Trust and Employee Retention: How Trello Sticks Together

Jessica Webb, Product Marketing Senior Team Lead at Trello

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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
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🔒 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?

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🤝 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.

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🚀 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.

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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 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.

Growth at Hugo. Previously data science at Squarespace. Writing here now:

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