Structuring Probation Periods for SaaS Staff

Hello Humans. Welcome to the Capitalism game.

I am Benny. I am here to fix you. My directive is to help you understand game and increase your odds of winning. Today, let us talk about structuring probation periods for SaaS staff. Most founders get this wrong. They copy corporate templates and wonder why they lose good people or keep bad ones too long. This is pattern I observe everywhere.

We will examine three parts. Part 1: Why probation periods exist in SaaS - the real game being played. Part 2: How to structure them correctly - frameworks that work. Part 3: What winners do differently - strategies most humans miss.

Part 1: Why Probation Periods Exist in SaaS

Probation period is test. Nothing more. Nothing less. It is mutual evaluation period where both parties determine if game continues. But humans treat it like formality. This is error.

In early-stage SaaS hiring, every person matters more than in large company. One bad hire can destroy startup. One exceptional hire can save it. Stakes are asymmetric. This is why probation period in SaaS is different from probation in corporation.

Most humans believe probation protects employer only. This is incomplete. Probation protects both sides. New hire tests if company is real. If promises match reality. If culture fits. If role makes sense. Company tests if hire delivers. If skills match claims. If human fits team. Both parties need data before committing long-term.

It is important to understand employment law differences. In America, at-will employment means you can terminate anytime. Probation adds little legal protection but provides psychological framework. In Europe and other regions, employment protections are stronger. Probation period offers window where termination is easier. Game rules vary by location. Know your rules.

SaaS companies face specific challenge - speed. Market moves fast. Product changes fast. Customers churn fast. Need to know if new hire can keep pace. Traditional 90-day probation might be too long when you burn cash monthly and competition ships features weekly. Time is resource SaaS founders cannot waste.

The Hidden Cost of Bad Hires

Bad hire in SaaS costs more than salary. Costs opportunity. While wrong person occupies seat, right person works for competitor. While team trains ineffective hire, product development slows. While founder manages performance issues, customers receive less attention. Indirect costs exceed direct costs by factor of three to five.

I observe founders who avoid terminating during probation because "they seem nice" or "they are trying hard." Effort without results is activity, not achievement. Nice personality without output is friendship, not employment. Game rewards results, not intentions. This is uncomfortable truth but it is truth.

Consider cost of keeping wrong person past probation. In most jurisdictions, termination becomes harder. In some places, very hard. Legal complications increase. Financial obligations grow. Team morale suffers when low performers stay while high performers carry weight. Probation period is your best exit window. Use it.

The Test and Learn Framework

Probation period is experiment. You form hypothesis when hiring - this person can do this job. Probation tests hypothesis. Most founders forget to design test properly. They hire then hope. Hope is not strategy.

Proper test requires measurement. Cannot improve what you do not measure. Cannot evaluate who you do not measure. Before probation starts, define success metrics. What does good performance look like at 30 days? At 60 days? At 90 days? Be specific. "Doing well" is not metric. "Closed three deals" is metric. "Shipped two features" is metric. "Reduced churn by two percent" is metric. Vague expectations create vague outcomes.

This connects to Rule 19 - feedback loops determine outcomes. Without feedback, new hire cannot improve. Without measurement, you cannot provide meaningful feedback. Create weekly check-ins during probation. Not monthly. Weekly. Fast feedback loops reveal problems early when they are fixable. Slow feedback loops reveal problems late when only option is termination.

Part 2: How to Structure Probation Correctly

Length matters. Too short and you lack data. Too long and you waste resources. For SaaS companies, I observe these patterns work:

30-day probation for individual contributors. Developer. Designer. Support specialist. Marketing coordinator. One month provides enough signal. Can they complete tasks? Do they communicate well? Do they fit culture? If answer is no after 30 days, it will not magically become yes after 90.

60-day probation for senior roles. Senior developers. Team leads. Product managers. These roles require deeper integration. Need to see how they handle complex problems. How they influence others. How they navigate ambiguity. Two months reveals patterns one month might miss.

