I wasted $40K on a senior engineer who quit after 4 months

We needed to scale our engineering side and bring on another engineering resource. We had some traction, things were moving good, and I thought maybe hiring someone senior would help us scale faster. So I posted the job on LinkedIn and couple other platforms, slowly started receiving some good resumes. Me along with my co-founder went through some promising resumes and shortlisted candidates who looked solid. We screened a few and finally shortlisted one who ha dpreviously worked at a MAAG company and had a strong background, good references, and seemed like he knew what he was doing.

My co-founder took the interview, had some call with him and after feeling assured, we shared him the offer letter and onboarded him.

After four months in, he told me it wasn't working and he wanted to make a switch.

At first we setup an internal call with him to understand what went south. We couldn’t change his decision and I started blaming him. Then I blamed the market and then I finally realized I had really no idea what I was doing when I first hired him. 

I had written this vague job description about "wanted someone who can own the backend" and "driving technical decisions" but never actually defined what that meant and any specifics. What's he supposed to ship in month one and what will the third month look like? What decisions can he make without me? What does success even look like? I had no answers to any of this and it was horrible.

He had come from a place where things were structured. We were the total opposite. I just dropped him in and hoped he'd figure it out. Of course it didn't work.

So we needed to hire again but now I was paranoid about screwing it up twice. We posted on LinkedIn, shared with some discord groups and some other places. We got hundreds of resumes and most were completely irrelevant. I tried asking around in some founder groups and on Reddit, got a few intros but nothing really clicked.

We also spoke to two recruiting agencies thinking they might help us take this load off our shoulders and get us some better candidates. Both of them were slow, it took them weeks to get back to me, and when they finally sent candidates over it felt like they hadn't really listened to what we really needed. They were just sending resources to make a placement. One agency wanted 25% of first year salary upfront. We're bootstrapped, that's insane.

At this point I'm stressed and running out of options. A founder friend from valley mentioned he'd used some platform to hire engineers and it worked out. I wasn't against the idea but I'd heard mixed things. I was more worried about making the same mistake again regardless of where someone was from.

We anyways ended up talking to them, mostly out of desperation. Company's called Uplers. The first conversation was kind of frustrating because the person wouldn't even show me the candidates yet. They kept asking me to define the role better first. What does this person own? What's the first milestone I wanted to have? What level of independence do they need? I just wanted to see resumes but they kept pushing back.

But looking back that was probably the most valuable part. It forced me to actually think through what I was hiring for instead of just reacting.

Once we got clear on that stuff they started screening people on their end. Few days, they only sent me 2-3 candidates at a time who'd worked at early stage companies before like ours. If I didn't like them they'd go back and find more. No pressure.

We thought of doing a short paid project first, maybe 2-3 weeks, before committing to anything full time. That really helped a lot. You see how someone actually works, how they communicate when things aren't clear, how they handle feedback. Personally, I felt this was way better than just having interviews (no offence).

The guy we hired is still here, been about 14 months now. He's really impressive. Now thinking about this, I feel the difference was I actually designed the role properly this time. He knew what he was responsible for, what the role looked like and what were the success metrics, and how we'd work together.

I'm not saying everyone should hire the same way I did. Different things work for different people. But the core lesson for me was that where you find someone matters less than knowing what you need them to do before you start looking.

If you can't explain what you want someone to accomplish in their initial few days, you're probably not ready to hire yet and thats the same advice I give to budding entrepreneurs. This learning costed me $40K..

I am curious how other founders are handling situations like this? Has anyone else had an early hire not work out?