Are you considering taking a position at a startup? Or are you already working for one, and it’s nothing like what you’ve experienced at a more established company?
I know this sounds like the intro to one of those “you may be entitled to compensation” commercials. Sorry to say, no compensation here — but I would like to share with you some mistakes that are easy to make when you work for a startup.
How do I know? I’m currently a startup and small business consultant, but much of my career was spent making these exact mistakes.
1. Letting a small budget hold you back
I always struggled with this one. I had big goals and ideas about what needed to be done to get there, but I’d put them on the back burner until there was more room in the budget. The problem: there’s almost never more room in the budget.
Think outside the box: what tools do you already have available that you can adapt? Are there less expensive tools or platforms you could use? Could you build what you need yourself?
I remember the first time I was introduced to Zapier, years ago now, by the CEO of the startup I was working for. Our budget was what Flo Rida would call low, low, low, low, and I had been begging them to bring another person on to help with the workload. The CEO’s response? My very own Zapier login. I entered the world of automation and never looked back.
The answer won’t always be automation, but chances are there are tools out there that are within your budget and will give you the nudge you need to follow through on all those big ideas.
2. Using your voice incorrectly — or not at all
At a startup, you already have a spot at the table, so use it.
A wise man named Erik Hatch once said, “Your best employees are your biggest pains in the butt.” So be (like I am) a pain in the butt. But when you’re speaking up, make sure you’re not coming across as a know-it-all.
I often had an aggressive style of communication; I would let you know what I was thinking, when I was thinking it, and exactly how I was thinking it. Not surprisingly, most people are put off by this type of communication and will just tune you out. So, as you can imagine, this didn’t get me very far. It was about as good as not using my voice at all.
What I came to realize — the hard way — was that everyone has their own communication style. I started asking people what theirs was, and anytime I wanted to raise a point about something or share my opinion, I would try my best to communicate it in the way the other person would be most receptive to it. It’s all about using your voice effectively so it drives your desired impact.
3. Waiting to have things handed to you
At a startup, you have the ability to pave the way for astronomical growth — for both the company and yourself. But not everything will be laid out for you: you’ll have to put your Nancy Drew hat on and find those growth opportunities.
Now’s the time to get creative and take initiative. This can feel uncomfortable; it did for me at first, mainly because I didn’t want to overstep any boundaries.
Here’s my advice. Spend some time observing what’s going on at your startup. Are there any pain points you’re noticing? What are your company’s goals for the quarter?
Write out a list of things you’ve noticed. Include what could be done to solve these problems or gaps you could fill — it doesn’t matter if you have experience in it or not. Then, present that list to your leader, and ask which items might be good for you to go after.
I always found this was a great way to take initiative while making sure I wasn’t completely going off into left field or stepping on anyone’s toes. It also allowed me to understand what the priorities were and which big initiatives I should be focused on.
4. Staying within the confines of your job description
Unless told otherwise, your job description is probably just a general guide of what the company needed weeks or months before you came on board. Now they have even more that needs to be done — and a lot of it’s probably not within your formal job description.
Did they hire you to write social media content, but now they need someone to write sales emails? Go ahead and raise your hand for that challenge; you’ll be surprised at how much your current skills might translate into other areas.
Years ago, I was hired by a startup to facilitate their customer onboardings. I walked in on my first day, and the CEO said, “We want to see what you make of this role.” It became clear that onboarding customers was only going to take about 10% of my time; it was up to me to figure out how I was going to spend the other 90%.
I could have easily stayed within the bullet points of my job description and made it really easy on myself. Instead, I saw this as a learning opportunity that doesn’t come around often. I started listening, observing, and asking questions. What were the immediate needs of the company? Where could I step in? What were others working on?
Soon, I had my hands in pretty much every area of the company, going far beyond what I was originally hired to do. It not only allowed me to get some intense hands-on experience, but it also helped the company build a foundation in various areas and get a grasp of their needs before hiring more specialized people.
I can confidently say that I wouldn’t be where I am today if I would have just stayed within my job descriptions and not dabbled in various areas. It would be like if Taylor Swift had stuck to country music — and no one wants to imagine a world like that.
5. Not setting boundaries
Work isn’t an all-you-can-eat buffet, but it can quickly become one if you let it. You see a lot of opportunities pop up, and you’re really hungry to prove yourself, so you want to pile it on. But pretty soon, you’re going to start getting really full and feeling kind of miserable.
As someone who used to think that lack of sleep and no days off were badges of honor, I know you can’t produce consistently good work if you’re biting off more than you can chew. My burnout reached the point where the mere thought of opening my laptop made my skin crawl. I hadn’t taken a vacation where I was offline in over three years. I had been working 12-hour days and through most weekends, I ate lunch at my desk, and I checked emails in bed.
Despite this earth-shattering realization that what I was doing to myself was completely unhealthy, I was still hoping that when I brought this up with the founder of the company, he would pat me on the back and say, “We wouldn’t be where we are without you putting in all those endless hours and weekends.” Instead, he looked at me and said, “I never asked you to do that.”
It stung, but he was right. He never asked me to compromise my sanity and my days off, but I did it because I thought that’s what would make us successful. In reality, it was doing the opposite. Moral of the story: take time off, enjoy your weekends, and set your boundaries.
6. Being inflexible
Things move fast. Like faster than Jimmy John’s delivery. One second, you’re neck-deep in an industry analysis, and the next, there’s a complete change of direction and it’s all-hands-on-deck for a sales presentation, forcing you to leave your industry analysis in the dust.
This can be frustrating, and I’ve let my frustration cloud my ability to see the bigger picture. I was always fighting the quick change.
I remember a time when I was in fact working on an industry analysis. We were pretty confident that we were going to target a new industry and needed the data and my analysis to back up why this was the best move for us.
