“Tell me about yourself”. Three (surprising) strategies to nailing the one question you can expect.

We all know it’s coming.  The “Tell me about yourself” question you can expect at the beginning of a job interview.  And no matter how much you might plan and practice your answer, it’s hard to find the fine line between natural and prepared that shows that you are an interesting, authentic human with a unique perspective and life experience. 

We’ll leave the effectiveness of the question to another post, but needless to say it’s your big shot to tell your story.  

And yet, I know that whenever I’m playing my answer over in my head I’m more likely to think about the things that I omitted, the slip-ups, and the tangents, than I am to think about how that story sets up the rest of the conversation. 

So we started to think if there were better ways to answer that question and per the Sidekick way thought about ways we could bend the expectations slightly to paint a clearer picture of that question’s intent.

And we came up with three strategies:

1.  Acknowledge the shape of your story - One of the things that any interviewer is looking for off the bat is self-awareness.  Here’s one way you can demonstrate it.  Resumes, LinkedIn profiles, and even the answer to this question sometimes presumes that our life stories occurred in a very linear way.  And we know they don’t.  So call that out!  Be open with the fact that although you took away lessons, life didn’t necessarily turn out as intended.  That’s ok! That makes you human and quite frankly more relatable.  So acknowledge it. Be honest about it.  And notice how the energy of the conversation shifts.

2. Focus on decisions, not accolades - Sometimes in telling our stories we get stuck in the bullets on a resume and not in the space in between.  But what an interviewer is more likely trying to glean in a first question is how you’re thinking.  Your decisions tell that story.  So make that story about why you made certain decisions and what you learned from them.  That’s ultimately how you can show, not tell, an interviewer that you are not only a deep thinker, but also self-aware enough to have integrated your life lessons along the way.

3. Differentiate between your intentions and your experiences - Bringing these first two points together, this question allows you to demonstrate that you are a realist and recognize that even though your decisions came with intentions, that your most rich life experiences exist in the gap between your intentions and your realities.  Shine light on to those experiences.  They often are not on a resume, but they speak to your humanity.  And they’ll paint the most authentic picture of the real story that answers “Tell me about yourself”.

The Best Startup Employee: The Cross-Functional Misfit

At Sidekick we’re always trying to figure out ways to help people tell their stories and to ensure that those stories give insight into people’s potential. 

Oftentimes the people who find the most success working for small companies are individuals who have found their way into their role via a specialty (e.g. product, marketing, engineering, etc.), but soon discover their passions loom larger than their lane. They look for ways to employ their skills to help seamlessly integrate their function into the overall organization. As a result, their ideals find a home in sowing the seeds of their company’s culture.

These ill-defined folks are perfect for a smaller organization looking to scale their team given they have the capability and willingness to wear many hats while also providing functional expertise. After six months (!) of meeting over 150 candidates we’ve learned that this group of people are also looking for tools that can better tell their story when applying to jobs, and we’re finally giving them a name:  cross-functional misfits.  

No matter the audience, when we share that moniker we typically get a knowing smile. In fact, we suspect that a decent number of people working in tech would identify themselves that way. 

We have the privilege of working with these misfits every day, and here are some qualities that tend to stand out:

English to English Translators - They typically find themselves drawn to roles that bridge multiple teams because they like interfacing between different audiences.  They love plugging in to the people side of business and recognize that most business problems are ultimately people problems.  For them, it’s about navigating the different incentives of each functional area and getting their coworkers pointed in the same direction.  They thrive on the challenges that are bound to show up when different incentives collide in shared initiatives.  And they’re exactly the personality type to solve the problem when a situation gets especially tough.

Eyes on the Prize - They’re highly motivated by reaching the end goal and will relish the opportunity to have a say in the overall project direction.  This often manifests when they position themselves on the cusp of different functions, which in turn allows them to communicate through coaching and teaching others about a less-understood side of the problem. They’re most successful when they’re given the responsibility to hit deadlines, prevent scope creep, and create a sense of ownership across different parts of the business.

Cultural Champions - Because they’re typically involved in so many facets of the business, they tend to be the types of employees who become your cultural ambassadors.  Not only are they natural coaches who enjoy the ins and outs of mentorship (and being mentored), but they find themselves in coordination positions because it gives them the opportunity to become better informal managers for the company.  You are also likely to find them stepping up when there’s opportunity to build cultural initiatives and will often jump at the chance to design team-bonding activities.  We’ve heard and like this definition of them but regardless of the words you choose to describe their impact on company culture, you know that you can lean on them to keep spirits high when the moment requires it.

