Planners’ Picks — May 12, 2026
Let’s commence with some summer suggestions in this issue of PP, along with enhancing your communication methods and working with more constraints.
:: Image of the Week
Don’t worry what others think; instead, try to improve from your own yesterday!
:: Work Culture & Team Development
Why managers feel stuck between process and people
Managers often feel pressure when they must enforce organizational processes while also supporting their teams’ real needs, writes Gloria St. Martin-Lowry.
Managers rarely sign up for the part of the job that feels like a balancing act. Yet it appears quickly once someone moves into leadership. One day you’re guiding a project forward, and the next you’re explaining a policy you didn’t create to a team member who is already stretched thin.
In moments like these, managers often realize their role sits squarely between two powerful forces: organizational processes and the people expected to operate within them.
For many lower-level managers, that tension becomes one of the defining challenges of the job.
Read more on this from Smart Brief:
:: Gratitude and Recognition
Finding the Light When Life Seems Heavy
Research continues to show that gratitude is one of the most powerful tools for building personal resilience. Studies have found that practicing gratitude can reduce stress, improve sleep, and help people recover more effectively from adversity by broadening their perspective and strengthening emotional resilience.
Chester Elton leads us on a journey to find gratitude regardless of the weight of the world.
:: Communication
Showing Up & Speaking Up
If there is one person on this planet who understands what it takes to create a Psychologically Safe workplace so people can speak up – it’s Shed. You won’t want to miss this event – Showing Up & Speaking Up.
In unsupportive, burned-out, and toxic workplaces where the tasks at hand and unrelenting changes rule the day, employees can feel powerless to use their voice. The amazing Stephen Shedletzky and Jen Marr break this down in her recent LinkedIn Live recording.
There are new critical skills we need today:
1. Knowing how to Speak Up.
2. As a leader, knowing how to Show Up and support those Speaking Up
Shed’s book is fantastic, and our conversations are always ones I long remember.
https://www.linkedin.com/events/7449608527494529024
“Three keys to more abundant living: caring about others, daring for others, sharing with others.” – William Arthur Ward
How to Communicate With Confidence & Ease
This episode will completely change the way you think about communication. What you learn will boost your influence and make you more confident.
If you…
Overthink what you said hours after a meeting,
Freeze up when it’s your turn to talk,
Or want to sound more confident without faking it…
This is your blueprint for better conversations at work, in relationships, and in life. Mel Robbins sits down with Dr. Alison Wood Brooks: Harvard professor, researcher, author, and one of the world’s leading experts on the science of communication.
Her course at Harvard Business School, all about communication, is one of the most popular classes there – and in this episode she shares the exact methods she teaches to students at HBS.
You’re going to learn the exact tools and strategies that will help you communicate with more confidence, ease, and clarity.
You’ll learn:
-What makes conversation feel so hard and how to make it easier
-The #1 mistake people make when they talk
-How to feel more confident even when you’re anxious, blanking out, or unsure of what to say
-Why we misread people constantly (and how to stop doing it)
-How to recover from awkward moments or miscommunication
-The skill every great leader, parent, and partner has in common
Whether you want to build better relationships, stop second-guessing yourself, or speak up with more purpose and ease, this episode will give you the science, tools, and confidence to do it.
https://www.youtube.com/watch?v=5yCqhY1D-VE
The Art of Active Listening | The Harvard Business Review Guide
You might think you’re a good listener, but common behaviors like nodding and saying “mm-hmm” can actually leave the speaker feeling unheard or dismissed. The truth is that mastering the art of listening involves a whole host of other skills as well. You need to do more.
See Amy Gallo’s take on active listening in this HBR video.
https://www.youtube.com/watch?v=aDMtx5ivKK0
:: Coaching
Employee retention starts with leadership: Why coaching beats managing
Coaching and clear communication from managers can help boost employee retention and engagement, writes Ryan Giordano, who offers strategies.
Employee retention has been one of the most persistent challenges across industries over the past several years. We’ve seen this struggle in tech companies and have also spoken with fleet organizations facing operational turnover. According to Gallup, “Manager engagement fell from 30% to 27% in 2024. Young managers and female managers experienced the largest declines. If managers are disengaged, their teams are too. Seventy percent of team engagement is attributable to the manager.”
It’s time to rethink the role of manager. So the question is no longer whether retention matters; rather, it’s how leaders can meaningfully influence it. The way leaders support their teams matters just as much as compensation, perks or job titles. Specifically, companies that emphasize coaching over traditional management are better positioned to retain engaged, motivated employees over the long term.
