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Some thoughts on hiring executives:

- Designing a process
- When to hire
- What to look for
- Interview Q's to ask
- Working w/ search firms

More thoughts here 👇
Know why you are hiring and what you're hiring for

Create 12-18 month roadmap & identify not just the people you need to hire, but the people you think you need to hire.

You'll come out w/ a list of 5 executives, and since you can't hire at once, you'll prioritize accordingly.
Counter: If you're not sure whether you need an exec, don't hire one.

Hire an executive only when it's clear that you need one: when you need to build out an org, accelerate hiring, and you need to scale & up-level your processes.
Know what greatness looks like:

- Aggressively meet world-class people at the position, regardless of where they are, so you can calibrate accordingly. They'll likely be happy to help you if you're doing well

- Use gathered data to write specs for the role & determine criteria
What do execs need to be able to do:

- Build organizations, often from scratch.

- Also be primary individual contributors.

- Act like an owner & be a team player
Understand whether role is value protecting or value creating, and spec accordingly.

CFO at SaaS company = value protection

CFO at Opendoor = value creation

Value protecting, hire for slope

Value creation, hire for experience

Hire the best person for the next 9 months, not the next 3 yrs.

i.e.:

If you find someone who's not good now but good 3 yrs from now, don't hire them. They won't or can't do what you need now

If you find someone who's good now but not in 3 yrs, hire them. You'll figure it out.
Promote from within when you can.

It's how you keep great people who would otherwise leave for better opportunities elsewhere. It also shows there is upward mobility in the org.

You can trust them. They already know your culture and have team buy-in.
Be careful hiring a big company executive for a startup.

The skill sets required for a big company exec vs a startup exec are very different.

Even the best big company execs often don't know what to do once they arrive at a startup.
If you know what you're doing, the odds of a given executive hire working out will be about 50/50.

That is, about 50% of the time you'll screw up and ultimately have to replace the person.

If you don't know what you're doing, it'll be way worse.
Use an exec firm for sourcing, but don't outsource your evaluation, selling, or knowing what you need in the 1st place.

No one wants to pay $100K to a search firm, but a great exec hire pays back orders of magnitude more than that

Avg time of search is 137 days, so start early!
Q's to ask:

If you were CEO at your last co, what would you do differently? (You want them to be an owner).

What's the business equation of your last company? (You want them to be strategic)

"Who are the people you'd bring along with you?" (You want them to be a talent magnet)
Best interviews are a mix of buying and selling.

Buying - Asking Q's, digging in

Selling - Painting a vision, expressing interest in specific candidate for a specific core part of that vision.

Qualify early: Why are they leaving? Why are they potentially interested in joining?
On Compensation:

Bring it up in the beginning briefly to assure you're in the same ball park, and then don't bring it up again until the end when they're sold.

"If we're meant to work together, don't want comp to be the reason why we don't."
After you hire them:

- Manage your executives. Even if you're 20 and they're 70. (e.g. Weekly 1:1s)

- But don't micro-manage (unless temporarily). If you feel urged to, it might mean you don't trust them. Dig into that.

- Ask people under them semi-regularly how they're doing.
When should you fire an executive

- When you no longer trust them to build their org & feel compelled to micro-manage.

- Judged by output of their org. Are they hiring? training?

- Andy Grove said you always fire a bad exec too late. If you're really good, 3 months too late.
Inspired by ideas in these posts, among others:

pmarchive.com/guide_to_start…

delian.io/lessons-2
This is a follow up to this deep dive on recruiting:
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