Tess Dixon

This week I talked to the terrific Tess Dixon!

Tess is currently a Product Design Manager at Condé Nast, but when I first met her she was Director of Support at Tumblr. She’s been with Condé Nast for about 6 months, and in leadership all together for around 8 years.

Thanks so much for taking time to talk to me today, Tess! I know you recently pivoted away from Support, but I couldn’t pass on the opportunity to talk to you about your time in the industry. Can we talk about your early days in CS first?

Sure! Just out of school with my Information Systems degree, it was hard to find tech jobs that didn’t demand experience. So I took the first entry-level job I could, doing QA for a small software company. I enjoyed QA, but it seems like my boss noticed I could write well and give simple instructions and lay things out in a bulleted list pretty quickly, and moved me to Support within a few months. I thrived there, and by the time I left three years later I had amassed a large amount of scripts that took us from doing mostly phone support to more and more email, and built out an online help center as well.

How did you eventually move into leadership?

I was promoted internally. At Tumblr, Marc LaFountain (one of Tumblr’s first employees) had started a small support team here in Richmond, VA and was just getting to the point where they needed an office when I joined the team. I was really lucky to have his amazing leadership and mentorship qualities available to me as I grew and learned there. I hired and managed my team starting in 2012, and was promoted to Director of Support in 2013 when he moved overseas.

When I started managing, it felt really natural and not like a big “transition” at all. Of course, I didn’t really know about Management as a discipline, but I had had good and bad bosses in the past. So I thought “Okay now I’m the boss of these folks so I better not mess things up for them.” That was really my motivation to put in 100% every day.

It was really easy,  just taking over the reins of an organization that I had already helped to shape and knew all the processes of. But I do think that things shift a little bit invisibly when you become a manager: even if you’re very well-liked and you have a communicative, comfortable relationship with your team, the moment you become a manager you’re suddenly seen as “the man.” So I think some people began holding back a bit when talking about work-related things around me, which is natural. I had to learn to ask very actively for feedback, and ask for it often. Even though I was the same interested and understanding person, feedback didn’t just naturally come out of the woodwork as freely as it did when I was officially a peer on the team.

Looking back now, what skills would you say make a good CS leader?

Being organized, because the tech world fancies itself both fast-paced and casual, so people act like they’re kind of allergic to structure. But human beings deeply need and want some level of structure, and want to know what the plan is and where they stand. Being organized and being a good communicator can help you with all of those things. 

Being a calm person at your core can help, too. In support, almost every request that comes in is considered an “emergency” to someone. So establishing what’s *really* an emergency, and what’s not, and sticking to those standards can help reduce panic, pressure, and the idea that they need to rush through every request and make sure that agents are able to give the proper amount of time and calm consideration to avoid mistakes.

I always assumed “By the time I’m in a leadership position, I’ll have it pretty much ‘all figured out’ and I’ll be really confident and know what to do most of the time,” but I think for most of us that’s just not going to be true. Certainly, when you start getting promoted you get to leave some of what’s perceived as “grunt-work” behind so you can focus on higher-level tasks, but those tasks are just as hard and much more is at stake. And I think most managers and directors are constantly learning from their own mistakes and failures and misconceptions, just as much as beginners are. So while I love leading people and processes and sinking my teeth into complex challenges, there have also been many days where I’ve said to myself “Remember how simple life was when I only had to help individual users all day and then go home and not think about work?”

So how easy is it to measure your success, and that of your team?

On a high level, asking the question “Are we doing the absolute best support with the resources we have available?” was always what mattered to me. That would depend on the business’ needs: whether they have a support team so that they can foster an online community, so that they can find and fix bugs, so that they can clear the ticket queue, so that they can build goodwill with their users, etc.

A support leader should track all the metrics they can, because although they don’t always tell the full story, they can be an indicator of efficiency problems or wins, and show you where to start looking in order to improve. Metrics have also been one of the only things that could get me traction with other departments in terms of prioritizing bug fixes and feature requests. I do think sometimes leaders can be too metrics-obsessed and stop seeing the human beings that work for them as human beings, and that’s uh…not good.

