I hope you had a happy holiday and end of 2025. I had a great year and am looking forward to an even better one in 2026. At this time last year I was preparing to leave Atlassian. This year I'm hard at work building a business, and really enjoying my freedom. My stress is lower and my happiness is higher.
I hope your 2026 is blessed with hard problems to solve that encourage you to grow 😁
"So remember this principle when something threatens to cause you pain: the thing itself was no misfortune at all; to endure it and prevail is great good fortune." -Marcus Aurelius in "Meditations"
One of the things I did over my time off for New Years is work on the service architecture for my business. I have a new contractor in sales, and it's forcing me (in a good way) to clarify what I do and why so that they can communicate this with the market.
I'm not done chewing on this, but I like where this is going. I'm going to share the draft visual I created with you so you can see what it looks like for now:
One thing that shook out of this exercise is that there's no Fractional COO offering. Part of that is because a Fractional COO is an undifferentiated offering. There are thousands of Fractional COOs out there. It also doesn't speak to an outcome, and I like driving towards outcomes.
Another thing I'm doing is designing an architecture that protects my time. I don't have this represented on the visual, but I will personally spend most of my time in the "Alignment" pillar that's higher leverage for me and requires my unique skill set. The other pillars will be delivered by my team, with governance and design involvement from me - not execution.
The thing I like most is how the pillars connect to each other. I drew this sort of like a hypothetical customer journey. A customer may buy something from the Entry pillar, like a financial model, which reveals a tension or uncertainty, which drives them to want help with Strategic Decision Work.
The alignment between strategy, budget, and execution creates conviction, and a desire for management systems (like OKRs and operating rhythms).
Those systems reveal constraints and a customer desire to deliver outcomes. Group 18 will own projects to transform how the business works. Those transformational projects will affect OKRs and the financial model, which requires ongoing Strategic Decision Work. In theory there's ongoing work for us for every client that's scaling.
The next thing I'm going to do is to elaborate on the Core Offers to enable my sales contractor to find and communicate with potential customers. Those customer conversations will re-shape the design of this service architecture. This is Product Market Fit for a services org.; once this gets locked in and resonates with customers - then we scale 😁
Kevin
A Quote
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The person who successfully struggles against weakness...may or may not become rich and famous, but that person will become mature. Maturity is not based on talent or any of the mental or physical gifts that help you ace an IQ test or run fast or move gracefully. It is not comparative. It is earned not by being better than other people at something, but by being better than you used to be. It is earned by being dependable in times of testing, straight in times of temptation.
I received a sweater made from CashSoft fabric from the Gap for Christmas, which was in part inspired by how much a friend of mine raved about his outfit. They’re very sold out, but if you can find something, I think you’ll enjoy it. It’s very good work from home attire.
There’s something extremely satisfying about how these wooden puzzle pieces fit together. And because it’s made of wood, they’ve got high durability, letting you build these over and over again. The downside is the cost; you’re looking at around $115 for a 500 piece puzzle. I have two of these, and I think 2026 is the year I splurge on a 1000 piece one!
I wanted the ability to stand while working or in meetings, but I didn’t want to get a brand new desk given that my existing desks aren’t that old. That meant I needed a riser, but I didn’t want to get a crappy one. I’ve only been using this desk riser from Branch for a week or so, but so far it’s been very sturdy and does exactly what I need it to.
(enjoy this 5️⃣ minute read)
Deep Dive on Intuition
I’m a heavily left-brained analytical person. When there’s a problem, I’m equipped and enjoy analyzing the heck out of it. It brings me satisfaction and joy.
Because being analytical is a natural strength, I was always mystified by intuition. It seemed…weird. Where does it come from? How come some people seem to be born with it, and other people, like me, aren’t?
I also heavily discounted intuition. Why would I trust someone’s “gut” instead of going through a logical reasoning process? That’s irrational
What I’ve come to realize is that thinking of intuition as a mystical, magical, natural force is incorrect. It’s not mystical at all.
It’s your brain recognizing patterns faster than you can explain them.
As you see something more and more over time, your brain no longer needs to consciously process it. It comes subconsciously. That’s intuition: Compressed experience.
If intuition isn’t magic, where does it actually come from?
Intuition's source: exposure plus pattern recognition
Intuition is built.
And it reminds me of the quote, “Do you have 10 years of experience, or one year of experience 10 times?”
The point is that living life and going to work isn’t enough by itself to build intuition to its full capacity.
You need exposure, variation, and feedback - all repeated over time.
That means you can’t be intuitive in a domain where you have no experience. If you start investing after never having done it before and try to do it intuitively, you’ll be in for a rude awakening.
