Run onboarding from context to observed performance. Prepare the work before the new hire arrives, teach the foundation, put the person in front of real customers, and use each check to decide what happens next. Every checklist line should describe something a manager can watch, listen to, or read.1 The checklist then becomes a decision tool: it shows where the new hire can act alone, where another practice round is needed, and whether the plan is missing something.
Checklist at a glance
Use the checklist in work order. Each stage ends with an observable output, which lets you advance, repeat, or add coaching.
| Stage | What you are trying to learn | Example question |
|---|---|---|
| Before start | whether setup is complete | What must be ready before arrival? |
| Role and context | whether the person can explain the role, audience, and reason to care | Who are we trying to reach, and why? |
| Foundation | whether the person can explain the script and workflow | How would you open the conversation? |
| Practice | whether the behavior holds in a scenario | What would you say next? |
| Customer contact | what the customer said and what the person learned | What did you hear that changes your next question? |
| Verification | whether the behavior can be seen in work | Can I watch or listen to the next attempt? |
| Coaching | what needs another pass | What will you change on the next attempt? |
Prepare before the start
Finish the setup before anyone starts. The new hire should spend the first working session learning the role, with access and process ownership clear.
Complete the operational work before the new hire starts. The manager, sales operations team, enablement lead, and hiring partner should finish it before the start date.2 Have the first day ready with introductory and overview meetings with stakeholders, software access, weekly goals, and the other setup tasks the role needs.3
Confirm the role's core economics first.4 Give the person a simple, living sales playbook that can guide the first 30 days.5 Document how the team works together in working manuals.6 Revisit those manuals regularly as roles and work styles change.7 Until the information has a home in an HRIS or intranet, a Google Doc or Notion page is sufficient.8
Teach the foundation
Make the first teaching block useful and keep it close to the conversations the person will soon need to handle.
Start training with scripts.9 Cover market context, product confidence, process clarity, and live coaching so the new hire can create qualified conversations quickly.10 Give the new hire a clear ICP, best practices, playbooks, and templates before asking the person to find potential users.11
Build workshops around the essentials of the job.12 The decks do not need to be complex.13 Record the workshops because some may be reusable for future hires even as the content changes.14 Keep each workshop tied to an action the person must later demonstrate.
Put the new hire in the work
Bring the person into the work while the material is still fresh. Scenarios and live exposure reveal gaps that a completed lesson can hide.
During onboarding, require every sales representative to talk to customers and ask questions.15 Add shadowing of sales representatives' calls and competitor website review.16 Before live work, use skills assessment technology and selling scenarios to expose strengths and weaknesses.17
After each exercise, ask what customer problem the person heard, which question opened it up, and how the person would respond next. Listen for whether the next question follows the answer, and watch whether the next action matches the stated workflow. Move on when the person can repeat the behavior without prompting.
Verify and coach
Count training as complete when the person can show the behavior. Turn each topic into an observable check and use the result to choose the next exercise.
Remove any item that cannot be verified by watching, listening, or reading.18 Write each check around a behavior, such as explaining the audience, handling a scenario, or asking a customer question. Record the proof, the gap, and the next practice task.
Build the foundation with a structured training plan, then layer coaching on top.19 Advance when the behavior is visible in the work. Repeat the exercise when the person knows the explanation but cannot yet perform it.
What not to do
Review the plan for these failure modes:
- Topic coverage and attendance do not show that the person can perform the work.20
- Product training, a login, and a list alone do not constitute training.21
- Limit product training because too much product training is counterproductive.22
- Product managers, technical leads, and the leadership team should participate alongside the sales manager.23
Before the new hire arrives, define the proof for each stage and assign a reviewer.