Lessons Learned from 230 interviews

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Today’s read time: 27 mins

Over 9 months (October 2022 - July 2023), I completed 230 interviews and 8 presentations across 75 companies.

Many people have asked about my experience and learnings so here they are, written as a letter to my former self. In essence, it’s the guidance I wish I could’ve had.

While I can’t promise this advice will land you your next job, it may help you understand the confusion and navigate the turbulence.

Here’s what I’d tell myself:

You were just laid off for the first time. While the embarrassment and fear you feel right now is normal, you better own it and get over it quickly.

If you don’t, you’re going to squirm every time someone asks you, “so, what has you looking for your next role?” That question will become your least favorite question and, unfortunately, the most common one you’re asked. If you stay in the embarrassment and fear, dread will carve itself through your body even in anticipation of being asked.

At first, you won’t even notice the subtle ways you’ll try to dance around it - “Hmm, yeah six years there. “Uhh, yeah, mutual, mutual, for sure.” “Uhh, next adventure.” With each skirt, that embarrassment and fear will seep deeper-and-deeper into your subconscious.

It’ll take weeks for you to recognize that the reason things seem off is because you’re not looking truth directly in the eye.

I’m here to tell you, though: you don’t need to wait weeks to look it in the eye. You can confront it and immediately own what happened. Once you do, you get to choose how to see it and make sense of it. For example:

• Instead of seeing it as you being laid off, you can see it as your role being eliminated.

• Instead of seeing it as an indictment on your value, you can see it as an indictment on challenging market realities and sub-optimal business decisions. 

• Instead of feeling embarrassed in isolation, you can feel shared compassion for the thousands of other (tech) workers who were laid off.

• Instead of seeing it as a situation that happened to you, you can see it as one that happened for you.

• Instead of fearing prospective employers will view you less desirably, you can see this moment as a chance to be viewed more desirable by building (and showing) resilience and grit.

• Instead of hiding from what you’re most insecure about, you can openly and eagerly shine the light on it.

You might find that what appears to be a shadow is actually a ray of light. Once you confidently own your reality, watch it spill positively into other areas of your life.

We don’t experience “objective” life; we experience the life our minds project. In other words, our life is what our minds focus on so be extremely cognizant.

For example, are you envisioning your interviews going well or tanking? Are you thinking about your amazing qualities or ruminating on areas you might lack? Are you operating from a not enough mindset?

And, fundamentally, are you seeing interview questions as an interrogation or as an opportunity to reinforce your experience, skills, knowledge, mindset, interests, etc.?

Do this, if nothing else. Simply switch two words - adopt an “I am” mindset instead of an “am I?”  mindset with respect to your worthiness, qualifications, and capabilities. Work to maintain it, especially when things aren’t going the way you envision because it’ll seem that way for months. Create within you a confidence unshakable to the events happening outside of you.

Your mind produces 40,000+ thoughts each day, many barely registering conscious levels. While you certainly can’t change all of them all, you can change some. Everyone else close to you believes in you. You need to, too. 

You’ll be asked 50 shades of the same question, “what do you offer us?”

Remember: nobody is going to make this case for you. I mean, you’re mostly talking to strangers who glanced at your resume for 30 seconds (or not). They have no clarity or conviction as to what you’re capable of.

So whether you like it or not, an interview is a sales pitch and the product is you.

To pitch effectively, you need to know your differentiators. Unfortunately, that’s hard to do. For example, have you ever noticed we don’t even really know how we do the things that we do best? It really is a life-long journey to discover our gifts and we can’t really do it ourselves.

Fortunately, you have a variety of tools to help you get on it. Remember when you emailed 20 friends and former classmates and asked what your unique gifts are? Remember that Strengths Finder exercise? Remember that leadership training survey when you first became a manager? You have a ton of ammo.

Go bucket all that qualitative information into themes and position them within the context of the company and the role. Who cares if most skills would be labeled “soft” skills by the world? They’re human skills, and they’re the ones that matter most in 21st century work environments. Lean fully into them.

