10 ways to find your voice on a startup rocket ship

This article was written by Bonnie Low-Kramen.

Can you imagine that even Amazon began in a garage as a startup? Jeff Bezos’ Seattle garage. Now Bezos is one of the wealthiest men in the world, and his garage is a local tourist attraction. Of course, many of the most recognizable brands (Uber, Instagram, and Facebook, to name a few) started this way, too–but mega success is not the result of most startups.

Startup companies, by definition, are exciting places to work. Still, they are not for the faint of heart or for people who require predictability. In Sheryl Sandberg’s book “Lean In,” the former COO of Facebook shared one of the best pieces of advice she ever received: If you are offered a ride on a rocket ship, don’t ask which seat. That’s what startups are like. They all require a leap of faith from those who climb aboard.

One CEO commented, “Working for a startup is like trying to build the plane while flying it.” Change is a constant, as are stress, pressure, and high emotions. So, while we know the names of the high-profile entrepreneurs who head these famous startups, what does it take to be the worker bees who help make their vision a reality? How has the journey gone for them?

Worker bee-dom

I was one of those worker bees, and I understand first-hand the exhilaration and the exhaustion. I began working with actress Olympia Dukakis in 1986 when the world did not know her name. When Olympia offered me the job to work as the publicity director for the Whole Theatre in northern New Jersey, I didn’t hesitate to say yes. I know the feeling of meeting a visionary and believing in my gut that she was the real deal. I trusted that the work we would be doing together was more significant than mine. The moment was unique, and I knew she was special. Saying yes to this middle-aged woman in ripped jeans and the fire in her eyes was one of Steve Jobs’ dots for me.

My instinct was right. Olympia went on to win an Oscar for her performance in the film Moonstruck co-starring Cher and Nicolas Cage. I worked by Olympia’s side as her Personal and Executive Assistant for twenty-five years. We often needed to figure out what to do, but we decided to fly the plane together. We both trusted each other. Sometimes when I made minor mistakes (and there were many), she would say, “Bons, we’re not saving lives here. We’re in the show biz. It’s acting smacking. I’m like a good plumber. Relax. Nobody is going to go to jail over this.”

This could be rule number one for CEOs to build loyalty in the staff of start-ups and all companies, for that matter. Make it safe for your team to screw up from time to time. Smile and mean it when you tell them they will not go to jail.

Start-up culture

The culture of startups is only for some. The executive assistants I train say that startups require wearing “many hats,” especially at the beginning when the team is skeletal. What that means is that on any given day, the EA has HR responsibilities of running payroll, paying vendors, and organizing interviews, marketing responsibilities of updating the website and creating social media graphics, and office management responsibilities of ordering supplies and getting quotes for laptop computers and mobile phone calling plans. In addition, these responsibilities include the EA tasks of managing the executive’s calendar, taking minutes at meetings, and planning a fundraising event for fifty potential investors. 

Is this high pressure? 1000%. Extended hours are the status quo, and burnout is a high-risk factor. However, these same EAs say that it is worth working on a project you believe in and having a front-row seat for watching the next “big thing” being born and having a hand in making it come to life. 

Stress, anxiety, and short tempers can run rampant in this fast-paced environment. All staff must begin working for a start-up with eyes wide open, clearly understanding why The entrepreneur hired them in the first place. Finding your voice is a must-do.

Here are ten ways to find your voice, save your sanity, and love your job at a start-up.

1. Research the players

Thanks to the Internet, learning about the key players in a startup has never been easier. Know who they are, understand what they have done before, and how their project is financed. You need to know the reputation of the people running the show. These are vital business questions before you buckle up on your flight suit.

2. Pace yourself and say what you need

Think of your work life as a marathon and not a sprint. It doesn’t matter who you are. The great equalizer is our 24 hours each day. That’s all we get, so be realistic about what you can humanly accomplish. At the risk of sounding like your mom, get as much rest as possible, remember to eat more than fast food, and remind your executives to do this, too. For example, if you need to work out several times a week at a particular time, say so at the interview, and then do it. The time to create healthy boundaries is from the beginning, even at a startup. Then, everyone will respect you for doing this.

