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  • Sean Ryan

It's YOUR Time, Take it Back!!

Reclaim your calendar by empowering your team

Do you feel like your calendar is running you, not the other way around? Are you frustrated trying to “manage your time,” only to have reality lay waste to your best-laid plans?

I hear this a lot. Leaders have a lot of priorities that come at them fast and furious, fighting for attention.

In ‘Top-Down Bottom-Up Time Management: Getting the Right Things Done In the Midst of Chaos,’ our signature priority-setting program, I’ll often start the first session with a simple question.

“How many of you are looking for more work?”

Of course, not one hand goes up, not once, in over 30 years of asking. But I do get many knowing smiles from leaders who feel there aren’t enough hours in the day. As somebody once said, “If you can’t get your work done in 24 hours a day, you might have to work at night!”

Think of how it feels when you’ve got that rare blank space on your planner. Or that feeling of joy when a non-essential meeting gets cancelled, giving you that gift of time? (By the way…if the meeting is “non-essential,” why is it on your calendar in the first place?!?!)

What if you could give yourself more of that? With delegation and discipline, it’s possible.


There are two traditional schools of thought when it comes to time management.

The top-down approach that emerged in the 1960s focused on effective planning, allocating your time to align with your priorities.

Then there’s the bottom-up school of thought, which our team affectionately calls “managing the mess.” This is about putting everything you have to do into the buckets and being super-efficient.

Here at Whitewater, we see a lot of value, as well as gaps, in both of these approaches.

So we took the best of both. Our approach blends the top-down approach, allowing you to focus your efforts on the most highly leveraged activities for your time with the efficiency of bottom-up planning that accounts for the messy realities of life, such as interruptions and the unexpected. This hybrid gives leaders the ability to manage both their high value-added priorities AND the dozens of stimuli coming at them in a rapidly changing, often high-stress environment.

That sweet spot in the middle is your planning center, and we’ve seen how, instead of constantly being in reaction mode, it gives you the tools to proactively plan and build the skills to set long-term goals and then translate them into high-impact daily and weekly activities.


Delegating is at the heart of our hybrid time management model, and for good reason: the best classic case studies on time management highlight it as the great differentiator between leaders who control their time and those who do not.

There’s MacGregor, Arthur Elliott Carlisle’s classic 1976 case study on the super-organized manager of a large refinery who has so much white space on his calendar he’s free for leisure. While the golf references and all-male workforce date the article, the author’s observations on the value of what he terms “participative management techniques” are as relevant as ever.

As Carlisle noted, many leaders think they are good delegators, but their behavior indicates otherwise, as they hold on to the lion’s share of decision-making.

Contrast this with “MacGregor” (an alias and an easter egg, referring to Douglas McGregor, author of The Human Side of Enterprise from 1958), who strategically, systematically refuses to take on his subordinate’s problems, the work he rightly sees as theirs, not his.

Relinquishing decision-making is easier said than done. It brings with it the risks of learning, namely mistakes. But to MacGregor, it’s worth it when mistakes are framed as learning experiences and decisions as growth opportunities. Or, in more modern times, as an executive coaching client of ours likes to say, “Why should I deprive my team members of a development opportunity by doing their work for them?”


MacGregor challenged the prevailing idea, then and even now, that a leader’s role is “chief decision maker” for those who report to them. MacGregor saw his job as setting clear performance objectives and staying informed about how his team was measuring against them.

He’d “quit making other people’s decisions” to be a proper supervisor. MacGregor saw his time as a scarce commodity, so he guarded it with an intentional and disciplined managerial system that provided clarity around quotas and budgets, so objectives were clear. He prioritized communication in the form of weekly Wednesday reports and Thursday meetings.

As he told the author, “A lot of managers feel that they have to keep proving to their people that they know more about their subordinates’ jobs than the subordinates themselves by doing their work for them. I refuse to do that anymore.”

Who’s Got the Monkey?, William Oncken, Jr., and Donald L. Wass’s oft-cited 1974 Harvard Business Review article provides a compelling visual representation of problems and work in the form of a monkey.

How do you keep them from ending up on your back?

It’s all about developing your team’s initiative.

“When you encourage employees to handle their own monkeys, they acquire new skills—and you liberate time to do your own job,” the article states.


The most effective managers of time share some common traits. They:

  • Set clear goals for themselves.

  • Identify the highest priority actions that lead to the accomplishment of those goals.

  • Adopt a weekly or longer scheduling horizon to ensure they structure their time for those important activities.

  • Constantly ask: “What is the best use of my time right now?”

  • Adapt daily.

  • Recognize that people are the most important thing, and prioritize decisions to spend time on important “people” issues as the need arises.

Building these habits takes time and discipline.

  1. For a few days, keep a time journal. Write down every task you do in those days.

  2. Write a list of your top three goals and prioritize them.

  3. At the end of the week, map your tasks on the simple, four-quadrant time management matrix. Along the top, make two boxes: Important and Not Important. Along the side, add two more: Urgent and Not Urgent.

  4. What is both not important and non-urgent? Those are low-hanging fruit for elimination or outsourcing.

  5. Next, check out your Important and Urgent categories. What can you stop doing to make more time for your high-priority goals and activities? If it still needs to get done, does it need to be done by you?

If you follow this simple exercise, you’ll likely be surprised at how much more spacious your planner feels and how much more focused you are at getting the right things done.


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