Also, broaden the definition of “strengths” and “skills”. As Kevin Kelly astutely points out, “at your funeral, nobody will talk about your achievements, they’ll talk about what kind of person you were while you were achieving.”

So, it’s not just what you did or what you can do; it’s also about how you maneuver in the world and how you impact others. Clarify and articulate your unique mindsets, values, interests, and personality traits. After all, those are all showing up to the table with you.

“Know thy gifts.”

-Me and/or maybe someone like Shakespeare or Seneca, though unconfirmed

Unlike a funeral, an interview is one place where your achievements will be discussed. It’s time to provide evidence you’ve put those unique gifts to use!

First things first, remember the successful things you’ve done. That log of milestones and wins you kept from your last two jobs? Clutch. Now look across it and ask yourself:

• When did I deliver phenomenal results?

• When did I crush expectations?

• Where did I add 10x value?

• When did I innovate?

Choose, say, 6-8 of those examples or stories and write out your answers using the STAR format. When you get to “A” (actions), be specific on the actions you took to drive impact. Think about what you did compared to, say, what someone else in the same position might’ve done (or not done). Every aspect of your example ought to convey a sense of impact, contribution, and value. These examples will likely cover 80% of the “tell me about a time you …” questions you’ll be asked.

Remember, too, interviews are words. It’s not what you did, it’s how you convey what you did. You’ll be tempted to think you can wing this part but you can’t. Plus, the best performances are when the presenter has prepared so deeply as to give off the appearance of winging it. That’s your aim, though it’ll take time.

Admittedly, you’ll be way off at first; saying things like “I was blessed to be promoted to lead our team of customer success managers!” You said nothing there about why you got promoted or what impact you had. Maintain a keen eye for improvement and you’ll end up with this much better version:

Similarly, at first you’ll blankly say, “Oh yeah, as a CSM I worked a ton with data!”. A sleepy and hollow version compared to this later description:

Okay, you get it: find and articulate the damn words. 

After 3-6 months people around you will say, “You must be so good at interviewing!” Sure, practice might make perfect. Or, as they say in golf, it might make permanent, by reinforcing the same mistakes or ineffective patterns. The difference lies in the degree to which you continually learn, pay attention to what works and doesn’t, and tweak your approach. You’re your own coach; it’s fully up to you.

Clear communication requires clear thinking and clear thinking requires clear writing. Write out your specific actions, focus on your impact, and continuously improve.

What we can do seems astronomically more relevant than what we can’t. Oddly enough, though, interviews are one place where people tend to explore and latch onto what we can’t do.

Most advice about weaknesses says to focus on how you compensate for and/or improve on them. Meh. Yes, you need to be aware of them so, sure, think about the critical criticisms you’ve received in the past.

Beyond that, though, my advice is to change your relationship with your “bugs”; to, again, see them differently.

Here are two ways to do that:

1. See that, perhaps, a bug isn’t an inherent weakness but instead results from a strength being throttled up too far

Too much of anything comes with a downside. For example, while you strongly value people’s strengths and advocate for your teams, when taken too far it can sometimes put you in a difficult position when demanding excellence or addressing performance issues. Strengths and weaknesses are two sides of the same coin. The ol’ yin-and-yang.

2. See that, perhaps, a bug is itself a strength

In other words, how might those past criticisms actually have been misconceptions? For example, you’ve heard you’re occasionally slow to make decisions. What if, actually, it’s that you’re a creative problem solver? That you’re uniquely able to gather and understand multiple perspectives and you’re skilled at ensuring the right problem is being solved? Or that you’ve heard you’re too laid back, especially with executives. However, what if that demeanor enables you to disarm others, connect authentically, and build trust more quickly? And what i you’re able to read rooms and throttle that light-heartedness up or down depending on the energy you perceive?

By thinking about our so-called criticisms, flaws, and weaknesses in a more comprehensive, nuanced way, you can see the ways in which your bugs may actually be beneficial.

I talked earlier about the not enough mindset and here I want to share that “not knowing” something can also be a feature! It enables you to see things with fresh eyes and notice and question long-accepted assumptions. You’re less shackled to previous experiences, beliefs, and conclusions.

