9 hiring lessons we learned the hard way

Denym Bird

Before starting HeyThere, Alex and I built Paintvine. Over the 5 years we have spent building that business, here are 9 lessons about hiring that will change the way you hire. We guarantee it.

1/ Don't rush to hire

Let's say you've got three candidates. You give candidate number one an offer & he rejects. Candidate number two drops out of the process, leaving you with a choice: hire candidate number three or start the monthslong process again. 

Every single time I've hired number three, I've been burned.

2/ Map the Matrix

Know what type of hire you're making: 

1) A unicorn: high experience, high critical thinking

2) A dice roll: low experience, high critical thinking

3) A kitchen timer: high experience, low critical thinking

4) A bust: low experience, low critical thinking

3/ Obsess over the JD

Most people treat job descriptions as a formality. Something you create to appease HR & post on your site. 


Wrong. A JD is: 

- The #1 way to know what you're hiring for 

- The best guide for interview questions 

- Forced accountability during the process

4/ Know the stakes of senior hires

Execs can 10x your company or destroy your company. 

Big learnings hiring execs:

- Botched hire sets you back 6mo minimum

- They are a magnifying glass: more costs, more A or C hires, more focus or confusion

- Trust is their greatest currency

5/ What people say > how they say it

Alex and I have always said SALES is the #1 skill you can have in life.

We still believe that. But it can also be a huge blindspot when hiring. 

Great storytelling used to distract me from imprecise thinking & other red flags. 

What people say is what matters most.

6/ Decision journal big hires

Bad hires are inevitable, but hiring success % should improve over time. 


Document hiring decisions & review 6mo later. 

For a template: subscribe to my new startup show (link in bio). 

Tmrw's episode will link to my decision journal.

7/ Long interviews are good

Leaders fear extensive hiring processes. 

They worry: 

- candidates will drop out.

- need to hire ASAP.

- too much free work.

Our view: 

- candidates dropping out is a good filter.

- see tweet 2 about rushing.

- so start paying at a certain point.

8/ Trial to full time is powerful

Some of the best hires we've ever made started as freelancers or consultants. 

This approach doesn't work for everyone. 

But when it does, it's an amazing way to de-risk a hire.

9/ Know your blind spots

I've had to hire for many roles I knew nothing about. 

So how could I assess whether a candidate was good or bad? 

Here's what I did: 

1) Talk to 5-10 senior people with the right experience 

2) Have the #1 of those senior people join the hiring process

And that's it, good luck out there!

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