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Tim Arnold on Leading with AND
07/06/22 • 25 min
Today’s conversation with Tim Arnold explores the gray areas that organization leaders encounter when faced with questions that don’t have black and white answers. We seem to be conditioned from an early age to see life in terms of either/or, right and wrong, good and evil, especially when it comes to problem solving. And there’s nothing wrong with this. In fact, it’s an incredibly useful tool for leaders to have. But what about the gray areas? What if polarizing the issue only makes it worse? How do we navigate questions of fairness, values, and creating win-win outcomes?
Dane and Tim discuss how to balance some of these values that often feel paradoxical. Should we lean towards greater responsibility, or more freedom? The answer can be both. Tim shares his own experience with learning to balance the need for stability within a company with his own inner drive to be constantly changing things. With a both/and mindset, he is able to successfully maintain both these seemingly conflicting values.
Tim has over two decades experience running a for profit business and a homeless shelter, and he has learned a lot about how to manage the complexity of tensions that arise within organizations. Currently he works as a speaker and author, helping others learn the tools for leadership success. His latest book is Lead With AND: The Secret to Resilience and Results in a Polarized World.
You can learn more about Tim by visiting Lead With AND
[2:17] Tim tells us his background and what led him to write his book.
[5:42] How it can be a benefit to shift from either/or to both/and thinking when it comes to solving complex problems.
[8:34] Tim gives a real-world example of an organization finding the balance between freedom and responsibility in order to successfully live out its values.
[12:53] Does this kind of thinking come more naturally to certain personality types or people of a certain age or maturity level?
[15:51] Young children see in terms of black and white, good and bad. The ability to navigate the gray areas is something we learn to grow into.
[17:45] Most leader personality types tend to do the either/or thing by nature, so they need to learn both/and thinking as a second language.
[20:24] Tim introduces his assessment tool that helps people successfully identify tensions and gives insight as to how to manage them, available at leadwithand.com
[21:59] Ignoring both/and thinking is like insisting to only inhale without ever exhaling. You’ll suffocate.
Today’s conversation with Tim Arnold explores the gray areas that organization leaders encounter when faced with questions that don’t have black and white answers. We seem to be conditioned from an early age to see life in terms of either/or, right and wrong, good and evil, especially when it comes to problem solving. And there’s nothing wrong with this. In fact, it’s an incredibly useful tool for leaders to have. But what about the gray areas? What if polarizing the issue only makes it worse? How do we navigate questions of fairness, values, and creating win-win outcomes?
Dane and Tim discuss how to balance some of these values that often feel paradoxical. Should we lean towards greater responsibility, or more freedom? The answer can be both. Tim shares his own experience with learning to balance the need for stability within a company with his own inner drive to be constantly changing things. With a both/and mindset, he is able to successfully maintain both these seemingly conflicting values.
Tim has over two decades experience running a for profit business and a homeless shelter, and he has learned a lot about how to manage the complexity of tensions that arise within organizations. Currently he works as a speaker and author, helping others learn the tools for leadership success. His latest book is Lead With AND: The Secret to Resilience and Results in a Polarized World.
You can learn more about Tim by visiting Lead With AND
[2:17] Tim tells us his background and what led him to write his book.
[5:42] How it can be a benefit to shift from either/or to both/and thinking when it comes to solving complex problems.
[8:34] Tim gives a real-world example of an organization finding the balance between freedom and responsibility in order to successfully live out its values.
[12:53] Does this kind of thinking come more naturally to certain personality types or people of a certain age or maturity level?
[15:51] Young children see in terms of black and white, good and bad. The ability to navigate the gray areas is something we learn to grow into.
[17:45] Most leader personality types tend to do the either/or thing by nature, so they need to learn both/and thinking as a second language.
[20:24] Tim introduces his assessment tool that helps people successfully identify tensions and gives insight as to how to manage them, available at leadwithand.com
[21:59] Ignoring both/and thinking is like insisting to only inhale without ever exhaling. You’ll suffocate.
Previous Episode
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Amit Gupta on Optimism in a Pessimist's World
Amit Gupta is an entrepreneur, writer, and serial optimist. He’s also a personal friend of Dane’s, and in this episode, Dane and Amit discuss the past, the present, and - with Amit’s own brand of optimistic clarity - the future.
