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  • Writer's pictureWilliam Buckingham

How to Structure Effective System Trainings

Why systems/process trainings rarely work, and how to make these better.

When it comes to training new CSMs, there’s essentially two types of training: functional and system.

Functional training: covers how to perform the core functions of the role. How to pitch, present, and follow up on customer business reviews is a great example. These trainings look at how to execute the customer-facing functions of the role. Often these focus on soft skills.

System training: covers how to use all the different systems and processes to meet the requirements of the business. These trainings teach how to translate the functional actions CSMs have taken into meaningful data and insights for the business.

Essentially, functional training covers how to do your customer-facing role, and system trainings teach how to show the business you indeed did your customer facing duties.

The issue is…. System trainings rarely seem to work.

Several times I’ve heard CS Enablement professionals state something along the lines of:

“We have some incredibly thorough courses on XYZ Software, but unlike our other courses, it just doesn’t click. We still have CSMs months later missing the basics of these key platforms and essentially not using them. How can I make these trainings stick?"

This is a meaningful issue because when CSMs have poor system trainings, the following outcomes are almost inevitable.

  1. Decreased CSM morale and retention. CSMs want to feel supported by their team members and their tools. When the system which are meant to serve them leave them frustrated and investing too much time on administrative tasks, morale suffers and CSMs might even wonder if it would be easier elsewhere.

  2. Bad data hamstrings leadership. The actions CSMs take in systems becomes the data leadership uses to coach performance, forecast the business, and drive product strategy. When CSMs inconsistently enter data into these systems, leadership either puts their trust in bad data or does not make data-driven decisions due to a lack of trust in that data. Either way, the optimal decision isn’t being made.

  3. Low ROI on expensive systems and processes. Enterprise software isn’t cheap. When a business decides to purchase a tool, it needs to achieve a return on that expense. For CS tools, this can only be achieved by the CSMs using these as intended. When this doesn’t happen, we see expensive tools which don’t deliver the insights or impact which were intended.


So, we know the core problem is that system trainings often don’t work, or at least don’t work well.

But why is that? Why are these trainings so ineffective?

It helps to reflect on a CSM’s experience with systems.

CSMs use several internal-facing software systems to execute their day-to-day responsibilities. Let’s look at the different types of software systems CSMs typically use, and a few examples of each.

  1. Customer Relationship Management(CRM) software (SalesForce, HubSpot, etc.)

  2. Customer Success software (Gainsight, Churn Zero, Vitally, etc.)

  3. Customer Support Case/Ticketing software (Service Cloud, Zen Desk, etc.)

  4. Contract Software (DocuSign, Conga, etc.)

  5. Bug and Feature Request tracking systems (Jira, Product Plan, Aha, etc.)

  6. Implementation/Project Management Software, often for onboarding and services engagements (Baton, Monday, Trello, OpenAir, etc.)

  7. Sometimes there’s even separate software for surveying customers (AskNicely, ‘Nuffsaid, etc.)

  8. Commission/Bonus Tracking (Xactly Incent, etc.)

  9. Billing/Accounts Receivable systems (let’s hope they aren’t spending much time here)

  10. Expense Reporting (Concur, Expensify, etc.)

That’s 10 right there. Of that 10, I say 5 are absolutely industry standard upon hitting a certain maturity level. Having a software solution for CRM, customer success, customer support cases, bug/feature tracking, and project management really become table stakes at a certain point.

It takes a lot to learn and become proficient in five software applications. Especially when you know there’s another five or so that are less impactful to your role but also must be learned.

All these systems must be used effectively by the CSMs… but learning 5-10 different software systems seems a bit daunting and certainly boring. Sitting through a 2-hour SalesForce or Gainsight training sounds mind-numbing. If we want CSMs to effectively learn, retain, and apply what is taught, we must do better than “boring” and “mind-numbing”.

System trainings are often plagued by three primary issues.

First, these trainings usually lack the context needed to ensure CSMS understand the importance of these systems and processes. The lack of this meaning and importance reduces the level of engagement when learning these systems. Less engagement leads to lower retention and application of what was covered (but not actually learned).

Second, system trainings are typically too long. If you think of your CRM or customer success software, how long would the training need to be to cover everything a CSM needs to be able to do in each of these? That’s a long training. I deeply appreciate SalesForce, but place me in a 2-hour training about it, and you better provide caffeine and snacks.

