Originally published as an Advisory Hour Substack post on 2026-09-02. This first-party site copy preserves the original text and public supporting media beside Leadership OS.
Original post
Stretch Goals
A stretch goal is the goal you set after you map out everything that needs done. It is the goal that is only possible if you squint and turn your head to the right. An ambitious goal after the goal of the ambitious thing. “Wouldn’t that just be the thing?” There’s a 50/50 chance your mind may be rebelling against the idea of a “work goal beyond the outcome itself.” Your brain is protecting you and it is wrong.
Brain-psychology mixes with social pressure to rail against the concept of stretch goals. The immediate retort you’ll get in a corporate setting is “what’s the functional difference between work that needs done and a stretch goal?” These people are right to ask and operating with the wrong lens. The work output (of finishing the tasks) is an outcome that happens as people go in pursuit of pushing their capabilities. If you don’t challenge others, or yourself, then you just meander about the same low-orbital pattern of behavior that you did the prior twelve weeks.
A leader pushing back against a stretch goal is saying “I don’t want individual/team to grow, and instead I want the work outcome to be completed by Friday. I need the outcome more than I need individual/team to grow.”
The very existence of a stretch goal asks us to imagine completing the work as a secondary activity. The truthful primary: What capability are we trying to create in pursuit of the work outcome?
Lessons from my own past
When I am put into a situation of building team capability it’s often very clear the immediate work that needs done. The real art is setting up and getting buy-in on stretch goals. “Stretch Goals” need to be marketed, prominent, clear, and achievable-and hard. Change is not easy. If the standard operating process is easy, then it’s a sign there’s little growth where it counts. Is your team growing if they work on the same unit of work week after week? Of course not, and it might even be a motivation of the manager of that person. If a person’s capabilities outgrow that work, then the subordination would seek bigger challenge, a raise, or possibly even a new job. The manager, sandwiched in an unwinnable situation, picks the outcome that causes them the least amount of work: don’t change anything. If an organization isn’t growing, it’s usually because its people aren’t.
Let me provide a couple vague examples where I’ve run stretch goals and when I haven’t. Let’s see if you identify your own organization in either camp.
The Stretched Contributor
I needed to build an activity in an organization around a specific domain concept. It was an exciting new Thing that would fundamentally improve X and then unlock Y. The organization leaders agreed and mixed a few chosen individuals. This newly formed team included talented actors who had specific out of domain skills. The Thing was somewhat new, but it was also unique. On the surface, the Thing was the task.
In my designs that went unspoken: the team were undertaking a project that wasn’t just about building a new Thing. Any of the organizations teams could build a Thing. Instead, I wanted to ensure the team could stretch their capabilities in a way that individuals in this team could become leaders in or around that domain long after. The best outcome was to dissolve this “Thing creation team” in favor of seeding them in the organization.
When structuring the work for the team, I took in a high-level idea and broke it down to the tasks that needed done. This is playbook technology product management. In the margins, I pushed it further. It wasn’t just about the tasks of that project, but rather an escalation of stretch concepts. I wanted to push this group to think bigger. The point wasn’t to complete the project we were working on. I was building contributors to the future enterprise value of the organization.
Today these individuals have risen up in the ranks, and each leads a significant chunk of the organization they work for. I have no doubts that they would do well in any team-and have themselves capabilities that could still be brought forward. I’ve repeated this playbook several times and always conclude the same: when given the nature of work, and an ambitious goal, participants will rise towards it.
The goal cannot be financial or performance. I argue these are outcomes of capability.
The “BAU” Contributors
The project was like the hundred that had come before it. The nature of the work was for the team to take in the product design, disassemble it into a working system, and then repackage it into the mainline product. The participants involved had well-oiled the result to a point that the work was predictable before it ever saw the engineers. “Oh, this much complexity is probably two days of work, and this other one closer to two weeks.”
Every week was the same for this team. They saw a level of consistency with the work outcome. There was never a stretch goal. There was merely the next set of tasks to complete. The result is that the team members never had a reason to strive. The result of this didn’t show up in the completion rates or performance of the team. In fact, all (and I mean all) of the KPI showed a team that was performing brilliantly. Except the real detail was hidden inside.
The participants of this team never grew beyond their bounds. The consequence of this is that without such opportunities for development, the team members increasingly grew dissatisfied and the only clue to this emerged in annual “how are we doing?” surveys. The most exciting days for the members of this team weren’t the annual survey, but rather the re-organization. Absent a challenge to grow beyond the task outcomes at hand, the team grew stale in knowledge and capabilities.
“We’re looking forward to the re-organization just to work on something different.” is often told to me by members of these teams. Absent stretch goals to help guide capability of a team, there’s a “safe fallback” to getting the immediate work done. And that work must be done. It’s just when there isn’t an opportunity for that team to think bigger, on harder and bigger problems, then it’s a local optimum trap. The stretch goal is the ladder you provide the team to unlock more value in the firm. Sometimes though, the people are the cog, and the organization is a cog moving machine. It is what it is.
But if leaders start asking, “We seem to have a growth problem? What’s causing that?” maybe the answer is hidden in the details, or not yet scribbled along the margins.
