Here’s a question - do you consider important milestones within your customer’s business calendar when planning onboarding?
Often when a big customer signs there is pressure to launch quickly.
But here are some things you don't know…
Their finance team starts year-end closing in three weeks.
Their IT team has a major infrastructure upgrade next month.
And their annual sales kickoff is in 90 days.
We meticulously plan our onboarding steps but often overlook the natural rhythm of our customers' businesses. This can have a huge impact on their success with your solution.
This misalignment leads to delayed implementations, reduced stakeholder engagement, and compromised user adoption.
But it’s not all doom and gloom!
There is an easy way to address this potential pitfall.
It takes some proactive work before onboarding starts and will make your onboarding experience even more effective.
So block out some time in your own calendar to implement this ASAP. ↓
🧪 The Project: Business Calendar Alignment
This project should be effective for any size of customer from enterprise to startup.
The more you know about the customer’s business, the better you can arm yourself to create valuable and timely experiences.
Step 1: Map the customer calendar
Develop a simple questionnaire for your kickoff meetings that captures key business timing factors:
When does their fiscal year start/end?
What are their busiest periods (e.g., month-end, quarter-end)?
When are their major internal events (annual planning, sales kickoffs, team retreats)?
What industry-specific events affect their availability (tax season, retail holidays, important conferences)?
When do they conduct internal audits or compliance reviews?
This can be part of your process for post deal close and pre kick off call.
This will allow you to begin the kick off call highly informed about their business with a solid plan for their onboarding.
They will be impressed that you even thought about it.
Then when you execute an effective plan based on these details they will be blown away!
Step 2: Analyse the onboarding phases
Once you have the relevant information regarding their business milestones, create a simple table that highlights the phases of your onboarding program and the best and worst time periods for each phase.
Example of how this can look:
Phase | Avoid Periods | Optimal Periods |
Kick Off | Quarter/year-end closing | Early in fiscal quarter |
Product Training | Month-end processes | Mid-month |
Integrations | IT freeze periods | Start of quarter |
Data Migration | Financial closing periods | Fresh fiscal periods |
Get more specific when you create this by adding in dates and additional timeframes for complete clarity.
This is for your internal use, but if you feel like it would benefit the customer to see how you are thinking about their success during onboarding, feel free to show them!
Step 3: Think about flexible timelines
Start with your standard timeline for onboarding. This will be the basis for all of your processes.
The aim is to be able to shift onboarding phases based on specific customer calendars without disrupting your processes too much.
Could you delay the kick off call to avoid conflicting with a big industry event they are attending?
If so, what other information or setup can you do with, or for them, to show the momentum of onboarding?
Examples: collate assets in a repository, set up their account with all the relevant users, create personalised videos to introduce users to the new solution, create templates relevant to their business and goals.
The options are endless - get creative!
🔍 NOTE: Be cautious of extending onboarding too far into the future.
You don’t have to avoid all customer milestones that can cause problems.
But being aware helps you better navigate them as and when they arise.
Step 4: Create a handover framework
Create a detailed handover regarding customer business milestones for whomever takes over beyond onboarding. This is a vital exchange of information.
Examples:
Check-in schedule - executives want these ahead of quarterly business reviews.
Stakeholder communication plan - monthly adoption metrics, bi-weekly usage stats delivered in an easy to digest format.
Key milestone tracking - plan expansion discussions around customer budget cycles, quarterly business reviews to align with planning periods.
Share the information you collated in Step 2 and be specific on dates or timeframes as well as actual key events.
You want to make sure that the customer continues their world-class experience beyond onboarding.
You achieve that through effective and detailed communication between internal teams.
🤓 The Analysis
This project is about finding effective ways to leverage your customer's natural business rhythm to drive success during onboarding.
You have an opportunity to transform onboarding from disrupted experiences that are out of your sight to strategic plays by having a deeper understanding of how their business calendar looks.
The most successful onboardings are not rigid.
They have a proven foundation for the experience but can ebb and flow with the customer’s needs in order to reach the most successful outcome.
What you'll achieve with this project:
Reduced onboarding delays
More predictable project timelines
Longer term bought in customers
Increased user adoption by launching at optimal times
