The Hard Truth of Working At a Startup

Written by Dave Bailey

Filed under culture management psychology

Startup working environment

Here are some expectations your team wish they knew before joining your company.

Every manager knows the anxiety that comes with the question, ‘Have I set clear enough expectations?’

But often, team members struggle and things don’t go according to plan. The answer frequently appears to be, ‘No! We need clearer expectations!’

When expectations aren’t met, everyone becomes a little more miserable. Tom Magliozzi illustrates this in his famous equation:

Happiness = Reality (minus) Expectations.

But why are expectations so hard to set?

One problem is that we don’t even recognize many of them until they become unfulfilled — which is when they suddenly come to our attention. And when you consider just how complex real life is, there always seems to be one expectation that slips through the net.

A new way to think about expectations

A big misconception about setting expectations is that it’s a monologue by expectation-setter to expectation-receiver. But in most cases, it’s a dialogue.

We all suffer from the ‘curse of knowledge’ in which we unwittingly assume that other people know the things that we know. To counteract this, we need to be willing to share information and ask questions in both directions.

My work as a CEO coach has given me an insight into the common yet subtle expectations that take time to become clear — and typically only after the expectation wasn’t met.

That’s why I’m sharing some of the rarely-said-out-loud expectations that might exist in your company. I hope they provoke a dialogue between managers and teammates and help to clarify hidden expectations before they become issues. Think of it as the memo that you never received.

This isn’t a complete list, nor is it a universal list — many of these expectations may not apply to your company. However, you’ll notice pretty quickly that there’s a theme:

The number one expectation in a startup is that you’ll be proactive.

With this in mind, here are 24 hidden expectations that you might find at your startup.

Managing your own work

1) Onboard yourself

Most startups don’t have an HR department, and onboarding is routinely forgotten, especially in the early stages. Make a list of the documents you’ll need before joining, and once you’ve joined, invite your colleagues for a coffee to better understand their roles. If your startup has READMEs, read them! You could even go the extra mile and create a resource for your next future colleague. Employees who onboard themselves instantly stand out to management as a godsend.

2) Remove or ignore blockers

There’s always a reason behind being blocked. Maybe you’re missing the information, data, or approval to move ahead. However, you have to figure out a resourceful way to keep progressing. In the majority of cases, mistakes are more valuable than inaction, so don’t be afraid to make them. 

3) Automate repetitive tasks

Every engineer knows the acronym ‘DRY’ — Don’t Repeat Yourself. It’s bad form to duplicate lines of code when they could be wrapped into a single function. The same applies to work in general. If you’re faced with an ongoing, repetitive task, look for ways to automate it. If you’re late to the automated workflow party, check out Zapier.

4) Adopt a problem

Let’s be clear: every startup has more problems than people . . . and teammates who adopt problems without being asked are the most valuable.

If you catch yourself thinking, ‘Someone should fix that,’ the someone is probably you.

Managing your manager

5) Prototype

The earlier you seek feedback, the cheaper it is to adjust to it. This underpins the whole idea of the MVP (minimal viable product), but it applies to work too. Imagine you’re asked to write a presentation. One approach is to show your deck only when it’s ‘perfect’. But the better approach is to get feedback on the outline first, even if it feels uncomfortable.

6) Feedback upwards

You’re probably thinking, ‘This is impossible! How am I supposed to give feedback to my manager?’ Regardless of how hard it seems, your manager will almost certainly expect you to give it if you have it. Many managers — perhaps naively — think they’re pretty easy to talk to, but in any case, if you don’t give feedback, they won’t know about any issues and nothing will change. Test the waters in an upcoming one-on-one with this: ‘There’s something I wanted to make you aware of. Is now a good time?’

7) Account for progress

Accountability just means providing an account of what’s going on. It sounds easy enough, but when someone asks you to explain what’s happening, it can feel scary (especially when your response is likely to be ‘slower than expected’). You should expect to answer difficult questions, these three in particular, which set up an accountability loop:

  • What will you do?
  • When will you do it?
  • How will I know?

8) Adjust to your boss’s style

Some managers are hands-on. They like to be kept in the loop, perhaps via a summary email (often called an EOD or EOW). Others are decidedly hands-off. They want you to take the lead and bring them in only if you’re stuck. If you can hold your judgement on what style is ‘best’ and adjust to how your manager operates, you’ll both be happier. If you really can’t deal with your boss’s management style, you might be happier finding a new boss. 

Managing your perception

9) Reframe complaints as opportunities to improve

There’s little room for complaining in a startup, especially when there’s so much that can make you unhappy. Instead, convert your complaint into an observation — consider its impact and try to find a way of improving the situation. You’ll come across as proactive rather than negative. A useful question to reflect on is: ‘How am I complicit in creating this situation?’

