Interested in joining a startup? There’s a couple things you need to know first.
Startups are hard. Working at a startup is equal parts addicting, rewarding, frustrating, and confusing. I should know, I’ve worked in senior roles at four different startups over the course of about five years and have some insight that should help you on your way whether you’ve been retrenched because of the pandemic or just looking for a change.
1. Can you thrive in chaos but work towards structure?
For those coming from a more rigid, already highly organized and segmented work background, the idea of the freedom and chaos of a startup can sound exciting and liberating. It is, but it comes at a cost. If you’re coming in as a leader you must be prepared to embrace chaos and have a plan to implement structure and process that can scale.
If you’re coming in at a junior level, you need to believe in and trust that your leaders have this plan and are providing you with goals along with the ability to explore what works within the framework of the brand mission.
Regardless, you won’t always know what you’re supposed to do and you need to be proactive and constantly experiment to succeed.
2. The people involved early ARE the company culture
Lets say the startup you’re considering joining is 10 – 20 people. The entire team is handpicked by a few people. The company “culture” is only as defined as that small group of people have made it, whether they’ve been around for six months or two years. It is a different thing to work closely with a small number of people that comprise the entire company than it is to work for a department in a large corporation.
You will spend a lot of time with these people. Are you patient enough in dealing with different personalities? Do they check their egos at the door? Better yet, are you able to check your ego?
Company culture of an early stage startup is heavily defined by the founders. Who the founders are as people will tell you what the team will be like.
So if these guys are the founders…
…you pretty much know what you’re getting yourself into.
There will likely also be a clique of people who knew each other prior to the new venture, so if you don’t know them then it’s potentially like going back to primary or secondary school and figuring out what table to sit at during lunch.
Again, the ability to be proactive in building relationships here matters even if we’re talking about doing it virtually.
3. How much do you know about the founders or CEO?
Do your homework. At an early stage startup, having faith in and trusting the founders or CEO is equal to if not more important than believing in the brand, product or whatever it is the startup is pushing for.
If for example if this is the CEO’s first foray into startups and the company hasn’t officially launched or is only a couple of years old, understand they’re going to go through a learning curve and growing pains. In this case, you need to look to see if they’ve been an agent of change and forward thinking in previous roles. Do they have the endorsements of not just their peers but of previous direct reports? Do they spend more time talking at conferences and boosting up their profile than actual organizational and leadership experience?
A CEO of a startup absolutely must have experience in building teams and then managing those teams. If they don’t have this experience they need to be smart enough to hire people who have those capabilities (and trust them fully) or have a co-founder than can. You need to make a judgment call, and to help you do this you need to gently inquire about the “past successes” of the founder or CEO. Some CEOs are just given money to start something but haven’t the foggiest of clues as to how to get it done because they’ve never done it before.
If you can’t ask directly, then ask around and do some research into the CEO and not just the company.
Do you have confidence in the CEO or founder’s ability to represent the company both to current investors, potential investors, the media, clients or possible clients and those in your industry? Especially during a global pandemic where economies are fluctuating and stability is scarce? The founder and CEO is your pitch person. They’re the ones who are out there getting the company money to build, grow and sustain. Some CEOs are better at this than others.
4. Make sure the startup has the right investors
Or at the very least are pursuing and targeting the right investors and not “random” money. Knowing who the investors are and their track record is incredibly important when considering the longevity of the company and the support it will have. You can have a successful brand or product, but if the CEO and product is not aligned with investor expectations then the startup has the potential to run into big trouble in the future around meeting misaligned expectations.
Additionally, if you’re interviewing for a position at an early stage company and they’re being shady about who their investors are and what their expectations might be, be wary.
5. Keep your grand plan to make millions in check
One of the main reasons people consider joining a startup is in the hope of eventually eventually making more money than they’ve ever dreamed of. Everybody has dreams of a startup going full unicorn and making you millions, but the reality of it is much less encouraging.
Don’t expect to make millions. Don’t expect to make it big or make a dime over your base salary or bonus. The likelihood of a startup truly making it and you getting a fat payout are rare.
That’s not to say that you shouldn’t negotiate for all the equity you can possibly get. You absolutely must do this if you even want that chance at a payout.
Do not accept an offer if there’s no equity they’re prepared to give you right away on day one. If they tell you they’ll have something three months into the job for you, don’t accept the offer. Why? Because you don’t know if that three months will turn into six…or never. It’s a startup, things happen. Priorities change and unless you get something on the table in writing at the very beginning you’re putting yourself in a bad position to negotiate later.
Equity can also be meaningless if you’re not planning on sticking it out, which means that if you’ve misjudged the CEO, company culture or if it was the right long term fit for you, then if you took less salary in the beginning but more equity, you’ve just done yourself a disservice.
6. Know what you’re getting out of it before getting into it
Because the majority of startups won’t make you those millions, be prepared to not make those millions to ride out pandemics on a remote luxury island.
