Last week, I presented on a panel at True Blue Blazing. The subject was Lessons Learnt from the worst projects ever.
Many people told us that they would have loved to know more so here is a quick checklist of what to do if you want your next project to succeed.
1. Don’t do it on the cheap
- Trying to save money by using volunteers, interns, or in-house staff who’ve never touched Salesforce before is the fastest way to triple your costs later.
- DIY might work for flat-pack furniture, but not for enterprise technology.
If you think hiring an expert is expensive, try hiring an amateur.
2. Don’t put all your eggs in one basket
- The classic “Train the Trainer” trap: one super-user attends training because “everyone’s busy,” and then they leave. Suddenly, no one knows how the system works, and all the process knowledge walks out the door.
Spread training across all users. Document everything. Set yourself up for success.
3. Measure seven times, cut once
- Discovery isn’t a luxury — it’s insurance.
- Spend time in the problem - don’t jump right into solutions
- Projects that skip proper discovery and stakeholder engagement end up rebuilding halfway through.
Invest the time upfront. It’s cheaper than rework later.
4. Clear ownership
- When everyone thinks someone else owns it, no one really does.
- Projects without a captain drift — decisions stall, priorities conflict, and accountability disappears.
Assign clear ownership and decision-making authority from day one.
5. Executive Buy-In
- If leaders aren’t visibly aligned, teams won’t be either.
- Mixed messages from leadership create confusion and kill adoption.
When executives sing from the same hymn sheet, everyone else learns the tune.
6. Check Credentials
- Choosing a partner or consultant based purely on price is a false economy.
- Choosing the right implementation partner or consultant is one of the biggest success factors in any digital transformation project.
- Price does matter, but value, experience, and fit matter far more.
Check credentials, reference check as you would an employee, and make sure they have current happy customers who can vouch for them.
The Moral of the Story
Every failed project leaves clues. If you don’t learn from them, you’re destined to repeat them.
Because projects don’t fail — people let them.