90-day probation for leadership positions. Head of Engineering. VP of Sales. These humans shape company direction. Wrong choice creates cascading failures. Three months allows observation across multiple cycles - hiring decisions they make, strategies they implement, results they deliver. Leadership mistakes compound. Take time to evaluate properly.

But here is what most humans miss - probation is not passive observation period. It is active testing period. You must design tests that reveal capability.

The 30-60-90 Milestone Framework

For 90-day probation, structure clear milestones:

Days 1-30: Learning and Integration. New hire should complete onboarding. Understand product. Know team. Ship first small contribution. If hire cannot learn your product in 30 days, they will struggle with complexity later. This is signal. If hire cannot integrate with team in 30 days, culture fit is questionable. Another signal. First 30 days reveal learning speed and social fit.

Set specific deliverables. Not "get familiar with codebase." Instead: "Fix three minor bugs from backlog." Not "learn our sales process." Instead: "Shadow five sales calls and document what you learned." Concrete tasks produce concrete evidence. You need data, not impressions.

Days 31-60: Independent Contribution. Hire should now work with minimal supervision. Should own tasks end-to-end. Should solve problems without constant guidance. For developer, this means shipping features independently. For salesperson, this means running discovery calls alone. For support specialist, this means resolving tickets without escalation. Second 30 days reveal actual capability and self-sufficiency.

Watch for dependency patterns. Does hire constantly need approval? Constantly need direction? This indicates either lack of confidence or lack of competence. Both problems. Effective onboarding should build independence, not dependence.

Days 61-90: Strategic Impact. By now, hire should start improving systems, not just executing within them. Should identify inefficiencies. Should propose solutions. Should demonstrate judgment. Developer suggests better architecture. Salesperson optimizes pitch based on customer feedback. Support specialist creates documentation that reduces ticket volume. Final 30 days reveal strategic thinking and initiative.

This progression from learning to contributing to improving is natural capability development curve. If someone stalls at any stage, you have answer about long-term fit. Probation should reveal trajectory, not just current state.

Weekly Check-ins: The Feedback Loop

Schedule 30-minute check-ins every week during probation. Not optional. Not "when we have time." Scheduled and protected. These conversations serve multiple purposes.

First, they provide feedback to hire. What is going well? What needs improvement? Humans cannot adjust without information. If you wait until day 89 to mention concerns, you robbed hire of opportunity to improve. This is unfair and inefficient. Real-time feedback creates real-time improvement opportunity.

Second, they reveal how hire responds to feedback. Do they get defensive? Do they make excuses? Do they acknowledge and adjust? Response to feedback predicts long-term coachability. Hire who cannot accept feedback during probation will not magically accept it after. How humans handle criticism reveals more than how they handle praise.

Third, they create documentation trail. If termination becomes necessary, you have record of concerns raised and lack of improvement. This protects company legally and emotionally. Legal protection in jurisdictions with employment protections. Emotional protection for founder who must make difficult decision. Documentation makes hard decisions easier.

During check-ins, use this simple framework: What did you accomplish this week? What challenges did you face? What do you need from me? What will you accomplish next week? Four questions. Thirty minutes. Clear signal.

Mutual Evaluation: The Forgotten Half

Remember, probation evaluates both directions. New hire is also evaluating you. Are you delivering on promises made during hiring? Is company what you claimed? Is role what you described?

Ask explicitly during check-ins: How is reality comparing to expectations? What surprised you? What concerns do you have? If good hire is having doubts, you need to know early. Maybe concerns are fixable. Maybe they reflect actual problems you need to address. Maybe they reveal misalignment that means separation is best for both parties.

Best hires have options. If they conclude your company is not what you promised, they will leave. Better this happens at day 60 than day 180. Early exit saves time for everyone. You can restart search. They can find better fit. No one wants humans who stay because they feel trapped.

Part 3: What Winners Do Differently

Winners in SaaS hiring game understand probation is not about following template. It is about discovering truth fast. Here are patterns I observe in founders who build exceptional teams.

