The Harsh Truth of Interviewing & Hiring Product Managers w/ Willis Jackson, Founder of Middle Mile and former 1st PM at Grove Collaborative

Willis Jackson is a long-time PM and founder in Silicon Valley. He was 1st PM at Grove Collaborative which IPO’d earlier this year, VP of Product at Apto, and he’s currently working on his new startup, Middle Mile. On this episode, we cover terrible PM interview practices, the key fundamentals of hiring you need to follow, how to ask behavioral questions the right way, making good PM assignments, and how to build your resume like a pro.
Unfortunately, the product management interview process at most companies is poor. Navigating the interview process, or creating a good one at your company is a tall task.

In this wide-ranging interview we cover both perspectives to help you think about both the perspective of the interviewer and the interviewee.

For the interviewer:
  • If you know you'll be hiring down the road, start planning now. Think about the skills you want, the values you want, and the process you'll follow. 
  • Interviewing is a skill. Spend time reading and learning how to do it well. 
  • It's much easier to create your interview plan in small, incremental steps leading up to when you need them than being buried, desperately needing help and spread too thin.
  • Avoid puzzles, brain teasers, and hypothetical situations that are nothing like the job they'd have. Research shows it has no bearing on evaluating candidates effectively.
  • If you're going to make an assignment, make it:
    • A reasonable time request (a few hours, not days worth of effort)
    • Consistently applied to everyone (don't give one person a day and someone else 2 weeks)
    • Involves what the job would really include. (Willis's example is a plan after an experiment / launch fails) 
    • Extremely clear what you'll evaluate them on and what you will not. (Like whether you care about design or format)
  • Be proactive in communicating with your recruiting team. Enlist their help and expertise to find & close great candidates.
  • Remember that hiring the wrong person is extremely expensive in time wasted by your team, cost on your budget, and setbacks on your projects. 

For the interviewee:
  • Make your resume succinct and include data & numbers as much as covering skills and actions
  • If you do not have numbers now, start working on it now. Get in the habit to look up numbers and see what work you did has moved the needle.
  • Your resume becomes talking points and great questions in the interview.
  • Prepare good questions to ask an interviewee to make sure the company does the kind of product management you like doing.
  • Reflect on your current job regularly. Willis recommends weekly journaling on subjects like:
    • What wins have you had recently? What happened?
    • What did you learn from a project that recently didn't go well?
    • What do you enjoy about your work and want future jobs to also offer you? 
    • What's changed over time in my notes?

Helpful links mentioned in this episode:

Learn more and connect with Willis Jackson

Learn more and connect with Jason Evanish:

Topics covered with timestamps:

(0:44) - Introducing Willis Jackson 
(2:18) - The different types of Product Management and how they affect interviews
(8:09) - How would you recommend a PM build up their hiring and interview skillset?
(12:30) - What resources would you recommend to learn how to do this well?
(17:15) - What are your thoughts on some of the ridiculous hypothetical questions we’ve seen in this industry?
(26:51) - The importance of networking, reputation and interviewing stories
(38:33) - What have you seen specific to assignments for candidates?
(52:43) - How do you feel about discussing company-specific problems with candidates?
(59:13) - How do you look at candidate resumes and how would you recommend people craft their resume?
(1:13:41) - As an interviewer, how can you signal what you’re looking for from a candidate?
(1:22:45) - How can a candidate figure out and advertise what they do and don’t love to do in Product Management?
(1:28:21) - Final thoughts 
The Harsh Truth of Interviewing & Hiring Product Managers w/ Willis Jackson, Founder of Middle Mile and former 1st PM at Grove Collaborative
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