My first 30 days as a fractional CTO: the checklist

The first month sets the tone of any engagement. Move too fast and you recommend things you don't understand yet. Move too slowly and you're an expensive observer. This is the checklist I follow.

#Week 1: listen before touching anything

• Founders and leadership: where the business is going in the next 12 months, and which technical problem keeps them up at night.
• The team, one by one: what slows them down, what they'd fix first, what they're afraid to touch.
• Customers' view: the top support tickets and the complaints sales hears. They tell you where quality really hurts.

Output: a one-page summary of goals, pains and constraints, shared back with everyone I spoke to.

#Week 2: the technical audit

• Architecture: how the main pieces talk to each other, where the data lives, what's a single point of failure.
• Code and delivery: how a change gets from a laptop to production, how long it takes and how often it breaks.
• Cloud and costs: what runs where, who has access and what each part costs.
• Vendors and contracts: what you depend on and how hard it would be to leave.
• Security basics: secrets, backups, access, and whether anyone has ever restored a backup.

I'm not grading the team. Most problems I find are reasonable decisions that outlived their context.

#Week 3: the roadmap

Every finding goes into one of three buckets:

1. Fix now: risks that could hurt the business soon (data loss, security holes, a fragile release process).
2. Build next: the changes that unblock the product roadmap.
3. Leave alone: things that look ugly but aren't worth the time today. Saying this out loud is half the value.

Each item gets an owner, an effort estimate and the business outcome it serves. If I can't link an item to an outcome, it doesn't go on the roadmap.

#Week 4: start executing, together

• Pick one or two quick wins the team can ship in days, to build trust in the plan.
• Agree on the working rhythm: when I'm available, how decisions get made and documented, what gets reviewed.
• Start the first structural item hands-on, alongside the team.

#The goal

From day one the goal is a team that doesn't depend on me. Every decision gets written down, every standard gets automated where possible and every hire raises the bar. If the company still needs me in the same way after a year, I haven't done the job well.