How should one evaluate a company before joining?

Building A New Product? Here's What You Need To Ask!
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Once a company has indicated that they want to extend an offer, I do an extensive Reverse Interview process with the company. Even if that isn’t possible in your situation, a reasonable company will accept your request to speak with 3-4 people for 30 minutes each. Ask for it.

Shreyas Doshi
How can you evaluate the caliber of people at a company before joining it? Here are 10 tips:
1/ Quality of their interview questions. Pay particular attention to their follow up questions. The quality of an interviewer’s follow up questions is a good indicator of rigorous thinking. Did they just ask obvious follow up Qs or insightful ones? Did they make you think?
2/ Overall rigor of the hiring process. If they aren’t rigorous when hiring you, if the process to get an offer seems “too easy”, they will do the same for future hires, leading to a progressive lowering of the talent bar. A very onerous hiring process isn’t a good sign either.
3/ Quality of *their* responses to your questions. Are the answers honest, nuanced? Do they express vulnerability? What is the clarity of their thinking? Are they generally good listeners? etc Preparation & presence is key. You need to conceive good questions & intently listen.
4/ Watch the tone & style of their communication at least as much as the content of the communication. Make sure it is aligned with your values and preferences (e.g. do you sense hubris? arrogance? fake caring? too sales-y? too transactional? adequate empathy? etc.)
5/ Background of the people who already work there (look on LinkedIn & Glassdoor reviews). Specifically, look for past evidence of clearing a high bar. This isn’t about fancy colleges or prior employers. Have they created something from nothing? Leadership activities? etc.
6/ Once a company has indicated that they want to extend an offer, I do an extensive Reverse Interview process with the company. Even if that isn’t possible in your situation, a reasonable company will accept your request to speak with 3-4 people for 30 minutes each. Ask for it.
7/ Ask the hiring manager who s/he thinks are the best 3-5 people at the company. Who best represents the company’s culture, values, and operating approach? Ask to speak with a subset of them to help inform your decision. (this is my most favorite tip)
Not only does this provide great signal on what the company’s best people are like, but if you accept the offer, it also gives you ready-made relationships with some of the best people at the company, which will be very useful for you when ramping up and also over the long term.
8/ For mid-level to senior roles at startups, you should be able to speak with a board member or investors. If a startup declines this request for a senior role (VP or higher), treat it as a yellow flag. Many investors say very positive things, so try to “hear between the lines”
9/ If it’s a B2B/enterprise company, speak with the company’s customers (e.g. friends/former colleagues who use the company’s product). Besides asking about the product, ask them about the caliber of people they’ve interacted with at this company and any cultural red flags?
10/ Know that assessing the caliber of people at a company from the outside is part art, part science. During a typical interview process, you will have picked up 100s of subtle signals that will inform your gut feeling about just how good the people are. So listen to your gut.
Bonus: A high caliber team isn’t just a collection of smart people. The most accurate indicator of the caliber of people at a company is the quality of its execution. So be sure to track the product & the comms that the company puts out publicly. Look for insight, quality, pace.
And if you are a founder or leader at a startup, most of these tips are applicable to you, but in reverse. Consider them as you design your hiring process, train interviewers, and devise policies on how you will support candidates who want to learn more about your company.

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