Building bridges: How to be a better manager by connecting with people

Interview with Anne Hjortshoj, Senior Director of UX at CarGurus
October 4, 2022
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Anne Hjortshoj is a product design leader with an accidental specialty in spinning up new teams. During her 20+ year career, she’s successfully led the design and product teams in industries disparate as automotive, cybersecurity, online education, financial services, politics, and advertising. Anne is Senior Director of UX at CarGurus, leading the team she founded three and a half years ago. Keep up with her via @annesaurus on Twitter or at

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When you’re ready to get to the next step in your career and move from IC to engineering management, you need to know how to navigate the tech ecosystem. Management requires a whole new set of skills that you’ll need to pick up quickly, so how do you prepare for the switch? What are some things you can do to make the transition smoother?

This week we interviewed Anne Hjortshoj, Senior Director of UX at CarGurus, to learn how she successfully leads teams. Read on for her advice on how to become an effective manager.

What was the biggest challenge going into the manager role? 

The biggest challenge I encountered when I switched to management was to learn how companies operate at the higher levels, and to apply that knowledge to how I relay information to the people I manage. It’s important to be able to distill things like changes in company direction truthfully and credibly, in a way that isn’t alarming or anxiety-provoking, with the context that is appropriate for an individual contributor-level person to have, so that they have the information they need to feel confident in the work that they’re doing, and in the company that they’re working for.

As a non-managing individual contributor, the mechanics of how a given company works isn’t all that clear, especially if it’s a large company; things seem to just “happen,” on high, kind of like weather. Because of their position in the organization, individual contributors are likely to miss a lot of important context around business and organizational decisions, so it’s easy for them to distrust what they’re hearing. Good managers provide that context.

If you’re interested in building muscle in this area, try having conversations with highly-aware colleagues who are managers (or directors or VPs). You can also spend some time studying your company’s org chart in order to understand the role and reporting structure of each group. If it’s difficult to find one person who understands the whole picture (spoiler: it usually is, no one person will have a perfect understanding or a unified perspective), you should reach out to a few people who are likely to understand different parts of the organization well. 

What’s your advice for ICs who want to connect with people outside their immediate org?

The success of any organization is dependent on the relationships that are fostered across the company. If you remain isolated within your own sphere of operations, you will lack useful context-setting information to bring back to your team (and for yourself!).

Networking tips:

  1. Make an effort to get to know people outside of your immediate circle of peers within the larger company.
  2. Have spontaneous 1-1s: spark up a conversation with someone you find interesting and get to know them professionally and personally. Eat lunch with them if you’re in the office, or have a one-off 30-minute Zoom call.
  3. Slack is more than just a workspace; you can use it to get to know your colleagues. It’s a great way to connect with people in a less formal manner than during a meeting, to build trust and work better together.

What was your transition to becoming a manager like?

Before entering management, I worked as an independent consultant for 10 years, helping various companies with user experience design. At a certain point, I realized that my learning had plateaued, so I started looking for companies to join where I could access a path to management. I took a job at Blue State Digital, a company that at the time was half marketing consultancy and half software company; BSD had never had designers work on the software side of the business, and their product needed attention. So I went from zero to 100: After joining as head of design, I quickly became head of product, and did a ton of work around enabling design and modernizing the software development process at the company.

After BSD, I moved on to a security startup called CloudLock, where I again spun up a new design capability and team. A year later, we were acquired by Cisco. Cisco is  a company which grows by buying other companies, which means there’s a mashup of all kinds of different cultures within the same giant organization (85,000 people, at the time I worked there). People at Cisco work really hard to reach across those cultural lines in order to engage each other. 

After leaving Cisco, I came to CarGurus, where I have been building a design team since late 2018. We reached critical mass as far as being able to more or less staff project teams about 18 months ago.

As a design manager, how can you continue to engage with your craft?

I don’t push pixels myself at this point, but I do engage with my craft in the macro sense, in that I enable and support great design outcomes from my group. Instead of designing an interface, I’m designing a situation in which my team can be successful. When I switched to management, I picked up a lot of skills that enable me to support other people, remove obstacles so that people are enabled to do their work successfully, train my team to problem-solve on their own, and generally deal with the operating system that is human beings trying to work well together. 

The other side of my role is to drive and synthesize design strategy across the company, so that our products reflect what the company is trying to achieve. Strategy might come from my team, from me, my peers, our C-level and board, or a particular sales team need. It all needs to be synthesized and articulated in a holistic way, and reflected in our products. So, in this way,  I continue to practice the craft of design, even as a manager. And of course, to do this successfully, I depend on the relationships I’ve developed over time, within the company I work for. 

Keep up with Anne at @annesaurus on Twitter, or at Anne is hiring!

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