Break people’s frames to reset their perspectives

Wes Kao on excellent craftsmanship and raising the bar as a leader

A June 2024 episode of Marketing Against the Grain

“As leaders, part of our job is to break people's frames. … If you are able to reset frames for people, they're able to then see through that new lens.”
–Wes Kao

Quick Summary

Wes Kao is an entrepreneur and marketer known for her writing on leadership and startups. Before she co-founded the edtech company Maven, she co-founded the altMBA program with the author and marketing expert Seth Godin. (Side note: If you’re a fan of Seth Godin, you might enjoy these sketch notes on his ideas about feeling significant at work.) On Marketing Against the Grain, Wes shares tips for succeeding in marketing and beyond with Kipp Bodnar and Kieran Flanagan of HubSpot.

You can catch the complete episode (45 mins) on YouTube.

Key Takeaways

• Great craftspeople pursue “side quests.” That’s what Kieran calls the side projects common among many high-performing craftspeople and marketers. For example, Wes wrote a blog for many years and Kieran developed a YouTube channel about sneakers with his brothers. (You could also think of side quests as side hustles, but they don’t necessarily need to be monetized—”passion projects” might be a better synonym.) Why do side quests? They’re a way to develop both your skills and interests. And a side effect of sharing about them: unexpected career opportunities. Kieran credits his side quest with helping him stand out and get hired at HubSpot later on.

• Thanks to the internet, it’s easier than ever to build a public portfolio of your work. Side quests often double as examples of your work and expertise. As Kieran says, “The beauty of marketing in the digital era is that you don't have to wait for someone to give you a job to build an incredible portfolio of work.”

• Creating great content requires doing the work. While the lack of gatekeepers makes it easy to share your work, you shouldn’t expect to find instant success. “A lot of people think that enthusiasm and confidence are enough to get to where you want to go,” Wes says. “But there's a lot of skill involved.” Achieving excellence requires ongoing practice and iteration to get better.

  • A related point here: Keep going, even if no one’s paying attention. “For the first 10 years of writing online, no one read my shit,” Wes shares. “I was still doing it because it was an amazing way to sharpen my own thinking, clarify my thoughts, and explore things that I thought were intellectually stimulating and interesting. … I think a lot of people get discouraged with doing anything because they think that, ‘If I only get five likes on it, then that's going to be embarrassing.’ But who cares? Just do it.”

• Great leaders still get their hands dirty. In the traditional marketing career trajectory, advancing typically means moving from doing tactical work to strategy and management. But according to Wes, “It's really important to not get too far away from primary data [as a leader], because often you are able to see things that your direct reports don't see.” In short, great leaders maintain their craft. They’re not above doing the work that might ordinarily be delegated to on-the-ground reports.

  • “If you're not good at the craft, it's very hard for you to give specific feedback on the work output of what your team members are doing,” Wes points out. Kieran also shares a LinkedIn post he wrote related to this topic.

  • Kipp adds that “the best craftspeople and leaders are also just great students of culture.” In other words, they often have strong observation skills and good taste. They recognize excellence and appreciate good work, often diving into the details when something piques their interest.

• How to raise standards for your team. Describing her experience working with Seth Godin as transformational, Wes says Seth helped raise her standards both for herself and of others by giving direct feedback. She shares an anecdote about being challenged to review a stack of books within two days, a much shorter time frame than she’d originally anticipated. Initially thinking it was impossible, Wes then considered how she might achieve it if necessary. The situation exemplifies "breaking the frame," or challenging existing assumptions and finding new ways to approach problems.

  • “As leaders, part of our job is to break people's frames,” Wes says. “If you are able to reset frames for people, they're able to then see through that new lens.” The idea is to help your team see things from new perspectives, which can often raise their standards. Kipp adds that holding someone to a high standard can help develop them.

• Being direct ≠ being rude. Being “direct” is sometimes used as an excuse to say things without thinking about others, and coming across in a rude or abrasive way as a result. According to Wes, this is a lazy way of being direct that doesn’t usually benefit anyone. “It's pretty entitled to say an abrasively direct thing and then just expect people to come along and understand or do the hard work of understanding you,” she points out.

  • To give direct feedback effectively, use the TACS framework: tactical, actionable, concrete, and specific. Wes offers this framework as a better way to approach directness, noting that it’s all about “sharing your logic, rationale, and thought process.” The goal of giving feedback, after all, should be to align on something for a better outcome—not to confuse someone or hurt morale.

• Strategy vs. strategic thinking. Wes highlights the difference between these two concepts and how they play out in the workplace. First, there’s strategy—the high-level thinking and planning involved in tackling a certain problem or project. It’s a big-picture and macro-level approach. Strategic thinking, on the other hand, is all about the details of execution. You might use strategy for monthly, quarterly, or annual planning, but strategic thinking is used on a daily basis.

  • Why this matters: In the marketing world, we often conflate leadership and higher-seniority roles with strategy work. But strategic thinking is just as important, even when you’re not responsible for developing a high-level strategy. “Not everyone is responsible for crafting a high-level strategy,” says Wes, “but I would say that everyone is responsible for strategic thinking.”

Thoughts

It’s been a minute since I wanted to do sketch notes for a more marketing-centric conversation, but I so appreciated this podcast for its discussion around direct communication.

The legendary Steve Jobs was not known for being particularly kind in the workplace. In fact, he told his biographer, Walter Isaacson:

“I don’t think I run roughshod over people, but if something sucks, I tell people to their face. It’s my job to be honest. I know what I’m talking about, and I usually turn out to be right. …

I feel totally comfortable saying, ‘Ron, that store looks like shit’ in front of everyone else. Or I might say, ‘God, we really fucked up the engineering on this’ in front of the person that’s responsible. That’s the ante for being in the room: You’ve got to be able to be super honest.”

His brilliance aside, that’s a big yikes for me. And yet, some people model Steve Jobs’ behavior. (Maybe the thought is that doing so will make them as successful as him?)

Working with incredibly blunt people is certainly not my ideal, so I really jived with Wes’s TACS framework and overall point about directness: Being rude and direct is lazy. It’s much more effective when you share your rationale and ideas for improvement. Otherwise, that Steve Jobs level of directness is basically just an excuse to be mean.

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–Joyce