How to answer the most important question in any Customer Success interview

The recruiter was kind. He explained that they liked to do things a little differently than a typical tech interview; instead of pre-written questions, they dedicated 45 minutes to one open-ended question.

“Tell me your story.”

At first I was psyched at such a simple prompt. I hated those typical “tell me about a time” interview questions — both asking them and answering them. I always longed for interviews that let me turn it into a conversation, not an interrogation. This was exactly what I’d always wanted — my question to stumble or shine.

A few minutes in, I realized I was in trouble. It’s an easy prompt — deceptively easy.

And now I was babbling for way too long about a job I left 2 years ago.

I started to panic as my story slipped away from me, and by the last 5 minutes I still had way too much to cover. I knew I was doomed.

Needless to say, I didn’t get the job.

All the mistakes I made in that interview can be traced back to one decision: I didn’t properly prepare. It’s a question any interviewer could ask — and one that most would — yet I had never sat down to write out a coherent narrative. I had never considered how I wanted to represent myself, what I wanted to be sure to cover.

I learned from this experience to not just write out my thoughts ahead of time, but to structure them so that I am representing myself well, so that I am tying my history to the company’s needs. I learned that answering this question well set the tone for the interview and my hiring experience.

It’s been years now, and I’ve been on the other side of the interview, seeing too many candidates make my same mistake over and over, and frankly, I’m tired of seeing it. Once I figured out how to answer this question, it unlocked a lot of opportunity in my career, and I hope it can do the same for you.

Pre-Write Exercise

First, before we dive in, I recommend you do an exercise.

Open a Google Doc or take out a blank sheet of paper, take five minutes and write out your career story. Write out what you think a recruiter would expect to hear, what you think makes you look like a successful candidate.

Try to do this before going through the rest of this article for the best results — I want you to get your instincts and your voice onto paper first, without my influence.

The goal here is to give you a first draft — so that when you are ready to apply the framework, you are editing, not crafting.

Ready? Let’s dive in.

The Your Story Framework

The Framework is 3 parts:

• Hook

• 2 Roles, 2 Wins

• Connect the Dots

Each part is best prepared individually, and then put together to form a smart, confident answer.

Each part has exploratory questions and examples to help you define it for yourself.

Hook

The goal of the Hook is to immediately engage your interviewer, to give them something memorable to associate with you, and to define who you are, by something other than paraphrasing your resume.

That’s not to say that your hook can’t include your work experience, but it shouldn’t be about what you’ve done, but who you are, what you’re about. You want to define you, before they can define you.

Consider your audience. How you develop your hook is going to depend on the type of company you’re applying to and what they stand for.

Look at the founders and executives for an idea of what the culture will be like. Some founders like to position themselves as Thought Leaders in their industry, or in the SaaS industry in general. You can find their writing or talks and draw from the way they define themselves as inspiration. Thought Leader execs attract and hire Thought Leader senior and mid-level leadership, who tend to attract and hire Thought Leader employees. If you find yourself interviewing for a company like this, you want your hook to be opinionated, philosophical — take a stand (that aligns with their stands!) and speak to the industry, rather than achievements.

On the opposite end of the spectrum, execs that don’t make a lot of noise online may indicate a different kind of culture, likely valuing experience and skillset over presentation. In an interview with this kind of company, you want to be practical, tactical. Getting into the “theory” is probably not going to impress the hiring team.

Basically, you want to know what kind of person they are looking for and make sure that’s reflected in your story.

A great hook invites questions. Think about a way to describe yourself that would invite questions. This shouldn’t be bullshit: you’ll want to be prepared to go deeper, with specific examples of how, what and why.

Hooks I’ve really loved as an interviewer are ones that highlight something unique and memorable and make me want to ask questions: How did a financial investigator become a CSM? Please tell me more about the dog rescue you founded, or your swordfighting hobby! As an interviewer, there’s value in watching someone talk about what lights them up, and it helps me remember them after weeks full of interviews.

But if you don’t have some interesting and unique personal detail, that’s ok — I don’t! A hook I’ve personally had great success with is: “I consider myself a builder, here’s some examples of what I’ve built.” This works for me because:

• it’s true;

• it speaks to what I’ve done but also what I’m looking for;

• I am most often applying to startups, where they value a building skillset.

