Your Workplace Transition Survival Guide


Whether you’ve decided to take the plunge into startup land after years in a big corporation, or chosen to move from a tiny startup to an enterprise position, there may be a few bumps along the way as you learn how to work with your new boss and team. Here are a few tips to help you find success in your new role.

When going from startups to enterprise…

Become Familiar With the (Slower) Pace: Because the enterprise usually operates at a slower pace than startups do, it’s important to realize that there are more levels of decision-making. Things can take a lot longer to get implemented. “In startups, if you have an idea you just do it to. You can get really frustrated if you have the same expectations for what you’re building in a larger organization,” said business consultant Pamela Slim, author of “Body of Work: Finding the Thread that Ties Your Story Together.”
The additional levels of decision-making stem from your choices having an impact on a larger scale. “It’s worth it sometimes to take a little more time to slow the process down because it’s going to be impacting more people and you don’t necessarily have the resources to redo the work,” Slim continued. Changing your expectations for how long things will take can save you some frustration.

Adapt to Hierarchy: If you’re moving to a structured organization from a flat startup, it’s important to respect the hierarchy in place. “In [the] enterprise, people actually often do care a lot about their role and their level and who’s involved in the process, so if you skip over people or leave people out or don’t respect hierarchy, sometimes you can be seen as being subversive where maybe you’re just trying to be speedy and get stuff done,” Slim said.

“Anyone going into a more hierarchical structure needs to pay attention to understanding the corporate culture and the operating pecking order,” added executive coach Michele Woodward, who recommends observing how people interact for the first month that you’re in a new role.

It’s also a good idea to ask your colleagues or boss how common processes work, and who’s involved in decision-making. Getting to know people and what types of things are important to them (and why) is crucial since there is a lot more consensus-building required to be successful in the enterprise.

Keep Sight of the Problem You’re Trying to Solve: Because there are many more people involved in the enterprise than there are in startups, it’s easy to lose sight of the business problem you’re trying to solve. “There are more people involved, things get more complex, and people will add things to the scope to try to make it a fit for everybody,” Slim warned. “Part of your role as a good strategic partner is to keep focus on the problem you’re trying to solve. Otherwise, you build these crazy, unwieldy applications or solutions that aren’t really what the business needs.”

After listening to everyone’s opinion, come back with some clear, thoughtful recommendations that help people understand the implications of what they want you to build. Respectfully speaking up about the technical implications of certain features and where problems may arise is far preferable to silently creating software that doesn’t address the problem the company wants to overcome.

When moving from an enterprise to a startup…

Adapt to a Flat Structure: “I’ve seen people totally freak out when there’s not a visible hierarchy,” Woodward said. Taking a step back and observing the totality of the startup will help you transition from a rigid structure to a flat or fluid structure: “How do people interact? What gets results? Do that, even if your past experience is 180 degrees different and feels uncomfortable. Allow yourself to adapt to the new culture so you can amp up your success more rapidly.”

Don’t Wait For Instructions: Since bosses don’t necessarily tell you what you need to do in a startup, you’ll have to figure some things out on your own.

“You have to quickly assess what needs to get done. It’s considered your responsibility to figure it out,” Slim said. This is very different from enterprise, where “division goals role down to department goals and then roll down to individual goals, so there’s a lot more clarity about what it is that you’re going to do.”

Assessing the situation and creating a plan can often put you in position to solicit feedback from a startup boss or team—but you’ll have to do your own legwork, first.

Prepare to Ship: In many enterprise gigs, writing flawless code or creating detailed project plans are valued. In startups, shipping a product is key.

“In enterprise, you have more resources and checkpoints. You’re trying to minimize mistakes, or engineer them out of the process. It can be career-damaging thing if you try something or ship something and it doesn’t work, so often in enterprise you’re trying to mitigate risk, and to wait until it’s hyper-tested,” Slim said.

Startups are the opposite: you have to release products into the market and then fix what doesn’t work. Since getting something into the hands of customers (even if it’s imperfect) is crucial, burning time to perfect products before shipping will most likely result in failure. “You just don’t have that luxury of time. You have to bring it out to market and then test it,” Slim added. “Culturally that can be a huge shift.”

So after sketching an idea and running it by your boss or team, start building. Time is of the essence.