What capability do we need in pursuit of the work outcome?
This is the guiding north star of a stretch goal. It’d be too easy to set a stretch goal that’s “oh instead of building X in Y time, we’ll do it in Z time!” This is an error. More work, less time, harder work are not stretch goals.
A stretch goal is a problem that inspires capability change in the individual.
Let me take you mentally back to the very beginning of this post. At the very top of this article I have a mountain with a rocket on it. I encourage you to take that image later and reflect on it with ChatGPT or another AI tool. There’s a lot of perspective hidden inside that image.
Imagine yourself ascending such a mountain. Each and every lap upwards and around the mountain you solve customer problems X and Y. Owing to this, you’re rewarded Z. The laps continue.
Is the point of your work to continue hill-climbing the value you already have? I can’t answer that for you. Maybe it is and maybe that’s the extent of your intended purpose for the outcomes you have going. Here’s a test for you that brings our rocket ship image back into frame.
If you hill-climbed that value all the way to the top, and found a fully-fueled spaceship waiting for you at the very top-what would you do? Would you board the spaceship or would wave as it blasted off to ever growing heights?
Optimization has a point. There are times in life when it’s useful to go deep and optimize the heck out of a system. I’ve more than my fair share of looking at making systems leaner, faster and a heck of a lot meaner. However, there are times where perspective needs to shift: transformation is a fully different thing. Capability building is a function of transformation.
Business as usual optimizes the organization for what you already have. Stretch goals are part of the capability building toolset. A toolbox of building capabilities in others, but also yourself. Have you considered that such a thing exists? Slow down reading for a moment and reflect on that. What toolbox of capability building do I have for myself or in others? What words describe it?
If you don’t have such a toolbox, then let me provide one now. It can be done today.
Personal Transformation
An easy way to reach individual transformation is to just task yourself with reading more books than you quantifiably read over the last five years. For example, I set myself up with a task to read a very large number of books this year-but with a caveat: the books were to be specifically outside my interests. If your brain was like mine, it’s already mustering up a list of excuses. “Ugh”, “I can’t stand ‘GENRE’.”, or “You’ll never catch me reading ‘CATEGORY’”.
Go to the category, find the smallest book on the shelf, and read it.
Owing to this self-directed punishment, I’ve observed changes: I’ve grown and learn so much by adopting this stretch goal. It wasn’t just reading, I just began reading as much as I could and then continued. I read books I hated every single page of reading. The book only counted if I made it to the last page.
Some books are so much in opposition to who you are as a person that you can feel the tortune of turning each and every page. One such book is on my bookshelf. Even now I eyeball that book with such incredible disdain. However, it forced me into a space where I overcame the hard thing. Lot of people will claim you shouldn’t fully read a book you understand in the first several pages. I disagree. On page 270 might be a gem of an insight in a book that you otherwise loathe-an insight that just unlocks a block in your life in such a profound way. Incredibly, I discovered there are types of books I love to read that I never otherwise would have found. And it all happened from a stretch: read 1 book from every category in the bookstores in town.
The recipe is simple and you’ll be different because of it. Visit your local bookseller. Pick three books out of three categories you’d never read (for whatever reason). Then read those books. And then repeat it again when you’re done. Do this for one year and you’ll be surprised at what you learn.
But if you want to give in to your mind’s argument that reading takes too long, well, there’s other ways in 2026 to identify a stretch goal. It can be one relevant to your existing projects, too.
What is YOUR stretch goal?
If you have any history with your AI tools, then there’s a great opportunity hidden there. Send this article to your AI tool (or copy and paste the content), and ask “What would be a great stretch goal for me based on our projects and past conversations? Provide a list of resources I’d need and why you think that stretch goal works better than others.”
I’ve done this and received back an incredible contemplation. I won’t provide it here to avoid polluting my own projects with yours. Start a new chat and just paste in the text I have in bold in the prior paragraph.
If you feel it’s a really novel stretch goal and that others might benefit, feel free to share it below in the comments.
The Rocket on the Mountain
The rocket on the mountain has so many stories hidden inside the one image. I’ll provide another here just as a closing thought.
In sport, it’s very common to climb a mountain only to realize that you need to break patterns and skills back down to climb a different mountain. This happens because there is only so much time in the day to build on only so many skills. You’ll build up a certain set and then reach the relative top and realize: “I need to fully re-work myself from the ground-up.” This is not a meta-reflection everyone has or is even willing to entertain.
Where-ever you’re at in life you’re either climbing a mountain or standing at the top. And the top can be a lonely, and somewhat scary place. The spaceship is there, ready to take you to your next adventure and to ascend yet another mountain. You might even contemplate building a bridge between two peaks just as a way to explore the area.
When you reach the summit there’s a hidden danger. Winning feels better than becoming a beginner. That slick spaceship isn’t about just jetting your off to “the next adventure”. It is about abandoning who you are so that you can seek who you might be.
The summit of the mountain is a campsite, not a home.
Connected work
- Core Beliefs: Humans: Read the operating beliefs behind ownership, growth, and high standards.
- Leadership and Scale: See how leadership changes as teams and systems grow.
- Leadership Anti-Patterns: Recognize the habits that keep capable teams stuck.