Amit is, in his own words a “relatively successful entrepreneur”, though we would argue his success is more than relative. Among other various startups, he is the founder of Photojojo, an online photography store which he sold in 2014 after recovering from an aggressive form of leukemia. From there, he began exploring his creative side as a science fiction author, which is what inspired him to develop his most recent project with fellow writer and business partner, James.
Sudowrite is an AI writing tool that Amit and James invented to help writers get real-time feedback and suggestions. His hope is that not only will their program help people overcome writers’ block, it can also help solve some of the issues of isolation that writers experience.
You can learn more about Amit and Sudowrite here:
[2:57]Amit tells a bit about his history as a tech entrepreneur, from playing around with HTML in college to his first startup and working as an intern with Seth Godin.
[5:08]Amit tells a story about a traumatic event that happened to him with some friends on the train tracks, which Dane says shows not only Amit’s resilience, but also that he hasn’t led a charmed life of the entrepreneur destined for success..
[8:07]In 2011, Amit was unexpectedly diagnosed with an aggressive form of leukemia, throwing him into a whirlwind of treatment and recovery, and subsequently began a national campaign for stem cell donation awareness.
[12:44]“Suffering is never an inevitability, it’s a universal human experience. But those who suffer and respond to suffering, in a way that somehow transcends the suffering is the kind of person that I want to learn from.”
[14:02] After his recovery, Amit changed the course he had been on and began to write science fiction, to pursue a passion for imagining a world made possible by technology.
[15:39] “The fiction that we're deluged with is so often dystopian. And it really concerns me that if we are just seeing the imaginations of our most creative people being devoted to how terrible the future could be, we're not going to be able to dream other ways that could be wonderful.”
[20:13] Amit shares some of the ways that getting sick changed his perspective and choices in life, and how he struggles to remember what the things are that really matter.
[22:21] The book Replay by Ken Grimwood is a reminder of the universal possibilities that exist for each of us in this life.
[24:10] Amit introduces us to his newest creation, Sudowrite, an AI-based creative writing tool.
[29:00] Dane admits to gushing when it comes to how cool Sudowrite is, and how much it could change the landscape for writers and open up new possibilities.
[32:14] Amet shares his thoughts on where he thinks the future is going.
Next Episode

Gerald Leonard on High Performance Workplace Cultures
Gerald Leonard has had a diverse career filled with creative pursuits and technical education. The magic happened when Gerald was able to draw a throughline from the success of small jazz ensembles to the success of tech teams and businesses. It all came down to knowing how and when to lead.
When you’ve played for years or spent that time developing your IT skills, you become an expert. While those skills are absolutely necessary for success in your chosen field, you also need an understanding of how your role must adapt. On a team, each person is an expert in their niche, but it’s only by coming together and supporting each other that the team can achieve its goals.
Putting together the various pieces of the success puzzle and creating powerful teams combines creativity, neuroscience, culture, and, of course, a little jazzy improvisation. Finding your way there can help you truly live your life “in the zone.”
If you’d like to learn more about these concepts, Gerald Leonards’ books Workplace Jazz and Culture is the Base cover these topics in more detail.
Timeline:
[4:08] Gerald details the eclectic road of specialties he’s walked and explored throughout his life.
[6:58] Choosing between pursuing a life on the road and being with his kids allowed him to slow down. But it was all meant to be and came back around later on.
[7:50] Balancing local concerts and starting a career in IT as a consultant showcased his natural talent for project organization and a mastery for adaptation.
[10:50] IT teams were changing and getting smaller. Gerald saw the similarities between playing with a small ensemble and working with concentrated tech teams.
[13:00] Culture and talent, incorporating not only the players on the stage but the audience, are the keys to succeeding at initiative changes.
[15:15] Gerald discusses the framework for his book, Culture is the Base.
[18:12] Leadership and collaboration are all about trust- trusting yourself, the process, and each other. Building that trust and establishing common ground is essential to creating strong teams.
[24:24] Being in the zone and learning to be in that flow state with a group of others. It’s about synchronizing with your team and melding those brainwaves.
[26:53] Gerald elaborates on whole brain integration and how it relates to coming together and finding that synchronistic groove. Outside of music, where it can naturally occur, there is a way to practice whole brain integration.
[30:05] How Gerald’s faith interacts with his daily routine and path toward success.
[33:20] Gerald talks about finding your purpose and direction. Consider what you want your mark to be and how you want your life celebrated in your old age.
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