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Selecting the Right Training Strategy for Customer Success Management

Nine questions a CS leader should answer before buying or building training, from desired outcomes and gap analysis to ROI and implementation.

PDF, 16 pagesFor: Team leaders2026 edition
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Summary

The short version

TLDRNine questions a Customer Success leader should answer, in order, before buying or building CSM training. Each question lists inputs, activities, outputs and hints.

First published 2021. Second edition 2026.

What's inside

9 topics in 16 pages

  • Q1 What do you need to achieve?
  • Q2 Where are you now?
  • Q3 What are your gaps?
  • Q4 What capabilities are required? (with a capability explainer)
  • Q5 How will you fulfil these capabilities?
  • Q6 What are your practical challenges?
  • Q7 How do you gain the authority to proceed?
  • Q8 How will you measure impact and ROI?
  • Q9 How will you manage the strategy?
Key takeaways

5 ideas you can use this week

1

Start with outcomes, not courses

Define each outcome by quality (what it is), quantity (how much) and deadline (by when), then rank them before you look at any training.

2

A gap is to-be minus as-is

Document where the team is now by group, compare it with the target, and rate each gap 1 to 5 or 1 to 10 so you fix the important ones first.

3

Not every gap needs training

A capability is process, people and tools. Some gaps need a new process or tool instead; record those separately.

4

Write a business case they will read

Executive summary, purpose, outcomes, expenditure, roadmap and appendices. Keep it on cost, time and ROI; put detail in the appendix.

5

Decide how you will measure first

Pick KPIs before you start: participation, progress, certification outcomes and changes in performance. Measure ROI where a financial link is meaningful.

FAQ

Questions

CS leaders planning training for a team, before they talk to any training provider.

It is 16 pages. Working through the nine questions with your team usually takes several short sessions; the guide suggests doing a little at a time.

No. It is vendor-neutral. It helps you decide what you need and how to measure it.

Product, Industry, Customer Success and Personal Qualities. The guide lists example capabilities for each.

Customer Success Week, until 18 October

CCSMP Full, all 5 levels, $487

Levels 1 to 4 plus Level 5 CPD. The offer ends Oct 18 at 23:59 Dublin time.