March 8th, 2021David Fleischman

Land the Job with Storytelling

Hi there, I'm David Fleischman and I've been living in the tech world for a long time. As someone who has been helped by a lot of people, I'm always motivated to do the same. I recently moved companies and went through a lot of interviews making this a good opportunity to document the patterns I've seen and used in my processes. As anyone who works with me knows, building learning loops and constantly testing is core to who I am. Successful interviewing, as is the case with just about anything, is about preparing with a strategy and improving every time.

When you're interviewing for a position, you generally are in one of two scenarios:

  1. You need a job and don't have a ton of choice or time. You're graduating soon, or you know you need to switch roles because staying is no longer an option.
  2. You're lucky enough to have a choice. You either are in a great role, but looking, or have a number of possibilities. You're one of the lucky ones, enjoy it!

This article covers the first scenario above but applies to both.

The key to a successful interview is telling a story - your story. Humans are fundamentally driven by narratives and stories. Everyone loves a good story. Positioning yourself often feels like it's about numbers and brand names, but ultimately it boils down to whether HR or the hiring manager believes people at that specific company will want to work with you and if your story adds up.

Think about how you tell your story. Why did you make a move? What did you learn? What do you hope to learn? How do you hope to grow? How to help others? Your LinkedIn profile, CV, and the story should set up this model.

With a few exceptions (engineering roles in particular), everyone invited to interview likely has the skills necessary to qualify for the role. While you are always being measured on skills, you're also being measured on fit. The best way to convince companies you are a fit is to research them well, and understand why your particular story makes you the best candidate for the role.

As a reminder, if you fall in the first bucket and don't have a choice, the first and simplest rule to know is that you love every company you talk to. As the saying goes, beggars can't be choosers and neither can you until you get some competitive offers.

As we're all taught, every good story has a few common elements: a protagonist, an antagonist, a beginning, a middle, and an end. Good interview stories are centered around you as the protagonist and business challenges as the antagonist. You, as the storyteller, must have specific examples of how you grew or learned - how your story has evolved.

Being specific is extremely important. No one would care about Harry Potter the boy who did something and maybe killed someone. We care about the boy who lived who transformed from a lonely orphan to a giving hero who laid it all on the line for friends and family he met on his journey.

Nobody cares that I just worked at Microsoft, they want to know what I did and how I learned. My answer is always that I started off so junior that I didn't have a job title that matched. However, I did everything nobody else wanted to do with a smile on my face and learned from those around me. Today, I'm comfortable at all levels of an organization as that experience taught me empathy.

The same is true for interview candidates. No one cares about that guy who maybe learned something from his school club, they care about the candidate with the amazing story. This is not to say that you need to drone on for hours - every story needs to have tangible results. If you were an individual contributor, that boils down to statements like "I achieved this." If you were a manager, it's all about what your team achieved together. Turning around a failing flight business at Expedia, along with describing the learnings and failures along the way is much more interesting than just showing numbers. Speak honestly on openly.

Teaching you how to tell your story is impossible. Your story is yours and you're the author. If there is interest in this concept, we can spend more time detailing the techniques involved. Until then, there are some tips below on general interviewing.

As a good storyteller, it is important to read the room. Regardless of whether you're in an in-person interview or remote interview, you want to confirm that you answered the given question. Simply asking, "Did that answer your question?" should be sufficient.

Asking questions like this shows a sense of humility that can go a long way in interview processes. It is a good way to engage the room and more importantly stop yourself from talking so much that the interviewer has to interrupt you to ask more questions. A good interview is part skill assessment and part conversation. This technique builds in the "breaks" to facilitate that conversation.

One of the best ways to stand out from other interviewees is to be genuinely curious and inquisitive during the interview. People love talking about themselves, and getting a recruiter or hiring manager to open up is a strong way to build rapport. Asking about their experiences at the company, their careers, or how they might solve a problem engages interviewers in purely human activity; expressing themselves. You can then build on that conversation to create connections.

LinkedIn stalking is good. Find out what you can about your interviewer and bring up any people you might know in common or shared interests. This connects you with your audience.

Something you can do early on to help with crafting your story and questions is to ask the recruiter what they're looking for beyond the job descriptions. Oftentimes, job descriptions will have skills they're looking for but won't list if they need a strong individual contributor or aggressive leader to turn around a team.

Having this information allows you to craft your approach and to tease out more of the company culture. Good recruiters and hiring managers will tell you a lot at these moments.

As you become more senior in your field, it's less likely that companies are hiring senior managers because everything is going really well. They're usually hiring because they need a leader to turn around a situation, and understanding that context can be key for your interviewing process.

When interviewing there are also some easy to follow ground rules:

  • Never speak poorly about a previous employer - not only does this set a bad tone for the interview, but it also reflects poorly on you. Instead, talk about what you learned from the role and how you grew as a contributor or manager. There are a ton of lessons if failure. Lean into those. A great phrase to use when asked why you're looking; I've learned a lot and I'm grateful for the experiences, but I've decided I want to learn insert your story here.

    Not everything has to be professional rationale either. Sometimes it can be personal reasons such as family or change of interest. For example, when I left my role at Apple, on paper it made no sense. The iPhone was amazing, I had a great role and Apple was growing really fast. For years, everyone I spoke with asked me why in the world would I leave Apple with a super skeptical tone - searching for the "bad." My answer was honest, simple, and personal. I loved working at Apple (true story) but my family was really unhappy with our living situation so I put them first. The answer builds trust and shows humanity.

  • Do not bring up compensation early in the conversation - while compensation is obviously an important factor to any job search, potential employers do not want to feel like that's your primary motivation. Remember, you have a story about why the company is a perfect fit for you, and that story usually revolves around other factors than compensation. There's plenty of time to discuss compensation later in the process.

  • Send thank you emails within the day - this should be table stakes to any interview, so don't be one of the candidates that forget. Ideally, each thank you note should contain something specific to the interview that will help them remember you as a candidate. If you had a really strong story, this is where you tie it into your email to leave a lasting impression. If you can't get to the folks who interviewed you, at least send a thank you to the recruiter and ask them to thank the team.

If you use these tools, you'll have a stronger chance of getting the position you're interviewing for, or worst case, you've learned to be better. If you're lucky enough to have the luxury of choice, you'll need to have a framework for how to evaluate them. I talk about that in part 2 of my interview series, which will be out soon.

Ready To Get Started?

David Fleischman

David is the VP of Product at Compass. He has an extensive career in tech and was one of many program managers for the iPhone.

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