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"Everything on this growing list is on fire. Urgent AND important. I need more hours. How am I supposed to keep up?"
– Late-night inner dialogue of a scaling executive
I was recently coaching a CXO…
whose company had roughly 10x’ed this year. He pulled up his quickly expanding TODO list to show me what he was up against. Every task was tagged “high priority.”
Like many high performers, he found success in being the ultimate go-to fixer, the one who is so reliably excellent that every hard problem gravitated to his plate. Being everyone’s preferred fire-putter-outer had turned his carefully built work systems and inbox-zero into a mess no Eisenhower Matrix could rescue.
For leaders in fast-moving organizations, chances are, if it’s on your list, it’s important load-bearing work. It all lights up, unhelpfully, at the same brightness.
Well, It Used To Make Sense.
Think back to your last real planning session. You sat with the whole picture in front of you and decided what this year was actually for. Your priorities were clear then because the noise was softer; you could see the grand vision, and the goals were fresh and exciting.
Then the quarter started, and other people's priorities encroached on your inbox, your Slack channels, and your calendar. Each one was reasonable on its own, but together they dissolved your clean list into a stuff-I-need-to-figure-out-at-some-point soup.
The problem goes mostly unnoticed until a task falls through the cracks or post-summer rush holds up a mirror. At that point, nearly everyone reaches for the same diagnosis: I need to start over, be more disciplined.
That might be only partly true.
The Equation Has Two Sides
Time = Priorities.
It’s easy to be tricked by the tidiness of this formula and think of every failure as a “not enough time” problem. Read it as an actual equation, and it’s easier to see the fuller picture: if your time and your priorities have drifted apart, either your time isn’t going to what matters or your priority gauge is off.
The goal is to notice the gap and work out which side needs fixing.
That fix seems as easy as a snap of the fingers, but in the midst of overwhelm and self-recrimination, when you’re in fight-or-flight mode, clear, strategic thinking is nearly impossible.
Every fix I can think of requires a (mostly) settled mind. So, before you dive into the work, breathe and give yourself grace, because your list is genuinely more than one person should be expected to do.
Side One: Is This Actually A Priority?
Priorities have a shelf life, but they don’t often announce their expiration date. Some may not be time-bound, but might be an idea you had once, a nice-to-have you inherited, or something you said yes to in a hallway that’s ultimately unnecessary.
At face value, they’re all important, and solving for “most important” gets us stuck in an unhelpful loop. Instead, I use the LNO framework. It helps you categorize where your time goes relative to the impact it generates, and you decide how you measure impact (money, time, productivity, etc).
Leverage — Activities where your return on time is multiplied (e.g., building systems, coaching others, strategic decisions, setting expectations teamwide)
Neutral — Return on time is one-for-one. For instance, you investing an hour to get something done saves someone on your team one hour
Overhead — Necessary but not value-generating (admin, logistics, reactive tasks)
The goal is to maximize the time you spend on the highest leverage items. So instead of asking how much a task matters, ask what you unlock by doing it. The answer tells you which letter you're holding:
"It multiplies" = Leverage. Those get calendar time and your real effort.
"It gets the thing done" = Neutral. Do it well enough, then move on.
"Not much, but it has to happen" = Overhead. Batch it or shrink it, and be honest about whether anyone would notice if it stopped.
Then make one more pass over the Leverage items and ask: Does this have to be on my list?
A task can be genuinely high leverage and still belong on someone else's plate, and the instinct that says "this is important, so it's mine" is the same instinct that overfilled your list in the first place. Handing a leveraged task to someone who can grow into it isn't demoting it. That's you multiplying through someone else’s time instead of your own.
Pro tip: The highest leverage item isn’t always work-related. I worked with a founder grinding himself into the ground; his highest-leverage item turned out to be daily exercise. If he didn't move, he didn't sleep, and if he didn't sleep, he was a grump to work with, and his decision-making degraded all day.
So when searching for your highest priority, check your blindspots; it might be disguised as the thing you’ve filed under “I’ll fit it in when I can.”
Side Two: The Honest Record
Now for the other side of the equation: how you’re actually spending your time. Generally, we rely on memory or the vague sense that “I really should be working on that other thing” to keep us on track.
But this quickly gets inaccurate. Your calendar, on the other hand, doesn’t care about your stated priorities; it just reflects what is:
The 5-Minute Calendar Audit
Open the last month of your calendar.
Color every block of high-leverage work BLUE.
Look at the resulting field of color. Was there enough blue there to move anything, or is it a few thin splotches running through an ocean of everything else?
Now color the month ahead of you, as it currently stands, and ask whether it is blue enough.
If it isn't, congratulations, because you have just found your gap, laid out in color. If there’s not enough blue, you have to schedule it.
“Schedule more blue” sounds too simple to be worth saying, and that’s why it slips under the radar. We tend to treat a priority list as though naming the work were the same as making room for it. We tend to shoehorn those priorities into an already crowded calendar and assume it will somehow all fit.
The reality is your high-leverage items need deliberate action: schedule more blue.
You Scheduled It; It Still Didn't Happen
Start with the same question side one asked: Is this still a priority? If the answer is yes, then be honest about what's making it hard. Usually it's one of two things.
It's too big to start.
You sit down, the thing is enormous and shapeless, and forty minutes disappear into your inbox instead.
I had a founder name "create the product strategy" as his high-leverage task and conclude he'd need a full, uninterrupted week to do it (which, at a company that size, was never going to happen). So we looked for two-hour blocks (the shortest timespan he’d need to enter a deep-thinking frame of mind) scattered across a couple of weeks.
Each block had a specific job: Not "work on strategy," but "sector 3 competitive analysis." That specificity gets you started faster, and it makes the block considerably harder to move, since "strategy time" reads as flexible to everyone, including you.
Something eats the block every time.
If the same two-hour blocks get edged out three weeks running, the problem is more likely to be the slot than your discipline.
Some of my clients have moved their thinking work to the very start or the very end of the day, because that's the only stretch when nobody needs anything from them. Others keep the slot and defend it by shutting off notifications for the duration.
What works here depends a great deal on how your particular brain operates. Some people need only to see the block on the calendar. Others need someone waiting on the other end, whether that's a chief of staff, a coach, or a colleague to think out loud with.
Whatever it takes, the point is that you're the one who has to notice the gap and build the thing that closes it.
From Fixer To Architect
The instinct that made you excellent at this job is the instinct to run at whatever is burning brightest. It is fast, it is responsive, and for a long stretch of your career it was exactly the right instinct to have.
At this executive level, it stops scaling, because the volume of bright things now exceeds you and always will. The shift being asked of you is to go from the person who does it all to the person who does what’s most leveraged. Your calendar won’t correct itself, your priority list doesn’t update on its own, and no one else can see the gap between them.
You can. And at the highest altitude, that’s the bulk of your job.
REFLECTION
What is on your list right now that was a genuine priority when you wrote it down and isn't one any longer? What would it cost you to cross it off today?
Looking at your current TODO list, which item, if it moved this month, would make two or three of the others easier? That one is your high leverage item.
What is the smallest and most specific block you could put on next week's calendar, with a real job attached to it, that a meeting couldn't casually bump?
Keep reading, keep leading,
Jess
P.S. If The Left-Hand Column has resonated with you, consider supporting my work by clicking on one of the ads below. It's a small action that has a big impact!
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