Planners’ Picks — October 27, 2026
It’s scary how much we love curating this newsletter for our audience — we also appreciate those who come out of the woodwork with suggestions for content!
Today we live in crescendo, promote team effectiveness in our teams, and compare sports teams to work teams in our resources this week. All treats; no tricks!
P.S. GO BREWERS!
:: Image of the Week
:: Self-Leadership Development
Why some introverted leaders advance, and others don’t
One of the greatest disappointments of my career was not getting a general manager role for a team I had been leading as the interim manager. I had the expertise. I knew the business. I had strong people leadership skills, and I believed my results would speak for themselves.
They didn’t.
The person who got the role had less subject-matter experience, but she possessed something I lacked: visibility, influence, and a strong network.
At first, I was frustrated. But as I worked with my new boss, I understood why she had been selected. She had strong relationships across the organization, the trust of senior leaders, and access to information that helped her anticipate change. Over time, I saw how much value those strengths brought to our team.
The lesson was humbling but important: Leadership advancement requires more than competence. It requires influence, visibility, and relationships.
As introverts, many of us believe that doing great work should be enough. Unfortunately, that isn’t how most organizations work.
Leading Through Uncertainty, Managing vs. Governance, and Why Curiosity Beats Expertise
What do you hold onto when almost everything is changing? David Kenny — co-founder of Digitas, former CEO of Nielsen, and one of the most sought-after board members in tech and media — has a simple answer: find your true north and don’t deviate from it.
In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni go deep with David on the leadership questions that are defining this moment: how to manage fear within teams, why AI makes curiosity more valuable than expertise, and the difference between managing and governance as a member of a board. He also makes a data-backed case for diversity as a winning business strategy — and shares what the 38 CEOs he’s developed have taught him about resilience, failure, and what it actually takes to lead.
https://open.spotify.com/episode/5Tb5nyzFyrUznZPaC3DlNV
“Proceed until apprehended” – Hazel Symonette
How to Live Life in Crescendo
The challenges of leadership can seem plentiful: lack of trust, fizzled communication, chaotic changes, a monsoon of technological innovation. But it doesn’t have to be overwhelming. In this recap of a conversation between Doug Conant and Cynthia Covey Haller, the two experts discuss how you can reframe your thinking, achieve actual success in a noisy world, and hit all the high notes as a leader.
https://conantleadership.com/most-important-work-is-always-ahead-live-life-in-crescendo/
:: CSN’s Book of the Week
How to Be Good at Life
“How to Be Good at Life” by Ben Meer is a practical guide that emphasizes the importance of building effective systems to navigate the complexities of modern life. The book aims to help readers achieve more while experiencing less stress.
You’re making thousands of decisions a day. You’re fighting algorithms designed to steal your attention. You’re managing passwords, subscriptions, and deadlines—complexity your brain was never built to handle. And somewhere in there, you’re supposed to exercise, eat well, and maintain friendships.
No wonder life feels harder than it should.
The happiest and most successful people don’t have more willpower than you. They’ve learned a skill most of us were never taught: building systems. This book is the missing manual.
Ben Meer—dubbed “The Systems Guy” by Forbes—spent years studying what separates people who consistently thrive from those who merely survive. Drawing on behavioral science and systems thinking, he introduces DRIVE, a five-step method for turning any goal into a working system.
Key Concepts:
The DRIVE Method
At the core of the book is the DRIVE method, which consists of five steps designed to transform goals into actionable systems:
- Define: Clearly articulate your goals.
- Reverse Engineer: Break down the steps needed to achieve these goals.
- Implement: Put the systems into action.
- Validate: Assess the effectiveness of your systems.
- Evolve: Adjust and improve your systems over time.
Life Engines Framework
The book introduces the concept of Life Engines, which are seven key areas of life where systems can be applied:
- Health
- Relationships
- Career
- Money
- Emotions
- Mind
- Environment
Practical Tools
Readers will find over 40 plug-and-play systems that can be implemented immediately, including the System Sunday ritual, which helps maintain organization and productivity throughout the week.
Benefits of the Approach
By focusing on systems rather than sheer willpower, the book suggests that individuals can achieve a sense of calm and clarity. The ultimate goal is to bridge the gap between who you are and who you want to become through effective system-building.
This book serves as a comprehensive toolkit for anyone looking to simplify their life and enhance their productivity.
See more straight from Ben at https://benmeer.com/book/
“A good heuristic when making a big decision: would choosing this make me feel more alive?” – Isabel Unraveled
:: Work Culture & Team Development
Healthy Teams website offers tools to foster team effectiveness
Teams on campus have a new resource to help them be more effective, especially at times of change or when presented with new challenges and opportunities. The Healthy Teams website offers self-guided exercises and resources to help teams work through the issues they may face at every stage of team development. A trained facilitator is not required to engage in the team exercises. The website encourages team members to view team development as an ongoing process and a shared responsibility. The self-guided tools found on this website equip team members to co-create team cultures that foster belonging, accountability, and engagement. The Healthy Teams website is offered by Learning and Talent Development and is designed for members of any team, including departments, units, committees, research teams and task forces.
The New Ways to Thrive at Work Now, According to Adam Grant
For decades, there has been a predictable formula for success in the white-collar world.
“Knowing more than other people was what made you valuable in knowledge work by definition,” says Adam Grant, the bestselling author and organizational psychologist at the University of Pennsylvania’s Wharton School.
Artificial intelligence upends that typical career edge. In an era of information overload, the ways in which professionals prove their worth at work will likely cease to be effective, he argues.
