The Startup Gut Check: A Quarterly Operating System Audit
By
Culture doesn’t collapse overnight. It drifts, quietly at first, until one day you realize the damage has taken root.
After a merger between two companies I helped build, we thought we had alignment. But without rhythm, without direct connection, and without shared clarity, the cracks widened fast. Trust broke. Communication stalled. People left. And the culture we thought we’d protected began to unravel.
That experience forced me to rethink how I define and maintain culture. It’s not just a vibe or a set of values on a wall. Culture is a system. And like any system, it needs rhythm and attention to stay healthy.
Toxicity crept in and with it came bullying, intimidation, and even lying. Through a handful of seemingly simple decisions, I’d structured our team in a way that allowed for the toxicity to creep in while simultaneously “elevating” myself from the day-to-day.
I had no idea how bad things had gotten. People were too afraid to tell me, let alone ask for help. For those of you who don’t know me, I think I am pretty easy to talk to and try to be genuinely curious (vs defensive) in the face of feedback. But that didn’t matter because the trust had been broken. The damage was done. Unsurprisingly, business performance was also affected. It was a hard time.
But once I finally realized the state of things, we moved fast. Toxic people and practices were immediately removed and we began the process of healing. I spent a lot of time one-on-one with team members to hear their frustrations, fears, and discuss where to go next. We engaged in group coaching with an organization that I cannot say enough positive things about, Crafted Leadership. Bit by bit, we rebuilt trust from the ground up. We each had an active say in what our culture would and has become.
That experience forced me to see culture differently. It wasn’t just values on a wall; it was our operating system. And like any system, it needed a rhythm to stay healthy. Over time, we began to codify this into something we could return to again and again. Not a one-off fix, but a repeatable rhythm: a quarterly audit.
Here’s how it (currently) works. Work happens in three phases that are designed to flow into whichever existing goal-setting systems you might use (OKRs, KPIs, EOS, etc.). Each phase covers four domains: clarity, energy, support, and the long view. In other words, this audit is one way to put Sustainable Momentum[LINK] into practice, making sure our ambition is matched with stamina and our growth with sustainability.
Phases
- Leadership pre-work: This step is critical. Before a group discussion, the leader(s) must do an internal audit by answering the key questions to each of the four below domains as candidly as possible. Be brutally honest, then decide what to bring to the team.
- Team conversation: A group discussion to walk through the key questions of each of the four domains to gather feedback and ideas. The focus is curiosity, not bravado.
- Upfront agreements: Turn decisions into explicit agreements the whole team opts into.
The Four Domains
CLARITY
Quick caveat: this domain assumes that you have a clear direction, a north star, for the business. If you don’t have that, figure it out first. From there, focus on whether everyone understands their role in reaching the north star and how to measure their progress. This may seem obvious but even with repeated championing of a north star, people often have trouble recalling it, let alone understanding their role in relation to it. Leaders often assume the vision is obvious. This is the moment to check: does everyone actually see it, and their role within it?
Key question:
What is the main goal of our company, and how specifically do I help us achieve it?
ENERGY
Once everyone is clear on how they uniquely impact the business, it’s time to examine where everyone’s energy is going. Are they spinning their wheels on something that could be automated? Do they regularly spend time on tasks they hate? Are there things they think are no longer necessary to do, or new things that should be done? The goal here is to eliminate the noise and things that drag you down. It’s the only way to avoid burnout. And it’s the only way to create space for creativity, joy, and learning. This is the fuel that keeps your team moving toward the north star.
Key question:
What do I do at work that energizes me and what do I do at work that drains my energy?
SUPPORT
Next up is to take a hard look at your specific systems. Do your systems reinforce your team? Does your team add value to your systems? Or is the team white-knuckling to keep broken systems alive? Systems here can look a lot of different ways. From your CRM dashboard to how meetings are scheduled to how the team makes requests of one another. A healthy support setup is multi-directional and is clearly modeled by the leaders. It also requires sufficient trust and candor to acknowledge when help is needed and to gracefully receive feedback and help. I see this play out in the leader–EA relationship all the time. When that partnership is strong, it’s a microcosm of what great support looks like: clear systems, trust, and the freedom to focus on what matters most.
Key question:
How can I contribute to the support structures of our company, both in the giving and receiving of it?
CONTINUITY
This is a time to pause and confirm your quarterly goals are continuing to point towards your north star. Quarters fly by, and quarterly goals are by definition short-term. Ensuring you have continuity across time will help everyone to feel more aligned and as a critical piece of the building momentum. When you find misalignment (and you will), this domain provides a clear platform to match up your short-term with the long-term.
Key question:
Did last quarters’ goals and our newly discovered ideas align with our north star?
Following the group discussion, you’ll have more great ideas and solutions in mind than you have time for. But you’ll also have greater clarity and alignment to bring with you into your quarterly goal-setting process. Plenty of people have built complex goal-setting systems, many of which are great. I don’t want to recreate the wheel, but my hope is that the above process acts as the alignment primer. It clears roadblocks and feeds the right energy into whatever system you use. With the cognitive congestion cleared, goal setting becomes practical instead of just theoretical.
Sustainable momentum is possible. Growth that fuels itself without burning people out. It requires marrying your ambition to intentional structures, within your teams and your life.
This rhythm isn’t just for me. It’s for the team. The point is not to check a box. It’s to stay close enough to hear what’s going unsaid and align before it’s too late.
I share all of this not because I have it perfectly figured out (far from it) but because I believe leadership practices should be collective experiments. This audit is one such experiment, a way to reject the false choice between ambition and rest. It’s a way to build a system where both can coexist. Closer to the kind of momentum that doesn’t just build, it endures.
Next week, I’ll share what it’s like to move from building systems in theory to actually living them inside a company.
How would you answer the key questions above?
And who else would you discuss this with?
