Hiring Is a 50/50 Bet. Plan Like It.
“I’m great at hiring — and I’m still wrong half the time.” — Molly Graham, startup exec and operator
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Most hiring frameworks sell you certainty. Scorecards, culture interviews, performance predictors — they all promise you can know who’s a fit before they join.
But here’s the uncomfortable truth, straight from operators who’ve done it across Google, Facebook, Quip, and PE-backed roll-ups:
Even great hiring processes are right only about 50% of the time.
Seriously - think about the department around you. Think about the C Suite you work with. We can all envision “that” hire.
So if you’re running a PE-backed company with a rather urgent value creation plan, the question isn’t just “Are we hiring the right person?”
It’s: “What will we do when they’re not?”
The beauty and the horror of tech companies is that your most previous asset walks out the door at the end of each day.
As operators who deal with risk adjusted bets for a living, it’s funny that we are so bad at both assessing and actionizing these types of hiring scenarios, especially since they make up more than 70% of our cost structure.
The Cost of Being Wrong
In a high-accountability, high-velocity operating model, a mis-hire isn’t just a people issue — it’s a P&L risk.
Lost quarters of momentum (ever hire a new, flashy CPO who put the company a year behind your product roadmap?)
Strategy delayed or derailed (OMG, how do we get out of Europe?)
Morale drag on adjacent teams (Let’s just avoid working with Sally)
Rehiring cost (often 1.5–2x total comp hit when it’s said and done)
Sponsor confidence erosion (is it because smart people don’t want to work with these leaders? What’s the deal?)
When the mandate is growth and margin — there’s no room for passengers.
Years ago, when I was at Data Domain, we adopted a goal for recruiting that we only wanted drivers, not passengers. The slogan was based on a Volkswagen commercial at the time: “On the road of life there are passengers and there are drivers. Drivers wanted.”
-Frank Slootman, former CEO of Data Domain, ServiceNow, and Snowflake
In high-output orgs, being a “passenger” doesn’t mean you're lazy — it means you're not accelerating outcomes. And that’s the fastest way to fall behind.
Operators Know the Odds. They Plan for It.
Here’s what top execs and CHROs do differently when they recognize hiring is a probabilistic bet:
1. Run a 90-Day Validation Plan
You don’t need to know if they’ll be perfect. You need to know if they’re directionally right — fast.
Write out what success looks like by day 90. Not just tasks, but:
Cross-functional engagement
Decision hygiene
“Velocity of understanding” — are they ramping or flailing?
Define 3 things they should be doing by week 6 that can’t be faked.
If they’re not doing them, they’re not working.
The big thing here is making it KNOWN to everyone (new candidates and existing hiring managers) that this is how the org works. It normalizes “failure” in the sense that you don’t have to shuffle someone out the door under the cover of night. It’s just how you operate as a company to safeguard your pace of hiring.
2. Pair Every New Hire with a ‘Block Buddy’
One team I know has existing employees walk through each onboarding block with the new hire. So if you are joining the finance team, for every block of your onboarding a different member of your new team will sit in with you (virtually or in person). What are the benefits?
Builds connection through casual interaction (proverbial “water cooler” talk)
Refreshes fundamentals for the veteran (sneaky!)
Promotes shared accountability for onboarding quality (they’re your teammates, too)
Onboarding shouldn’t feel like passive info consumption. It should be active repetition with relational glue. And this gives people a chance to assess one another and start to build bonds in those “water cooler” moments.
3. Enable the Manager, Not Just the Hire
Many misfires happen not because the hire failed — but because the manager wasn’t clear, ready, or supported.
Before the offer goes out, have the manager answer:
What will success look like in the first 30–60–90 days?
What’s the single biggest risk in this hire?
How are you going to unblock them in week 1?
Every hiring plan needs a parallel manager enablement plan.
If someone is going to use +$100K to hire someone, they should be willing to take a beat and memorialize the above.
4. Watch for Cultural Lag Indicators
Bad hires rarely implode publicly. They erode quietly.
Watch for:
Slowed decision speed (why are they holding onto the ball so long?)
Invisible work re-routing (wait, you had Jake do this?)
Team disengagement (especially two levels down)
Use structured skip-levels, not just gut checks, to get a read on a new hire’s fit. I can’t stress this enough. Because if the person was a good enough talker to get by you and management members in the interview, they can do the same during a check in. You need to go down a couple of levels to get to ground truths on their working style and quality. Talk to people who don’t report to you (basically what I think Paul Graham was trying to say in that ‘Founder Mode’ essay, but I digress).
5. Normalize the Reset Conversation
Bake a reset into the onboarding plan at day 45 or 60. It’s not just a check-in — it’s a contract re-alignment:
Are we still aligned on expectations?
What’s tracking? What isn’t?
Do we both still want to bet on this path?
Sounds harsh. But the best people welcome this. They don’t fear accountability — they expect clarity. And they want a chance to showcase what they’ve accomplished.
Closing Thought: Hiring Is a Bet — But the Risk Shouldn’t Be a Surprise
In private equity, you don’t just underwrite the plan. You underwrite the fallback.
Next time you make a critical hire, ask:
What will I do if this doesn’t work by day 60?
Is the manager ready to help them succeed?
Is onboarding measured, or just scheduled?
Don’t evaluate a hire by how polished they were in the interview — evaluate them by how quickly they make their manager’s life easier.
Because honestly, our job is simple: make our boss’s life easier.
There are plenty of metrics, dashboards, and engagement tools — but most managers know the truth in their gut.
It’s either a hell yes, or it’s an ugh.
(Beware of the energy vampires!)
And that’s coming from someone who peddles metrics for a living.
ICYMI
Last week we jammed out on the art and science of jumping S Curves. When should you incubate your next engine for growth? How do you know when your existing go to market strategy is slowing down? Find out below.