Third is the fact that system trainings are often one-and-done trainings. These are structured as a singular training session or course. The problem comes in the form of the Ebbinghaus’s Forgetting Curve. In short, it explains that people forget what they learn over time, with the bulk of forgetting happening immediately after the learning occurred. We take a system training, move onto the rest of our onboarding, and then hope we recall all of it when we use the system later.

Bad news is we rarely remember.


So let’s take a look at an example.

The following is a high-level overview of a few new hire trainings. By no means does this cover the full list of what a CSM must learn. The extent of which is too long for this article and would dilute the point being made.

Typical, separated curriculum:

Managing Customers:

  • Completing Customer Onboarding

  • How to Run check in Meetings

  • Conducting Quarterly Business Reviews(QBRs)

  • Leveraging Support Cases

  • Handling Product Escalations

System Trainings:

  • SalesForce

    • Finding newly sold accounts

    • How to track onboarding completion

  • Gainsight

    • Exporting usage data for check in meetings

    • Recording check in meetings

    • Setting up recurring QBR triggers

  • SalesForce Service Cloud

    • Viewing and reporting on support cases

    • Editing Support tickets.

  • Jira

    • Viewing and Reporting customer bugs and feature requests

    • Escalating bugs and requests.

What are your thoughts?

I’ll share with you mine.

This feels like too much system training. Even though I know the Managing Customers Training is likely more detailed and harder to master than the System Training, I’m still not stoked to see so much system training for administrative work. I’m a CSM, I want to get in front of customers – not learn and use systems.

Additionally, you can see how this example embodies some of the core issues we want to avoid.

The system trainings happen after, and unrelated to the functional training the CSM is receiving. This reduces the CSM’s understanding of the importance of these systems.

Additionally, with these trainings separated from the functional training, we must restate the actual context of why and when we use these systems and processes. This can add significant time to a training, which can negatively detract from the learning experience.

While we can’t see the duration of these trainings, I can see there’s many software systems to learn – probably a long time spent covering these. The length of these is going to crush my engagement and retention as a new CSM already taking in so much new information.

Lastly, you learn each system and then you move on to the next. One and done. The forgetting curve will come in hot on all these.

We can see that this structure is wrought with many of the characteristics which learning and development(L&D) research has proven detracts from effective, long-term learning.


So, what's the solution?

How can we do better as enablement professionals?

The first guiding principal is: Don’t make it about the system.

The second is: Make it about the CSM’s function and goals at the company.

Essentially, whenever possible, don’t separate functional and system trainings.

The key is to incorporate system trainings into your functional CSM trainings as much as possible.

Creating a course on how to retain customers? Add to the curriculum: updating health score, renewals, and risk in the customer success software.

Creating a course on how to manage customer escalations? Add to the curriculum: creating and finding product bugs, set up alerts for unresolved tickets and increased ticket volume.

It’s a simple solution – make system training part of functional trainings so it shares in the perceived importance and relevance of functional training.

Let’s look at how we would do this for our previous example. Below is how I would restructure that content. Note, the [bracketed] text is there for you, the reader. It shows where those system trainings reside, yet we keep the structure and messaging focused on the actual functions and goals of the CSM.

Managing Customers

  • Completing Customer Onboarding

    • Know when a new customer is coming [SalesForce]

    • Drive smooth, efficient onboarding

    • Always know the status of onboarding efforts [Baton]

  • How to Run check in Meetings

    • Leverage customer usage data [Gainsight]

    • How to conduct and what to cover in check ins.

    • Communicating with the Account Team [Gainsight- Timeline and CTAs]

  • Conducting Quarterly Business Reviews (QBRs)

    • Save time automating QBR triggers [Gainsight – Recurring CTAs]

    • How to prepare with the Account Team [Functional + Gainsight C360]

    • Present data which matters to the customer [Gainsight, Service Cloud, Jira]

    • Delivering the QBRs – Best Practices

    • Following up on and driving action items [Gainsight – Email Assist]

    • Executing action items internally [Gainsight, Monday, and Jira!]

  • Influencing Support Cases

    • Know when a case is escalated or not getting resolved [Service Cloud]

    • Know when support cases are linked to a bug or feature request [Service Cloud and Jira]

  • Handling Product Escalations

    • Know when bugs are causing increased support cases [Service Cloud and Jira]

    • Improve customer sentiment by knowing when bugs and feature requests are resolved and delivered on [Jira]

This structure attaches system trainings to meaningful CSM responsibilities. It also breaks up system training to be dispersed throughout the functional training. In the same regard, it actively combats the Forgetting Curve by providing multiple opportunities to cover same systems and features.

