing to remember is that their life has taught them that this is the way to show up. This is what makes them feel safe and prepared. Instead of asking them to take on all the risk, you have to understand what would have happened in someone’s life that made this thing that is frustrating to me, be safe and prepared for them. You flip it again. When you flip it again, that person is frustrating to me. I am equally as frustrating to someone else but I can do something about me. I can’t necessarily change them.

[bctt tweet=”Embrace the fact you are equally as frustrating to others as you are.” via=”no”]

You can change your reaction to how you react to them. This is interesting because of your background. You have a Master’s in Education and you wrote this book, Good Enough Now, which is an innovative and practical guide to ridding yourself of self-doubt, self-limiting beliefs and habitual excuses. What did you learn from your degree in education that helped you with this book or did it have any impact at all?

I was amazed at all of the connections that I was making. My husband is an environmental ethicist and philosophy professor. He’s always giving me different little passages or something that strikes his fancy. As I was writing the book, “William James is popping up. George Burns’ movie is popping up.” I started seeing all these connections and so I put them all together because together everything led to the work that I was compelled to do. Most of my Master’s degree studies were on identity development and the process that we go through in identifying each and every one of our identities. As soon as they synthesize with us, we then have to start over with a new thing we learned about ourselves. Working with adult learning and college-age students and the development that happened as we begin to adult. It’s connected to the theories of the book but mostly I pulled from my audiences, my participants that I used probably too many individual stories of my own mistakes. The book feels very naked and vulnerable to me. I started the work to do the audiobook and enough time has gone by so I’ve reread my book and there are a couple of pieces in there where I’m like, “I don’t think I know I decided to share that story.”

I am going through a lot of rereads and I know what you’re talking about because you go, “I forgot I even put that in.” You can read it twenty times and then there’s so much content that you forget what’s in there. What I talk about is similar and I can see why it felt that we would be good to connect on this. There are many people that have difficulty in team situations. I’ve had a lot of team training that I’ve done and I’ve had a lot of teams in the courses I’ve taught. Teams can be challenging because you want a diverse team to come up with a diverse product. If you have everybody the same on the team, you get a not-so-exciting product in the end. Everybody freaks out because they don’t get along because they’re diverse. How do you help teams? Have you done anything with them?

I’m about to do a retreat for an entire department of a hospital here in Boston. I work with teams to show what they’re doing well because we typically only focus on what is going poorly. If you embrace the fact you are equally as frustrating to others as you are by others, then what you’re able to realize is often what good frustrating people can provide balance off your own weaknesses. One of the activities that I do when I do either corporate work or something like that and they have a search committee. Once people fit themselves in the model, I take the strongest from all three archetypes and put them in a room instead of having one person pull together eight of their friends. When we talk about “diverse teams” that we look different typically, we all want to be on a committee together. Often what happens is the original search committee is all in the same place in the model. They end up reviewing resumes and interviewing people and bringing someone in who matches their place on the model, which means those are the only people they’re going to align with. They’re instantly outliers to everybody else in the organization.

I get permission. Scratch the search committee which a lot of people get excited about because they were volatile to be on that in the first place. I pick the three strongest from the three different archetypes. I know that it’s working when at the first meeting it’s silent. Their arms are crossed and they don’t understand why I would think the three of them would want to work together, but have those three people review the resumes and interview candidates. If they could agree on someone, they’re going to be deeply connected to three different types of people in the workplace and they will last longer. My dare when I work with organizations is that if you’ll let me do this, I guarantee you it will happen faster. The person will be brought on and they’ll last longer. In a year, if that person is no longer working there, I will give them their money back and I’ve never given anybody’s money back.

You go around to organizations now. Do you have your own company? Who do you work for?

TTL 290 | Breakthrough Sessions
Breakthrough Sessions: Recognize that your life created both strengths and weaknesses and that combination makes you feel safe and prepared.


I work for myself. I tried to work for other people and found out that was not a good fit. I’m self-employed.

How do you get your customers? Who is your ideal customer?

Living human beings who want to be better and also have a checkbook. I spoke with professionals from national headquarters for fraternities and sororities, so all associations and nonprofits. I’m doing a hospital and I will be working with meeting planner organizations and organizers of conferences in the mid-Atlantic. I talked to a dental association and I’m excited about starting to work with dentists. The truth is that humans need support being humans and so why limit yourself? The person on the plane next to me asked, “How do you get more business?” This goes back to curiosity. How I get more business is I have to be good at a small thing and do it a lot. That’s what I do.

Do you advertise or do you do word of mouth?

I do mostly word of mouth. I have the privilege of working much that it’s hard to do much more than word of mouth. I don’t have that much time but I intentionally set goals each year that helps me decide new directions or new places. I’ve been focusing on periodical publication, radio and podcast interviews because it keeps me on my toes and it’s exposure to a lot of different markets. We’ll keep going but mostly I would say it’s word of mouth.

You’ve been on at least a podcast a week for how long?

The goal was originally to do one a week because of scheduling issues. I tend to say yes anytime somebody was interested. I’ve been on 164 podcasts in 2018.

What’s the biggest difference from this show? Are they all similar?

They fit clearly into the model. There are some people who are incredibly detailed and incredibly specific, maybe even micromanage-y. You have to prove what kind of microphone you’re using. You have to fill out a huge question here. Do all these things ahead of time but that doesn’t mean the actual interview they know how to pronounce my name, they know that I’m a speaker, they know I wrote a book. That’s upfront but that doesn’t necessarily mean how they show up as they’re interviewing. There are other people that have a following and are interested and excited to introduce and see where it goes and much more free-flowing. Often, they are asking the most insightful questions.

