You Made the Hire. Now What?
You spent weeks finding the right person. Fast forward three weeks and something feels off. Not catastrophically wrong, just... off. They're nice. They're trying. But you're not sure.
This is the moment most leaders get wrong. Not the hiring. Not the firing. The part in between.
Paddy Lambros, former Talent Director at Atomico: "I don't think I've ever seen somebody who's had a really bad first month turn it around and become a top performer." Meanwhile, Olivier Gaudin built SonarSource to 800 people with zero managers and, when he noticed a values disconnect, froze hiring entirely to fix the environment. Roland Siegwart at ETH Zurich takes the opposite view: "Brilliant people can learn extremely fast if they are given the context."
Who's right? Having spoken to dozens of founders on this podcast, we think neither extreme works on its own. The real question is: Were your expectations clear from the start? And is the learning curve real?
Below is a framework built around three checkpoints - Week 1, Week 2, and Month 3-4 - to help you answer that honestly.
How to Set Expectations Before a New Hire Starts
This is where most leaders already lose. They know what the role is called. They have a rough sense of what the person should do. But they haven't defined what success actually looks like at month three.
Before your new hire walks through the door, answer these questions. Write them down. Be concrete, not aspirational.
What should this person have accomplished by month three?
Not "gotten up to speed" or "integrated with the team." Specific outcomes. A salesperson should have closed X or built Y pipeline. An engineer should have shipped Z. A marketing hire should have launched a first campaign. What are the tangible milestones?What does performing in this role look like on a daily and weekly basis?
What meetings are they in? What decisions are they making? What are they owning? If you can't describe the rhythm of a good week in this role, you're hiring for a title, not a function.What does this person need from you in order to succeed?
Be honest. Do they need context you haven't documented? Access to people you haven't introduced them to? A clear mandate you haven't articulated? The gap between what you expect and what you've actually set up is where most "performance issues" are born.What would make you say "this isn't working" at month three?
Define the red lines now, while you're clear-headed. When you're in the fog of month two, you'll rationalize. Having this written down keeps you honest.
This isn't just useful for evaluation. It's useful for hiring. If you can't articulate what great looks like in this role at month three, you can't assess candidates either. The backwards thinking starts before the job posting goes live.
What to Look for in a New Hire's First Week
Week One is not about performance. It's about signals: does this person show up in a way that suggests the trajectory will be there?
Think back to the first week and reflect honestly:
Energy and intent
Did they arrive with genuine curiosity about the company, the product, the team?
Not performative enthusiasm, but real questions that showed they want to understand how things work here.Did they take initiative to orient themselves, or did they wait to be told what to do?
In a startup, the information isn't neatly packaged. The people who thrive are the ones who go looking for it.How did they handle the inevitable chaos of a first week?
Every startup onboarding is messy. Did they roll with it, or did you sense frustration that things aren't more structured?
Early relationship signals
Did they proactively reach out to teammates, or only interact when required?
Noa Perry Reifer, who built people and culture functions at On and Neko Health, makes a sharp observation: relationships in a new company don't come naturally. You have to invest in them deliberately. The people who get this start building connections from day one.Did you observe any friction?
Not conflict, that can be healthy, but a disconnect in how they communicate, how they respond to feedback, how they handle ambiguity.
Are you being honest with yourself?
Did you set them up for a good first week?
Did they have the access, context, and introductions they needed? Or did you assume they'd figure it out because "that's what startup people do"?Are you already explaining away small concerns?
"It's only week one" is a valid statement. But notice the instinct. Are you observing, or are you already making excuses?
How Fast Should a New Hire Start Contributing?
By week two, you should see the first signs of contribution. Something that signals this person is starting to convert context into action.
Paddy Lambros calls this "time to first value" and argues it should happen on day one: a salesperson shadows a call, an engineer commits something useful. The principle is sound even if the timeline is generous: the faster someone contributes something real, the faster they build confidence and the faster you get signal.
Contribution
Has this person delivered anything tangible yet?
Even something small: a first draft, a first call, a first piece of code, a first analysis. What matters is whether they moved from absorbing to producing.Did they push something forward without being asked?
Spotting a broken process, suggesting an improvement, asking "can I take this on?" Paddy's observation is that the best people "knock on your door and say 'this is busted, what the hell?'" That instinct either shows up early or it doesn't.If they haven't contributed anything yet, why?
