Questions Worth Sitting With in 2026
Reflections from a rollercoaster year working alongside early-stage founders.
by Micaela Kamp
In moments of uncertainty, I’ve learned not to rush toward answers.
My instinct is to ask deeper questions about the situation in front of me - not as an academic exercise, but as a way of making sense of complexity when answers are incomplete.
2025 was a year of uncertainty.
Markets shifted. Behaviors changed. Teams felt the weight of doing more with less. From my seat, the founders who navigated the year most thoughtfully weren’t the ones with the cleanest plans. They were the ones asking better questions.
Questions don’t slow progress; they determine direction. As we step into 2026, these are some questions I am carrying with me as the year unfolds.
1. What hasn’t evolved at the same pace as the rest of the company?
Founders know their company won’t stay static. The vision evolves. The market responds. The business grows up.
What’s less obvious is that not everything evolves at the same speed.
As customers mature, sales cycles lengthen, and stakes increase, the work changes. It moves from proving something works to figuring out how to make it durable. From momentum to maintenance. From speed to structure. But those shifts don’t happen evenly across the company.
Some parts grow up quickly. Others lag behind, still operating on assumptions, systems, or expectations that made sense earlier. These imbalances aren’t a failure of leadership. They’re a natural byproduct of growth.
The friction founders feel at this stage rarely means something is broken. More often, it’s the tension created when parts of the business are still optimized for an earlier version of the company, while others have already moved on.
The work here isn’t to “fix everything.” It’s to notice where the pace of evolution has been uneven and to decide, intentionally, what needs to catch up next.
Carry this into 2026: Make note of the parts of your company that have evolved the fastest and what hasn’t kept up. The gap between those two is often where your next set of leadership and systems decisions belong.
2. Where does the business still rely on me instead of a system?
Most of the founders I work with understand that they can’t be the critical infrastructure of the business forever. They know that building something durable means eventually removing themselves from the middle and replacing effort with systems.
What’s harder is when and how to do that in real time, especially inside resource-constrained, fast-moving companies.
As growth accelerates, founders often step in out of necessity, not ego. Decisions need to be made. Momentum needs to be protected. And when time or headcount is tight, being the system can feel like the most responsible option in the moment.
And that tradeoff makes sense… for a while.
Over time, the cost creeps up quietly. Decisions bottleneck. Progress slows. The founder becomes the place everything routes through (again), carrying more than the system was ever designed to hold.
Carry this into 2026: Pay attention to what breaks, stalls, or escalates when you step away. Those moments aren’t failures. They're signals pointing to where the next system needs to be built.
3. Where do we need alignment more than acceleration?
When founders told me they wanted momentum last year, it was often after a long stretch of reacting. Momentum wasn’t about moving faster. It was about finding footing again.
What they wanted was relief: from too many competing priorities, from shifting definitions of success, from the feeling that everything required urgent attention.
The breakthrough didn’t come as acceleration. It came as alignment. Fewer goals. Clearer ownership. Decisions that didn’t need to be rehashed every week.
Carry this into 2026: Ask where alignment would do more for you than speed. Because clarity doesn’t slow growth. It gives it something solid to stand on.
4. What metrics am I optimizing for NOW?
Most of the founders I worked with in 2025 were thoughtful about metrics. They tracked performance closely and understood that numbers shape behavior.
What got harder as their companies grew wasn’t choosing the right metrics. It was keeping them current as the business changed.
Hierarchies shift. What mattered most at one stage can quietly lose relevance at the next. New constraints appear. Tradeoffs change.
Without an intentional moment to step back, metrics have a way of drifting out of sync with what actually matters. It isn’t because anyone isn’t paying attention, but because the company is moving faster than the measurement framework keeping up with it.
When founders paused to explicitly reevaluate what they were optimizing for, the tension made more sense. Tradeoffs felt more intentional: whether that meant prioritizing margin over top-line growth, stability over speed, or focus over expansion.
Carry this into 2026: Make space to revisit your metric hierarchy. Be clear about what “winning” means at this stage of the company, and let your dashboards, goals, and conversations reflect that reality. When metrics are aligned with where the business actually is, everything else tends to feel steadier.
5. What am I protecting because it’s familiar, not because it’s working well?
This question came up at almost every inflection point I saw this year.
Founders weren’t holding onto things that were obviously broken. They were holding onto things that once worked but had begun to falter.
They weren’t ignoring problems. They were protecting past wins. What made these moments hard wasn’t a lack of data or intelligence. It was attachment.
Letting go felt risky. Strategically and emotionally. These choices were familiar; tied to earlier wins or early identity. Familiarity can give false comfort, especially when the alternative means stepping into uncertainty without a clear replacement yet.
What I kept seeing was this: clarity comes after something is let go, not before.
Carry this into 2026: pay attention to what feels heavy, over-defended, or harder to justify than it used to be. That tension is often the signal that the company is ready to evolve, even if you don’t yet know exactly what comes next.
Carry Questions, Not Just Answers
The year ahead doesn’t require perfect plans or final answers.
It requires a way of navigating complexity without rushing to simplify it.
What matters most is staying in conversation with the questions that shape how you decide, where you focus, and what you’re willing to reconsider as conditions change.
These questions aren’t meant to be resolved all at once. They’re meant to be returned to; as your company evolves, as new information emerges, and as the year unfolds. Over time, they have a way of clarifying what matters next.
———
More About RevUp Capital
RevUp Capital invests in B2B and B2C companies that are revenue-driven and ready to double down on growth. We deploy cash and capacity to help companies grow from $1-3M to $10-30M, quickly and efficiently, using a revenue-based model. Companies enter our portfolio with $500K-$3M in revenue, a strong growth rate, and a team that’s ready to scale. Our typical investment range is $300K-$500K.
More at www.revupfund.com
How We Invest
We built RevUp to invest into B2B and B2C companies ascending the $1M-$10M growth curve. We know from experience—and from the stellar performance of our portfolio—that this curve can be conquered. But, having the right resources and support along the way is critical to success.
RevUp combines non-dilutive investment with hands-on support to help companies build stronger, more scalable infrastructure for growth. And, we do it using a non-dilutive model. Our goal? Give companies the best shot at success while preserving founder equity, optionality, and autonomy.
For more info visit here.
About the Author
RevUp Capital Director of Platform Micaela Kamp is an accomplished growth marketer and content architect with 10+ years of experience helping early stage companies share their stories. Over the years, she has used her ability to question everything and a belief in storytelling to build strong foundations for scalable growth for founders.