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Troubleshooting

When to call Tinkso for Claude Cowork help

Honest guidance on when Tinkso adds value to a Claude Cowork rollout and when you can self-serve. Custom connectors, multi-function rollouts, regulated functions, stalled pilots.

Updated 2026-04-25Read 3 min

TL;DR. Most Cowork problems are self-serve. Outside help pays back for custom MCP connectors, multi-function rollouts, regulated functions, stalled pilots, or your first packaged skill. We grade ourselves by whether the client doesn't need us at month four. If they do, we got the handover wrong.

When you do not need outside help#

  • Adopting workspace pattern, CLAUDE.md, and the prompt library.
  • Standing up a single-function pilot with a sponsor and pilot owner already in place.
  • Onboarding 1–10 new operators.
  • Troubleshooting common errors (Section 08 of this bible).
  • Picking the right plan tier.

The bible exists so you can do all of this without us.

When outside help typically pays back#

  • Custom MCP connector. Your function depends on a SaaS without an official connector, and the data flow is complex enough that "we'll just use the file pattern" fails.
  • Multi-function rollout. You're scaling past Wave 1 to three or more functions in parallel and don't have an enablement function yet.
  • Regulated function. Security, audit, or compliance documentation is heavy and your team has not done this before.
  • Stalled pilot. Week 8 has passed and adoption has not taken; outside diagnosis is faster than internal triage.
  • Custom skills. You have a workflow that wants to become a skill but no one in the team has packaged a skill before.

What we will not do#

  • Take over your rollout. We coach the pilot owner; we don't replace them.
  • Sell you Cowork licences. You buy from Anthropic; we charge for implementation.
  • Run a 6-month transformation. Our typical engagement is 4–6 weeks per sprint.

How to brief us in 30 minutes#

A short call covering:

  • Current state — which functions, how many seats, how long live.
  • Pain — what isn't working.
  • Constraints — budget, timeline, regulatory.
  • Success — what would "fixed" look like in six weeks?

We come back within 48 hours with a yes, no, or modified-scope answer.

What an engagement looks like#

Sprint-shaped:

  • Sprint 0 — Observe (1 week)
  • Sprint 1 — Foundation: workspace, governance, first prompts (2 weeks)
  • Sprint 2 — Skills + connectors: the technical build (2 weeks)
  • Sprint 3 — Onboarding + handover (1 week)

Total: 4–6 weeks per function. Not a six-month commitment.

Tinkso's take#

We grade ourselves by whether the client doesn't need us at month four. If they do, we got the handover wrong. The bible is written so the handover is real — every page is something you can do yourself, with us coaching when the situation actually requires outside experience.

Want this delivered, not DIY'd?

Tinkso runs the deeper engagement behind the playbook on this page. Book a 30-minute call.

Last reviewed: 25 April 2026 · The Cowork Bible · Tinkso