You don’t need a different hook for every interview. You can prepare a baseline hook, and adapt it as needed, as you do more research.

You can also prepare a few different hooks, and pick which one makes the most sense ahead of your specific interview. I’d recommend having something that works for each of these categories (and some can overlap!):

• something very professional, for more buttoned up companies;

• something fun, for more casual companies;

• something that is very philosophically-focused;

• something that is very practical and achievement-oriented.

Questions to help you develop your hook:

• What’s a unifying principle, value, philosophy you work toward?

• What matters to you?

• A pattern you’re particularly proud of? 

• Did you have a unique path to Customer Success?

• Do you have a unique hobby or skill?

• How do you like to brand yourself?

• What books have you read about company culture, the industry, etc that helped shape you?

2 Roles, 2 Wins

The interviewer has already read your resume, maybe multiple times. This not the place to describe what you did in that job day-to-day, but what you achieved. This is where you brag, where you highlight metrics or projects or something to show what you have accomplished. Don’t repeat the bullets on your resume, show that you know what the most important bullets are, and to put them fresh in the interviewer’s mind.

Pick your two most important roles, and 2 wins from each role (so 4 total). Especially if you’ve had a lot of different roles, this rule of thumb helps you keep it simple: speak about the two most important roles on your resume – in most cases that’s your last 2 roles, but you should focus on your 2 most relevant roles — and then highlight 2 wins each.

Keep it simple. This shouldn’t be too long — remember this is one part of one answer to one question, so you want to keep it snappy.

“As a CSM at X, where I retained 95% of my book year over year and launched a customer education series. In my role at Y, I developed the playbook to increase account expansion by 25% and developed a methodology to scale my book from 40 to 75 clients without impact to churn.”

When in doubt, tie it back to the job description. This is the perfect place to pull out similarities to the job you’re applying for, where you make sure to hit keywords from the job description and your application, especially if this is a first round, where they may not be as versed in the role itself, but are looking for specific green flags.

Questions to help you define what to share:

• What 2 roles are the most similar to the role you are applying for?

• What were your biggest quantitative highlights from each role?

• What’s a significant project you worked on?

• What kind of customers did you serve?

• What’s a skill you developed?

Connect the Dots

Connect you and your experience to the job. You want to answer the question “why do you want to work here” before they can ask it. Find a way to explain how your background, and what you are seeking, make you a good fit for them.

Look for language in the job description. Think of interviews like an open book test — they tell you what they want to hear from you, so make sure you’re paying attention. The “What We’re Looking For” section has exactly what you need to say to demonstrate how and why you are the right fit.

Be honest about what you want. There’s a temptation to only focus on what you think the interviewer wants to hear. But there is power is honesty! An interviewer can often sense it, and it helps you weed out roles that you wouldn’t enjoy.

Once, after talking about how I liked to build and get my hands dirty in process, an interviewer told me “We’ve got it all figured out already, we just need someone to execute.” Perfect — it was not a good fit for me!

This is your opportunity to do that — and an added bonus is that it is a sign of confidence to clearly articulate who you are and what you want. You benefit just by stating specifically what you are looking for.

Questions to help you define what to share:

• What key phrases from the job description fit you and your experience?

• Have you done the specific job they are looking for before, and how?

• What kind of environment do you want to work in?

• What matters to you in a job?

• What excites you about this role, in comparison to other roles?

All Together Now

Once you’ve completed the 3 distinct parts, you want to put them all together. They may be perfect as is, or you may want to adjust the language a bit so it flows nicely. But once it’s together, you’re done.

Now, it’s just time to practice. Here’s what I like to do:

• For every interview, I open a Doc and name it “Company Interview Prep.”

• I add in all the questions I want to prep, with “tell me your story” being my first question.

• I don’t copy and paste it from somewhere else, I type it from memory. I find that this helps me answer more naturally, and it becomes easier to recall, because it’s not like I can read from a script for my interview.

• I’ll say it out loud a few times, which helps me catch any awkwardness, feel more confident, but also to commit it to memory.

• If I really want to go the extra mile, I’ll do it a second time, starting with blank sheet and typing my answers from memory.