office woman quits job

The When Ways to Retain Talent

Evan Allgood

Editor's Note: We love Daniel Pink’s book, When. Great insight, great writing, great justification of afternoon naps. His insights don’t just apply to our individual personal and professional lives (and schedules), but also those of large organizations. We’ve talked elsewhere here about the importance of purpose, autonomy, security and the behavioral underpinnings of employee engagement. This article reflects upon how a book that keeps jumping into our consciousness reinforces the notion that those and other behavioral insights have tremendous power to shape the relationship between worker and company


A recent letter to The Cut asked, “Should I Quit My Boring, Well-Paid Job?” Almost all of the writer’s work responsibilities had been commandeered by a colleague. Disappointed and disengaged, she weighed leaving her job for more challenging terrain – or sticking around for the high salary, flexible schedule and absence of stress.

The letter and its response reminded me of the “When to Quit a Job” section of Daniel Pink’s 2018 book on timing, When. Pink asks: “Is your current job both demanding and in your control?” For the person considering quitting her boring, well-paid job – who has repeatedly asked her superiors for more to do – the answer of course is no, neither. Pink calls this “the worst [scenario] of all.”

I don’t begrudge the writer her cushy gig, but it’s embarrassing that an agency would pay someone so much to do so little. And it’s sad that a (seemingly) smart, competent person who wants to work hard is likely to jump ship for lack of stuff to do.

By inverting the questions in Pink’s guide, companies can learn some valuable lessons about engaging, retaining and developing talent. Here are a few.

1. Challenge, but don’t micromanage.

This advice might seem obvious, but as evident from the letter to The Cut, some employees just have nothing to do. I have a friend who worked for one of the world’s largest auto manufacturers, made six figures, and for years begged his boss for like, a task. They never gave him anything, so now he works much harder for a rival car company, where he’s exponentially happier.

Pink writes:

The most fulfilling jobs share a common trait: They prod us to work at our highest level but in a way that we, not someone else, control. Jobs that are demanding but don’t offer autonomy burn us out. Jobs that offer autonomy but little challenge bore us.

A slow day at work can be nice, but string together a few dozen or hundred of them and you can practically feel your brain atrophying.

On the flip side, there’s nothing professionally challenging about a boss sending five Basecamp reminders a day, or Slacking someone all the time for updates on every little task. Give an employee something to do, then leave them the hell alone to do it.

Give an employee something to do, then leave them the hell alone to do it.

2. Align work with long-term goals.

Though many employers like to ask, “Where do you see yourself in five years?” during the interview process, it’s less common to check in after someone has been hired to see how their plans may have shifted (or if they were finessing the truth in the first place to get the job). That’s a problem, because, as Pink notes:

Ample research from many countries shows that when your individual goals align with those of your organization, you’re happier and more productive.

One of the saddest anecdotes from The Cut’s letter was the author taking professional development courses that were paid for her by her company … but she had nowhere to apply these new skills at work. If someone took the time to see how this person was feeling, what her goals were, and why she was taking these courses, they could probably get a great return on the money invested in her education. Instead, she is twiddling her thumbs, thinking about bolting and writing letters to The Cut.

By brushing up on an employee’s ambitions, one can better tailor the employee’s role to their strengths, make their work more fulfilling and keep them around.

By brushing up on an employee’s ambitions, one can better tailor the employee’s role to their strengths.

3. Allow employees to do their best work.

Outlining an ideal management style, Pink paraphrases Stanford professor Robert Sutton:

If your boss has your back, takes responsibility instead of blaming others, encourages your efforts but also gets out of your way, and displays a sense of humor rather than a raging temper, you’re probably in a good place.

The getting-out-of-the-way here echoes #1 above: Don’t babysit or handhold.

And don’t take credit for someone else’s work. I’ve had bosses who were eager to accept praise for their employees’ ideas/words/designs – but who went dark when it was time to take responsibility for giving those employees the wrong direction, or for botching a project. For whatever reason, these bosses also made the worst jokes. (Editor’s note: Knock knock. Who’s there? This. This who? This is an obvious attack on the integrity of my jokes.)

Don’t be that boss or your employees will flee to the nearest four-star Glassdoor company.

4. Sync pay raises to work anniversaries.

In 2014, Entelo analyzed one million employees’ job histories and found that workers are most likely to leave around their one-year anniversary at a company. They are next-most likely to leave around their second anniversary. Then their third. “You get the idea,” Pink writes.

Why? There are a few reasons:

Pink also notes, “One of the best ways to boost your pay is to switch organizations.” So as work anniversaries approach, employees may leave because they’re dissatisfied, they want more money or both.

To mitigate these feelings, employers should try to sync pay raises to work anniversaries. By doing so, the employee who asks themselves, “What do I have to show for the past X years?” can at least say, “Well, I’m making more than I was X years ago, and they seem to appreciate my work.”

Money isn’t everything, though. If employers fail to tap into the other, more intrinsic work motivations given a nod by When, a raise is unlikely to keep someone from leaving, finding a new job or spending their energy writing letters to the editor and reading books about timing.

Evan Allgood


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