December 16, 2025
The essence of leadership is the ability to shift from being driven by past patterns to being driven by a vision of the future, and then bringing others along with you. There are a number of skills associated with this process, but none that are quite as important as how we set, communicate, and execute on goals.
At the core, when we set goals we are doing two things:
The importance of this is beautiful, because it means that if you master the meta-game of setting and achieving goals, you will have mastered the core process of leadership. But the truth is that the vast majority of people struggle to create and achieve their goals.
In this article we will discuss some of the most proven methods for defining goals, the roadblocks that get in the way of achieving them, and what to do about it.
Goals can originate from authority figures, social pressures, comparison, incorrect assumptions about the world, or any number of other external sources. They can also come from our dreams, an internal desire to change, suffering caused by repeating patterns, or other internal sources.
While the initial motivation for a goal can come from an external force, it is the internal relationship that they have to our vision of our life that has the biggest impact on if we achieve them.
Said differently, the more we’re able to tie a goal to the future that we truly desire, the better. This brings us to our first roadblock - working towards goals that aren’t meaningful to us.
While it would be great to have everything that we do in our lives be completely dictated by our desire, that’s not the reality for the majority of people. To be a part of a team or system, you are at some point going to need to submit yourself to an external goal or vision. That can be bad news because goals that are externally imposed can feel more like obligations than opportunities, especially if they feel disconnected from your values.
Knowing that, what can we do?
Practice We start by reflecting on the life that we aim to create. You can do that by answering two questions:
This is a key piece of the process that should not be rushed or taken lightly. If this is approached conscientiously and with the intent to design your life, what you will get at the end is a vision that’s really meaningful to you, and a list of things that need to change to make it a reality.
That list of things becomes the field that you will work from when creating your goals. In many cases, succeeding in supporting the organization that you’re a part of is instrumental to creating your vision. If that’s the case, you can consistently revisit this vision when that organization imposes goals.
If succeeding in this organization is NOT critical to your vision, then you may end up with a goal to separate. In either case, you will have intrinsically powered motivation.
You may also find that you have a list of 50 different things to address, which is an introduction to another powerful roadblock.
We’ll discuss other constraints later, but it’s important to acknowledge at the outset that cognitive resources and time are limited. That means that setting too many important goals at once is a recipe for disaster.
Overloading yourself (or your team) with too many competing priorities will create: shallow effort, decision paralysis, schedule conflict, abandonment of goals that seem less important, and a general decrease in performance.
A good rule of thumb is to pursue no more than 1-3 major goals simultaneously. I classify a major goal as something that takes longer than a week to achieve, involves learning new skills, and / or necessitates a change in perspective or beliefs.
At the core, when we set goals we are doing two things: Review your list of improvement areas. What thing, if improved, would bring about the most progress toward your vision? Make that the priority, and do this up to 2 more times.
Now that you have a short list of improvements that would contribute massively to building your vision, it’s time to turn them into daily behaviors and start chipping away. To level set before getting into that process, here are a few proven methods for verbalizing, visualizing, and solidifying these improvements as goals.
This is one of the most common, simple, and powerful methods for clarifying your goals. SMART is a method that says goals should be Specific, Measurable, Achievable, Relevant, and Time-bound.
Instead of: "Improve customer relationships"
SMART version: "Increase our Net Promoter Score from 42 to 55 by December 31st by implementing quarterly business reviews with our top 20 accounts and resolving support tickets within 24 hours."
This goal is specific (NPS increase, QBRs, response time), measurable (42 to 55, top 20 accounts, 24 hours), achievable (incremental improvement with clear tactics), relevant (customer relationships), and time-bound (by December 31st).
The OKR method was popularized by Google in the 90s. It's designed for setting inspiring, aspirational goals while maintaining clear measures of progress. The framework encourages ambitious thinking and creates alignment across teams and departments.
Objective: A qualitative, inspiring statement of what you want to achieve
Key Results:3-5 quantitative measures that indicate you're making progress (typically aiming for 60-70% achievement)
Review cadence: Usually quarterly, with weekly check-ins
Objective: Become the most trusted partner for K-12 districts implementing 1:1 device programs
Key Results:
1. Increase customer retention rate from 85% to 95%
2. Achieve an average implementation timeline of 45 days (down from 90)
3. Generate 40% of new revenue from customer referrals
4. Reach 90% participation rate in our professional development workshops
Notice how the objective is inspiring and directional, while the key results are specific and measurable. If you hit 65% on each key result (81% retention, 68 days, 26% referrals, 59% participation), that's still significant progress toward becoming a trusted partner.
WOOP is a scientifically backed method developed by psychologist Gabriele Oettingen. It works through a technique called mental contrasting, which combines positive visualization with realistic obstacle planning. Research shows that people who use WOOP are 30-40% more likely to achieve their goals than those using positive thinking alone.
