Sales Management
Most founders wait too long, misdiagnose the problem, and either fire the wrong person or keep the wrong person. Here is the 5-step framework for diagnosing, coaching, and deciding — fast.
Most founders skip step one and go straight to step three. That is where the cost accumulates.
When a salesperson is not hitting their number, the instinct is to intervene immediately. The problem with that instinct is you may be solving the wrong thing. Underperformance has four possible root causes: the salesperson lacks the skill, the salesperson lacks the motivation, the sales process is broken, or the quota and ICP were set incorrectly. Firing a salesperson who has a broken process is an expensive mistake. Coaching a salesperson who has the wrong motivation wastes your time. Diagnosis comes first.
Most founders let underperformance go on too long because they are uncomfortable with direct feedback. They drop hints, adjust territories, or quietly reassign accounts. The salesperson rarely understands what is actually wrong until it is too late to fix it. A direct conversation means two things: you name the specific gap (not 'your numbers are down' but 'you closed zero deals from your last 12 discovery calls'), and you ask the salesperson to explain what they think is happening. You need both the data and their perspective before you can know what to do next.
The most common mistake in managing underperformance is keeping someone in a vague performance conversation for months. There is no timeline, no clear standard, and no defined consequence. The salesperson stays in place, morale on the team suffers, and nothing changes. A 30-day performance window with written criteria removes the ambiguity. The criteria should be activity-based and outcome-based: a specific number of discovery calls, a specific number of qualified deals entering the pipeline, and a specific close rate on opportunities already in stage. The standard has to be achievable. The timeline has to be real.
If the diagnosis points to a skill gap rather than a motivation or system problem, coaching is the right intervention. Coaching the wrong thing wastes time for both of you. If deals are stalling between discovery and proposal, the issue is likely qualification or solution presentation. If deals are stalling at close, it may be price objection handling or urgency creation. Identify the one specific bottleneck in this salesperson's process and focus your coaching time there. Do not run general sales training. Run deal-specific coaching on the exact stage where the breakdown happens.
At the end of the 30-day window, you have two options: the criteria were met or they were not. If the criteria were met, acknowledge it and raise the bar for the next 30 days. If the criteria were not met, the conversation you need to have is clear. The most common failure mode here is extending the timeline. If a salesperson did not meet the criteria in 30 days, adding another 30 days rarely produces a different result. It usually means you are postponing a decision you have already made. Make the call based on the evidence you set out to gather, not on how long the person has been there or how much you like them personally.
Underperformance in a small sales team is expensive in two directions. The obvious cost is the deals you are not closing. The less obvious cost is what the underperformance does to the rest of the team. When a salesperson is not being managed, everyone else on the team sees it. Standards drift. Accountability weakens. The people who are performing start wondering why they bother. The cost of delay is not just the missed quota. It is the signal it sends to everyone watching.
The most important thing to get right before any performance conversation is the clarity of your expectations. If you have never written down what a good month looks like for this salesperson, the conversation will be subjective — and subjective performance conversations rarely produce change. Start with the accountability document and the quota criteria before you manage to them. See what a sales accountability document looks like →
Getting this diagnosis wrong is the most expensive mistake you can make. Here is how to tell the difference.
No written ICP or qualification criteria defined for the team
This specific salesperson is skipping qualification steps the rest of the team follows
The sales process has never been documented or trained
The salesperson knows the process and is not following it
Every new hire takes 9 to 12 months to ramp up
This salesperson is ramping slower than everyone else hired at the same time
Quota was set without benchmarks or historical data
Other salespeople on the same quota are hitting it consistently
Pipeline reviews happen irregularly and lack accountability
This salesperson does not show up prepared or act on agreed next steps
Lost deal debriefs never happen — nobody knows why deals die
This salesperson loses deals that similar salespeople close at the same stage
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.
Managing underperformance is one of the most common conversations I have with founders in the first weeks of an engagement. They usually already know what needs to happen. They have been putting it off. Part of what I do is give founders the framework and the data to make the call they should have made weeks earlier, and to move forward without second-guessing themselves.
Thirty days from the moment you identify a specific, measurable gap. Not from when revenue started declining. The moment you can name a precise metric that is not being met, you start the clock. Waiting longer rarely produces new information. It usually just means you have a longer conversation to have at the end and a bigger cost to absorb in the meantime.
The fastest test is to compare this salesperson's results against everyone else on the team using the same process. If your other salespeople are closing at 30% and this person is closing at 5%, that points toward a person issue. If your entire team is closing at 5%, that points toward a system issue. If you only have one salesperson, compare their conversion rates by stage against your own historical conversion rates from when you were selling. The data tells you where to look.
Say the specific number. Do not open with general feedback or soften the lead. Say: 'Over the past 90 days your close rate on qualified opportunities is 8%. The team standard is 25%. I want to understand what you think is driving that gap before we talk about next steps.' Then stop talking and listen. You need to hear their explanation before you decide what is actually broken. Most founders do the opposite: they deliver a diagnosis before they have collected the data.
A PIP makes sense when two things are true: you believe the performance problem is fixable, and you have not yet had a direct conversation with specific criteria. A PIP is not a formality before termination. If you have already decided, skip the PIP and have the honest conversation. If you have not decided and the problem is addressable, a 30-day PIP with clear metrics gives both sides the information they need to reach the right outcome.
Ready to formalize the process? Here is how to write a sales performance improvement plan →
In 30 minutes I can help you diagnose whether you have a person problem, a process problem, or a quota problem — and give you a clear next step that does not cost you another quarter.