A new sales rep can finish the onboarding deck, pass the product quiz and still struggle to run a useful customer conversation. Product knowledge is only one part of becoming effective in the role.
The manager needs a way to see what the rep can do, identify where they need support and give them suitable opportunities to practise. In hospitality and travel-tech, that includes understanding how the customer operates and what a purchase would change for the people doing the work.
Start with the tasks the rep must perform. Build the training and coaching around those tasks.
Define what ready means
Choose a small set of observable skills. A new rep might need to explain the target customer, open a relevant conversation, investigate a problem, demonstrate the right part of the product and agree a next step with the buyer.
Make the standard specific. "Understands discovery" is hard to assess. "Can establish how the customer handles the process today, what is causing difficulty and who needs to be involved in a change" gives a manager something to observe.
Include the ability to recognise a poor fit. A rep who can explain why an opportunity should not progress is learning valuable commercial judgement.
Agree these standards before the start date so the new hire and manager are working towards the same expectations.
Prepare the essentials before day one
Check access to the CRM, calendar, demo environment and approved customer materials. Assign a manageable set of accounts with a clear reason for their selection. Confirm who can answer product, pricing and implementation questions.
Prepare a small library of useful examples: a strong first conversation, a deal that was disqualified and a clear customer handover. Use recordings only where recording and training use are permitted. Anonymised notes can serve the same teaching purpose.
Explain why each example is useful. Asking someone to watch a long list of calls without guidance leaves them to guess which behaviours they should copy.
Teach the customer's working day
Ask the rep to describe the customer workflow before rehearsing the product pitch.
For hotel software, that might mean following a reservation from booking to arrival and understanding who handles changes, guest messages and exceptions. For a tours platform, it might involve availability, booking channels and the handover to operational staff.
The exact workflow depends on your product. The exercise should reveal where the proposed change touches existing systems and people.
Bring an implementation or support colleague into the discussion. Ask what customers find difficult after signing and what information they wish sales collected earlier. Turn those answers into practical discovery questions, while keeping unapproved promises out of the sales conversation.
Give the first month a working rhythm
Use a plan that combines learning, practice and customer exposure. The following is an example, rather than a universal deadline:
- First week: learn the priority customer segment, observe selected conversations and practise the opening and discovery questions.
- Second week: lead parts of live conversations with support, record clear CRM notes and send follow-ups for review.
- Third week: run suitable conversations, demonstrate against a confirmed customer problem and manage agreed next steps.
- Fourth week: review the developing pipeline, identify skill gaps and agree the next coaching priorities.
Adjust the pace to the role and sales cycle. An experienced rep entering a new sector may need more customer context than basic sales training. A first-time seller may need smaller practice steps and closer supervision.
Avoid making access to live work depend on memorising every feature. Choose low-risk opportunities and increase responsibility as the rep demonstrates readiness.
Coach one behaviour at a time
Protect regular manager time in the diary. Use a short review of a real conversation or a focused role-play, followed by a specific practice task.
Ask the rep to assess their own work first. What did they learn about the customer? Where did the conversation become unclear? What would they change?
Then choose one improvement. If the rep moves into a demo too quickly, practise the questions needed to understand the current process before showing the product. Review the next relevant conversation to see whether the change appeared.
Give feedback on something observable. "Be more confident" provides little direction. "Pause after the customer explains the problem and ask how it affects the team" gives the rep an action to try.
Measure progress without hiding the context
Time to first deal is useful, but it needs a clear definition. Record the rep's start date, when they received usable accounts and whether the first win came from an inherited opportunity.
Track leading milestones too: first independently led discovery, first well-qualified opportunity and first complete handover. Review the quality of each milestone rather than counting activity alone.
Compare similar roles, territories and opportunity sources where possible. Keep individual results visible when the team is small; a single unusually quick deal can make an average look more meaningful than it is.
Fix the recurring obstacle
If several new hires struggle at the same point, inspect the process. They may be missing a clear pricing explanation, reliable demo setup or access to the person who answers technical questions.
Keep a simple record of those obstacles and assign an owner to each fix. Update the onboarding material while the learning is fresh.
For your next hire, start with three things: observable readiness standards, a first-month diary with protected coaching time, and a short list of useful customer examples. Then use the rep's actual work to improve the plan. That creates an onboarding process the manager can run, measure and refine.