Wish: I want to become a leader who gives regular, meaningful feedback to my team.
Outcome: I imagine my team members feeling supported and clear about their development. I see myself having natural, helpful conversations about their work. Our 1:1s feel productive rather than awkward. Team members are improving visibly because they're getting the guidance they need.
Obstacle: The main internal obstacle is my discomfort with difficult conversations. I worry about saying the wrong thing or damaging the relationship, so I avoid giving feedback that might be hard to hear.
Plan:
The power of WOOP is that it acknowledges both the aspiration and the reality of achieving it, then creates automatic responses for when challenges arise.
Each of these methods has advantages and disadvantages, and are best suited for specific scenarios and timeframes. Since we've started from a visioning process, it's likely that some of your improvement areas are so broad and time intensive that it's not immediately apparent how you can start to work on them.
This brings us to our next roadblock, and a method for overcoming it.
If you are unable to connect goals to your daily life, the odds of you forgetting them, or pushing them aside for more urgent tasks are high. To overcome this challenge, use a combination of the methods above to break the goals into bite sized, daily chunks. I call this process the vision cascade.
Let's say you've identified that becoming a leader who develops people is critical to your vision. Here's how you'd cascade that down:
5-Year Vision: I'm a leader known for developing exceptional talent. My team members consistently get promoted and attribute their growth to our work together. I've created a culture where feedback is welcomed and people feel supported in taking on new challenges.
Annual Goal (OKR format):
Objective:
Key Results:
Q1 Milestone: Establish consistent feedback rhythms and build my feedback skills
Monthly Goal (January): Practice giving feedback in low-stakes situations and build the habit
Weekly Goals (Week 1 of January):
Daily Behaviors:
Morning routine (after reviewing my calendar, 9:00 AM):
During team meetings:
After 1:1s (immediately):
End of day (4:45 PM):
Notice how the 5-year vision cascades all the way down to specific times of day and triggers. The daily behaviors are concrete, scheduled, and tied to existing routines (after reviewing your calendar, after completing 1:1s, and at the end of the day). This makes the abstract vision of "developing people" into something you actually do on Tuesday at 9:00 AM.
Inherent in the vision cascade is the need to measure success. Without objective measures, you won't have anything to evaluate your progress against, and you'll struggle to know whether your approach is working or needs adjustment.
Leading and Lagging Indicators
Creating measures is essential, but not all measures are equally useful. The ultimate outcome of your goal—the thing you're actually trying to achieve—is what matters most. But by the time you have that outcome data, it's already too late to change course.
These outcome measures are called lagging indicators because they're retrospective. They tell you what happened in the past. While lagging indicators are critical for knowing if you succeeded, they don't help you succeed.
The best leaders track leading indicators alongside lagging ones. A leading indicator is a signal that changes before the final outcome, acting as a predictor of success. Because leading indicators happen earlier in the process, they're more within your control. They either build confidence by showing meaningful progress, or they signal that you need to adjust your approach before you've wasted months of effort.
How to apply:
Using our feedback example:
Lagging Indicators (the outcomes you ultimately care about):
Leading Indicators (the behaviors and early signals that predict those outcomes):
If your lagging indicator is "80% of team members report feeling very supported in their development," but your leading indicator shows you're only having developmental conversations in 40% of your 1:1s, you know you need to change your approach now, not wait until the quarterly survey confirms what you already could have predicted.
Leading indicators give you control. They let you course-correct in real time rather than discovering six months later that your strategy didn't work.
As you create your leading and lagging indicators, you may discover that some constraints will limit your success even if you execute perfectly. The earlier you identify these constraints, the better. Running into an unexpected constraint mid-pursuit can kill your momentum, drain your motivation, and make a previously achievable goal feel impossible.
To surface constraints before they derail you, ask these questions about your goals:
The existence of constraints is normal and expected. They shouldn't necessarily stop you from pursuing a goal. Instead, address them in one of two ways: either change your goal so it's not reliant on the constraint, or make addressing the constraint part of your goal.
How to apply:
Using our feedback example, here's what constraint identification might reveal:
Question 1: What resources, tools, or access do I lack? You realize you don't have a clear framework for giving feedback. You've been avoiding it partly because you don't know how to structure the conversation.
Response: Add "Learn the SBI feedback model" to your January goals. Block 2 hours to study and practice before giving your first round of feedback.
Question 2: What competing priorities might interfere? You have five direct reports but your calendar is already overloaded with project work. Finding time for meaningful developmental conversations feels impossible.
Response: Either reduce your goal (focus on developing 2-3 key people instead of all 5) or address the time constraint by blocking recurring 30-minute slots for 1:1s and treating them as non-negotiable.