Plus, the world is changing so rapidly that much of what we currently “know” may be outdated soon. The problem with “knowing” is that when we think we already know, our curiosity plummets and so we never find out what needs to be updated. And, really, life is a never-ending series of updating what we know.

Lean into situations where you might not know and remember: nobody else actually knows either, whether they’re talking about your supposed weaknesses or, actually, well, anything!

2,000 words advising you how to tell your story and now I’m telling you to let go of it. Huh?

See, you’ll work on, communicate, and reinforce the “Phil Weiss career story” so many times you might be tempted to think it’s real when, in actuality, it’s a complete fiction; a creation of your ego.

As any buddhist would tell you, there’s no “self” generating thoughts or sensations. What we call “self”, Tara Brach explains, is actually a “series of thoughts and patterns of behavior that we’ve drawn together to create a story about a personal, individual entity that has continuity through time.”

Okay, you might be wondering, why is this important to recognize? Because the moment you decide ‘this is my story’ is the moment you stop learning about yourself. The moment you say “this is who I am” is the moment you’ve wrapped your identity up in your story and made yourself more rigid and less open to emerging ways of seeing yourself.

We hardly even notice we do this. For example, when you say “I hate mushrooms”, you tell the story of a self who has a fixed mindset of hating mushrooms through time. Just by simply adding today - “I hate mushrooms today” - you maintain an openness to changing your mind in the future.

A silly example, perhaps, but it points to the need to avoid creating and holding onto such fixed professional stories and identities - in this case, related to healthcare, innovation, customer success, management, startups, etc. How you’ll think and act in the future won’t resemble today, just like today doesn’t resemble the past. After all, not a single moment of our experience stays steady.

You need to hold your career story lightly, especially after hundreds of repetitions.

As someone who’s constantly on the search for questions to shake our mental snow globes, these interviews will be an ideal playground. Of the hundreds of questions you’ll be asked, a few will stay with you weeks later. Here are some:

• [For each of your last 2 jobs] On a scale of 1-10, how would your previous manager rate your work? If less than 10 what would s/he say it would’ve taken for your work to be a 10?

• What’s the biggest misconception people have about you?

• [At the end] What question haven’t I asked that I should and why?

• What was your costliest mistake and what’d you learn?

• Who were your best hires and worst hires and why?

• Who do you admire most and why?

Also, as you know, questions aren’t just a one-way-street; they help you learn about the company, team, role, etc. They’re also an important proxy as they signal to the interviewer how curious you are and what you’re curious about. As Voltaire said, “judge a man by his questions rather than by his answers.”

That said, get used to having a measly 5 minutes at the end to ask them! Due to their breadth and open-endedness, here are 3 I found to be valuable buzzer-beating questions:

• What are, say, the 2 most important things you think I need to know about either the role, team, company, or your customers?

• What’s on your whiteboard for the next 3-6 months?

• What’s your #1 piece of advice for me if I were to come into this role?

Another useful approach - especially when there’s a lot more you want to understand - is, instead of picking only one question, use the last few minutes to rattle off your 5-6 burning questions. You’ll maximally signal your curiosity and, sometimes, too, the interviewer will offer to set up more time. Like all aspects of this season, take full advantage!

You’re going to encounter a ton of great practices and approaches. Here are some you’ll want to take with you:

• The recruiter who shares valuable feedback through the process, including the concerns she’s heard from the team. That truth is valuable.

• The recruiter who texts you encouragement before your case study presentation. Authentic advocacy is a breath of fresh air.

• The interviewer who ignores your resume to avoid preconceived notions and instead asks you to share your story without mentioning anything on my resume. Who we are as humans > who we are as skill sets.

• A two-hour career deep-dive with a hiring manager that’ll turn out to be 60% interview and 40% therapy as you learn about yourself in the process. Answering questions you hadn’t thought about before is the path to insight.

• When actions actually match the all-too-easy to mutter “I want this to feel like a two-way conversation” sentiment. Unfortunately rare, yet incredibly fruitful to interview a company.

• Short writing assignments, especially early in the process, that gauge your ability to synthesize, distill, and communicate. It’s nice when there’s space to provide thoughtful answers as opposed to just reflexive ones.