Absolutely! Reducing humans to lines on a spreadsheet is not going to help anyone in the long run. Considering those humans now, how did you nurture growth in your team?

At Tumblr we had a support-specific career leveling doc that we presented on and reminded people about regularly, as well as a career worksheet for anyone who wasn’t quite sure what their career goals were yet. There can be a huge misconception in support as in other industries that your manager basically has to die in order for you to grow in your career, which is of course total rubbish. It’s challenging to convince people otherwise, I guess because for what seems like all of history, popular depictions of career development only show people becoming managers, Directors, CEOs, etc. Trying to figure out what folks are interested in, where their skills shine, and developing unique paths for them (whether that’s a management path or an individual contributor path, whether it involves vertical or lateral moves or a combination, etc.) is hard and slow and unglamorous work but I think that’s the way to go.

And what about your own development?

For me, this really has to come from a variety of sources. I take in a lot via podcasts (really enjoying the Yonder and Design Better podcasts right now), blogs, scholarly papers, books, mentor relationships, and a smattering of tweets by industry peers and cool folks I’ve met at conferences.

The Support Driven Leadership Summit is probably my best recommendation. When I attended that in 2018 I had the distinct feeling of having finally found the most laser-focused conference available for support leaders. A lot of conferences you go to have a variety of stuff going on for both agents and leaders, and I do think it’s good to attend as many as you can and absorb as much as you can. But the Support Driven summit really had a lot of topics that were the exact types of things that senior managers and directors of support deal with on a daily basis, and I got a lot out of it. So if you add that experience to being a part of the Support Driven Slack community and being able to ask questions, answer questions, and watch discussions unfold there, you’ve got a very solid resource right there.

Do you remember any great customer experiences?

Any time a user goes out of their way to thank the agent, or writes back later telling us a great story about what ended up happening with their issue, or talks about how much they love the product in a post and tags us. At Tumblr, we used to sometimes get messages from people who had found their partner via Tumblr and ended up getting married, etc. Those were always super heartwarming and reminded us that we were there to support a magical platform where magical things happened.

There’s usually a dark side, too, right?

Yeah, sometimes. Anyone who harasses or stalks an individual support agent, who almost certainly isn’t even the person who came up with or could change the policy they’re mad about. Seriously, can you imagine what their lives must be like to feel like that’s a good use of their time? Eeeeesh.

You recently moved out of a support role and into a design role. What has that been like?

Yes, after my time at Tumblr ended last year, I started putting some feelers out and looking for remote support leadership roles. 

I ended up being approached by Condé Nast and was asked if I would be interested in managing product designers rather than support people, and I’m so glad I took that leap. 

The past few months have been so challenging and a huge learning experience, since entering any team without having come up in that discipline is a fish-out-of-water story. But what I’ve also found is that support and design have a lot of similar concerns (ever found yourself in a meeting where you’re the only person in the room advocating for the user? that happens to designers too), and so much of what I learned as a support leader is applicable here as I work closely with product designers, UX writers, and UX researchers. 

On top of that, the qualities that made me good at organizing the processes and initiatives of support teams are equally as useful in the tackling design operations and creating all the conditions necessary for designers to be creative and make good work. So on one hand, it was a little bittersweet leaving the support world since that was where I was comfortable and especially since I’m a huge proponent of support as a lifelong career. We’re living at an exciting time where businesses are starting to value support not as a cost center but as a core facet of their business. More support leaders are entering company leadership and even being named as CEOs, so the common misconception that the only way to grow from a support role is to become an engineering / marketing / product person is starting to die out. 

On the other hand, it’s been refreshing to do something completely different, and it’s been validating to see the skills I gained in support being put to good use elsewhere. I miss my dear team at Tumblr, many of whom had worked with me for the greater part of a decade and who I consider some of my best friends. But I’ve loved getting to know my new team at Condé Nast, who are creative, funny, user-centered people and in many ways have restored my faith in building tech for large audiences.

And last, how do you sign off?

Tess (Since 99% of the emails I send are internal, I tend to just put my name!)

Thanks so much, Tess! I really wanted to know how you’d got on since pivoting from CS, and I’m so glad to have had the opportunity to catch up!

More next time from another awesome CS Leader!