Solo founder check-in
For: Solo founders — running it alone, navigating the loop without a team to mirror them
Running it alone means no one mirrors you. Twelve questions on your work, your direction, your energy, and what you're carrying — for the founder who has to be their own coach, board, and HR.
- 12 questions
- 4 dimensions
- ~4-5 min
- Self · Peer · Both
Solo founders operate with a feedback loop nobody else in business has to hold alone. There's no manager to flag drift, no co-founder to argue with, no team to surface the unsaid; the failure modes are quiet, internal, and almost always invisible to the person living them. This template is the structured pause founders rarely take: an honest read across the four dimensions where things actually fail — the work, the direction, the energy, and what's being carried that hasn't been said. Run on yourself; or, if there's a person in your life who has the visibility (co-founder, spouse, mentor, board member), send it to them too. The cross-view is often where the highest-leverage signal arrives.
How it works
Run it on yourself monthly or quarterly — solo founders rarely get the prompt to actually stop, and the cadence is what makes the difference. If you have a co-founder, spouse, advisor, or anyone with real visibility into how you've been operating, the peer view often catches what the self view can't. Anonymous mode unnecessary — usually you'd want to know who said what.
What's inside — 12 questions across 4 dimensions
The work itself
momentum, learning velocity, validated progress
Direction & decisions
am I on the right path, with the right inputs?
Energy & isolation
sustainability, mental health, the lonely-at-the-top dimension
What I'm carrying
the unsaid stuff, what I haven't told anyone
The questions, in full
Every question is included below. You answer them yourself first, then send the same set to the people who've seen you work.
The work itself
- Q1Rating (1-5)
I'm making validated progress — my work is informed by real evidence from users / customers / market, not by my own theories.
- Q2Rating (1-5)
I'm spending most of my time on the work that actually moves the business — not on activity that feels productive but isn't.
- Q3Open answer
What's the one thing about your business right now where the evidence is strongest — and the one where you're working off conviction without evidence?
Direction & decisions
- Q4Rating (1-5)
The direction I'm pursuing is one I'd choose again today — not one I'm pursuing because it's what I started with.
- Q5Rating (1-5)
I have at least one external input I genuinely listen to — peer founder, advisor, mentor — not just people who agree with me.
- Q6Multiple choice
Looking at my big decisions in the last 90 days, the dominant pattern was...
- — Made them deliberately, with the right inputs
- — Made them deliberately, but I wish I'd had more inputs
- — Made them quickly under pressure
- — Avoided them — they're still hanging
- — Made them but I'm second-guessing now
Energy & isolation
- Q7Rating (1-5)
I'm operating at a sustainable pace — not running on adrenaline that I'll pay back later.
- Q8Rating (1-5)
I have at least one place where I can be honest about how this actually feels — not founder-Twitter / pitch-mode honest, but actually honest.
- Q9Rating (1-5)
The isolation of running this alone is something I've named and am actively managing — not just absorbing.
What I'm carrying
- Q10Rating (1-5)
There's nothing critical to the business that I'm avoiding because facing it would be hard.
- Q11Multiple choice
If I'm honest about what's been on my mind lately, the heaviest thing is...
- — Money — runway, revenue, fundraising
- — The work itself — am I building the right thing?
- — People — co-founder, hires, customers, key relationships
- — Me — energy, identity, why I'm doing this
- — Family / personal — the cost this is asking from outside the business
- Q12Open answer
What's one thing about the business — or about being the founder of it — that you haven't told anyone? What would change if you did?
The research behind these questions
Drawn from Eric Ries' The Lean Startup on validated learning vs vanity activity, Paul Graham's Y Combinator essays on founder time-allocation and conviction, Brad Feld's writing on founder mental health and sustainability (Startup Boards, Do More Faster), Jerry Colonna's Reboot on the interior life of being a founder and the costs of pretending it's fine, Ben Horowitz's The Hard Thing About Hard Things on the moves no one else can make, and Brené Brown's Dare to Lead on the courage to surface what's actually being carried. Each question targets a specific signal solo founders rarely surface to themselves.
References
- — Eric Ries — The Lean Startup
- — Paul Graham — Y Combinator essays
- — Brad Feld — Startup Boards / Do More Faster
- — Jerry Colonna — Reboot
- — Ben Horowitz — The Hard Thing About Hard Things
- — Brené Brown — Dare to Lead
Ready to run this round on yourself?
Sign up, pick this template, answer it about yourself, and send the same questions to the people who've been in the room with you. The gap between your view and theirs is where the actual learning lives.