4 Habits of a Successful Team.

Tony Guglielmi
4 min readJun 22, 2016

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In my relatively young career, I’ve worn many hats as a developer, designer, project manager, and manager. While this plurality of job roles provided unique challenges, I have been blessed to work with amazingly talented teams in the process. Each team all had different goals, but shared very similar habits that I believe cultivated their success:

1. Fail Loudly
We’ve all heard and embraced, “Fail Fast, Fail Often,” or the old Facebook motto of “Move Fast and Break Things,” but the key is not to sweep failures under the rug. It is important to talk about your failures just as much as your successes with your team so everyone has the chance to learn from others’ mistakes. Don’t be down on yourself, though, but rather ask and answer these questions:

  • What went wrong?
  • What actions do we need to take in the future to prevent it from happening again?
  • When will we set time aside to make this change? (This is meant for times when the project is a bit out of scope, but planning is the only way to set things into motion).

Failing loudly as a team garners a culture of communication, because it encourages ownership of actions and retrospection leading to improved processes and systems for the future. This is why sprint retros and post-mortems can be so advantageous to your team.

2. Mentor and Be Mentored
Having a Senior member mentor a Junior member pushes both to better themselves and build trust, while also strengthening emotional buy-in to the company. I believe it is important for everyone to experience being both a mentor and apprentice in order to have a chance to be humbled as a student and proud as a teacher.

Remember, mentorship does not need to be limited to the hard skills one uses in daily job functions or even between employees on the same team. One example from Imgur was a mentorship that took place between a Full Stack dev and a Senior iOS engineer. It was amazing to see how fast one can learn and transition into being a productive member on another team when you have a resource to lean on. This instance included an added bonus, as our Full Stack engineer transitioned to the iOS team and brought his knowledge of the backend API service, allowing him to share his skillset.

Whether this is a formal or informal system is not important. Mentoring builds confidence and confidence empowers. Empowerment is contagious and pushes team members to teach others.

3. Give and take critical feedback often and early
Critical feedback is a clear, balanced, and specific opinion on how to improve on any subject or issue. It is one of the toughest soft skills any team battles with. It is easy for feelings to get hurt or fear what the feedback could be. The keys here are to:

  • Do it often so the team becomes accustomed to the discomfort. (If it is comfortable then it isn’t meaningful.)
  • Give and take feedback so the team understands it is a reciprocal tool for all to use and grow. It is not a mechanism for judgement.
  • Feedback is balanced with both positive and negative points with actionable items for next steps. (Saying “I disagree” is not acceptable. Saying “I disagree with this point because…I feel like a better approach could be…” is.)
  • Do it early in projects. Critical feedback is best used to guide a team to a finished product and not as an afterthought a week before launch.

This ties in closely with “Failing Loudly”, but is worth outlining, as it is a critical asset to strengthen communication in a team.

4. Encourage Work/Life Balance
Many companies talk the talk, but don’t walk the walk. This is a touchy subject that can cause heated discussion, but balance of work and life happiness stands as the most important habit on this list. An unbalanced employee will be bound to burn out; unbalance doesn’t just affect them, but also their team members. It is not the company’s job to enforce balance, but as a community everyone has a stake in supporting it. Small ways to help promote balance are:

  • Be selective in your praise of those who burn the midnight oil. Do not always assume late night work is productive work. While it can be inspiring, it comes at a cost. By praising these individuals, you will inadvertently begin cultivating a work-a-holic culture where time is equal to productivity, which is not a true measure of success.

Remember that this choice to work late can be at the cost of that person’s family and friends; and ultimately their happiness. I would suggest assessing the situation on why that person is working late (if it happens consistently): Was there a badly evaluated project timeline? Is there a roadblock that is better brought to the team? Are there too many meetings, keeping them from being productive during the day?

  • Give a generous vacation policy. There are a lot of ideas on what is the best system such as unlimited PTO or accrual, but really whatever works and makes your team happy is all that matters. Sometimes the best thing for an employee is to have time away from projects and deadlines in order to have a fresh perspective on their return.
  • Balance comes from the top down. In my experience, the best way to support a work/life balance is for leadership to support it adamantly. The CEO at Hello Monday would always push me out the door when he left at 6 PM. He would exclaim, “Today’s work is done, Mr. Ohio! Go and enjoy your night; thank you for today.” It was a simple gesture but all that is needed.

A team’s habits on a day-to-day basis contribute to the bigger picture and betterment of its members. These habits are key to a successful and growth-oriented office environment, but they are not the only ones. Please feel free to share your thoughts from experience on any of the above or any I didn’t mention!

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Tony Guglielmi

Senior Software Engineer at Imgur, who loves creating joyful and useful products.