1/ Throughout my startup career, I’ve seen many founders have an aversion to sales. This is a mistake that can kill your startup.

2/ Sales is often viewed as either a saving grace or proof that the product isn’t good enough (because it should sell itself). Neither are ever true. Some common mistakes that result in...
3/ Mistake 1: Hire a sales rep before reaching product/market fit to get your initial batch of customers. This is a mistake because founders need to work through their MVP with early adopters to truly understand what it is they’re selling.
4/ Mistake 2: Reach product/market fit, need to scale, and rely entirely on self-serve. For enterprise products that require big commitments and internal shifts, almost no product is self-explanatory enough to sell itself.
5/ Mistake 3: Make a first sales hire who isn’t scrappy enough to help mold the sales process from scratch. Some salespeople are amazing at their jobs, but not cut out to establish the processes that others end up following. This skillset is what @rdedatta calls a “sales ninja”.
6/ At Twitch, we built an advertising sales team. We tried and failed several times before finding the right sales leader who had sold into the market before. The lesson here: if it doesn’t work at first, it might be how you are doing it (not the market’s fault). Keep trying.
7/ When I talk to founders about sales, I tell them that you need to get out there yourself and do your own initial sales to learn what your customers want.
8/ @rdedatta wrote a great piece about how to get first customers and hire a sales ninja: https://t.co/MFoL36DUFI

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1/ Here’s a list of conversational frameworks I’ve picked up that have been helpful.

Please add your own.

2/ The Magic Question: "What would need to be true for you


3/ On evaluating where someone’s head is at regarding a topic they are being wishy-washy about or delaying.

“Gun to the head—what would you decide now?”

“Fast forward 6 months after your sabbatical--how would you decide: what criteria is most important to you?”

4/ Other Q’s re: decisions:

“Putting aside a list of pros/cons, what’s the *one* reason you’re doing this?” “Why is that the most important reason?”

“What’s end-game here?”

“What does success look like in a world where you pick that path?”

5/ When listening, after empathizing, and wanting to help them make their own decisions without imposing your world view:

“What would the best version of yourself do”?
I like this heuristic, and have a few which are similar in intent to it:


Hiring efficiency:

How long does it take, measured from initial expression of interest through offer of employment signed, for a typical candidate cold inbounding to the company?

What is the *theoretical minimum* for *any* candidate?

How long does it take, as a developer newly hired at the company:

* To get a fully credentialed machine issued to you
* To get a fully functional development environment on that machine which could push code to production immediately
* To solo ship one material quanta of work

How long does it take, from first idea floated to "It's on the Internet", to create a piece of marketing collateral.

(For bonus points: break down by ambitiousness / form factor.)

How many people have to say yes to do something which is clearly worth doing which costs $5,000 / $15,000 / $250,000 and has never been done before.