Going from a big company to a startup? Here are three things you need to ‘unlearn’ to be successful

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People going from a big company to a startup, as a founder or an employee, severely underestimate the differences in how the work gets done. This is such a hard thing to explain that most of those who have been entrepreneurs or startup employees for a long time can’t identify and help those making the transition effectively. Every time I interview a candidate coming from a big company or advise an entrepreneur who just made the jump, I ask them: What do you think it’s like to work at a startup?

This is a very telling question. Often, I get a romanticized version of work at a startup (cue meme of “what my mom thinks I do vs. what I actually do”). They are hungry for autonomy, speedy decisions, fewer meetings, more innovation, etc. All of that is true. They balance that with the negatives: the lack of resources, potentially going out of business, and lower cash compensation.

Marcelo Calbucci.

These impressions are based either on hearsay or Dr. Google and they don’t capture the differences. At a macro-level, they get the pros and cons of working at a startup right; at the day-to-day working level, they mostly don’t.

Recently, instead of asking them what they think it will be like to work at a startup, I asked them what they need to unlearn to work well at a startup.

I can tell the question doesn’t work well during an interview. I get the deer-in-the-headlights stare. They can’t for their life understand why they would need to “unlearn” anything to work at a startup.

And here lies the reason many people fail to make this transition. You have to unlearn your old ways to be effective at a startup and that’s hard — harder than most people think. And the longer you spend in a big company doing things one way, the harder it will be for you to unlearn it and keep your mind open to new ways.

The unlearning of the old ways and the learning of the new ways doesn’t come organically. I often see struggles that last months and sometimes years for people to understand why things are not happening, why they are “failing,” why the product is not getting the traction that it needs, why sales are not happening, or why they can’t get their team to do what needs to be done.

I’ll highlight three ways the work is different (out of more than a dozen):

You have to go get it

Being self-driven is just not enough. You can be extremely self-driven and still find yourself in a position where the work is not happening as it should. At an established business, there is a “playbook,” written or not. Responsibilities and roles are better defined, market response is better known, and you have a high-level of confidence if you do “A” you’ll get “B.” It’s like paint-by-numbers. You’ll get a picture at the end.

Startups, even the ones that have traction, don’t have good playbooks for your role whether you are the CEO or the new intern. The playbook is constantly changing and because of that, if what you need is “B” at the end, you’ll have to try “A,” and if that doesn’t work you’ll have to try more things. In other words, not only you need be self-driven, you need to follow through and be outcome-driven.

It’ll feel lonely at times

Maybe that’s a little over-the-top, but the reality is that in a startup you’ll have to make a lot of decisions and get a lot of the work done yourself. That’s fine, that’s exactly why I want to work at a startup, you might say.

Well, let’s look at reality here. The support systems in established companies are put in place so you can focus on your core responsibilities. Things that you might consider “background” on your job come to the forefront. It could be HR benefits, office admin, accounting, etc.

But these are not really the ones that trip people over. What trips people over is how they had a “village” helping them get their work done. Let’s say you were a lead visual designer at a large company. You might have had other designers, copywriters, translators, style guides, functional specs, revision tools and processes, and many other things you don’t even realize you had to support you to get your work done.

At a startup, chances are you won’t have a lot of these tools, processes, and people to help you. You’ll make a lot of these decisions on the fly without much time to get someone to bounce ideas off of. And, you’ll make a lot of mistakes in the process.

You move fast, to a new direction

Even the worst startups are faster than the fastest big companies. The big frictions that slow down work are simply not there at a startup. It could be the convoluted decision process, which usually startups have none or light processes (see the previous paragraph); it could be the unnecessary concern about upsetting existing customers; it could be the excessive number of steps the legal, accounting, compliance, internationalization, and customer support teams put in place to make sure all the bases are covered.

Startups move fast. You heard that before. When applied to an individual day-to-day work, this can cause some frustration and discomfort. While at a large company, you have a kick-off meeting, followed by several rounds of conversations, decisions, proposals, and execution — at a startup, a lean version of that can happen in just a few days or even hours. That does sound exciting if you been held back by the slowness of your company, but it can be a burden of responsibility too big if you are making a handful of decisions a week, any of which could cause severe damage to the startup viability or to your career. The fear of failure really kicks in.

I don’t mean to scare people away from considering joining a startup but I want people to come with the right mindset that it’ll require to unlearn so they can be ready to learn the startup ways.

You might have been a vice president or a principal engineer at your previous company. Independent of it, the best strategy to transition and succeed at a startup is to be humble and assume you can’t bring the toolbox and tools you’ve been assembling for the last decade. You’ll need a new toolbox and you’ll acquire new tools as you go.

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