Note: You won’t be able to cover all aspects of a system training by spreading it through your functional trainings. For some systems, you’ll have to have a separated training. That’s okay. The goal isn’t to eliminate system-specific training, it’s to improve system training when possible.

If you’re feeling doubtful, I’ve included steps to implement this strategy.



Improved Performance and CSM Morale

The primary benefit is CSMs executing more consistently and performing better. Remember, the whole point of onboarding is for CSMs to know what the best practices are, how to effectively execute these, and when to do so. That’s performance.

When CSMs have more meaningful context for what they are learning and get to learn with strategic repetition, they are much more likely to remember why, when, and how to perform certain tasks. Additionally, when CSMs use systems effectively they gain in return meaningful data which they can use to further refine their performance. Confidently using these systems and gaining meaningful data from these reduces CSM frustration as they navigate their challenging, dynamic role.

Greater ROI on Systems

Software solutions aren’t cheap. (Did I already say that? Well, it’s worth saying it twice!)

To obtain a positive ROI, users must use the software. If the solution saves time, it only saves time if/when the CSM uses it. If it increases expansion rates 10%, it only increases this when CSMs use it. If it prevents churn by 1%, you guessed it, it only reduces churn when CSMs use it. The classic example of this is CRMs selling how much time will be saved forecasting, and then half your sales managers use spreadsheets to forecast – asking each rep to update deals row by row.

Driving greater, more consistent adoption of these systems pursues the desired outcomes and ROI which you targeted when you purchased the solution. This gets us to our next point.

Better Decisions

Decisions are rarely better than your data. The actions CSMs take in the many software systems they use become the critical datapoints for CSMs, CS leaders, Product, Sales, Support, Marketing, and others.

Data created by CSMs inform everything from Net Revenue Retention(NRR) to which customer types perceive the greatest value and which product bugs have the greatest impact.

If you need this data readily and accurately at the fingertips of your leaders, you need CSMs using your systems effectively.


Tips to implement:

  1. Get the learner's perspective. As with all enablement, get perspective from the learner audience. What matters to them? Focus on those matters and train on systems in this context.

  2. Incorporate these bit by bit. Don’t just decide that as of tomorrow all system trainings are moving to be components of your functional trainings. That’s not realistic and won’t work. You should… à

  3. Start with Fundamentals, and therefore your core CSM functions and systems. A great starting point is customer check in meetings. How can you transfer (or reinforce) some of your system trainings into your customer check in training? Next, try it with QBRs.

  4. Give a precursor to which systems will be reviewed. Don’t just randomly change subjects to a software program after discussing the soft skills of a CSM responsibility. When you start the session or course preface which software tools will be used and covered. For example “In this course you will learn how to deliver effective check in meetings to customers. We’ll review how to prepare for, deliver, and follow up on these important meetings. We’ll review a few critical tools and processes for completing check ins, such as Service Cloud reports, Jira queries, and Gainsight Timeline and CTAs.” Now the CSM knows these are coming, and why.

  5. Sandwich courses between live sessions. I find it most effective to give a high-level introduction and walkthrough of key software systems, let the CSM learn deeper specifics during the system portions of functional trainings, and then follow this up with a live session to re-review what was learned and how they are using the intended system. Again, this helps prime the context and combat the Forgetting Curve.

  6. When planning your curriculum, list functional and system trainings separately, then map the system trainings to functional trainings. The focus is functional trainings with system trainings incorporated. Its much easier to look at what must be learned for a function, and then slot in aspects of system training. Again, you’ll find you can reiterate some of the key system knowledge in a few different sections and



Effectively enabling CSMs is no easy task.

There is so much to learn – skills, processes, systems, etc.

When CSMs use the software tools as intended we see improved CSM performance, better decisions, and greater ROI on operational investments. We achieve this by leveraging the context and perceived importance of functional trainings to introduce and/or reinforce system trainings.

You'll still have separate system trainings - this is likely inevitable. The goal is to make system trainings more effective by relocating and incorporating more of these into functional trainings when possible.

It takes more creativity and planning when creating your enablement content, but the impact on long-term learning, retention, and application is well worth it.

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