With a new year comes new goals. Goal-setting is a universally accepted best practice because, as the old saying goes, “Shoot for the moon. Even if you miss, you'll land among the stars.”

This is inspiring but reductive. If you shoot for the moon, you could hit the moon…hard. You could crash land. And there you are, right where you wanted to be but not how you envisioned.

This is precisely what happened in 1999 with NASA's Mars Climate Orbiter. Built by the best minds from NASA's Jet Propulsion Laboratory (JPL) and other collaborating institutions, it carried state-of-the-art instruments to map the Martian atmosphere and surface. Together, they embarked on a journey that was supposed to add a new chapter in space exploration.

Then, the $125 million probe crash-landed on Mars.

The crash was attributed to the units of measurement used by different teams: Lockheed Martin engineers were using the imperial system (pounds-force), while NASA's team used the metric system (newtons). Beyond the failure to align on measurement, there were several instances where one or both teams failed to course correct. NASA scientists noticed that the Orbiter was drifting off course almost immediately, but managers demanded that the worriers and doubters "prove something was wrong."

Despite constant measurement and a clear vision of where they wanted to land, NASA allowed the probe to shift 100 kilometers off course at the end of its 500-million-kilometer voyage--more than enough to hit the planet's atmosphere and be destroyed accidentally.

The challenge with goals is that we drift off course from our intended path the second after we launch. Our trajectory is subject to the gravitational pull of other ideas, projects, and priorities. It takes immense focus to steer the ship, and that focus has to be on the right things.

Consider Blockbuster, which built a competing DVD delivery business positioned to rival Netflix’s, but a new CEO effectively killed the initiative to prioritize in-store experiences1. Blackberry lost its dominant position in the mobile phone market to Apple because it refused to de-prioritize the historically favored physical keyboards in favor of the immensely popular touch screens2. Kodak, once a titan in the photography industry, failed to prioritize the shift to digital photography despite having early technology for it because it was trying to protect its profitable film business3.

Prioritization is a superpower — one that can differentiate high-performing individuals and teams. More importantly, prioritization is a superpower that can be learned.

To be good prioritizes, we first have to learn why we suck at it in the first place.

The Gravitational Pull of Poor Planning

Certain biases often hinder good prioritization and thought patterns that can skew our perception of what matters. What seems evident at the moment is often instinctual, and what’s instinctual is lazy (see System 1 vs. System 2 Thinking from Definitely, Maybe).

Here are some common traps we fall into when trying to identify how to prioritize:

• Urgency Bias: We tend to prioritize tasks that appear urgent (like emails or phone calls), but they may not necessarily be important for long-term goals. This bias can lead to a reactive work style, where immediate tasks precede more significant, long-term objectives.

• Recency Bias (or Shiny Object-Syndrome): We often give more weight to recent information or tasks, assuming they are more relevant. This can distract from older yet crucial tasks that require attention.

• Overestimation of Capacity: There's a tendency to overestimate how much can be achieved in a given time frame, leading to over-commitment and neglect of critical tasks.

• Perfectionism: Those with a high bar for quality can fail to discern when that high bar is necessary. Over-emphasizing excellence when “good enough” is good enough can lead to misallocation of time and resources.

• Avoidance of Difficult Tasks (Bikeshedding): There’s a natural tendency to avoid tasks perceived as difficult or uncomfortable, even if they are essential. It’s a preference for activity over progress.

Sound familiar? Yeah, I thought so.

Biases are challenging to overcome, but this is where decision frameworks come in handy. We can’t eliminate the bias but can counteract it with structured thinking.

Prioritization Strategies

Here are some essential prioritization techniques to help you and your team consistently win.

1. The Monkey and the Pedestal

The big idea: Tackle the most significant, riskiest challenges first.

Why we need it: If your goal is to teach a monkey to recite Shakespeare on a pedestal, the last thing you should do is build the pedestal! You’ll be tempted — incentivized, even — to work on things that signal activity, even if it’s inconsequential to the goal itself.

