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How Creative Market’s CTO Encourages Cross-Functional Partnerships

Perspectives in Engineering

How Creative Market’s CTO Encourages Cross-Functional Partnerships

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Engineering leaders work with all aspects of their teams. They support and coach their teams, they manage incoming projects, and they are the outward face of their crew. But what if engineering managers’ primary role was actually bigger than that?

For Chris Winn, CTO and board member at Creative Market, engineering management actually is bigger than that. It’s largely about building partnerships with external stakeholders.

“I expect our managers to be great advocates, coaches, and mentors for their direct reports,” Winn says. “And they need to be a strong partner to me, as a CTO, to make sure that we’re building an excellent engineering team.”

But a large part of the effective engineering leaders’ efforts need to be focused outwardly from their team. “Engineering managers do a lot of things,” Winn says, “but one of their one of their most core responsibilities is to build partnerships with other leaders across the organization.”

Often in organizational structures, the executive team cross-pollinates what’s going on in their respective departments — sometimes even sharing the challenges they’re facing, and collaborating on the direction they’re setting for their organizations. And sure, managers occasionally talk to other managers on the other side of the office. But that’s not the sort of collaboration Winn sees his engineering leaders engaging in.

Engineering managers do a lot of things, but one of their most core responsibilities is to build partnerships with other leaders across the organization.”

Instead, he coaches engineering managers at Creative Market to proactively build partnerships with other stakeholders, such as Product and Design. He encourages interdependence and normalization of help-seeking between leaders of different teams

“Product and Engineering, specifically, is a critical partnership,” he says. “Partnership with Design is also really important, but engineering managers need to have strong partnerships with our product managers because they serve as a translation between product requirements and technical requirements.”

Winn expects engineering managers to be great partners to those different stakeholders, whichever department they call home. Let’s take a look at some of the ways that stakeholder partnership can take shape.

Collaborative roadmapping

Roadmapping is one of the highest leverage activities that Product and Engineering leaders can collaborate on to increase the output of their organization. As Winn says, the most effective roadmaps are those that are produced by cross-functional leadership teams.

“If that relationship is not strong, especially as an organization grows, that company is probably going to experience miscommunication around what’s supposed to be built, a feeling of misalignment, or friction between handoffs,” Win explains.

Creative Market’s leadership teams tackle product strategy together at a very high level. They start with the vision of where the company is going, discuss roadmap priorities, and then balance those priorities against the company’s financial goals. The purpose of these mind melds is to ensure that each of the shops is set up for success as best as possible.

Then, all the managers are brought on board—Engineering, Product, and Design alike. The managers are involved early on in the process, so they can provide meaningful insight into those priorities from a practical standpoint.

We put a strong emphasis on making sure that the engineers feel like they have a clear understanding of what we’re building, and why we’re trying to build it.”

“Engineering managers, for instance, are basically getting to a T-shirt size,” Winn explains. “They can say, that priority sounds great, but that’s a really large project. Is there a way that we can get most of the same ‘wins’ from a customer standpoint, while focusing our resources over here?”

With the managers’ involvement, the leadership team can get a better feel for what each team can fit into their quarter or their sprints. That way, there’s a lot of clarity and buy-in around what’s being built before the project has been assigned to someone.

“We create thorough product requirement documents, and we put a strong emphasis on making sure that the engineers feel like they have clear understanding of what we’re building,” Winn says. “Not only that, but why we’re building it — and why now, instead of in 3 or 6 months. What are the stories, and what are the all of the pieces involved? Is it going to impact another team? Are there any other stakeholders that need to be brought in before we start building this?”

By investing in research and outlining the details ahead of time—and where stakeholders are working together to “measure twice, and cut once,”—teams are able to ship better products, faster.

Calming the incoming request chaos

At some point or another, most organizations will experience external stakeholders (perhaps it’s Sales or Customer Success) try to sidestep the software team’s process for queuing tickets — and end up giving an engineer work that they hadn’t budgeted for in their sprint. Winn has taken various approaches to solving this problem at Creative Market and in the teams he’s led in the past — and as with any process, many of those that were successful elsewhere, weren’t successful in his current organization.

For Creative Market, the most effective process that Winn’s team has realized is to establish a single point of prioritization — if someone wants a bug to be fixed or has a recommendation to share, those requests need to go through one person (or team). That workflow is communicated externally again and again as the company continues to grow.

Winn explains how this works in his organization: “If you want something done, you need to go through Product. Product manages the prioritization of those requests, and documents all of them in one area. If something is going to get picked up mid-sprint, it still has to go through a product manager. The bottom line: everything goes through Product first. And it’s been really successful for us.”

This is something we talk about as a team, and a lot of our engineers really value this process.”

Winn acknowledges that there are exceptions, like when there’s a high-priority bug that needs to be fixed immediately. Engineering can respond to those requests — but they need to be few and far between (not every bug is high priority, and it’s important that external stakeholders and engineers are coached to be able to make those distinctions). But in general, most work goes through the product managers, so that the engineers aren’t facing constant “high-priority” distractions.

In this setup, engineering managers work closely with product managers to establish priorities based on the established roadmaps. It’s a continuation of the higher-level pre-sprint planning process. This setup doesn’t give Product power over Engineering; rather, Product is just the door everything comes through, but Engineering is involved with everything that comes back out.

“This is something we talk about as a team, and a lot of our engineers really value this process,” Winn says. “Perhaps some of them came from a place that didn’t value prep work the same way, or set them up for success. Engineers don’t want side-loading, because they know their development process is better without it.”

Autonomy, mastery, purpose — and being an effective storyteller

Creative Market is growing significantly, Winn says. And people across the organization are excited about the direction that their technology is going.

That combination right there—growth and interest—is a golden opportunity for engineering managers to translate their team’s work to every other stakeholder in the company, particularly those who don’t have a daily working relationship with Engineering.
?Software engineering is difficult to understand — and possible even more difficult to explain, especially to those who have little to no technical experience.

“We have be really effective translators,” Winn explains, “so we talk a lot about things through the customer lens or a shop’s perspective. How does the technology end up impacting our product and our customers? We try to tell our technology stories in a very relatable, human way.”

Sometimes, these stories can simply be presentations to people who are curious. For instance, Winn’s managers have done a presentation about some interesting technology that the company integrated in their system or workflow. It doesn’t always have to be about improving the product — highlighting changes to your process, new training programs, technologies, or even a company off-site can all be great ways of showing that your organization is thriving.

We have to be really effective translators. We try to tell our technology stories in a very relatable, human way.

Managers can also take the initiative to forge partnerships with teams outside of Product and Design (though this opportunity can be useful to strengthen those relationships too). Set up team talks, where engineering managers can interface with and translate the technology for different groups across the org. Establish partnerships with these other departments. Offer them context into the things you’re doing, independently and as a unit.

“I want our engineering team to always be getting stronger — on an individual and team level — especially as we scale,” Winn says. “Creative Market is growing overall, and there’s obviously a lot of the focus on the engineering team. People are excited, which is exactly what we’re striving for. There’s momentum, tons of opportunity, and a lot of it ties back to being able to effectively tell our story.”

By sharing that story, not only will external stakeholders have a better, trusting relationship with Engineering as a whole (and also understand how hard Engineering works), but they’ll likely be more excited about the organization’s direction and their role in it. That’s what communication and collaboration are all about. And those relationships can only strengthen your engineers’ work, your managerial effectiveness, and increase the company’s performance as a whole.