Future Founders - Ultimately, the characteristic that we see most in them is a desire to one day be founders of their own organizations.  Oftentimes in their career they’ve reached a place where they understand how functional areas might operate and connect, but want to go to a business where they can refine their skillset before heading off to their own company.  While it may be counterintuitive to hire someone who’s already thinking about their next gig, if you can promise them a medium-term opportunity to develop them into great entrepreneurs you’ll be getting an employee who not only will be a fan of yours for life, but will have a multiplicative effect on your organization.  Seeing the types of careers that you set up for your previous employees will demonstrate to other employees and applicants that they will learn and grow by being a part of your organization.  So building a business that supports future founders will give you a leg up in attracting the best candidates.

We absolutely love meeting cross-functional misfits at Sidekick because we recognize how hard it is for them to tell their job story.  A unique quirk of our onboarding process is that when we meet candidates we do not look at their LinkedIn profiles ahead of time, meaning that we allow for their career dreams to set the stage for our conversation. Our cross-functional misfit candidates thrive in open-ended environments and our process ensures that their distinct approach to job seeking becomes a highlight of their candidacy.  

Know someone who falls in this category?  Maybe you do?  We’d love to meet you and get you set up for the job ready to serve your professional growth.

Hopeefully these three strategies give you some additional approaches to consider when thinking about this predictable and yet complicated interview question. 

The one interview question worth asking:

Look. This is a weird time to be hiring.  Not only are we facing unpredictable markets and a possible unprecedented (cite Fortune study) downturn in the overall employment market, but companies are adjusting to an indefinite promise of working from home.  Especially now, hiring mistakes and cultural misalignments are more costly than they’ve ever been.

But, as we all know, during conscious-shifting moments opportunity abounds.  Now is exactly the time to be implementing forward-thinking tools and frameworks to attract and hire the best candidates. If you’re hiring right now, you’ve probably noticed your application volume spiking, underscoring how difficult it is to differentiate between resumes that start to look very similar at first pass.

At Sidekick we’ve always ended our interviews with one question to cut through the noise:

“What is something that is often hard for you to communicate about yourself in a first interview, but is key to understanding who you are as a person?”

A knowing smile tends to show up on our candidates’ faces when they hear it.  After all, it’s universal after an interview to feel like you missed communicating something important.  And so our question serves a few purposes all of which are key to the candidate’s experience and normally hard to obtain information:

1. You create permission for them to be themselves - The comedian Chris Rock used to joke that when you’re meeting someone for the first time you’re meeting their representative.  Giving someone permission to address something core to their humanity creates a moment, albeit brief, to step into themselves.  That simple act of permission will give you the chance to hear something from their heart and not their head, because they won’t be thinking about what you want to hear but rather what feels true to them.

2. It humanizes you - No matter how you structure your interview the power dynamic between candidate and company will always be there.  But this question gives you the opportunity to enroll them in a very human experience: it’s hard to tell your story.  By breaking down that power dynamic in a final question you leave them remembering that you made the interview experience as supportive as possible. 

3. They show you what matters to them - Whatever a candidate is drawn towards in regards to their answer will give you some insight into their personal priorities.  If you listen closely, you may get clues into the pitfalls, their key motivations, or even something they’re actively trying to work on about themselves.  However they answer, they’ll give you a unique look into their internal priorities, which ultimately tells you if their priorities will match up with what the role requires.

4. Puts them in control of “the landing” - As much as the job interview is about discovering what makes a candidate tick, it’s ultimately a chance for a candidate to express themselves.  So why not give them the chance to stick their own landing?  You’ll get an unvarnished, unpracticed answer that ultimately gives them the chance to feel good about themselves because whatever they shared feels authentic and true.  Putting that control in their hands, especially at the interview’s close, will leave them feeling ultimately empowered.

There are a million different permutations of how to conduct good job interviews, but we find that the above question is a great one that gets to the core of what drives a candidate at this moment in time.  That information is always important when evaluating someone’s fit and is especially right now as we consider how we build excellent teams.