Editor’s Note: 
This article is adapted from our podcast interview with Natasha Jen, originally recorded for Twos Talks and released on the Twos Studio YouTube channel. It has been edited for clarity and format.

In this episode of Twos Talks, Natasha Jen, partner at Pentagram New York, shares what she looks for when assessing designers. She discusses what she notices in a portfolio, how she reads a designer’s thinking, and the signals that show someone is ready to succeed in a high-level design environment.

Depth, Complexity, and Original Thinking

Jen pays close attention to how a portfolio reveals a designer’s judgment and problem-solving approach. She looks for projects that go beyond surface presentation and show clear layers of decision-making, development, and intention. Depth and originality matter to her because they point to how a designer thinks, not just how they style.

She explains this in her own words:

“Depth is really really important, because the depth of a project shows the ability to build out something that is perhaps more system based… I also look for a level of novelty. You can get a very good portfolio, but novelty is something that is so in the visual based that you begin to actually know a little bit more about this artist in front of you.”

Curiosity and Initiative

Jen looks for signs that a designer actively engages with the world around them. Curiosity often leads to initiative, and she connects this idea to her own early experience at Pentagram. In those first months, she took on tasks around the studio simply to learn how everything worked. That attitude earned her greater responsibility long before anyone formally asked for it.

“I had a lot of curiosities… I wanted to actually do everything, meaning I wanted to actually manage the studio… I didn’t ask for permission; I just did them.”

Soft Skills and Communication

Strong work alone is not enough for Jen. How a designer communicates, collaborates, and responds to feedback forms an equally important picture of potential.

“The work itself tells you a lot… but then there are other very important aspects such as personality, such as communication skills… You have to make a careful decision and then help improve these areas that need improvement.”

Understanding Potential and Growth

Hiring involves balancing what a designer has already achieved with what they could accomplish with support and guidance. Jen looks for signs that a person can grow into the role while contributing meaningfully to the team.

“You get a good sense during the actual interview… but never fully. You’re also taking a considered risk on someone. Knowing what the risks may be… a lot of times work is fantastic, but the person isn’t the best communicator. You take the risk and help them grow.”

How Top Designers Become Great Managers

For designers moving into leadership, Jen says the most effective managers are those who first excel at design. Strong design skills give them credibility and the insight to guide others.

“The best design managers are often times the best designers… we ended up being managers just because we know how to do this stuff so well.”