I spent weeks compiling all the research, putting together a SWOT analysis, making presentations for the board, the whole nine yards… only to be told that we weren’t going to be headed into a new industry after all, and I needed to move on to something else. I felt defeated and angry. It was time wasted — all that work for nothing.
Once I was able to get past my emotions, I realized it wasn’t actually a waste of time. Fast forward to today, and I still use what I learned during that project to help other businesses. Me being frustrated and angry was probably the most unproductive outcome of the whole project, as it held me back from diving into other projects. Not going into that new industry was the right decision in the end, and no amount of work would have changed that.
So, don’t be me — take it in stride and think about the skills you’ve learned.
7. Being wary of feedback
Feedback just hits differently at a startup. Like having gelato in Venice, Italy instead of the local coffee shop in Ankeny, Iowa.
At a startup, feedback is typically not formal: it’s maybe a little (or a lot) blunt and oftentimes on the spot. It can catch you off guard, and if you have a tendency toward the dramatic, it might feel like the end of the world. But as it turns out, it’s most definitely not the end of the world.
I was always the person who would ask for feedback from anyone who would give it to me. Whether it was positive or negative, I wanted to hear it all. Where could I improve? What was I doing well? Am I meeting your expectations?
And for the most part, the feedback I received was pretty positive. Just the pat on the back I needed to keep excelling and give my ego a little boost. But whenever I received negative feedback, it always felt like a punch to the gut.
On the outside, I took it very well. I would thank them for their feedback and tell them that I would work on it immediately. What was going on inside was a completely different story: I would go into a mental tailspin. “They don’t know the full story. That feedback just wasn’t fair.” I would find all the reasons they were wrong, and it would consume me.
Eventually, my mind would win out, and I wouldn’t actually work on whatever it is I was supposed to improve upon. As much as I touted that I was open to feedback, I really wasn’t. As a result, I limited my growth potential until I decided to actively change my mindset and my attitude.
8. Not over-communicating
Everyone is so buried in their own things that it may not always be apparent that you’ve got something handled or you’ve been working on a given project. Let people know. Talk about your ideas and plans and how you’re going to tackle them. And don’t be afraid to talk about your wins, too.
At first, I used it as a way to mitigate being micromanaged. If I could fill people in on what I was doing, how I was doing it, and when I was doing it, they wouldn’t come back later to check in on me. I also used it as a way to make sure I was working on the right things.
I’d fill everyone in on what I was doing and wait for someone to tell me that I shouldn’t focus on that, or alternatively, that I was on the right track and to continue doing the thing I was doing.
I quickly realized that it also helped avoid duplicate work. With everyone wearing so many different hats at a startup, there would often be multiple hands in one project. If you didn’t over-communicate what you were doing, you would end up working on the same thing as your coworker, which is probably in the top 10 worst feelings next to wet socks.
This is a learned skill. It took me a while to understand what over-communicating is and what it isn’t. I use the term “over-communicate” instead of simply “communicate” because there’s a difference:
Over-communicate: “Hey Kate, I just wanted to let you know that I am handling slides 5-10 on our monthly marketing presentation. It looks like you’re doing slides 11-20. I also made a note of that in our activity tracker. Let me know if you have any questions.”
Communicate: “Hey Kate, I’m working on some of the slides in the monthly marketing presentation.”
As you can see from the example, over-communicating is also about making sure everything’s noted in every communication channel (within reason). If you say it in Slack, someone who checks your project management app won’t see it. Keep that in mind.
9. Giving in to imposter syndrome
I can’t even remember how many times I’ve said, “I’m so not qualified to do this.” And I still let that thought bang around in my head sometimes. You are qualified.
You were hired because you’re worthy of a spot on a rocket ship. You may not know all the ins and outs, and maybe you’ll be Googling what “CPC” and “PPC” mean, while simultaneously setting up Google Ads.
All that matters is that you get comfortable with being uncomfortable and not having all the answers.
I mentioned that, at a past startup, I only had 10% of my job description clearly defined. I would love to tell you that I knew what I was doing and that I had countless years of experience under my belt to prepare me for that exact moment. In reality, I almost quit my first week.
I had a huge fear that they were going to “find me out” and realize that I was just a young kid who let the check engine light blink at me for months before getting an oil change (and only after my dad reminded me). They would inevitably fire me anyway, so why make it worse on myself, right?
I knew I was being ridiculous. I never lied about my experience or my skillset, and I didn’t misrepresent myself in any way during the interviews. So either (a) they were silly to hire me, or (b) they actually believed I could do it. The answer was a healthy mix of both. It usually is, and as long as you can fight back against that imposter syndrome, you’ll do just fine.
10. Specializing instead of generalizing
Every startup will need specialists — eventually.
But one of the best things you can do for your career (and for a small company) is to generalize your skills. That means learning and executing on marketing tasks while also juggling sales initiatives. Or onboarding users while also digging into data analysis.
Generalizing can teach you a little about everything and helps you see the full customer journey firsthand. It’s what helped me figure out what I actually wanted to specialize in and what my true talents were, while also saving the company thousands of dollars since I was tackling multiple job functions.
One area I always wanted to venture into was marketing. So, when a startup I was working for needed someone to take on the marketing initiatives, I jumped at the opportunity. Did I have experience? No. Was I really good at Googling? Yes. I dove right into watching courses, reading blog posts, and talking to professional marketers.
And you know what? I actually was successful. By that, I mean that we were making money off of our marketing initiatives and bringing in leads. There was just one problem: I didn’t like marketing.
I so badly wish I would have fallen in love with it and that it would have been a Hallmark movie moment. It wasn’t, but I still learned something immensely valuable while filling a role the company desperately needed filled.
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