Sales Management
Most PIP guides are written for HR departments at enterprise companies. This one is written for founders managing their first or second salesperson who want a process that is fair, specific, and actually produces a decision.
Done right, a PIP forces clarity on both sides. The goal is not to build a case for termination. The goal is to give the salesperson a genuine, documented opportunity to meet a defined standard.
A PIP that says 'needs to improve performance' is not a PIP. It is a complaint with a signature line. The only useful PIP starts with a precise gap statement: what the current performance is, what the expected performance is, and the time period over which the gap has been observed. 'John closed 2 deals last quarter. The team standard is 6 deals at an average deal size of $18,000. Over the past two quarters, John has closed 2 deals and 3 deals respectively, while other salespeople hired at the same time averaged 5 and 6.' That is a gap statement. It removes ambiguity and gives both sides the same factual starting point.
The success criteria of a PIP should be specific, measurable, and achievable. Achievable is important: a PIP that sets a standard nobody else is hitting is a setup for termination, not improvement. The criteria should cover both activity metrics and outcome metrics. Activity metrics: a minimum number of discovery calls per week, a minimum number of qualified opportunities entered into the pipeline. Outcome metrics: a specific close rate, a specific number of closed deals or revenue over the PIP period. Two or three clear criteria are enough. A PIP with ten criteria becomes impossible to track and enforce.
The timeline of a PIP should match the nature of the problem. If the issue is attitude, consistency, or following the defined process, 30 days is enough to see whether the behavior changes. If the issue is a skill gap, like converting discovery calls to qualified opportunities, 60 days gives more time for coaching to take effect. Shorter than 30 days is rarely defensible. Longer than 60 days is almost always about avoiding a decision rather than giving a genuine chance to improve. Pick the timeline that matches the problem and commit to it.
A PIP without weekly check-ins is just a document. The check-in is where the PIP does its work. Each weekly check-in should take 30 minutes and cover three things: progress against each criterion (with actual numbers, not impressions), what helped or hindered performance that week, and what specific coaching or resource the salesperson needs to succeed in the coming week. Document each check-in. Write a brief summary of what was discussed and what was agreed. Both parties get a copy. This documentation protects both of you and creates a real-time record of whether genuine support was provided during the PIP period.
The most common failure in PIP execution is extending the timeline when criteria are not met. If the salesperson did not meet the stated criteria in the agreed period, the right next step is a conversation about what comes next: either a transition out of the role or, in rare cases, a restructured role with different expectations. Extending the PIP almost never produces a different outcome. It delays the inevitable, keeps the salesperson in limbo, and signals to the rest of the team that the accountability systems are not real. Make the call on the agreed date based on the evidence you collected, not based on how the person made you feel during the check-ins.
Most of the PIP content available online is written for HR teams at large companies with formal performance management systems. It focuses on documentation for legal protection, HR sign-off requirements, and multi-tier escalation paths. That content is not useful for a founder managing a team of two or three salespeople who has never run a formal performance process before. The value of a PIP for a small team is different: it forces you to define what success looks like for this role, which many founders have never done explicitly. A PIP that ends in improvement is a better outcome than a PIP that ends in termination. Both outcomes depend on how clearly the standard was set at the start.
Before running a PIP, make sure you have the accountability document in place for your team. If you have never written down what good performance looks like for this salesperson, you are starting the PIP conversation from a position of ambiguity. See the sales accountability document framework →
These are the patterns that turn a PIP into a formality instead of a genuine management tool.
Writing goals like 'improve attitude' or 'communicate more proactively' with no measurable definition
Running a PIP as a formality when the decision to terminate has already been made
Canceling weekly check-ins because things are busy, which signals the PIP is not serious
Extending the PIP timeline when criteria are not met instead of making the agreed decision
Focusing only on outcomes (close rate) without inspecting the activity and process inputs that drive them
Not providing the specific coaching, tools, or information the salesperson needs to have a genuine chance to improve
I'm Louie Bernstein — I have 50 years in business experience, including 22 as a bootstrapped founder. My Fractional Sales Leadership business has been helping founders since 2017.
I have helped dozens of founders work through performance management conversations they had been avoiding for months. The most common pattern I see is this: the founder already knows what needs to happen and has known for a while. What they need is a clear framework and someone to walk them through the conversation with confidence. A well-run PIP is not a punishment. It is the most honest thing you can do for a salesperson who might be in the wrong role or missing the support they need to succeed.
Five things: a precise gap statement with specific numbers, two to three measurable success criteria, a defined timeline (30 or 60 days), a weekly check-in schedule with documentation, and a clear statement of what happens at the end of the PIP if criteria are met and if they are not. Anything vague is not a PIP. It is a conversation you had and wrote down.
Thirty days for behavior or consistency problems. Sixty days for skill gaps that require coaching to close. Shorter than 30 days is not enough time to see genuine change. Longer than 60 days usually means you are postponing a decision rather than running a genuine improvement process. The timeline should be set based on the type of problem, not based on how uncomfortable you are with the outcome.
Yes, if two conditions are true: you have clear evidence of underperformance against a known standard, and the salesperson understood what that standard was before you hired them. If your onboarding did not set clear performance expectations for the first 90 days, a PIP at month three is premature. Fix the onboarding expectations first and give a reasonable ramp window before measuring against full quota.
In most US at-will employment situations, a PIP is not a legal requirement before termination. The practical reason to run a PIP is not legal protection. It is clarity. A PIP forces you to define success in writing, give the salesperson a genuine chance, and make a decision based on documented evidence rather than a subjective call. That is valuable for you and fair to the salesperson regardless of the legal requirements in your jurisdiction.
In 30 minutes I can help you build the specific criteria for a PIP that is fair, defensible, and actually produces a clear outcome — without months of ambiguity on both sides.