“In order to remember it, one must have known it.” – Joan Didion
:: CSN’s Book of the Week Recommendation
Inside the Box: How Constraints Make Us Better
We live in a world that gives us seemingly infinite choices and prizes freedom above all else. We have an unprecedented number of options regarding what to do, who to be, and how to spend our time. All that choice is wonderful; it is also overwhelming. The irony is that total freedom can be paralyzing, and unlimited resources don’t necessarily lead to the biggest breakthroughs. In fact, overvaluing complete freedom can be disastrous for everything from starting a company to harnessing creativity to finding personal satisfaction.
David Epstein argues that all of us—individuals, businesses, institutions, even societies—can benefit from narrowing our options. He dives into the science and practice of constraints, exploring exactly when and how guardrails can be beneficial, whether we’re working with limited resources or using self-imposed boundaries to tap unexpected wells of focus and innovation.
Original, galvanizing, and deeply researched, Inside the Box tells absorbing stories of people and organizations that embraced constraints to transform themselves, and the world, as well as a few that struggled from a lack of limits. Epstein reveals how boundaries create breakthroughs, and how setting the right constraints can help you become the most creative, productive, and satisfied version of yourself.
“The law of sacrifice says: we let go of something of lesser value to make room for something of greater value.” – unknown
:: LinkedIn Learning
Tips to Reset on an Overwhelming Day: Gain perspective in the face of overwhelm
In this course, organizational psychologist Erin Shrimpton guides you through practical strategies to navigate a challenging day. Learn techniques to pivot when you are feeling overwhelmed. Explore ways to process thoughts and emotions in the face of challenges by evaluating your personal narrative. Plus, find out how you can shift your mindset to focus on what’s important, set yourself up for an optimistic outlook, and create a thoughtful, values-based way to respond to challenges.
Learning objectives
- Pivot when feeling overwhelmed.
- Develop strategies to reflect and process emotions.
- Learn skills to define personal priorities to maintain flexibility.
- Create a conscious strategy to find focus and move forward in the face of challenges.
:: Mental Health and Self-Care
An Awe Walk Through History and Possibility
Noticing the history and beauty around us can shift how we see ourselves—and our communities. An awe walk through Harlem reveals how the stories embedded in public spaces can spark connection, perspective, and a sense of what’s possible. What about in your locale?
https://greatergood.berkeley.edu/podcasts/item/an_awe_walk_through_history_and_possibility
“Be content with what you have; rejoice in the way things are. When you realize there is nothing lacking, the whole world belongs to you.” – Lao Tzu
:: Self-Leadership Development
Pressure is a Privilege
This from Douglas Conant’s recent newsletter:
Pressure is often viewed as a negative force in our lives. Understandably so: It can be an enormous cause of stress, forcing us outside the confines of the familiar. Yet I have found that each challenge also presents a series of urgent questions that help me to meet life and leadership with the zest they both demand.
In each tough situation, I ask myself:
· Do I engage in the face of this specific pressure? What are the benefits if I do?
· Do I have the capacity to respond to the stressors involved?
· Do I have the fortitude to give it my all, knowing I might fall short?
Responding to pressure in this way is like a game of truth or dare where each round is both truth and dare. And yet, the only way through it—the only way to really win—is to take an honest self-assessment, and then, whenever possible, respond to each of these questions with a resounding ‘YES.’
And while there may be times that it’s appropriate to say ‘no,’ I find that more often than not, I’m invigorated by the prospect of a “pressure test.” Life tends to expand when we meet challenges with a can-do spirit.
Over the last 50 years, I have come to view the inevitable pressures of leadership as a golden opportunity to do some of my best work when it matters most.
It is in those moments where the odds are stacked against me and my colleagues, when the heat is palpable and the stakes are high, that I delight in rising to the challenge. It is here that we can lift our contribution profile, lead by example, and thrive in the face of adversity. And if we falter, we can still take pride in the fact that we gave it our all. As Teddy Roosevelt said, if we fail, at least we fail while “daring greatly,” which is a better fate than joining the ranks of “those cold and timid souls who neither know victory or defeat.”
Ultimately, you can’t win if you don’t play. And if you want to win in life and leadership, you can’t always play it safe. Pressure is a privilege. You must step into the arena and do your darndest to come out on top. Here are three reasons why.
1. Pressure makes us better
They say, “necessity is the mother of invention.” I would also say that pressure is the mother of performance. This holds true across disciplines, whether you’re a tennis player, a Fortune 500 executive, a painter, or a parent.
We can be the most exceptional contributor on a ‘normal’ day. But when things get dicey, we’re forced to apply all the knowledge and ingenuity we can muster. And, if we’ve prepared properly through training, practice, and earnest effort, we can rely on that preparation to be agile and creative in the moment, which makes us better in the long-term.