3. Speaking truth to power

I train assistants where it is their obligation and responsibility to find their voice and speak up. It needs to be a part of any startup or significant corporation job. For many, speaking up feels easier said than done because people need to be trained to do it. Leaders are supposed to have all the answers, but they do not. In a startup environment, the staff is hired for their work, who they know, and what they know. At the interview, I strongly suggest asking straight out. When I see or know something that I think you need to know, how would you like me to tell you? And, are my opinions welcome? Listen hard to the answers about whether or not your voice will be heard and valued.

4. Ask detailed questions about the job description

When busy executives feel rushed, they often need more time to write down the total, comprehensive job description. This is very common and is also a set-up for failure. If this is the case, write the job description based on your conversations with the leaders. Then send your written job description back to them to clarify your role and responsibilities. Please only say yes once you agree with the leadership team about what exactly you will be doing. I urge you to be granular and ask; Will I be expected to work nights and weekends? Will you need someone to do personal tasks like walking your dog and picking up your kids from school? It is better to know the answers to these questions upfront. A universal red flag is a bullet that reads: Must have a thick skin.

5. Get your deal in writing

Worker bees are a business. You are offering a service. Be sure not to accept verbal contracts or handshake deals. Just like with the job description, insist on a written agreement. Handshakes are friendly too, but I know and have heard too many stories that include the sentence, “I don’t remember saying that.” If you have no written proof, you have very little recourse. 

Know if you are entitled to vacation or sick days, or do you only get paid when you work? Will you be working from home, in an office, traveling, hybrid, or combining all of these? How will your out-of-pocket expenses be paid? Will the company supply a dedicated laptop and a phone? Are you reimbursed for gas? In a startup, it is appropriate to include a clause to build a 6-month severance payment if the company fails. Those negotiating your startup employment with you will respect you for addressing these issues before committing and signing on the dotted line. 

6. When You’re Talking Money

Discuss how much you will be paid and how often and by what means you will receive it–bank transfer, check, Venmo, cash, crypto. Will you be a W2 or 1099 employee? Are there any benefits, such as health insurance or stock options? Is a Director of Finance handling this, or will you also manage the finances? Or will you be chasing down money with each pay period? This is your livelihood, and if you are like most people, you pay your bills. Therefore, it is imperative to speak up about the specifics of compensation.

7. Do a test flight

Since there are many variables with startups, offer to come in for a day to shadow the team. Or, you can offer to do a 30-day trial where you get paid to work, and in that time, everyone gets to know one another and see how you work together. Most EAs agree that they can tell most of what they need to know about the people and the project after 30 days. It is like dating before you get married. It is wise to do this, especially with a startup.

8. Do not reward bad behavior from anyone– Period

Yes, everyone has a bad day once in a while, and we can decide to offer kindness, a helping hand, and grace in those moments. However, workplace bullying, discrimination, and sexual harassment are not allowed continuously. 

These abusive and toxic behaviors are not to be tolerated by anyone, including our famous visionaries. You are an employee paid to perform the tasks for which the company hired you. You are a fellow human and deserving of being treated with respect, without fear for physical or psychological safety. In the interview, you can ask: How are you on your worst day? Then listen hard to the answer. For any questionable behaviors, document everything (in writing!) for possible future use.

9. Ask for feedback

Busy visionaries often need to pay more attention to the important step of offering regular feedback to the team. You need to know how you are regularly doing, but it’s not uncommon that you will probably have to be the one to ask for it. At the interview, ask; How often will we meet, and how do you give feedback? Hopefully, asking those questions will initiate a discussion about why feedback is essential.

10. Staff trains leaders

This statement may seem ironic and even counterintuitive, but it is true. One of the common denominators of our visionary leaders of startups is that they all have revolutionary ideas that end up changing the world and making millions of dollars. However, it does not mean that they are also excellent staff managers. Those are two entirely different skill sets, which is why they need staff. No one ever said that visionaries are good at managing others. The data shows that the average age that a leader receives their first training in managing people is 46. Staff often need to communicate with their managers by finding their voice to speak up about matters, such as giving regular feedback.
Given the current strong job market and the YOLO economy (you only live once), startup jobs are plentiful for skilled, resourceful, and ambitious staff. However, climbing aboard a rocket ship must be an intentional career move.