Wondering Toward The Good Work Life

It’s no wonder we’re feeling the friction we are: How we’ve learned to organize, manage, and do the work is perfectly suited for a world that no longer exists. Now is the time to figure out how to work in the world that does.

Written By
Drew Weilage
January 12, 2022

It’s no wonder we’re feeling the friction we are: How we’ve learned to organize, manage, and do the work is perfectly suited for a world that no longer exists.

On the other side of this overcomable conundrum is the personal satisfaction, professional success, and real progress we show up to work every day hoping for:

The Good Work Life.

It’s possible. It’s real. It’s just that it requires a committed willingness to rethink work.

And that’s the problem.

A Difficult Feat

We’re terrible at updating our views. Just absolutely terrible. It’s a fact of human nature.

However, the change(s) we need to make at work can only happen when we choose to deliberately open ourselves to the idea of updating our views about work … which often happens by first changing what we do.

Here’s an example.

Professional management agitator Tom Peters (a hero in this context!) introduced the American businessworld to a revolutionary idea in the early 1980s: Managing By Wandering Around. Because it was time for a shakeup.

Until then, if you can believe it, the mental model of many people in management positions, especially the most senior positions, was that their job was best conducted from behind a big mahogany desk.

It’s laughable now—now, people would ask whispering questions (blink twice and all that ...) about any manager tethered to their desk for longer than a couple of hours. 

It took Managing By Wandering Around, Tom Peters, and agitators of his ilk to push the rest of the work world into a new mental model of just what management should look like, with a simple nudge to wander. Now it’s common practice.

Well it’s time for another shakeup: Because it’s time to wonder.

Where Managing By Wandering Around is about getting out of the office and spending time with people doing the real work (for your learning and communicating and relating) ...

Managing By Wondering About is (doing those same things and) asking (to yourself ... and to others) if how we’re doing things (our approach to work) is, you know, the best way for us to do them.

(Prediction: They’re not.)

After a decade-plus of doing this sort of wondering about, I’ve found nearly every management practice (from what we believe to what we do) falls short (I use stronger language at happy hour) of helping us (that’s us as in you, and us as in an entire organization) achieve what we’re out to achieve.

Without the parentheticals: Work isn’t working. 

Not the meetings, not the approvals, not the silos, not the strategic planning, not the go-above-and-beyond requests, not the performance management, not the goal setting, not the weekend work ... okay, this list could go on and on and on ... but even the mental model (the hierarchical bureaucracy!) from whence it all originates isn’t working either! 

It’s high time to wonder why.

Managing By Wondering About is a mental model to do more wondering—“Why?” is a powerful question and curiosity is a powerful frame of mind—so we can discover and then change the work practices holding us back, particularly with the knowledge of two important and often ignored facts:

Healthcare changed again

We work in a fluxy world.
And since you already know The Transforming is always-happening and always-unfolding and not controllable by anyone, it will come as no surprise to learn: There’s more flux on the way. 
Yes, the pandemic was disruptive to our status quo and it has changed a lot of things. And also yes the pandemic has been an accelerant of existing forces reshaping healthcare for decades ...
... which are reshaping our organizations
... which is reshaping the work we do
... and, as a result, reshaping our jobs
... in ways that just about always have proven not to be for the better—not for the organization, nor for the people you work with, and not for you as an individual.
You get stretched, pulled, pushed, extended, and squeezed in an effort to get it all done and done well … because our approach to work hasn’t changed much from the 1950s.

How We Work Creates B-I-G Problems

Our approach to work today is built on the ideas of obedience in a 1950s classroom, efficiency in a 1950s factory, and military tactics of a 1950s fighting force. 
To be fair: 
But there are (at least) two B-I-G problems with the prevailing approach in our modern times.
One, it wears people out.
Two, well, the second argument is that it limits the potential of what an organization can achieve—but in all seriousness, what’s a healthcare delivery organization if every employee is worn the f*** out?

Taking Action

Healthcare changed, how we work hasn’t, and it’s holding us back.

So what successful navigation of The Transforming calls for, more than anything, is conceiving of a better approach to how we work … for the type of work we’re doing … and in the environment it’s happening in. There are better ways to organize the work, manage the work, and perform the work. It’s up to us to find them.

Managing by Wondering About is an entry point. It helps us recognize our reality, get curious about it, discover some things we didn’t know, and then, well, hopefully, provide inspiration to do something about it.

First we see. Then we do.

What we’re wondering toward is this: Creating the conditions for you and your team to do your best work. 

Because what we have now is not that.

So that’s the opportunity. 

That’s the leadership we need. 

And that’s where The Good Work Life is.

Here are five recommendations for getting started with Managing By Wondering About:

  1. What’s getting in the way of you doing your best work? Why? What’s the friction?
  2. Take a relatable work friend to coffee. Ask them the same questions.
  3. Wonder About: Take a walk (metaphorically or not) and talk to your team. Ask them the same questions.
  4. Consider the advice in here: “Better work right away this morning”. ​​
  5. Then only when you’re ready: Create a 15-minute daily recurring calendar appointment, invite just yourself and at a time when you’re most likely not to be disturbed, for “Learning From The Experts”. There are experts, past and present, Wondering About. Let’s learn from them.

Bonus 1: Have you introduced your team to Org Resilience and Better Work? 

Bonus 2: Questions (about anything)? Send me a note at drewweilage@gmail.com.

Through The Work is a talent development studio for healthcare leadership embracing The Transforming—the always-happening, always-unfolding state of change in your job ... and using it to make more of the change you know should be happening, happen.

The Transforming is the most important professional opportunity of our careers—one that will lead to new job opportunities, real change, and a transformed industry for all of us and everyone else.

My name is Drew Weilage and I work in healthcare, too. At Through The Work, I assist people like you with the skills, attitudes, and points-of-view to propel your professional success. It's personal training for a transforming world of work.

Oh, and pep talks! Get a pep talk when you need one: big day, bad day, or any day at all. Text me at 646-450-2465 or send me a note.

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