So what do you expect to get out of the experience if you never end up with that money at the end? This is an easy one.
Startups are a fantastic opportunity for career growth and to gain experience that is more difficult to come by in a corporation. This is the case even if you end up at one short term. You can still work it to your benefit.
You can get your hands dirty in a variety of ways. If you’re hired as head of marketing, expect that you’ll be doing more than what’s in the job description and embrace it. If you’re hired at an entry level position, do anything and everything you can and contribute where needed, as needed. You’ll get promoted if you excel.
Have skills in mind that you want to acquire before you start. Will the startup provide you with the ability to try new things? Are you prepared to realize you’re going to have to fly by the seat of your pants at times? But know if you’re prepared to learn then you’ll grow. So even if the startup doesn’t make it or if you don’t make it at the startup, or a better opportunity comes along then you’ll have expanded your skillset and hire-ability, which is especially important in today’s competitive global job market.
7. Decide if you want to be a leader
If you’re not already a leader, do you want to be one? The ability to grow at a startup is greatly bolstered by your ability to grow into a leader. When I’ve hired staff at startups I’ve always looked at the candidate and tried to determine their capability to continuously grow in responsibility, taking and incorporating feedback, their ability to handle failure and move on from it and their potential at currently or eventually being able to provide actionable direction to others. Those who sit on their hands and don’t constantly engage and interact are those that will get the least out of being at a startup.
Uncomfortable with managing people? Be prepared to get less out of a startup. If you’ve no experience managing people but have aspirations to do so then a startup is a fantastic opportunity to get the chance to grow and manage a team, which in my opinion is absolutely invaluable when it comes to career development.
8. Established or new managers should manage their team building expectations
For those leaders already experienced in building and growing teams, its best to manage expectations and understand burn rate needs to be kept in check. Team growth is something that should always be addressed as needs arise rather than filling holes that don’t yet exist. For the established leader, this is an exercise in patience but a necessary one. Growth isn’t equal to “hiring like crazy.”
You must be prepared to work on process and provide achievable goals to staff, to listen to them, to provide feedback and follow up on it even when you get too busy. This goes for a staff of two or 22.
If you can’t do that, be prepared to lose people, and if you lose people at a startup then you’re going to hurt the company much more than a company with an already established reputation.
9. Be prepared to work odd hours
It’s thrilling to work late into the night on a shared vision or project and succeed. The sense of accomplishment you get from it is addicting and immensely satisfying. But so is the satisfaction you might get from attending your daughter’s first day of school or spending time with your significant other or family.
There is such a thing as working smartly and not just working long hours because everybody else is. It is possible to have a life and work at a startup, but to do so requires a diligence in time management and organization that goes beyond your typical nine to five corporate gig.
For those looking at entry level roles at a startup, look for flexibility from your future manager whether or not it is a work from home gig. Your new boss might want you to work long, odd hours, but do you believe they’ll also accommodate you when you need it? This is important.
For all of the managers and leaders at startups out there, be as accommodating as possible as burnout is a real thing. Never assume that because employees have equity or because it is a startup that everybody wants to, or can, work crazy hours on a shared vision. This is made even more challenging when considering the various hurdles faced managing remote teams already concerned about their health and that of their family during a global pandemic.
So that’s a lot to think about…
There’s a reason why those who really dig into startups end up working at multiple startups or even launching their own. They’re the ones who are never satisfied and dream big. They look towards the future. They get a taste of “this is what a company should be like” and they want to try again and again. And eventually, they’ll make it. You’ll make it.
Consider all of the above when thinking about joining a startup but consider two things above all else:
- Does the startup give you an opportunity to do something you love doing?
- Even if it doesn’t work out, will you have grown in your career and experience as a result of working at the startup?
If you can answer in a positive way to the above, then you’re halfway there already.
It paints a picture in your mind, of some Utopian work environment (think Google HQ) with its play toys, colourful cube meeting rooms, slides, fireman poles and slushie machines. Not to mention riding electric scooters around the office to get your daily fix of cappuccino, while you’re at it don’t forget the dress code, ripped jeans, cool shoes no socks and a branded eco-warrior T-Shirt.
Sounds cool right?
Yes, if you believe in Unicorns like my 6 year old.
“These environments are very fast, unstructured, can be successful so strap in, prepare yourself and enjoy the ride”.
I personally have been approached by around seven start-up companies in the last two years, all within my field of expertise. It sounded great in the beginning, in fact amazing and the owner had more energy and enthusiasm than a Chimpanzee on Nitrous Oxide. Once I started asking questions, about the business and the owners the less I felt comfortable. In essence do your own due diligence and listen to your gut feeling. Ask yourself, should I leave my current job with security and benefits for something that sounds sexy, but could be risky. If you are a poker player and it feels good go for it. You only live once right?
“Grass is not always greener on the other side”.
Just like this old saying goes, there’s a reason for it. Make sure you get a 2nd opinion, hell even a 3rd. Maybe not from your mother-in-law perhaps.”