There’s a level of confidence that comes with being connected to a significantly larger idea than just, “What are we going to do for the next twenty minutes?” I would also say that there are other people that are doing it. They had the idea and they’re figuring it out as they go along. There’s not a plan. There’s not an audience but they did it. They bought the equipment, set it up in their office, now they got a show. All three of those people show up in our everyday lives. If we’re going to be honest, we’ve been all three of those people as well depending on the scenario. That’s what I mean by being good enough. There’s always going to be more prep or more education or more people or contacts or something. You can do the best you can with what you have some of the time.

You talk about many different things in your book. You say building on your strengths and in one of the courses I’ve taught in the past and one of my past books I wrote a little bit about StrengthsFinder because it was part of a course I’ve taught and I was writing about personality assessments. Do you focus only on strengths or do you do weaknesses too?

Both I would say. In order to self-assess which of the variables head, heart or action you show up with the most, you have to be able to determine which one you are. All three of them are problematic and desperately needed. It’s not about fixing your weaknesses and showcasing your strengths. It’s about recognizing that your life created that combination and that combination makes you feel safe and prepared and it could be frustrating to someone else.

A lot of people have a lot of self-doubts and limiting beliefs in different things. What you’re dealing with is important. I like the whole blending humor and all the things you do to make it a little different. There are many trainers that do the same thing and I love that aspect. I’ve had some people suggest taking improv classes to become a little bit better at communicating. What do you think of that idea?

Doing anything that scares you a lot is important because some people are like, “Improvs,” but it doesn’t scare them. I go to cooking classes. I’m a horrible cook. Cooking classes don’t scare me because it resulted in the food I get to eat. If we talk about doing new things, what you need to do is get yourself in a position where you are uncomfortable and at an edge so that edge is where you begin to know yourself. Question yourself, take risks and then make decisions. Did you like it or you didn’t like it? For improv, for some people that’s utterly terrifying. Do it. For me, it was formalized standup comedy that was scary to me because it’s a fireworks show with relatively tipsy people with high expectations for laughs. That felt riskier to me than learning how to make fried chicken.

Did you ever have a joke you thought that was going to be the greatest and it completely flopped? Is there one that you thought would be great and it was nowhere?

One of the things that you learn as a standup comedic is that every day you are working a story or a joke or a funny way of looking at things or a funny way of making connections. Every time I speak, at least 20% of it had never come out of my Facebook because I’m in the moment. I’m present. I’m making connections based on their questions or what’s happening out in the real world. If 20% of it has never been tested on human ears before, there’s a good chance some of it is not going to work. The comedic side of it is preparing for that. You hope you bomb so that you can learn from it, but you don’t want to bomb a whole show. If I test 20% new material but say that I bomb half of it, that only means 10% didn’t work.

Who’s your favorite standup comedian ever?

George Carlin. I was fortunate enough that I got to travel with him and do some shows with him.

Did you get to talk to him? I imagined he’s pretty quiet and introverted in real life.

Most comedians are because it’s all come out on stage. I had surgery and had to empty out my Netflix queue. David Schloss is a very dark comedian and I appreciate it. How much humor he was bringing to conflicts that you’re not supposed to be talking about, let alone laughing at.

It was so much fun having you on the show. I was wondering if you could share some links of how people can reach you and find out more about hiring you and also get your book?

If you go to, there’s general information about me and my book, etc. If you go to, you can take a little baker’s dozen silly questions but they are statistically relevant if you want to place yourself inside the model. If you go to, there’s a whole bunch of free stuff there including all of the activities and handouts from the book and the flowchart about making better connections. Thanks for having me.

It’s nice to have you on, Jessica. Thank you.

I’d like to thank Dan and Jessica for being my guest. Thank you so much. We have such great guests. If you wanted to know more about the book, Cracking The Curiosity Code or The Curiosity Code Index, you can find that at I hope you join us for the next episode of Take The Lead radio.

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About Dan Hoffman

TTL 290 | Breakthrough Sessions

Dan Hoffman is building, an idea that came out a sabbatical in Barcelona. Circles fosters deeper conversations to create enduring connections and learning. Dan loves growing companies, delivering great service, and applying technology. He believes that business is philosophy in action, culture eats strategy for breakfast, and learning is leverage. Dan has a lot of education and isn’t stopping. Dan joined a successful early Internet service provider that sold in 1998, founded and failed by 2000 with a venture-backed roll-up in Asia, and then started and grew M5. M5 became a pioneer in the cloud communications industry. After 12 years, Dan sold M5 to ShoreTel (SHOR) and worked there for a while before being selected as a 2014 Henry Crown Fellow and shipping off to spend two years with his family in Spain.


About Jessica Pettitt

TTL 290 | Breakthrough Sessions

Referred to as the “Margaret Cho” of Diversity Trainers, Jessica Pettitt blends politics, humor, identity, and local flair with big city passion and energy through direct, individualized, and interactive conversations. Her workshops, seminars, and keynotes don’t just leave participants invigorated but inspired and motivated to follow through with action to create change. Having traveled and lived in a variety of communities and environments all over the world, while also engaging with education as student, teacher, administrator, and active community member, Jessica uses her life experiences to take participants through a safe but confrontational process of examination, self reflection, and open dialog that is as challenging as it is rewarding.


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