Question 3: Who else needs to change their behavior? Your own manager never gives you feedback and doesn't value developmental conversations. There's no organizational support for what you're trying to build.
Response: You can't change your manager, but you can create support elsewhere. Find a peer who's also working on feedback skills and create mutual accountability. Or reframe: focus on what you can control (your own team culture) rather than waiting for organizational change.
Question 4: What would make this impossible even with perfect effort? If you have 12 direct reports and back-to-back meetings all day, weekly developmental feedback might genuinely be impossible without structural changes.
Response: This reveals that your goal needs adjustment. Either reduce the scope (bi-weekly instead of weekly, or focus on a smaller group), or escalate the structural issue (talk to your manager about right-sizing your team or reducing other commitments).
Identifying constraints isn't about finding excuses. It's about being realistic so you can either remove the obstacles or design around them before they stop you.
So far we’ve discussed the planning process for creating an ambitious goal. Simply putting this amount of effort into setting the right goals will have a huge impact on your performance. Connecting to a larger “why” will create more resilience, attaching your goals to a daily practice will keep them top of mind, and using a framework (or two) will provide structure and clarity.
Now it's time to execute, and there are a couple of roadblocks that show up here that can still derail your progress.
It's tempting to imagine that people who accomplish huge goals are just built differently—that they wake up every day filled with motivation to work. This isn't true, and believing it creates a harmful narrative that can lead to perfectionism or all-or-nothing thinking.
The fact is that motivation is an emotional state. It comes and goes, largely outside of your control. The highest achievers don't rely on motivation. They stack their habits, use commitment devices, and design their environment so that they make progress regardless of how they feel on any given day.
Using our feedback example:
Habit stacking: Instead of hoping you'll remember to give feedback, attach it to an existing routine. "After every team meeting, I'll identify one person to give feedback to within the next hour."
Commitment devices: Schedule your 1:1s at the same time every week and add "developmental discussion" as a standing agenda item. The structure removes the decision of whether you feel like having the conversation.
Environment design: Create a simple template for feedback notes and keep it easily accessible. When you notice something worth mentioning, you can capture it immediately rather than relying on motivation to remember it later.
The goal isn't to feel motivated every day. The goal is to build a system where motivation becomes irrelevant.
One of the most common things that stops people from achieving their goals is how they respond to imperfection. Maybe you've been there? You have a goal of working out consistently, but then unforeseen circumstances force you to miss a workout. Instead of making it up the next day or doing a lighter workout at home, you throw the goal out entirely.
This is especially insidious because it reinforces a story that you're not good enough or that you'll never hit this goal, making the pursuit even more challenging the next time. The reality is that any goal big enough to matter will present you with setbacks and blockers. If you let them stop you, then that narrative of never being good enough becomes true.
But you don't have to do that. Here are ways to prepare for setbacks:
If you accept that setbacks will happen and decide how you'll respond from the start, you'll be more resilient in the moment. This type of planning is inherent in the WOOP method.
In our feedback example: "If I have a particularly difficult week and miss giving feedback, then I will send one piece of written feedback to at least two team members by Friday afternoon. That keeps the momentum going even when the week doesn't go as planned."
Regardless of the setback's nature, your response dictates whether you get closer to your goal or further from it. Maybe you underestimated an obstacle. Maybe you missed something entirely in your planning. That's okay, as long as you're committed to learning and applying what you learned.
You had a feedback conversation that went poorly. Instead of avoiding feedback altogether, you reflect: "I jumped straight to criticism without acknowledging what was working. Next time, I'll start with what I appreciated about their work." The setback becomes data that improves your approach.
What empowers all of the change above is accountability to your goal. If you're blaming others for your lack of progress, you won't make the changes necessary to succeed. That's not to say other people can't impact your progress—they absolutely can. It means that regardless of what happens and how out of your control it is, you're the one who needs to adjust, reframe, and recommit.
If you've gone through the process of setting a meaningful goal, identifying constraints, and building daily behaviors, you're already demonstrating the capacity to change. If you need the extra push of accountability and ownership, here are things you can try:
Make a public declaration of your goal. Find an accountability partner who understands both what you want to accomplish and why, then give them guidance on how they can help keep you honest.
Tell your team: "I'm working on becoming a leader who gives more regular feedback. If you notice I'm not doing that, please call me on it." Or find a peer leader and check in weekly: "How many developmental conversations did you have this week? Here's what I did."
The key is making your goal visible to others in a way that creates gentle pressure to follow through. When someone else knows what you're working on, abandoning the goal becomes harder.
From creating a healthier lifestyle to hitting ambitious sales targets, people who master the meta game of setting and achieving goals have a massive advantage in creating the life of their dreams.
Achieving goals is a skillset, meaning it can be mastered with consistent, high quality practice. You can do it.
Photo by Mauro Gigli on Unsplash
