Just got a design offer? Here’s the biggest risk to your exciting new role.

Whether you’re a first-time designer or a seasoned pro, joining a new company carries all sorts of risks. Here’s a framework for identifying pitfalls — and how to recognize the biggest risk of all.

Jon Simmons
Published in
6 min readSep 19, 2022

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Joining a new company is an exciting time! Don’t let the title of this article get you down. It’s an accomplishment to have gotten an offer. Keep that enthusiasm — you’ll need it to help carry you through the inevitable challenges that arise from being in a new job. Focusing on the risk will help. Keeping your radar up will help you navigate the process of assimilating into a new company.

What happens if you aren’t aware of risk?

You don’t want to be like an a colleague of mine, who decided to exit a company after he received an angry email from the founder and CEO of a start-up he had recently joined.

He came in with lots of enthusiasm and jumped right into understanding the product, users, and customers. He was coming off a successful stint with a company where he was a sought-after designer in a similar enterprise space. He drove long distances to speak with customers and did well on an initial redesign of a key part of the product architecture.

He had wildly misunderstood the culture of the company.

In his previous role, he was used to having frank discussions about the direction of the product. So he carried this habit into his new role.

And here was his fatal mistake — assuming that the appetite of one company for direct feedback was the same at a completely different company. As it turned out, it wasn’t.

Let’s learn from his error.

As you might have guessed, he didn’t think much about what it would take to successfully onboard to this new company. He just jumped in. The action bias isn’t a bad default (especially in the startup world), but it can get you into trouble, as it did in his case.

So, let’s approach joining a company with some intention. Let’s define and refine the problem. Like any design problem, we want to:

  • Adopt a framework for assessing risk
  • Focus on the right things by prioritizing risk
  • Plan on mitigating known risks
  • Prepare to adapt to unforeseen situations

The problem is easier to understand if we view companies as closed societies, with their own patterns of behaviors, ceremonies, values and beliefs. The problem is that you are jumping into a new society, and you can’t really know what that means until your first day and beyond.

If you haven’t read it, I would highly recommend the book The First 90 Days (or, TF90D as I’ve affectionately dubbed it). It’s a self-proclaimed ‘onboarding bible’ — a well-earned descriptor.

TF90D — A guidebook for career transitions

In TF90D, the author, Michael D. Watkins identifies 4 common areas of risk that people encounter as they join a new company. And he identifies one monster lurking in the shadows waiting to devour you whole :)

Risk 1: Understanding the structure of the business

As product designers, we like to focus on the products and users of our products. Watkins thinks this is the easiest risk to identify, but I’m not so sure.

Here, many designers fall down.

And by this, I don’t mean how the business makes money (although this is important). Most designers I’ve worked with understand revenue and funding sources.

Business orientation also means how the company is structured — the various departments and silos. It also means how performance is evaluated. This can have a huge impact on your success.

Other important questions to think about — what career ladders are in place? How is planning done, and what tools are used?

It’s first because it’s the most easy to understand. It’s the most visible layer of a company’s patterns and beliefs. Let’s dig deeper.

Risk 2: Making good connections with stakeholders

New designers especially are in for a shock where this is concerned. They spend a majority of their time on portfolios and the technical parts of the interview process. So it’s a surprise when they get into a job and realize so much of success is about managing expectations, creating relationships and having a good line of communication to key stakeholders for their projects.

My advice to designers: turn off Spotify, get out of your seat, and go meet with people.

Even tenured designers get caught out by this. In the example from earlier, my acquaintance had 5+ years experience.

It’s easy to forget that stakeholders also means peers and people more junior in the hierarchy as well. Remember that some people punch above their weight, so to speak — their title belies their influence.

Stakeholders in general are easy to find and talk to — they are visible and thus, not the biggest risk factor. The big risk is something hidden, ephemeral, and deeply important to every organization of humans.

Risk 3: Aligning with real expectations

I love what Michael Watkins says in TF90D — interviewing is like romance, and working a job is like marriage. Which is to say, that expectations created during the recruitment phase are often based on assumptions and not actual fact. For designers, it’s the difference between what someone says to you in a research study, and their actual, observed behavior. Sometimes, people just don’t know themselves very well. What might look like a lie is actually just all-too-common self-delusion.

The gap between what you assume your mandate is and what it * actually * is can be the difference between success and failure in a role.

Mis-alignment of expectations is a huge risk. It’s easy to walk into a role thinking you understand what’s needed.

Still, wrong expectations aren’t the biggest risk.

You might be able to recover from mis-aligned expectations. Expectations are mostly easy to talk about, as long as you remember to talk about them. The biggest risk you face is something unseen, yet hugely consequential.

In an organization, the biggest risk to your success is the thing that separates the in-group from the out-group.

Your biggest risk: adapting to an unfamiliar culture

Culture is defined by Merriam-Webster as:

the set of shared attitudes, values, goals, and practices that characterizes an institution or organization

It’s been said that culture is everything we do, value and believe, but don’t acknowledge outright.

For this reason, culture is your biggest risk in joining a new company. Why?

  • It’s unseen
  • There’s no manual for culture — and if there is, don’t trust it (it’s probably not the real culture)
  • It’s not uniform — it’s different across teams
  • There can be all sorts of unhealthy biases and beliefs in a culture and
  • You won’t be able to change it

Culture includes things about how decisions are made, how power is distributed, and how promotions and other kudos are handed out. It is beliefs about the core structure of a company— an organizing set of values and beliefs.

My hand-drawn guide to company culture

This goes beyond being a ‘culture fit’ (which is typically a ephamism for poor hiring decisions).

Adapting to culture means quickly understanding and aligning with a set of beliefs and values that no one will come out and tell you directly.

It’s like trying to follow a road in total darkness with no headlights.

You can see the importance of illuminating your path by looking ahead and understanding the risks inherent in joining a new company. So map the risks, and come up with a plan to meet people, clarify expectations and assimilate to the culture.

Congrats on the offer! I hope this guide helps you find success in your new organization.

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Director of User Experience @ Atmosphere | SXSW speaker | Top-rated instructor at General Assembly