The Go-Live Gap, episode 1
Why do go-lives fail after the customer is live?
Lessons from close to 2,000 implementations, with Cheri Hewlett
Cheri Hewlett, AI-native operating leader and CPA; formerly implementation, solution consulting, and customer success
A go-live often gets recorded as a completed implementation when the customer does not see it that way, and the cause usually starts earlier than the project: the information gathered during the sales cycle rarely reaches the implementation team intact. Cheri Hewlett has worked across customer success, solution consulting, implementation, and product over nine years and estimates she has been involved in close to 2,000 customer implementations. She explains why "the value is obvious" is the most damaging assumption a services team inherits, why implementation gets blamed for outcomes it did not control, where AI belongs in implementation work, and the one thing she would change about kickoff.
Chapters
- 00:00 The go-live failure people explain away
- 01:20 Why sales-cycle information does not reach implementation
- 03:00 Cheri's background across the product lifecycle
- 04:28 What tends to be missing from project plans
- 06:08 The root cause of most implementation train wrecks
- 07:16 Early signals that a project is drifting
- 08:39 The most damaging assumption: the value is obvious
- 09:54 When the buyer and the end users want different things
- 13:08 Change management as the missing workstream
- 15:57 What implementation gets blamed for
- 18:28 Advice for early and mid-career implementers
- 20:27 Burnout, layoffs, and working differently with AI
- 22:39 Where AI belongs in implementation
- 26:13 The question leaders are not asking
- 27:25 Technically successful, felt like a failure
- 29:37 The one thing to change about kickoff
- 31:56 What to remove from kickoff
- 33:30 Mindset shifts and what you control
- 37:19 Career paths when upward mobility is limited
- 42:13 Proudest moments and parting advice
Key takeaways
From Cheri Hewlett, AI-native operating leader and CPA; formerly implementation, solution consulting, and customer success.
- Going live and being complete are different things, and the misclassification of a go-live as a finished implementation is the failure most often explained away.
- Most train wrecks share one root cause: assuming you understand the solve, building for hours, and presenting something that ignored a person's workflow, their data, or their ERP.
- The most damaging assumption is that the value is obvious. If the team solves for efficiency and the customer bought control and standardization, both sides can call the project a success right up to the churn.
- Early warning signs: the customer asking a stream of confirmation questions, and you having to over-explain what you are asking for. Both usually mean expectations have drifted.
- Change management is the component most often missing from the plan, and it continues after go-live. A clear, measurable business case from the sales cycle is the anchor that keeps a project engaged.
- Implementation teams get blamed for long projects and for churn even when the deal was over-promised or the business case was not written. Cross-department collaboration is the fix, since a sale that cancels is a loss for sales too.
- AI's best role in implementation is translation: from business value to configuration, and from sales-cycle conversations to the project team, so professional services can spend its time on advisory work and relationships.
- The one change to kickoff: define what you must know before the first call. Why they bought, which competitor or prior system they chose against, who the stakeholders are, and whether their objectives differ.
Questions this episode answers
What information should flow from sales to implementation?
Why the customer bought, what they chose against, the system they are leaving, the stakeholders and whether their objectives differ, and the observations that rarely make it into a project plan: availability, skill level, seasonality, and who was actually in the sales conversations.
How do you handle an economic buyer whose goals differ from the end users'?
Plan for change management from the start, secure executive sponsorship on the customer side, and set a recurring check-in with the sponsor, biweekly or monthly, to realign when the team drifts from the objective.
Where can AI help implementation teams without replacing them?
Cheri's examples are transferring sales-cycle context such as call analysis to the project team, translating a business case into configuration guidance, and taking worksheet inputs into the system, so the human time goes to consulting and relationships.
What advice does Cheri give implementation professionals who feel stuck?
Be curious about the workflow before and after your part of it. Much of a career is in your own control, and her own path was often horizontal before it was vertical. Write down what you enjoy doing and let that decide the direction.
Where Stipulate fits
Cheri's opening point is that what the customer said in the sales cycle rarely reaches the project team intact, and her kickoff fix is a template of what you must know before the first call. Stipulate reads the customer's Slack channel from the first conversation, keeps the commitments and decisions in one place, and carries them through to go-live and beyond, so the project team starts with the context and the lead can see when an engagement goes quiet.
About Cheri Hewlett
AI-native operating leader and CPA; formerly implementation, solution consulting, and customer success