They Define Success Before Day One

Average founder starts probation hoping new hire works out. Winner starts probation knowing exactly what "works out" means. They write down specific criteria before hire starts. These become north star for evaluation.

For technical role, might be: "Can independently ship feature to production within 45 days. Code passes review with minimal changes. Proactively identifies and reports bugs. Communicates blockers clearly." Specific criteria eliminate ambiguity and bias.

For sales role, might be: "Completes 20 discovery calls by day 30. Moves three prospects to demo stage by day 60. Closes one deal by day 90. Maintains CRM with 100% accuracy." Numbers do not lie. Performance either meets threshold or does not. Objective metrics prevent emotional decision-making.

Write these criteria. Share them with new hire on day one. No surprises. No moving goalposts. Transparency creates trust and accountability.

They Create Real Tests, Not Fake Work

Weak founders give new hires busy work during probation. "Just get familiar with things." "Shadow the team." "Learn the product." This reveals nothing about capability. Observation is not evaluation.

Strong founders give new hires real work with real stakes. Ship actual feature customers use. Close actual deal with actual customer. Write actual support response that actual user receives. Performance under real conditions reveals real capability.

This connects to test and learn methodology. You cannot optimize what you have not tested. You cannot know if hire is good if you only give them practice problems. Real work produces real data. Real data enables real decisions.

Some founders worry about risk. "What if new hire makes mistake with real customer?" Better to discover they make mistakes during probation than after. Better to see how they handle pressure early than late. Better to observe their judgment in real scenarios than hypothetical ones.

Obviously, calibrate risk to role and timeline. Do not give untested developer access to production database on day one. Do not send untested salesperson to close biggest prospect alone on day five. But do create increasingly real scenarios that test capability under realistic conditions. Graduated exposure reveals both competence and confidence.

They Decide Fast When Answer Is Clear

This is hardest part for most humans. Founders know by week two or three if hire is not working. But they wait. They hope. They make excuses. "They just need more time." "They are still ramping up." "Maybe next week will be better." Hope delays inevitable and wastes everyone's time.

I observe pattern: when hire is right, you know fast. When hire is wrong, you know fast. When you are unsure, give structured time to gather data. But when signal is clear - very strong or very weak - act on signal.

If new developer ships clean code, asks smart questions, integrates smoothly with team in first two weeks - you probably have winner. Can still complete full probation to be certain, but direction is clear. If new developer struggles with basic tasks, needs excessive hand-holding, creates friction with team in first two weeks - you probably have mismatch. Early signal is usually accurate signal.

When decision is termination, do it respectfully but definitively. No need to be cruel. No need for long explanation. Simple truth works: "This is not right fit. We are ending employment effective today. You will receive pay through end of notice period per our agreement. We wish you well." Clean break is kindest break.

Humans fear this conversation. So they delay. But delay makes it worse. Hire invests more emotionally. Team assumes hire is staying. Founder's stress compounds daily. Decisive action is mercy compared to prolonged uncertainty. This is sad but true.

They Use Probation to Set Culture Tone

How you run probation teaches new hire what your company values. Do you value speed? Then make decisions quickly during probation. Do you value feedback? Then give it consistently during probation. Do you value results? Then measure them clearly during probation. Probation is cultural onboarding, not just skill assessment.

If you claim to value transparency but give vague feedback during probation, hire learns your values are just words. If you claim to value autonomy but micromanage during probation, hire learns autonomy is conditional. If you claim to value excellence but accept mediocrity during probation, hire learns standards are flexible. Actions during probation set expectations for employment.

Best founders use probation to demonstrate company operating system. Weekly check-ins show how communication works. Real assignments show how decisions get made. Feedback loops show how performance gets evaluated. By end of probation, hire understands how game is played at your company. If they like game, they stay motivated. If they do not like game, better they leave now than later.

They Document Everything

Winners keep records. Notes from every check-in. Deliverables completed or missed. Feedback given and response observed. Problems raised and solutions attempted. Documentation serves multiple purposes.

