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Behind the Team: Trust and Employee Retention, How Trello Sticks Together
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Behind the Team: Trust and Employee Retention, How Trello Sticks Together

Chatting with Jessica Webb, Product Marketing Senior Team Lead at Trello

October 22, 2020
Conor Dewey
Growth at Hugo
Conor is a Growth Marketer at Hugo, an interface for centralized meeting notes that connect with your favorite tools. He has worked on data science and growth at internet companies including Mastercard, Unity Technologies, and Squarespace.

It’s easy to give lip service to trust and relationships because the results are hard to measure. But what would it look like to build a team that has quadrupled the median retention rate for talent in the technology sector?

Great relationships can translate into more effective teams and employee retention, but the biggest benefit is that it’s more fun to work in a company with great relationships and a strong sense of trust.

I was able to chat with Jessica Webb, Product Marketing Senior Team Lead at Trello, to discuss how they’ve managed to maintain team members for 4+ years in an industry where retention rates are notoriously low.

In this article, you’ll get practical advice on:

  • Practices for creating and maintaining trust among team members
  • Communication among teams that really works
  • Eliminating ego-driven behavior

Trello’s project management software platform has more than 50M registered users. The company was acquired by Atlassian in 2017 for $425 million. As Senior Team Lead in the marketing department, Jessica works with a group of 10 full-time team members and another 5-10 people who are pulled in depending on the specific projects.

Even with this lean team, Trello has worldwide reach among businesses and organizations. Jessica mentions that trust and caring are the keys to this level of efficiency on the team.

In our interview, she goes beyond run-of-the-mill thought leadership and gets down to practical steps that can lead to trust and caring within your team.

🔒 Making it real; making it safe

First and foremost, caring has to be real. How much time do you take in your meetings to ask what’s going on in people’s lives? When they answer, do you listen, or does everyone just say they are fine?

Jessica says that at Trello, meetings start with a check-in:

We have a bi-weekly full team meeting. We call it the “Club Marketing Meeting.” We always make time in that meeting to talk about our highest highs and our lows and share the progress updates. What’s essential is that we remember that we're humans and it’s safe to acknowledge that part. What that means is that we know each other so well we know each other's work styles so we can predict what will be needed in terms of support. And that's been super helpful especially in a time like this where there's been a big emotional change for the world around us.

To maintain emotional safety, the team has a specific practice of giving everyone the benefit of the doubt. “You might be assuming something but you actually don't have the context. So we constantly push for clarification.” When there’s a misunderstanding, a team member will repeat what was said, and say what they understood or interpreted, and then get feedback on whether their interpretation was correct.

By using this technique of inquiry instead of assumption, the team gets deep into one another’s motivations and is able to reconcile issues quickly. This habitual inquiry makes it easy for everyone to say what’s on their mind because they know if they are misunderstood, the other party will ask for clarification.

🤝 The role of trust

In our discussion, Jessica wasn’t conceptual about the idea of trust. Trust comes from knowing what you can expect from people, that they will deliver, and that they care. Trust is built up over time, as the team works together and gets to know each other’s strengths--and it also comes from being willing to step up and compensate for one another’s weaknesses.  

Care is the knowledge that your team members will sacrifice their own self-interest for that of the team or the goal. When someone cares, they put your interest before their own.

The Trello marketing team is a group of people that is so creative and collaborative and there's no egos. We are very much here with shared mission and vision, and people aren't protective over their projects. If somebody comes up with an idea but doesn't have the bandwidth to support it, they're more than happy to to have somebody else take it to the finish line. I feel like we're kind of like the baton races where you're passing it to the next person.

Creating trust in cross-functional teams is a matter of contribution, and again, Jessica’s insights were that it’s not necessarily about doing something for other teams, but about providing useful perspectives. She noted, the product team was skeptical about having participation from marketing in some of their meetings.

By providing useful perspectives and inputs to the meetings she was able to build up trust among the team. In other words, thinking about how to give support to others rather than how to get support was the fundamental basis of building cross-team rapport.

🚀 4 meetings keep trust alive

Trust can be built through a number of different types of meetings. Here are the four types of meetings Jessica cited and how to leverage them to build trust and care in the organization.

Team “club” meetings

Bi-weekly meetings aren’t just status updates. Trello’s marketing team uses regular meetings to share challenges and triumphs, including the personal side of what is happening for them. Asking about the best and worst parts of their jobs allows them to support one another and also play on one another's strengths. The meetings include auxiliary team members as well as the core team members, so nobody is excluded.

Personal check-ins

Regular work meetings include a check-in to get people settled into the meeting and to handle what people are dealing with. If someone is having a particular challenge, the rest of the team really listens and supports them. It’s not a check-in just to make everyone feel good. In other words, it’s not enough to ask someone how they are--you have to want to know how they really are and listen to the answer.

One-on-ones

“One on ones are some of the most valuable meetings in terms of getting to know one another,” Jessica says. One on one meetings should be standard practice for every manager, but again, she emphasized that allowing people to be human and not just a “worker” is what makes the difference in the long term.

AMA with the chief

Trello has a regular monthly meeting where all employees can ask the organization’s co-founder anything. Some call this a “Fireside Chat”. What’s important about the meeting is that it’s not an update — it’s designed completely around the questions that employees want to ask leadership. Knowing that leaders are available as a resource on a regular basis also fosters the environment of caring and trust.

😰 Busy is no excuse

Taking care of one another as individuals is simply part of what she sees as the job of a manager and the team members themselves. It’s not relegated to some official function but integrated into the day-to-day workings of everyone. Caring is pervasive, not a job.

The marketing team at Trello is one of the most productive in the industry and given their rate of growth, they’re extremely busy. Again, that doesn’t appear as an excuse on Jessica’s radar. She did mention that everyone is clear about their time limitations, so they don’t take on more commitment than they can handle. Making time for one another is simply built in.

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Conor Dewey
Growth at Hugo
Conor is a Growth Marketer at Hugo, an interface for centralized meeting notes that connect with your favorite tools. He has worked on data science and growth at internet companies including Mastercard, Unity Technologies, and Squarespace.

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