• Speaking of thoughtful answers, mock presentations are often cringy. They don’t have to be, though! What you’ll find works 10x better is simulating an internal prep meeting as opposed to a mock client meeting. Here, you’ll walk interviewers through a client presentation and your rationale (e.g. “here’s where I’d cover data insights, what I would highlight, how I’d show it, why I’ve crafted it that way, etc.”). Interviewers ask 'how would you handle XYZ?' as opposed to asking it as a fake client and it becomes an actual dialogue. This approach reduces stuffiness and awkwardness and interviewers can actually ascertain how you think as opposed to how you perform improv.

You’re also going to run into some wacky practices so, one, prepare your mind for them and, two, leave them far behind. Here are four:

• The company whose auto-rejection email will say, “it was great getting to know you!” even though you won’t actually speak with anyone. More broadly, get ready for algorithm rejection!

• The company who, following 6 interviews, a case presentation, and references calls, ghosts you. Ironic that the company itself is in the recruiting business!

• The company that moves you forward to the presentation stage then back-tracks as they re-configure their interview process on the fly.

• The company that says “we just need you to meet this one more person” 4 times, ending with a tally of 11 interviews.

Lastly, you’ll identify 4 key questions to work through in order to thrive in this season:

1. To what degree can you develop equanimity?

The ups-and-downs of even a short job search can be extreme so think about what a 9 month search will be like. Avoid getting too high or too low during the journey. A call goes great? Cool, onto the next one. A call goes terribly? Cool, onto the next one. Keep your expectations high but your hopes low. While a few situations will test you, remember the half-life of a strong emotion is seconds, not days. Avoid the emotional roller-coaster.

2. How peaceful can you be even while the “I need a job” problem remains unsolved?

To borrow from the Stoics, this season is a test from life. You can’t put happiness, peace, and relaxation on the back-burner, making it dependent on landing a job. That’s yet another example of the “once I” mindset - "Once I a job, then I can relax.” Once you land a job, there will be a variety of other stresses - heck, likely from the job itself.

See that happiness, peace, and relaxation are available right now, even as you navigate through this challenging period.

You can’t make your well-being dependent on things outside of you. Life’s guaranteed to keep throwing curveballs at you; it’s simply a matter of what and when. This one’s a trial run and how you handle it sets the tone for your future self. This period of uncertainty is a prime time to build resilience and cultivate a deep, intrinsic source of well-being and contentment.

3. How will you handle a fully blank calendar?

How you fill your days is how you fill your life and, for the first time in years, you have nothing to mandate a loaded calendar.

It won’t be overwhelming for you as long as you follow your curiosities. Your interests across the intersections of your curiosities provide a blank canvas to overlay your abilities and skills. Creating and tinkering with ideas will give you something to hold on to and deeply satisfy your intellectual curiosity and thirst for work.

Plus, without even realizing it, you’ll build a website, create a guide on building team culture, give a talk on customer success in health tech, start a book summary library, launch a newsletter, and write 15+ posts on the intersection of work and well-being. Simply put: keep following your curiosities.

Plus, in the age of the internet, what’s more powerful to show your capabilities - a one page resume or a portfolio of posts, guides, content, etc.? Duh.

4. How will you deal with the unknown?

One of the biggest challenges you’ll face is dealing with the unknown, specifically the channel that informs you when the amount of unknown is decreasing: email.

Email is the place you go to find out whether you’re getting closer to your goal - Did I get an interview? Am I moving forward? Are there meetings to schedule? What’s the latest? You can only know by checking email so you’re going to be tempted to check it a lot. You’re going to struggle with emotional and physical boundaries. You may even become convinced you’re addicted to email.

Regardless, what’s clear is you’re desperately trying to reduce the amount of unknown in your life. All that makes you is human. Two things that'll help considerably are (1) deleting email from your phone and (2) not checking email before noon. An app called Inbox When Ready will help with the latter boundary. Most of all, be as easy as you can to yourself. I mean that about the constant email checking and the experience in general.

With deep love and gratitude,

Your future self

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