When to use it: Large, complex projects with multiple dependencies or uncertain futures.

Learn more: Google X Blog.

2. The Eisenhower Matrix

The big idea: Ensure critical tasks are completed by segmenting your to-do list based on importance and urgency.

• Delegate tasks that are urgent but don't require your expertise

• Delete tasks that don't add measurable value and distract from core tasks

• Do urgent tasks that have material consequences if not completed timely

• Schedule tasks that aren't urgent but usher in long-term goals

Why we need it: Intuitively, we know we should do what’s important and urgent, but in practice, we don’t structure our work this way. Instead, we substitute “importance and urgent” with “recent and frequent” because those are appropriate proxies.

Imagine a manager with an Exec Team presentation tomorrow, an upcoming team-building activity in a month, a backlog of emails, and Slack messages from various colleagues throughout the day. What typically happens is the emails and Slack messages continue to demand the manager’s attention, meaning she dedicates less time to the Exec Team presentation (Urgent/Important) and the Team-Building activity (Not Urgent/Important), such that what matters most gets rushed.

Using the Eisenhower Matrix, the manager can box out time to focus on what matters and batch unimportant tasks like emails and Slack messages.

When to use it: Personal task lists.

Learn more: Invest Your Time Intentionally with the Eisenhower Matrix (Forbes)

3. Can/Should Matrix

The big idea: Many teams are so focused on what they CAN do that they forget what they SHOULD do.

Why we need it: We tend to over-emphasize extremes — what we can do OR what we should do — and rarely think about the intersection of these two spectrums. Teams may know what’s important (what they should do) but hyper-focus on the blockers that prevent them from achieving the goal to perfection. When blocked, they’ll over-rotate what they can do with little regard to how it positions them to achieve their long-term objective.

The Can/Should Matrix thus does two things:

1. It reminds us that the top of our list should always be what we can and should do (Boxes 2, 3, and 5).

2. It forces us to identify how to unlock capabilities preventing us from what we should do (e.g., what shifts Box 1 to 2 or 3?).

When to use it: Mid- to long-term team goals.

Learn more: The Beautiful Mess - Can Do vs. Should Do

4. The LNO Framework

The big idea: Achieve leverage in your work by allocating your prioritizing tasks with higher return-on-investment

Why we need it: We tend to conflate “being your best” with “doing the best on every task.” It’s nonsensical — the email confirming you can attend the 8 a.m. meeting doesn’t require the same effort as the email pushing the team to rethink their product strategy — but the perfectionism bias lives on.

Shreyas, the creator of this framework, uses this example of a Product Manager’s to-do list to emphasize how the time allocation changes once you think about leverage.

Before LNO:

After LNO:

When to use it: Daily / Weekly tasks.

Learn more: Shreyas’s Tweetstorm.

5. Big Rocks

The big idea: If you start filling your time with sand and pebbles (minor tasks and secondary responsibilities), you won't have room for the big rocks (your most important priorities).

Why we need it: Consider this a longer-term version of the Eisenhower Matrix. The concept is similar - what’s important should be prioritized over what’s unimportant - but you swap out Urgency for Impact (or leverage if you want to think about this in conjunction with LNO). The biases are the same — we tend to focus on what’s recently come across our desk or what conversation has sparked on Slack — but being intentional about what matters allows us to keep these new ideas in perspective.

When to use it: Long-term team goal planning.

Learn more: The Seven Habits of Highly Effective People, Steven Covey.

Conclusion

No one will join us on a journey if we can’t articulate how where we’re going is better than where we’ve been. And no one will join us again if we don’t take them to their promised destination.

We must ruthlessly prioritize to resist the gravitational pull of distractions along the way. We must never lose sight of our goal and find the most straightforward path.

No one is born to prioritize, but leveraging the abovementioned techniques will help you develop into an expert navigator.

Godspeed, fellow travelers.

 Thanks to Roman Eskue for graciously reviewing this post to help me improve it before publishing!