How to prioritize (when everything’s a priority)

The famed Eisenhower was supposed to be the panacea for all of our prioritization problems.

With its handy quadrants, it was meant to be a beacon of clarity and focus.

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I mean, if you chopped off anything deemed “not important” (i.e. the bottom half) life would be so much less… stressful.

But here’s the rub.

Raise your hand if a scatter plot of your to-do list (Eisenhower-style) looks more like this:

That client proposal? Due in 4 hours.

The offer letter? Candidate needs it by EOD.

The new onboarding program? Crap, that was due last week.

It turns out that when everything is important AND urgent , the Eisenhower Matrix stops working.

So how do you prioritize, when everything is a priority?

All outcomes are not created equal

The Eisenhower matrix had a fatal flaw. It doesn’t account for impact.

Yup, the matrix doesn’t actually tell you what is important (particularly if you lop off the bottom half). The impact of a task is not assessed, which makes it impossible to prioritize accordingly.

Here are 4 approaches to make your level uo your prioritization skills.

Approach #1: Assign a value to every task

Benjamin Franklin was onto something when he introduced the “Time is Money” aphorism in Advice to a Young Tradesman.

“Remember that time is money. He that can earn ten shillings a day by his labour, and goes abroad, or sits idle one half of that day, though he spends but sixpence during his diversion or idleness, it ought not to be reckoned the only expence; he hath really spent or thrown away five shillings besides.”

A standard to-do list will use a High / Medium / Low classification to measure impact. Our own $10K Work framework takes this a step further by adding leverage. Here, we can draw on the wisdom of Archimedes who said:

Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.

Remixing these concepts (into a nifty matrix) produces the magic of $10K Work which can easily be implemented into any task-management system in under 20 minutes.

Approach #2: Use “Even-Over” statements

If you don’t choose your priorities, your priorities will choose you. Life is about making intentional trade-offs. Even-over statements can help you make these trade-offs explicit.

But first, let’s set the record straight: We’re not talking “ice cream over broccoli.“ Nope. We’re talking about having to choose between two really good options.

For example, let’s say you’re looking to move into a new apartment. There’s probably a bunch of things that you want, such as:

Proximity to school
Proximity to work
Safety
Being in a cool neighborhood
Good local dining options

Now we all want The Unicorn. We want it all. But in practice, that’s probably impossible. (It either is prohibitively expensive, or doesn’t exist.) Which forces us to make a trade-off.

Everything on the list is a good thing. But we’ll have to make our priorities explicit. This list might morph to include:

I value safety EVEN OVER good dining options
I value proximity to school EVEN OVER proximity to work

If the unicorn appears, great. If it doesn’t, at least you’ll have a useful rule of thumb for prioritization. We’ve been thinking about how to use Even-Over statements in RadReads. Some of our ideas include:

We value product quality EVEN OVER execution speed
We value mental health EVEN OVER maximizing employee output
We value sustainable growth EVEN OVER faster profitability

Approach #3: Measure Return on Effort

If you were in the business of building widgets, you’d measure how many widgets you produce. But you wouldn’t stop there. You’d look at the inputs, notably time and money.

Task management frameworks fail to look at the input cost of a task. Sure, some of them have “duration” as a metric. But even then, it tends to be more descriptive.

A more precise approach to prioritization would consider the inputs, specifically the effort. This can be done with a simple ROE (i.e. Return on Effort) calculation.

To illustrate this, lets use a simple example of two competing tasks: a Tweetstorm versus__a YouTube video.__

The Tweetstorm will take 30 minutes and will generate 10 new sign-ups (estimated).
The YouTube video will take 10 hours and generate 150 sign-ups.

Next, estimate the return on effort :

Tweetstorm: 0.33(i.e 10 sign-ups / 30 mins)
YouTube video: 0.25 (150 / 600)

The ROE recommends that you focus on the Tweetstorm first. Remember, this is a prioritization exercise. It doesn’t mean you won’t do the YouTube video, it just impacts the sequencing.

Here’s an example of how we use this approach over at RadHQ (and one we implement for our consulting clients):

Approach #3a: Add Probabilities to the ROE

As you consider longer-term tasks a new challenge arises. What if the pay-off is uncertain? This happens all the time in business, where you may be choosing between adding a new product line, re-designing a workflow or investing in a new marketing campaign. Clearly some of these “outputs” have riskier paths.

To account for this variability, we can attempt to refine this analysis by adding a probabilistic layer. Let’s revisit our simple Tweetstorm vs. YouTube video example. What if you’re__90% certain the YouTube video__ will work, yet only 25% certain about the Tweetstorm?

Here’s the new math:

Tweetstorm: 0.33 * 25% = 0.08
YouTube video: 0.25 * 90% = 0.22 (aka the winner)

Doing this analysis in your task management system is probably overkill, but acts as a quick mental heuristic if you’re still stuck in prioritization limbo.

Approach #4: Understand the dependencies

If a task unblocks a subsequent action, it increases in value. If I need to sign-off on a product roadmap, our product management, ops and marketing teams are all in “standing mode” until I’ve done my part. These dependencies need to factor into the value of the tasks on my plate.

In the post Ruthless Prioritization, Brandon Chu emphasizes the importance of “unblocking” other teams:

If you’re optimizing for the company’s ROI above your product’s— which you should be — you’ll now need to assess the cumulative ROI of not just your project, but the dependent projects that you unblock in order to make the correct prioritization decision for your team.

He demonstrates the cumulative ROI with this powerful visual:

Source: Brandon Chu

Unblocking: A manager’s number one job

As I’ve reinserted myself back into a management role, I’ve realized that I am usually the blocker for a series of downstream tasks. Since one of my hats involves being our Chief Marketing Officer , I often need to review copy, rewrite headlines, develop campaign framings and analyze customer research. Until I complete these activities, many things can’t “go live” or get “launched.” Most days, my job feels like air-traffic control (which I thoroughly am enjoying).

However, there’s a tension here. It makes it much harder to do Deep Work and therefore my attention always feels fragmented. Strong internal communication protocols and clear response expectations can really alleviate this fragmentation.

Approach #5: Are you connected to your why?

This last prioritization tool is obvious, yet easily overlooked. Do you understand how a task moves the needle to a bigger why? This problem is particularly acute in large organizations, where many employees feel like they’re a languishing cog in a corporate hamster wheel.

As the CEO of RadReads, I’ve struggled to balance the tension between our daily activities, our intermediate goals and our long-term vision (while simultaneously fighting off Shiny New Toy Syndrome). We’ll save this for a longer post, but we’re clear on our Mission (help high-performers lead more productive, examined and joyful lives) and our quarterly OKRs (via Christina Wodtke’s Radical Focus framework).

I don’t love OKRs, but our two Objectives are:

Establish Supercharge Your Productivity as the engine of sustainable growth
Establish Product-Market-Fit for our consulting business

Each of these has 2-3 Key Results that we track each week to ensure we’re on focused and moving in the right direction.

This approach can also be applied at the personal level, with a simple $10K Question:

Do you know what you want and why you want it?

If every task is viewed through this lens, you’re on the fast track to prioritization.

And if you haven’t asked that question, welp, there’s your highest priority!

Our upcoming cohort of Supercharge Your Productivity _teaches these advanced prioritization techniques. Enrollment opens in a few weeks,join our waitlist and secure $498 of launch bonuses. _