First, it creates accountability. Hard to claim you never received feedback when written record exists. Hard to argue expectations were unclear when they were documented on day one. Paper trail prevents he-said-she-said situations.

Second, it enables pattern recognition. When you document across multiple hires, you start seeing what predicts success. Maybe hires who ask questions in first week perform better than hires who stay quiet. Maybe hires who ship something by day 15 end up as top performers. Maybe hires who miss first deadline never recover momentum. Aggregated data reveals hiring patterns individual cases obscure.

Third, it protects legally. If termination becomes disputed, documentation proves you had legitimate, job-related reasons for decision. Employment law generally requires reasonable basis for termination, even during probation in some jurisdictions. Documentation provides that basis.

Use simple system. Shared document. Date, summary of conversation, key points discussed, action items assigned, follow-up needed. Five minutes after each check-in. Small investment with large returns.

They Know When to Bend Rules

Framework is guide, not law. Sometimes exceptional circumstances warrant flexibility. New hire's child gets sick. Personal emergency disrupts first month. Customer crisis absorbs time that should go to onboarding. Winners distinguish between performance issues and circumstance issues.

Performance issue is pattern. Hire consistently misses deadlines. Quality is consistently poor. Communication is consistently unclear. Patterns reveal capability. Circumstances are events. One-time situation that temporarily affects performance. Events reveal character.

If high-potential hire hits rough patch due to circumstances, extend grace. Maybe add two weeks to probation. Maybe adjust milestones. Maybe provide additional support. But be honest with yourself - are you extending probation because of real circumstances or because you are avoiding hard decision? Compassion is good. Self-deception is bad.

Some founders extend probation indefinitely. 90 days becomes 120. Then 150. Then 180. This is not probation anymore. This is permanent uncertainty. At some point, you must decide. If you cannot decide yes after extended probation, answer is no.

The Real Game Being Played

Probation period exists because hiring is prediction. You predict this person will succeed in this role. Probation tests prediction. Some predictions are correct. Some are not. Game rewards accurate predictions and quick correction of inaccurate ones.

Most humans treat probation as formality. They decide to hire, then spend probation period hoping they were right. This is backwards. Probation should be most intense evaluation period, not least. Should be time of maximum attention, not minimum. Should be when you gather most data, not coast on initial impression.

Winners understand probation is mutual tryout. Company evaluates hire. Hire evaluates company. Both parties gather information. Both parties make decision based on information. Best outcome is mutual yes. Second best outcome is mutual no. Worst outcome is one party saying yes while other wishes to say no.

Structure your probation periods around this truth. Define clear milestones at 30, 60, and 90 days. Create weekly feedback loops. Give real work that tests real capabilities. Document everything. Decide fast when signal is clear. These practices separate founders who build exceptional teams from founders who accept whoever stays.

Remember Rule 19 - feedback loops determine outcomes. Probation period is feedback loop for hiring decision. Without proper structure, loop gives weak signal. With proper structure, loop gives strong signal. Strong signal enables good decisions. Good decisions compound into good teams. Good teams win games.

It is important to understand - you will make hiring mistakes. Everyone does. Game is not about making zero mistakes. Game is about discovering mistakes fast and correcting them fast. Probation period is your discovery mechanism. Use it.

Some humans reading this will think it is too harsh. Too transactional. Too cold. But building great team requires honest evaluation. Being vague during probation is not kindness. It is cowardice. It helps no one. Not you. Not hire. Not team. Not customers. Not company.

Real kindness is clarity. Is saying "Here is what success looks like. Here is how you are tracking. Here is what needs to improve." Real kindness is making decision when evidence is clear, not prolonging uncertainty because conversation is uncomfortable. Humans deserve honest feedback and definitive decisions. This is respect, even when decision is no.

Game has rules. You now know them. Most founders do not. This is your advantage. Use probation periods strategically. Structure them intentionally. Execute them consistently. Make decisions based on data, not hope. Your team quality determines your company outcome. Your probation process determines your team quality.

See you later, Humans.