Interviewing upwards

People don’t quit bad jobs, they quit bad managers.

– some person on the internet (probably)

I really like my job. I get to spend perhaps an hour with someone before they’ll receive the ability to change that quite a lot. Given my first reaction is resoundingly negative, let’s calmly remove some risk from the situation. Here’s some thoughts in no particular order on being on the interview loop for your own manager, having recently gone through this odd exercise firsthand.

🙏 First, I am so thankful for the folks I asked for advice. While no one I’d asked had directly been in a similar situation, the suggestion to write some things down had tremendous impact to being thoughtful first and anxious second. Y’all listened to my questions, deliberately questioned my anxieties, and provided advice beyond anything I could have asked for. In particular, these two thoughts were the most insightful for me.

📚 My friend Jy asked me to consider what makes a good manager with something along the lines of “Well, what do you want out of working with this person? Write out what you need from a manager.” The simple act of putting thoughts to paper was clarifying. Nothing written was terribly new or novel, but it helped shift perspectives to “look at all the things I don’t like doing that I won’t have to do” and “look at how much I value that work.” It also helped me come up with a couple talking points I wanted to take away from a conversation. The top few were along the lines of

• Attending meetings that don’t scale to be attended by all individual contributors any longer
• Maintaining the “tribal knowledge” that hasn’t been written down (or updated since it changed)
• Prioritizing all the tasks that are both important and not the core job of helping folks try the product out. There’s a lot of things that fall in that category like correlating product feedback across users, building new demos, talking to partners, being on interview loops for neighboring teams, unblocking teammates, etc.
• Political maneuvering I found to be exactly ZERO FUN that one time I made a run at people management - performance reviews, talent calibrations, team responsibilities, expense report reporting, etc.
• … and so on …

🌱 My friend Keith Hoodlet gave another guide point to “build trust from the start, then work backwards with questions”. This helped me think through what’s not on the job description that’s every bit as important. His notes on leadership and staying technical , navigating the challenges and benefits of going between people leadership and leadership as a deeply technical individual contributor, were also incredibly insightful. This helped me work backwards to consider how I’d (attempt to) steer our conversation.

• Can we give each other some space to communicate? How does our conversation flow?
• I try to only “drive” an interview for about half of our time, then let the other person steer the conversation. Where are we going in that time?
• When I push the edge of your technical knowledge, can you say that you don’t know? We’re all human, can’t know it all, and communicating in good faith isn’t as easy as it sounds.

📓 Here’s what I was trying to pull out of these brief conversations when asking somewhat open-ended / story questions.

• Have you done this before? Tell me that story. I’d open by asking about something from that resume and see where we go from there.
• Why people management? There’s a ton of career options that rely on your leadership skills, why this one?¹
• How do you work with other teams? Usually I’d pull on something mentioned before - like product teams or the sales leader or <insert one of many other teams we interact with pre-sales>
• How do you manage downwards? Upwards?
• How does that change based on seniority of those teammates?
• What’s your technical background look like?
• What’s your experience across the public sector verticals?

🪞 Panels and committees can be frustrating and expose your own blind spots. I said “wow, never saw that in this person” way more often than I’d thought. The panelists in other roles all saw different traits from folks. I knew this to be true from being on loops for tons of other folks, but everything seemed a bit more important this time around - almost like the couple roles I’d been the hiring manager for.

🌀 There will always be another opportunity to manage people. The number of exceptionally ambitious young men with zero management experience who were crestfallen by this knowledge was astonishing to me. For real y’all - keep being great at your job. Learn everything you can about the business and people and process around you. You will be actively dodging management opportunities for the rest of your career. 😊

🙅🏻‍♀️ “If strategic doesn’t work out, I’ll apply for the Fed role because I’ve done some Fed deals before.” Multiple people said this to my face … wtf?!² Public sector sales is hard enough without someone in management thinking it’s a good spot to just chill until “something better” opens up for the private sector. Doing a job you don’t like is normal, but most folks would rather work with others who want to be on the ride too.

🤗 I expect to be asked why I’m not in consideration for the manager role above me. There was a massive difference in how folks asked about this. Most were compassionately curious. There were some exceptions though - ranging from awkward to outright condescending. I was judging how tactfully this was navigated.

🤖 The AI recorder bot that joined my interview calls was helpful at a high level, but not much assistance on any individual interview. The notes it generated were lackluster, but verbose. It was more of an edited transcription than notes for later. However, the statistics it provided were actionable and insightful. It was great to see a pair of colors along the video replay time, a summary of how much each person talked, and how often we went back-and-forth in conversation. It also gave a rough words-per-minute metric on how fast each of us were talking. This was useful for pacing conversations, how I trended over time, and how interactive the conversations were.

👐🏼 Professionally, I’m a pretty open networker. I expect to be found on LinkedIn, my website or public talks, etc. Happy to chat about it to a (very small) extent, but let’s not lose focus here. This chat isn’t about me - how do we work together? After a bit, it seems a little weird because the whole point is that I want to hear all about you.

🕵🏻‍♀️ I definitely crawled everyone’s professional network and literally any socials or other public information I could find. I was doing this anyways to help bring on great folks I may not be close to, but it was insightful to see how much this varied across people.

• Do you have a blog or other public work history? Great! I’m digging in.
• I may have done some warm outreach to folks we may have in common to get more of a gut check on what it’s like to work for you.

💗 Lastly, who we are in interviews is probably not who we are working together day to day. Interviews are stressful, awkward, and merely a teeny tiny window to what it’s like to work together. This is both unnerving and hopeful. I’m trying to be hopeful.

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Footnotes

🤖 I’ve had a ton of fun messing with the new AI image tools. This one is a “make this a watercolor” of a photo I’d taken of cornflowers in the garden a few years back.

1. Huge pet peeve of mine - “management” and “leadership” are not synonymous. I’ve had decent managers that had no “leadership” about them and great colleagues that had no formal authority yet wielded influence beyond anyone with folks under them on an org chart. Leadership isn’t defined by your spot on the org chart and management is a job with a façade of authority to it. Sometimes the two overlap, sometimes they don’t. 😊 ↩

2. FWIW, none of the folks expressing this sort of opinion were hired for either role. I’m grateful that that feeling towards an oft-maligned vertical was expressed early and wish those folks all the best. 💌 ↩