Seeing a lot of posts here about switching CRMs so I figured I would share what I have learned running migrations across HubSpot, Salesforce and Pipedrive. Most failures are not technical. They are planning gaps. Here is the breakdown.

Where migrations actually go wrong

• Data mapping, not data volume. The problem is rarely "too many records." It is mismatched field types, custom objects with no equivalent in the target system and duplicate or dirty records that get faithfully copied over instead of cleaned.
• Underestimating integration debt. Every Zapier zap, webhook and third-party app connected to your old CRM has to be rebuilt, not just "migrated." Teams find this out mid-project, not during planning.
• No rollback plan. If cutover day goes sideways, you need a way back. Skipping this is the single most common cause of "we migrated but now we are firefighting for two weeks."
• Treating it as an IT project instead of a change management project. The tooling is the easy part. Getting sales and support to actually use the new system with clean habits is the hard part.

Sequence to follow

1. Audit before you map. Inventory every custom field, workflow, and integration in the source system. Flag what is actually used versus legacy clutter. Do not migrate dead weight.
2. Clean at the source. Dedupe and standardize data in the old CRM before export. It is far easier to fix there than after import.
3. Migrate in phases, not all at once. Start with core objects (contacts, deals) in a sandbox, validate, then move workflows and automations, then integrations last.
4. Run parallel for a defined window. Keep both systems live for a set period (one to two weeks typically) so you can catch what broke before fully cutting over.
5. Train on workflows, not features. Do not just show people buttons. Show them how their existing process maps to the new system.

Timeline reality check: for a mid-size team (50-200 users, moderate customization), budget six to twelve weeks. Anyone promising a clean migration in a weekend is either overselling or you have a very simple setup.