What do you wish you’d considered before joining a startup?

8 things I wish I’d known before working at my first startup.

Photo courtesy of WOCinTech

Six years ago I was ready for a different work experience. My resume was chock full of traditional administrative positions that paid the bills but held little interest or excitement. After years of managing books and executing other people’s ideas with which I felt no affinity, I was ready for a shift.

I wanted to be deeply connected to my work, work with a product I felt invigorated by, and to be a part of the bustling startup community I had fallen in lust with from my internet spectator seat.

When I was lucky enough to land an interview for a role that fit my-work-at-a-startup objective, I allowed my excitement, assumed good fortune, and some deep rooted personal issues to distract me from taking the time to reflect on if the job was a fit for me.

Scouring the web you’ll find article after article espousing advice to would be founders for consideration before they start up. But a deep search will reveal little from those of us who are not, and do not presently aspire to be, in the founder’s seat. This feels askew to me, especially when you consider the number of team members compared to founders at startups. Let’s change that. I’ve captured here eight considerations I wish I had known back then, but I hope you’ll do more than just consider my learnings — I hope you’ll be inspired to weigh in with what you’ve learned from your experience.


Interviews work both ways.

I was brought up with this idea that once you apply, the only desired outcome was to receive an offer for the job. Period. The idea that the interviewing process also existed for you to evaluate if it was right for you was never mentioned. Even more so, since the entire process of interviewing was about your ability to interview, you would never want to do or say anything that would be potentially risky — like making the interviewer uncomfortable or inviting a level of transparency that might reveal a poor match.

If I’m going to invest my most valuable resource — my time — into something, there is absolutely no reason to skimp on the exploration of what I’m really getting into. Interviews are an opportunity to see how a team and their culture, a product or service, and their practice of working aligns with my interests, aspirations, values, and lifestyle. Every bit as much as it is for a potential employer to evaluate how my skills, aptitude, working style, communication, and motivation match their plans and desired goals.

Me freezing up and pretending to be something I’m not in an effort to crush the interview process serves neither myself nor my future team. If my prospective employer isn’t open to hearing and earnestly responding to my inquiries, do you really think they will do so once I’ve signed the contract?

Know your shit. Own your shit.

I entered my first startup with a powerful, underlying motivation that has taken me years to fully unpack: I could make up for feelings of inadequacy and incompleteness through work. I was not ready to explore, let alone own that part of my shadow the day I first interviewed to join a startup. But I do believe some red flags would have been exposed had I taken a pause in my “I want to work at a startup” drive to review the landscape within me.

Years of self-examination have brought me to a better understanding of my key motivators, values, and core needs.

One of my core values is integrity. At it’s core, integrity for me is being honest and accountable to your word. One of my more tenuous manger relationships was largely due to the fact that he would agree to do things, then not follow through. One day as we were running in circles around this issue again, he told me outright “it just doesn’t matter that much to me to do what I say.”

Since that experience I’ve made it a point to ask any potential manager the question, “Is staying true to your word important to you?” If I receive a response that feels genuine and in line with my values, I go a little further saying, “That’s terrific. Integrity is one of my principal values and a key factor in building a trusting relationship for me. I also know that sometimes things are out of our control and we are unable to follow through. Can you share how you communicate with your team when something like this happens?” The response itself is important, but I also pay close attention to how they react to the question — I want colleagues who aren’t afraid of a little self-inquiry.

I’m not advising that you need to travel a life’s journey before making a career change. Stopping for an hour before you ship off your resume or walk into an interview to review your values, explore your motivations for wanting a position, and review what your needs (beyond compensation) from an employer truly are can be a powerful compass to guide decisions.

If you think this sounds like a great idea but you’re new to a practice of self-inquiry and don’t know where to start, a great guide is the Core Needs Inventory from The Center for Non-Violent Communication. Simply reviewing the list and noting those which resonate with you can be a powerful experience.

Communicate what you need.

Things I work best with:

A clear understanding of company vision.

A clear understanding of how my work fuels the company vision.

An agreed upon framework of how we will evaluate whether my work is successful.

Regular, structured communication on status, wins, failures, and challenges of work.

Agreement that conflict is natural and can be navigated consciously.

Mutual respect that we are all humans having human experiences, and that doesn’t get put on pause just because we cross the office threshold.

Space and support for learning new skills, and personal growth and development work.

Flexible schedule with agreed upon regular periods of complete disconnection.

Access to sunlight. Vitamin D is my soul fuel.

Leadership matters. Immensely.

I’ve had the opportunity to lead and manage teams a few times in my career. Here’s the truth of it: More often than not, I’ve been downright awful at it. The more I share my experiences and have honest, open discussions with other leaders — of both small teams and large companies — the more I know I’m not alone.

Leading others is really, REALLY hard work. And it’s work that many startup founders turned CEOs (particularly first timers) and managers have zero experience, training, or practice with. The leadership learning process can manifest itself in a wide spread of results ranging from hilarious hijinx to violent behavior that reverberates through the entire team.

