Iterative Interviewing: Hard-Earned Lessons from the Job-Hunting Trail

The same concept applies to job searches and interviewing.

This is also closely related to the idea of “Always Be Interviewing“:  Product leaders learn and grow with each experience, leading to a better eventual outcome.  So, interviewing more often leads to more iterations, which means quicker evolution, right?

With that in mind, I would like to share some hard-earned interviewing lessons that can hopefully spare you some cycles:

It’s Good to Have Friends
We all know the dismay and disappointment at spending lots of time creating a really nice customized resume and cover letter for a specific role… and then never hearing anything from the company.  It’s the curse of LinkedIn’s “Easy Apply” – it creates a torrent of job applications that makes it really hard for recruiters to find your needle in the haystack.

Lesson Learned: It’s not just about the numbers, it’s about the network.  Friends and former colleagues can be an awesome resource during your job-hunting endeavor.  This is where LinkedIn and your professional network can be the difference between getting noticed and silence…  With just a few exceptions (see “old frenemies” below), I have found that reaching out to former colleagues and friends is THE.MOST.IMPORTANT.WAY to get a conversation started.  I would like to also use this moment to say THANK YOU to all the friends who have helped in the past and are helping now!
 

Energy and Caffeine
I went into an onsite interview last year fired up and ready to explore how I could help a local software company move things forward in their product management team.  The interview room included the head of engineering, the recruiter, and their strategy leader.  After going through the standard questions “How do you prioritize the roadmap?” etc., I was in the room alone with the recruiter.  This is the part where I should mention that I’m an energetic person (and I’m part Italian)- I get excited when I’m talking about something I’m passionate about, such as product management!  As we spoke, I actually fell out of my chair because I was so dramatic with my gestures.
Lesson learned: If you are naturally full of energy, do not also caffeinate yourself! 
(I had quickly finished off a Mtn Dew Voltage soda (with ginseng!) before walking into the interview)

I recently got to late-stage interviews for a product marketing opportunity.  I had some great conversations with the hiring manager – we built a really good rapport.  I knew they wanted to fill this position quickly, and I was eager to help.  So eager that I rushed to interview in person early in the morning after a late-night flight back from one of the industry’s biggest tradeshows (which is in itself an exhilarating and exhausting time).  Long and short: The “cold open” interview was with one of the key people in the company, and they did not seem to be in a particularly good mood.  Unfortunately, with my jet lag, I wasn’t able to pivot the way I would normally and stumbled a bit.  This killed off an opportunity that I still think would’ve been a great fit.  In the end, there wasn’t a rush: It took them a few months to eventually fill the position.
Lesson learned: Don’t rush things – if it’s meant to be, it’s meant to be – interview when you are at 100%.

Old Frenemies Sometimes Should Stay Old Frenemies

Though I have lived in 14+ places in my life, my key formative experiences were in the Midwest:  I trust people. I see the good in people. I am optimistic (think Ted Lasso).  I recently went further into the interview cycle for a product marketing role with a company that SEEMED to be a great fit.  They had a local office, they seemed to have the need for someone with my background, I had a nice opening discussion with the hiring manager, etc.  A “bonus” was that some of the key people in the company were former colleagues from way back in my career.  That being said, one of these former colleagues seems to have a grudge that they just can’t get over.  I think it all comes from an episode 20+ years ago when I was selected for an internal transfer that they also applied for.  That seems to have led to years of quiet animosity and, now, even passive aggressiveness.  I’m pretty sure that they sabotaged this opportunity.  Not everyone is from the Midwest, I guess.
Lesson Learned: Some people will never change.  It’s a big world out there and sometimes it’s best to just avoid people with negative energy.

 

Don’t Go First
I was recently in a group interview with two potential colleagues.  Once we all got on the web meeting, we all looked at each other “Who should go first?”.  This was apparently their first group interview during this cycle.  I was eager and enthusiastic so I just jumped forward to introduce myself.  However, as I started speaking, I realized I wasn’t sure if I should just stick to a professional introduction, or give a little more about my personal life.  I ended up jumping back and forth and the result was a little awkward – Not a great start to a late-round interview.  
Lesson Learned:  Let others talk first, especially in group interviews.  It helps take the nervous edge off to first learn more about the other people.  Also, “mirroring” is a thing: Sometimes it’s best to get the read on the other people in the room before jumping forward so that you can match their demeanor.  Finally, letting others go first means you have an opportunity to find potential connection points based on their introductions.  

 

A few years ago, a friendly connection at a venture capital firm put me in touch with a key hiring manager at one of their local portfolio companies.  I did a ton of research on the ~20-person company and its industry and built a whole business case that introduced the product marketing function into their organization.  The problem?  The trajectory of the company was in the wrong direction: Even with a great business case, they simply were not in a position to hire me then, and they ended up closing their doors within the next year or so.  Though it would have been great to land the job at that time, it would’ve been a short stint.
Lesson Learned: When on the job market, finding the next job can seem like the #1 top priority.  However, it’s really about finding the right fit.  It’s important to understand the overall direction of the company before investing too much in aligning with its future.

Finally:

I recently had a great set of interviews with a company and a product role that were aligned on so many levels with my experiences.  From my perspective, it was hot and heavy: In just one short week, the hiring manager meetings went really well, and then moved to an interview with the wider marketing team.  I was really excited about this possibility.  I even learned that I was the first candidate to progress as far as I did through the interviewing process.  Then it suddenly went silent… days went by and it turned into almost a week.  Inspired by my son’s recent (and successful!) medical school admissions process, I drafted a “Letter of Intent” about how interested I was in the role and how I felt it totally aligned with my background and my career goals.  Then, after thinking more about it, I decided to NOT send the note.  I didn’t want to be overbearing or too pushy, so I kept the draft letter to myself.  Long and short, I then got the call from the recruiter a few days later that said the team really had lots of positives about me, they just needed to make a choice and, though close, went with a different candidate.  The haunting words were “They want to free me to pursue other opportunities”.  In retrospect, I may have been too cool and coy: I don’t think they quite knew that THIS was my dream job!
Lesson Learned: To quote Billy Joel: “Tell her about it!” If there’s really a strong fit, it’s okay to let them know how much you would love to move forward.  Of course, don’t be overbearing, but, when it is really close, I think it’s also important to lay it on the table and share how excited you are.  Looking back, would you rather say to yourself: “If only?” or “I put it all out there”?  After years of the job market being in favor of workers, perhaps employers would like to feel a little love, too?

 

What do you think? 
What hard-earned lessons have you learned from interviewing?