DEAR STAGE 2: We’re a Series B company scaling our GTM team and trying to evolve our interview process to make sure we’re maximizing time with candidates, getting to decisions faster, and actually screening for the skills we need. How has interviewing or hiring changed in an AI-native world? ~INTERVIEW FATIGUE
DEAR INTERVIEW FATIGUE: Talent is always top of mind, but even more so right now. We’re all feeling the push to find efficiency, drive AI adoption, evaluate our teams and then train, retrain and uplevel. Every board meeting I’ve been in this year has had a variation of this topic - do we have the right people for the next stage of growth? Do we need to change our hiring profile? How should our hiring process evolve?
This week I chatted with Scott Peyser, a Stage 2 LP and Head of Revenue Strategy, Operations and Readiness at Asana. Scott’s team runs RevOps, GTM Excellence, Solutions Engineering and full cycle SMB sales. He’s built and rebuilt sales interview processes at scale, and as we dug into this topic, he was adamant: “the tools may have changed, but the traits that make someone great at this job did not.”
Many people are assuming we need to start again and completely rethink how we hire for an “AI-native team”, but Scott’s push is really to get back to the basics - define the job, be clear in what you are hiring for, understand how you are going to evaluate it and then do that consistently at scale and over time.
I want to share 2 takeaways from our conversation that are particularly actionable - the first about Asana’s interview process and the second about Scott’s interview learnings throughout his career:
1. Define the traits (and what good looks like)
Scott is in the process of revamping the interview process for GTM hiring at Asana. He started by bringing the sales leaders together for a whiteboard exercise: each leader listed everything their best sellers do well and generated a list of about 45 items total. Then everyone marked their top 5. The lists converged on five qualities:
Curiosity and questioning
Grit and accountability
GM mindset
Resourcefulness
Business acumen
With a short, specific list everyone agrees on, the interview process becomes more focused. As Scott puts it: “You can be prescriptive, but if the prescription is wrong, it doesn’t matter.” Once you have the list, you need to take the time to write a shared definition of what good looks like. This work is critical to laying the foundation for a great interview process and candidate evaluation.
If your team isn’t screening for anything specific it’s because nobody ever defined what a strong answer sounds like. When five interviewers each bring their own favorite question with no shared definition of what good looks like, you get (near-total) overlap and almost no signal on the candidate.
Asana also moved to live working prompts. One example: “a customer is at risk and you’ve only sold into a single buying center. How do you triage the risk and expand into a second buying center, live, in the room?” For leadership hires, they hand over a take-home data exercise: here’s our data, we’re planning for 2027, what’s missing, what would you want to make a real structured decision? That puts GM mindset and business acumen under actual pressure, instead of asking for a story about the last time someone showed them.
2. Hiring like Scott
Scott has hired a lot of people in his career and I wanted to hear what has worked for him. Regardless of role or company, Scott personally screens for two things when hiring a new member of his team: intellect and drive. And he has 2 questions he likes to ask every candidate:
“You’ve obviously been really successful. What do you think’s prevented you from being more successful than you’ve already been?” People who point to something internal (a skill gap, a habit, a blind spot) have a shot. People who point to a bad territory or an unsupportive manager don’t. This question is a read on accountability - does the candidate look to internal or external factors? Do they look for things they can control or play victim?
He also asks candidates to imagine the job worked out: “In a couple weeks you’re with family and friends and they ask what you’ll be doing. How do you answer?” People who’ve actually done the work on your company and your market answer specifically. They’ve thought about what the job will entail and can envision themselves doing it. This one really surprised me, but it’s easy to imagine someone going through the motion of an interview process without actually internalizing the work.
This was a very grounding conversation for me because it brought back the basics. I can almost guarantee someone in your interview panel is asking “how do you use AI in your sales process?” as if the answer is a proxy for talent. Yes you want someone who is using AI, but that’s because they are curious and motivated and will use whatever the current tools are available to succeed.
Until next week!