“The currency of success is shifting under our feet,” says Grant, the author of a coming book, “Vibe: The Secrets of Strong Connections in a Lonely World.”
“If you can stay light, and stay loose, and stay relaxed, you can play at the very highest level—as a baseball player or a human being.” – Bill Murray
What Can Sports Teach You About the Game of Life?
Are you using every opportunity to prepare your team members for the game of life? Take your cue from the great coaches in all sports and at all levels. They use sports to teach their players valuable lessons.
Life is a continuing competition in which excellence wins. Therefore, it’s better to learn how to compete when the consequences are small.
This article was geared towards children, but applies to you, me, and our teams too.
https://www.franksonnenbergonline.com/posters/what-can-sports-teach-you-about-the-game-of-life/
:: Recognition and Appreciation
Gratitude as a Leadership Practice
Gratitude isn’t just a seasonal gesture—it’s a value that transforms relationships, team dynamics, and organizational culture. While Thanksgiving season often reminds us to “give thanks,” leaders who practice gratitude every day model a deeper truth: recognition and appreciation are not just soft skills.
At WISL, we believe gratitude as a leadership practice is about creating a culture rooted in awareness, humility, and connection.
https://wisconsinservantleadership.org/gratitude-as-a-leadership-practice-servant-leadership/
:: Productivity and Innovation
What’s The Biggest Daily Motivator? Progress.
You rarely lose motivation because the work got harder. You lose it the moment you can no longer see yourself moving. Writing down three small wins a day is the cheapest way to keep that in view.
“Time will multiply whatever you feed it. Good habits make time your ally. Bad habits make time your enemy.” – James Clear
:: Communication
Active Listening as a Leadership Strength
Last week, Shelly Vils Havel of SHape LLC and Rich Gassen of CSN presented to the IT Leadership Program at UW–Madison on Active Listening as a Leadership Strength. There were a lot of valuable takeaways from the chat, and we also shared a participant guide with several resources included. We referenced several resources, including concepts from Heather Younger, in her classic book The Art of Active Listening.
What’s one challenge you need more practice in overcoming when you are listening to someone?
>> Distractions
>> Interruptions
>> Wanting to Respond
>> Uncomfortable Subject/Difficult Conversation
See our participant guide and resources document here to assist YOU in your next active listening situation: https://lnkd.in/gwWPAC6R
:: Upcoming Events
How 6 Critical Practices Create High-Performing Teams in Higher Education
Join bestselling author and leadership expert Victoria Roos Olsson as she reveals how the best higher education leaders achieve both at the same time.
Grounded in global research across sixty countries and refined through thousands of real-world implementations, Victoria will introduce core concepts from the groundbreaking new book, Expect a Lot, Care a Lot. She will equip you with a clear, proven system for driving performance while strengthening the people who make it possible, whether you lead a small campus committee or a large university division.
During this webcast, you will learn how to apply six critical practices to move your teams into the highest levels of engagement and performance:
- Align Purpose and Performance
- Communicate as a Coach
- Delegate for Growth
- Fuel Growth with Feedback
- Manage Energy
- Maximize One-on-Ones
Date: November 4, 2026
Time: 2:00-3:00 pm CST
Understanding Your Identities and Experiences
Each of us brings a unique blend of experiences, identities, and values to the workplace—and they shape how we see the world, interact with others, and how we participate and contribute to our teams. In this course, you’ll have the opportunity to reflect on your own experiences, identities, and values and consider how they influence workplace interactions, culture, and perceptions. You will also explore how these factors can shape our assumptions and perspectives. Finally, you’ll be introduced to a practical tool designed to check for and navigate assumptions effectively.
Why should you attend:
• Explore your individual experiences, identities, and values.
• Build awareness of how identities, experiences and values shape perceptions and workplace dynamics.
• Learn how to check for assumptions.
Part of the Thrive@UW Program , open to all UW–Madison employees. Select Offerings to determine which dates are virtual and which will be held in a classroom;
Dates: November 5 (in-person), December 3 (online)
Introducing SEAT: UW–Madison’s Change Management Framework
Change is a constant at UW–Madison, and supervisors often play an important role in helping employees understand and navigate what is changing. Whether the change involves a new process, technology, policy, organizational structure, or way of working, how people experience and respond to change can have a significant impact on successful adoption.
Developed collaboratively with campus partners, SEAT (Stage, Engage, Act, Thrive) is UW–Madison’s practical Change Management Framework and Toolkit. In this session, participants will take a closer look at the framework, explore the tools and resources included in the toolkit, and consider how SEAT can help them think through and support the people side of change.
In this interactive session, participants will:
- Explore the four stages of the SEAT Framework and how they can be applied to different types of change.
- Discover practical tools and resources in the Change Management Toolkit that can help leaders and teams navigate the people side of change.
- Consider how SEAT can help them prepare, engage, and support employees through changes affecting their teams.
Presented by Jen Erickson of the Office of Strategic Consulting.
Jen’s Bio
Jenny Erickson has more than 20 years of experience in community, organizational, and leadership development. As Capacity Building Lead in UW–Madison’s Office of Strategic Consulting, she develops learning experiences and practical tools that help campus teams lead change, strengthen performance, and build healthy workplace cultures. Previously, Jenny served as a professor and community development educator with UW–Madison Division of Extension, partnering with organizations to identify needs, develop solutions, and evaluate impact.
Date: November 19, 2026
Time: 10:00-11:00 am
Online via Zoom Link