Is it because the onboarding didn't give them a path to contribute? Or is it because they're waiting for perfect conditions that will never exist in a startup?
Learning speed
Are they asking better questions this week than last week?
The quality of someone's questions is one of the most reliable signals of how fast they're learning. Week one questions are about orientation. Week two questions should show they've built a mental model and are now probing deeper.When they got something wrong or received feedback, how did they respond?
Did they absorb it and adjust, or did they get defensive or deflect?
Are you coaching or just watching?
Are you coaching or just watching?
This is the question Noa Perry Reifer also urges leaders to ask themselves every morning. If you're silently evaluating without giving direction, the problem might be your leadership, not their performance.Have you given them direct, specific feedback yet?
Not "you're doing great" and not "I have some concerns." Have you told them concretely what's working and what isn't? If not, you're withholding the one thing that could accelerate their trajectory.
When to Let a New Hire Go (And When to Double Down)
This is the real decision point. By now, you have enough data. The question is whether you're willing to look at it clearly.
Pull out the milestones you defined before day one. If you didn't define them, and be honest, many leaders don't, reconstruct them now as best you can, and note that the lack of clarity is itself a finding.
Is the learning curve real?
This, in our experience, is the single most important signal. Not where the person is today, but the slope of the line.
Looking at the trajectory from week one to now, is there a consistent upward curve? Are they measurably better at their job today than they were a month ago? Two months ago?
When they hit walls, and everyone hits walls, did they push through? Did they ask for help? Did they find a way? Or did they stall and wait for the wall to be removed?
Is the gap between where they are and where your month three milestones said they should be closing? Widening? Static?
Roland Siegwart's insight applies here: brilliant people learn fast if you give them the right environment. If the learning curve is steep and real, that matters more than where they started. But if you've given them the environment, the context, the coaching, and the curve is flat - that's your answer.
Did they meet the milestones you set?
Go back to the milestones you set before day 1. How many have they hit? Be specific.
For the ones they missed: was it a capability gap (they couldn't do it), an effort gap (they didn't try hard enough), or an environment gap (you didn't set them up to succeed)? Be ruthlessly honest about all three.
Paddy's "stick or twist" question: If you could rewind and choose between rehiring this person or going back to market, what would you do? If the answer isn't an immediate "I'd rehire them," sit with that.
How to have the performance conversation
This checkpoint is not just internal reflection. It's the point where you sit down with the person.
Jonas Muff, founder of Vara, describes the shift that changed his leadership: he stopped finding ways to soften, contextualize, or delay difficult conversations and started going directly in. Not aggressively. Directly. "Embrace the emotions that come with it," he says. The conversation is uncomfortable, but the alternative, avoidance, is worse for everyone.
Can you articulate exactly what needs to change, by when, and what support you'll provide? If you can't be that specific, you're not ready for the conversation yet. Go back to the milestones.
Have you separated the person from the circumstances? Lina Chong's observation: sometimes the issue is genuinely that nobody on the team has the experience for the next stage of the company. That's not a personal failing. But it does need to be communicated openly: "This is the next stage of the company's journey, and this is what it requires."
What Now
There is no universal right answer on when to invest more and when to let go. Anyone who tells you otherwise is selling you a framework that doesn't survive contact with reality.
What we've heard across dozens of conversations on this podcast is a pattern:
the leaders who build great teams are the ones who are clear about what they expect, honest about what they see, and willing to act on both, whether that means doubling down or making a change.
The tool is not the decision. The tool is the clarity that makes the decision possible.
Two principles worth carrying with you:
Define success before you need to evaluate it. The time to set expectations is before day 1, not when things feel off. Work backwards from month 3: what does great look like? If you can't describe it, the problem starts with you.
Watch the slope, not the point. A person's position on day 30 matters less than the trajectory from day one to day 30. A steep learning curve paired with genuine willingness to push through hard moments is worth more than a polished start that plateaus.
The perspectives in this framework come from conversations with founders, investors, and operators across the Follow the Gradient podcast. If any of these resonated, the full episodes are worth your time:
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Follow the Gradient is a weekly newsletter and podcast by the serial founders Melanie Gabriel & Christian Woese about how to scale a business from Europe while staying sane.