10) Assert yourself (but not too much)

Entrepreneurs are an assertive bunch that often see the defence of their ideas as a challenge. The surprising truth is that they like (and need) a well-reasoned challenge, and even get frustrated when people don’t stand up for their own ideas. If you’re not naturally assertive, look for opportunities to assert yourself, linking your ideas back to your goals. On the other hand, if you’re naturally assertive, learn when to sit back and listen. This goes for leaders too.

11) Know the product, know the numbers

You might not work in the product team, but you should know what it does, and how it works. Similarly, you ought to know which metrics are important to the business (or your goal) and how you’re performing. If your startup has a dashboard, memorise the numbers. If it doesn’t, build one.

12) Get to know your colleagues

Startups are a team sport and the strength of its relationships are as important as the strength of its individuals. Look for opportunities to learn about your colleagues. If there are social events, go to them. And if there aren’t . . . well, you know the drill!

Managing your own growth

13) Train yourself

When you’re a manager in a startup, it often feels like there’s no time to train your team. Embrace this by looking for ways to train yourself and develop new skills.

If there’s something you don’t know, your first stop should be Google!

Find a few blog posts on the topic and read them. Take a two-hour online course on Udemy. Look up free video tutorials on YouTube. And if you learn something useful, why not teach it to your team?

14) Find external advisors

If you expect your manager to have all the answers, you’ll be disappointed. Seek out and cultivate external mentors. One trick is to ask someone knowledgeable for advice on a specific situation. This will make them feel special, and since it’s about a situation rather than about you, they’re less likely to sugar-coat their opinion.

15) Lead your one-on-ones

One-on-ones are your meetings. If you don’t set the agenda, they’ll revert to status updates, which could be done by email. Carve your development needs into them: ‘I’d like to take fifteen minutes to identify and discuss my development needs. How’s that sound?’

16) Ask good questions

People often don’t ask questions because they falsely assume they should already know the answers. Try to ask ‘dumb’ questions frequently (with the exception of ones you can ask Google). You’ll find that these questions can make you look smart. It’s the questions where you assume you’re clever that make you look like an idiot.

Managing yourself

17) Look after yourself

It’s a fact of life that you are responsible for your own wellbeing. Only you can figure out what you need to stay happy and perform well. For me, it’s getting enough sleep, going to the gym, eating healthy foods, and spending time with loved ones. Book your needs into your calendar, proactively.

18) Say ‘no’ when you need to

Part of looking after your wellbeing is being able to say ‘no’ without feeling guilty. It isn’t always tyranny that stops us from looking after ourselves — it’s often simply the desire to say ‘yes’. And yet, saying ‘no’ can end up earning us more respect from others. After all, everybody knows how hard it is to do.

19) Embrace discomfort

There is no growth without discomfort. They are tightly coupled and any unpleasant circumstance offers opportunities for growth. In the startup world, uncomfortable situations might include failing, being held to account, or striving for something slightly out of reach. Seek them out.

20) Manage stress

Startups are a cauldron of emotions. You can expect to feel angry, frustrated, and overwhelmed at points. However, these emotions aren’t an excuse to take it out on your teammates. Learn to self-soothe by breathing deeply, taking a time-out, or doing whatever works for you. In my companies, I hold weekly team retrospectives as a way to (safely) vent what’s lifting us up and bringing us down. Want retros at your company? You know what to do.

Managing startup reality

21) Put in the hours

Startups aren’t known for their work-life balance. Neither are most creative people for that matter — I doubt Mozart was too concerned about me-time while writing his Fifth Symphony. Ensure your work preferences are compatible with the company. There’s no shame in not wanting to work long hours, but if that’s the case, perhaps startups aren’t the ideal environment for you. As a rule of thumb, budget for (at least) a couple of late nights per month at the early-stage.

22) Take a low salary

In a similar vein, if you want a high salary, don’t work for a startup. Small companies are rarely equipped to pay top-of-market wages. And how do you deal with a lower-than-desired salary? Live below your means. The appeal of startups shouldn’t be the salary . . . it should be the mission.

23) Your role will change

One way to think about startups is as a set of assumptions to be tested. Over time, assumptions change — and roles change too. In all likelihood, the role you were hired for will look completely different after three months. Go with the flow, and learn as you go.

24) Your role is temporary

This is an even stranger truth. If the company scales, the requirements for its leadership also change. This means the company may have to hire someone above you. (Note: this applies to founders too.) It follows from Peter’s Principle that your startup will grow to the level of your incompetence. Leave room for the possibility that you won’t be top dog in the future.

Take this list to your next one-on-one

Which of these expectations resonate with you? And which might resonate with your colleagues? You’ll never know unless you discuss it with them. Try using this list in a one-on-one, or as an agenda for a team meeting.

Something that became clear to me during the writing of this article is this: these are also the expectations boards have of their founders. So, we’re all in the same boat. Willing something into being demands a huge supply of proactivity from everyone.

How can you be proactive about being proactive?

Continue reading about startup structures: 

Originally published Apr 24, 2020, last updated Oct 18, 2023

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