The high cost of vague onboarding

I once hired a developer who had recently failed her probationary period at a well-known firm. On paper, she was exceptional; in person, she was sharp, driven, and clearly capable. I asked her what went wrong.

She told me that despite accepting the offer two and a half months before her start date, she “arrived” on day one (it was a remote role) to find she had no logins. She spent three days emailing people from her personal Gmail, only to be told her credentials were “in the queue”. When she finally got in, she was told to pick the top ticket from the backlog. No context, no introduction to the codebase, and no sense of who the user was. After days of sleuthing, she found the user, fixed the bug, and shipped the code, only for the user to tell her: “Oh, I don’t use that feature anymore.”

Her heart sank; her productivity followed. She didn’t fail that company, their lack of intentionality failed her.

The Myth of the “Coffee Chat” Plan

Many organisations mistake a calendar full of “introductory chats” for an onboarding plan. They pat themselves on the back for being welcoming while the new hire sits around feeling like a spare part. Effective onboarding isn’t about socialising, it’s about momentum.

To get a senior engineer or a new lead productive in weeks rather than months, you must be deliberate.

1. The Logistics of Respect If a new hire doesn’t have their hardware, their Slack access, and their IDE permissions on day one, you are telling them their time isn’t valuable. It is a basic hygiene factor. It makes them feel welcome and, more importantly, important.

2. The Living Task List Whether you use Jira, Trello, or a shared Apple Note, have a template ready with the onboarding process on there for the new hire. This serves two purposes: it gives them something to do immediately, and it introduces them to how your team actually manages work. On that list, include specific people they need to reach out to. Don’t introduce them; let them introduce themselves, but do give them a clue as to why that person matters to them. It builds agency from the first hour.

3. Modern Tooling and AI Exploration We shouldn’t be wasting days teaching people where the files are. Ideally your environment setup should be automated, but in the real world it’s often not. But for this first step they don’t even need to be able to build or run the code. Tech debt isn’t always bad, it’s part of a CTO’s strategic toolbox and I would say that having a great build/deploy/process is much higher up the costly tech debt ladder, because you release a lot more often than you onboard. But with modern tooling, containerisation and the rest, there isn’t much excuse for not automating environment setup too.

What this step is about is building some comfort. I encourage new hires to use an LLM - it really doesn’t matter much which one, all the good ones are great — to map the codebase. Let them use the AI to interrogate the logic and ask questions. But once they’ve got a reasonable big picture, keep it contained. Give them a specific area of the system to focus on within the first two hours to prevent them from drowning in the deep end.

4. Ship to Production on Day One Have them code something real. It can be a minor UI tweak or a logic fix of no great consequence, but it must be real. Getting code into production on the first day sets the tone for the entire tenure. It proves the plumbing works and gives them an immediate “win”. And if it was a user-facing fix, have them call up a user and tell them about it. Build relationships, confidence and self-value.

5. Breadth through Purposeful Problems Once that first win is in, repeat the process with at least two other unconnected parts of the system. This exposes them to different parts of the codebase, different Product Managers, and different sets of users.

Crucially, never say, “Go have a chat with X.” Instead, say: “Talk to X about their problem with the billing exports and come up with two ideas on how we might resolve it.” This turns a generic coffee meeting into a problem-solving session. It ingratiates the new hire to the stakeholder because they are immediately seen as a source of help, not just another face on Zoom.

After four weeks of this deliberate, high-tempo approach, your new hire isn’t just “getting up to speed”; they are already a core part of the engine. They feel valued and they bring value to your business.