You also can’t be intuitive when hiring your first employee. You haven’t had the reps and the closed loop to have built intuition. You need to hire lots of people, having hundreds of interviews - plus all the calibrations, performance management, and eventually promotions, stagnation, or exits. Then, after having all that experience and reflecting on the closed loop, you’ll begin to become intuitive in hiring.
"YOU are different, but I'm recognizing a potential pattern here."
As intuition is developing, you might start by literally naming the pattern. You’ll promote someone and say, “That was just like when we promoted [so and so],” or you’ll exit someone, and say, “This went down the same way as when we had to fire [so and so].”
Later you might meet someone, or be in a situation, and you’ll start to feel - hey, this pattern is happening again. Only now you’re starting to see it in advance.
This is great! You’re getting smarter and smarter, and your subconscious helps you by bringing the awareness forward without requiring the annoying labor of conscious thought, or needing to go through the full cycle.
But here’s the problem: Cognitive biases feel exactly the same.
The overlap between intuition and cognitive bias
Intuition and cognitive biases operate in the subconscious. Thoughts derived by either method will arrive automatically without conscious effort. Both can give a sense of confidence and may seem obvious.
This is why intuition can get a bad reputation. You may feel like you’re operating on intuition, but it’s really a cognitive bias coming through the same pathway. Your subconscious doesn’t tell you why it produced the answer; it just produces an answer.
Your job is to determine whether that answer came from trained pattern recognition, or a cognitive bias hijacking you.
Confidence is not a good proxy. Your subconscious will produce confidence regardless of source. Feeling “sure” is not evidence of being right.
"I'm 1000% sure I can't lose on this bet!"
To differentiate you’ll need to inspect the intuition. What experience do you have in this domain? Have you seen this pattern play out before? Do you have a closed loop to know how different paths turn out? Would I have this same feeling if some of the details changed?
Intuition isn’t an excuse to stop thinking. It’s just a data source, and one that must be interpreted.
Ignoring it throws away information, but blindly obeying it risks putting bias in the driver’s seat.
So how do you develop intuition?
Developing intuition deliberately
To develop intuition: increase exposure, close the feedback loop, and think in abstractions.
Increase Exposure: You need the reps across a variety of domains and experiences. That lends itself to saying “yes” to opportunities when they come up. Take on the project. Serve on the committee. Do the thing!
Your lived experience is really important, but you can also generate experience second hand. Read books, listen to podcasts, and have conversations with experienced people.
If you know me, you know I recommend books the most as they’re the easiest and highest density source. Biographies, specifically, can be really helpful because they’ll go through the detail of someone else’s lived experience.
Close the Loop: Going back to our interviewing concept, if you interview 1000 people, but don’t actually hire and work with them, then you’re not developing effective intuition. You might see patterns from repeated exposure, but you don’t know how to interpret them as good or bad.
If you have the exposure without the closed loop with feedback your confidence will increase, but your accuracy and effectiveness won’t.
Make sure you see things through to the end. Make sure you’re getting feedback in order to interpret the patterns.
Think in Abstractions: When developing intuition, be careful not to be too literal. Small, inconsequential details don’t break a pattern. If you’re governing a team project and things start to feel off, for example, don’t discount it because the team members are different, or the exact product/service your building is different.
You’re building a pattern library, and patterns are fuzzy. You need to think in a level of abstraction to get above the weeds.
But even trained intuition needs to be handled carefully in real decisions.
Intuition as decision input, not output
Intuition is often thought of as an output - you get a sensation and stop working because you've figured it out.
That's wrong. Instead, intuition should be thought of as an input.
In decisions, intuition will show up first. That’s makes it valuable - and dangerous. Leaders are at risk of stopping the work once their intuition speaks. They consider it the end, when it’s actually the beginning.
Instead of sharing your intuition and shutting down the conversation, treat it as data for your decision process.
Even with intuition, you still need to interrogate your decision. You need to seek disconfirming evidence and invite a challenge.
If you treat intuition as an input, then it informs a hypothesis. It becomes a prompt for investigation and a flag worth examining.
See the difference in these two statements: ❌ “Something feels off, so no.” ✅ “Something feels off, so let’s figure out why.”
Intuition can influence the process without dictating the outcome.
Call to Action
Intuition is a helpful complement to deeper rational thought and analysis. It’s something you earn through a life of experience, reflection, and pattern recognition.
Since intuition can look the same as cognitive bias, the goal isn’t to “trust your gut,” but rather to know when your intuition is trained versus just guessing.
Listen to your intuition this week. Where is it coming up and serving as a warning (or encouraging) signal? Where are you - like me - suppressing it in the name of conscious evaluation?
