Here is Rob’s next chapter!

At a recent offsite, I asked the room of senior leaders, “How many of you started your day yesterday with a clear plan?” A few raised their hands. Then I asked, “How many of you created that plan yourself — proactively — rather than letting your calendar dictate it?”

Fewer hands.

One of them — a founder-CEO — pulled me aside later and said, “I realized my calendar is basically a public utility. It’s there for others more than it is for me. My assistant, my team, clients — everyone plugs into it. But I haven’t treated it as mine in a long time.”

We stood there for a moment, looking at his screen, packed from 7:30 a.m. to 6:00 p.m. I asked him: “Which of these blocks of time is your work, your initiative, your agenda — and which ones are a reaction to the pull of people and activity around you?” His eyebrows went up as if enlightened.

Most leaders aren’t lazy or disengaged. Quite the opposite — they are constantly reacting. Overnight fires. Requests for help. Meetings. Inbox triage. Calendar conflicts. Their days are full... but not necessarily effective.

In Chapter ___, I gave you a time management plan for designing your Ideal Week. As with military battle plans, that Ideal Week inevitably changes beginning Monday morning. This chapter will address how you make adjustments on-the-go and spend your time most effectively each day.

The Leadership Challenge

To what extent did yesterday’s work feel more reactive than proactive? As you look at your calendar for today, how much of the activity on there is dictated by meeting invites, emails and texts that you need to respond to, and what others have identified as “fires” that need to be put out immediately? What is your plan for using any of the whitespace that you see in your schedule?

If you’re like many leaders, your calendar fills by default—not by design. Meetings multiply. Requests creep in. Before you know it, the day becomes a series of reactions instead of a sequence of choices. You’re moving fast, but not necessarily forward.

The real danger isn’t the chaos. It’s the drift. Important work gets edged out by urgent noise. And you lose the sense that your time—and your leadership—belongs to you. The result? You look up at 6 p.m. having been busy all day, but not quite sure what you accomplished.

Planning your day well is not about rigidity or complexity. It’s about ownership and intentionality.

The Leadership Opportunity

The goal here is simple: Begin your day with a plan. That alone — the act of choosing your day’s priorities ahead of time — puts you ahead of 80% of other leaders. The system or method you use matters far less than the fact that you have one.

Here’s how I do it, and how I coach others to do the same:

1. Block the Big Things — Before the Week Starts

If something matters — like writing this book — it has to live on my calendar. I created a repeating event: “Writing Hour,” 10–11 a.m., Monday through Friday. Do I keep it every day at that time? Not always. But because it’s there, it rarely gets deleted — just moved. It protects space for high-leverage work.

Your calendar isn’t just a tool for scheduling. It should be a tool for protecting what matters most.

2. Plan Tomorrow, Tonight

Every evening, I take five minutes to jot down tomorrow’s “1–2–3”:

1 — Most important task (the one that makes the day feel like a win)

2 — Urgent items I need to handle (so they don’t become true emergencies)

3 — Maintenance tasks (email, calls, prep work)

This version of the “1-2-3 List” comes from Greg McKeown’s Essentialism podcast and is deceptively powerful. It forces clarity, not volume.

3. Do the Hardest Thing First

Your willpower fades throughout the day. So does your decision-making capacity. If something is really important — having the hard conversation, preparing the critical sales pitch, reviewing details in the new budget — do it in the first block of your workday1.

Ask yourself: If I only got these 1–3 things done today, would the day still feel successful?

4. Say No Like a Grown-Up

You’re going to get meeting requests. Before saying yes, ask: “What’s my role here?” or “Would it still be successful if I weren’t present?”

If your calendar is full of “just in case” meetings, you’re sacrificing real work for comfort and appearances. Check that your ego - wanting to be wanted - isn’t overruling your purpose - why I am here and how I make my greatest contribution.

5. Put Time Limits on Everything

Email. Studying documents. Research. Even phone calls. Parkinson’s Law says tasks expand to fill the time allotted. So give them less time. You’ll move faster and stay more focused by keeping yourself accountable to the clock. If you get to the end of the allotted time and still need more, you can schedule it.

Try:

• Email triage: 30 minutes mid-morning, 20 minutes late afternoon.

• Callbacks: batched into one 45-minute block.

• Meetings: rarely more than 45 minutes unless it’s a true strategy session.

I routinely set a timer on my phone to be held accountable to get a task done and then move on.

6. Build Buffer Into Your Day

Don’t book yourself back-to-back. And don’t allow your admin to do it either. Even 10-minute buffers between meetings help you reset. Use them to walk, breathe, review your notes, or just look out a window and re-center. The higher you rise as a leader, these quiet moments are a necessity, not a luxury.

You’ll show up better in the next thing — with clarity and presence, not clutter and spillover.

7. Make your admin your planning partner

If you have an executive assistant, treat them as a strategic ally, not just a scheduler. Share your priorities, blocked times, and key objectives for the week. A great admin can help you protect your calendar, decline low-value meetings, and create margin. Take the time to educate them so they don’t just put new events in your calendar, but also keep unnecessary ones out.

Plan Your Day: Autopilot vs. Intentional

To paraphrase the late leadership guru Peter Drucker, planning your day as a leader isn’t about being super efficient. It’s about being effective. Your calendar should reflect your priorities, your responsibilities, your vision — not just your availability.

And that starts with having a plan.

Notes

1. Brian Tracy has written an entire book about not procrastinating — Eat That Frog! And Stephen R. Covey identifies “First Things First” as number three of his Seven Habits of Highly Effective People. Later he wrote an entire book on that concept, First Things First.