Meeting our growth edge from time to time is necessary. You may have heard the aphorism, “Life begins at the edge of your comfort zone.” Pressure naturally pushes us out of that comfort zone and invites us to grow.
We may feel our throats tighten and our nerves heighten when we faced with the sudden opportunity to pitch a dream client, or when a new, time-sensitive project falls into our lap. But that sensation of nervous energy can also be harnessed as excitement. What a gift that we can use our unique skills, insights, and convictions to move through a novel situation creatively. These pressurized conditions also sharpen our skills for the next challenge and improve how we lead in the spaces between. And if we do falter, as all leaders sometimes do, we’ll still be better for it.
One caveat: If your work environment leaves you wondering why things always feel like an unrelenting pressure cooker, that can prove unsustainable and counterproductive over time.Ultimately, you must try to cultivate an environment where there are only intermittent periods of high pressure, not near-constant fires to put out. In this case, whether you have the power to lead the organization differently, or feel called to move into a different environment entirely, is up to you.
Personally, I’ve almost always been able to mitigate the pressures of my work situation and I believe you can too.
Continue Reading “3 Important Reasons Why Pressure Is a Privilege”
The chains of habit are too weak to be felt until they are too strong to be broken. – Samuel Johnson
How To Improve Your Information Diet
Author David Epstein presents this week’s reader question, courtesy of David Robinson:
“I struggle with how to impose sensible constraints on how much content (newsletters, podcasts, non-fiction books, subscription feeds, etc.) I follow and regularly consume. I’m quite curious and could spend all day absorbing new insights. If you have some ideas on how to impose intelligent constraints in this mode of consumption I’d be quite grateful!”
David says he’s struggled with this exact issue. A useful constraint comes from deciding what not to consume. “I’ve tried two helpful things in the last year. First, I did the genomics-lab thing. I made a list of all the sources of information I regularly intended to consume, and the other things I intended to do in a day, and immediately realized it wouldn’t all fit. I then asked myself, if I had no choice but to cut this information-consumption list in half, what would go?”
Read this entire article, including a teaser to David’s new book Inside the Box, here: https://davidepstein.substack.com/p/how-to-improve-your-information-diet?publication_id=1024339&post_id=192368197&isFreemail=true&r=3c3hz&triedRedirect=true
:: Upcoming Events
New Career Development Course Launch
A new course, It’s Your Career: Having a Productive Career Development Conversation with Your Supervisor is now available to all UW–Madison employees. We want to let you know about this resource for you and the employees you supervise.
This 30-minute, self-paced course is designed to help employees reflect on their strengths, interests, values, and development goals. It guides them in creating a simple career development plan and prepares them to initiate a thoughtful conversation with their supervisor, mentor, or another trusted person. As a result, you may begin to see more employees reaching out to schedule career-focused discussions.
Research consistently shows that regular career development conversations increase engagement, motivation, and retention. Employees who feel supported in their growth are more likely to bring energy, clarity, and commitment to their roles. This course helps employees become better prepared with clearer goals, thoughtful questions, and a shared understanding that career development includes both success in their current role and preparation for future opportunities.
As a supervisor, your impact comes from listening, asking good questions, and helping employees explore learning opportunities, stretch assignments, and next steps that align with organizational needs.
We encourage you to:
· Support and promote participation in the course.
· Welcome requests for career conversations.
· Approach these discussions with curiosity and openness.
This is an online course you take at your own pace. Your engagement signals that career development is valued and that it makes a meaningful difference. View the course at It’s Your Career: Having Productive Career Development Conversations with Your Supervisor.
Summer Music Venues in Madison and Beyond
It’s time to start scoping the summer music scene in the area, from the Terraces (Memorial Union and Monona), to Olbrich’s Biergarten, to all of the local festivals with their beer tent bands, Dane County has you covered if you like to dance and sing along to great tunes.
We are featuring a couple options for your consideration:
Memorial Union Terrace Summer Line-up
https://union.wisc.edu/events-and-activities/event-calendar
We recommend the Young Dubliners and The Kissers on July 25! Mama Digdown’s Brass Band has been a staple in the area for decades too, and they will grace the stage on August 29.
Monona Terrace Concerts on the Rooftop
https://www.mononaterrace.com/event-group/concerts_on_the_rooftop
Our recommendation here is surely Granny Shot on July 9th for those of us who remember the 90’s hard rock scene, and Nauti-Nauti on June 4th for a yacht rock experience.
Got a suggestion for music in your area? Let us know!