If you’re going to commit yourself to someone else’s vision, understanding how the leader approaches leadership is indispensable. First and foremost, does the leader have a leadership practice? i.e.- Are they/what are they doing to strengthen their leadership muscle? Do they have a regular practice to evaluate themselves as a leader and cultivate their own personal development?

I also find it prudent to dig in to the following: Do they believe in top down management? Or do they believe in servant leadership? How involved of a manager are they? What leaders and leadership styles do they look up to? Do they believe in transparency? How do they give feedback? How do they receive feedback? How do they empower autonomy?

Mirroring is incredibly valuable.

See also: If possible, get it in writing.

Before my husband Eoin and I walked down the aisle we thought it would be wise to invest up front in sessions with a couples therapist. Why not ask an expert to help us lay the framework for a successful marriage?

It’s probably no surprise that the bulk of our sessions focussed on communication — the cornerstone of any relationship, marital or otherwise. One of the most useful, practical skills she introduced us to was mirroring: the art of recapping back to someone your understanding of what they communicated. It’s a simple, yet incredibly powerful tool to ensure you and your co-communicator remain on the same page.

In the interviewing-recruiting process a lot of information is discussed, promises are made, excitement and optimism is shared. Taking a few moments to speak or, particularly with key issues, put in writing your understanding from conversations can be transformative to the relationship. Imagine building your working relationship knowing you are a literally on the same page. It’s a powerful framework.

Actions speak louder than words.

I was surprised to find that working outside of traditional business hours was regularly expected at a job where during the interview process the hiring manager had emailed back and forth with me on weekends, late nights and holidays. I now pay close attention to time stamps.

A year ago a friend, a talented engineer, was in the late stages of interviewing with a company who asker her to complete a small project as a final test of the interviewing process. It was estimated that the project would take roughly eight hours of her time. When she shared this scenario with me, I was appalled to learn that there had been no offer of compensation for her time investment for the project, as this exercise was unexpected and followed several in person interviews. If someone doesn’t value and respect your time before your start, why would it change once you sign the dotted line?

Research and references are your friends.

Confession: That first startup gig, the one that ended in an epic burnout — I wasn’t the first to leave in distress. In fact, the company had a well known reputation for being challenging to work for and an extremely high turnover rate. I didn’t notice because I didn’t want to notice. I didn’t do the work. I was so attached to the idea that this was my “dream job” that I dare not risk bursting that bubble. I didn’t ask around, I didn’t take a peek on LinkedIn to see what the average employee life cycle was, I pretty much didn’t do anything responsible. It’s behavior that came back to cost me dearly. Take the time to do some quick searches online, put out a few feelers if possible, and genuinely reflect on other people’s experiences. There is no doubt that one man’s nightmare can be another’s nirvana, but fact gathering is just as much about crafting a well-rounded picture as it is about coming to a conclusion.

Be wary of false hope.

See also: equity as compensation is a risky road.

When I was losing my grip on reality burning out at a startup, I would delude myself that all the hard work and suffering would pay out once the company reached the next benchmark of success — moving targets including releases to team growth where work would be be more evenly distributed to profitability to the ultimate achievement: an exit. I was swayed by the siren call of what I now believe to be false hope.

Certainly life and work are rich with examples of working hard + overcoming obstacles = reward. The entire promise of startups is this formula. But it’s been my experience that startups produce a uniquely dangerous breed of hope mongering, where the reward is perpetually just around the corner. The problem is that the corner is in continuous motion and the reward, release, or rest consistently remain just out of grasp, keeping teams trudging forth for months, then years at a stretch.

One of the most common examples of hope mongering I’ve experienced is the overinflated importance placed on equity. When I received my first startup offer, my eyes became platters at the equity line, despite having no clear understanding of how equity, let alone venture capital, actually worked.

It was shortly after that appointment that many of the harsh realities of startups slowly came into focus. What success rates really are— less than 5% — , the hazy lines around how a successful startup is defined(ie- exits and acquisitions are often not good things), and what equity for a #5 or later employee at even a “hugely successful” exit really translates to on pay day. If this paragraph toils your tummy for even a moment, trust me, building knowledge in this area is your friend.

John Greathouse has an excellent, highly pragmatic post for team members to understand their equity that takes you through the mechanics of calculating what your options are really worth. If you’re an employee banking on your equity, even a little, I highly recommend you read it.

I still believe in and operate on hope in every aspect of my life. For me, it’s essential lest I slip into nihilism. But I practice a more measured operation of hope — one that arrives from seeking a clear understanding of facts and experience.


So here you have it, my best lessons earned through years of working in startups. I make no claim to be the expert here, and my experiences are few in retrospect. That’s why I’d love to ask you, The Medium community, to share your wealth of experience and knowledge:

What do you wish you’d considered before joining a startup?