Management: 5 Steps to a Happy Team

Shea Sulkin
Jun 27, 2019 · 7 min read

Let’s put it out there. Management is not for everyone. Most managers, while perhaps great leaders, are not great people managers. Yet others guide innovation, build great teams and grow incredible individuals.

If you’re interested in managing, first, ask yourself why. Do you want to be a manager or do want a promotion? The answer hopefully is that you want to be great at what you do and build on your own talents. For managers, that typically means a natural aptitude towards:

  • Listening (and by listening, I mean not talking)
  • Finding and growing others talents
  • Advocating for others

We all spend a great deal of energy finding the right career path, but once there’s a promise of promotion, it’s easy to gloss over asking yourself if the role is truly a fit. So stop. Ask yourself. We’ve all seen the effects of untalented managers.


Right from the start of my career, I learned the ripple effects of these managers. And it stuck.

My first boss fell into the terrible category— a lunch time drinker who pawned all work onto me. As an early overachiever doing the work of two, over time, feelings of resentment came to dominate my working experience.

My next boss was exactly the opposite, and what I was craving — extremely strict and incredibly motivating. At times I couldn’t stand her, but the past experience, and the speed at which I advanced, motivated me to stay with it. This was my first time seeing the effects of a great manager.

This set me up to see both sides of the coin. At 24, an interest was sparked and I was set up to mentor a new designer. Throughout my career, I’ve continued to enjoy managing, and a decade later, I manage a team of designers. While I may not be liked every day, I consistently receive thanks for the role that I play and hear that we have the happiest team around :).

Here are the top 5 things I continue to come back to in managing individuals and teams.


1. Start with Listening

When joining a new team, I want to get to know the individuals, how the team works and about the work itself. I meet with each person, usually to kick off our one-on-ones, then meet with the group. With the group I either use a Post-it style activity or a discussion to gather:

  1. What’s the day to day like?
  2. What’s working?
  3. What’s not working?

I’m not going to fix everything, but I want a pulse of where we are. I’ll gather my thoughts on team meetings and cadence and perhaps holes in process we could work towards. A typical cadence I like to start with is:

  • Weekly reviews
  • Friday retrospectives
  • Quarterly goals (with check-ins every 2 weeks)
  • One-on-ones (weekly or less)

The weekly reviews are to bring the team together, share any news and review the status of all projects. If it comes up that a team member has too much or too little work, this helps us shift work as needed. I also ask the team to share new work (easy to do as we’re designers) to keep us inspired and collaborating.

Friday retrospectives, goals and one-on-ones are detailed below.

Structure can be incredibly helpful, but too much is no bueno. Keeping an eye on the ability to adapt, I work these meetings in over the first couple of weeks. Just about anything is open to reassessment.

The message I want to set from the beginning is,

“I’m the leader, but this is our team. I want your feedback, I want us all to feel ownership, to feel motivated, to grow and enjoy this work.”

2. One-on-Ones

Ultimately, individual motivation can make or break a team. This makes one-on-ones the best place to start and the most important meeting to keep.

I like to follow a loose 10/10/10 (in which 10 minutes are dedicated to listening to the employee, 10 minutes for the manager to respond and 10 minutes to discuss together) with the following questions:

  • How are you doing? What’s going well? What could be improved?
  • How could I improve as your manager?
  • What are your motivations? Short-term goals? Long-term goals?

A separate post is coming soon all about one-on-ones.

3. Goals

Setting and maintaining team goals allows us to check in on what’s working and what’s not and find new ways to stay motivated and engaged. We aim to set goals quarterly and align (at least some) of our goals with the company goals or mission.

The first time the team creates goals, we start with a Post-it activity.

  • Intro: Each team member gets a stack of Post-its and a Sharpie (for visibility). I give a few examples of possible goals to get the juices flowing.
  • 5–10min Activity: Each person writes one idea for a goal on each Post-it. No bad ideas — it’s quantity over quality — and I join in as well. (Another option is a Start, Stop, Continue activity.)
  • Review: Each team member takes a turn sticking their Post-its to a white board and explaining each one. As we go (or at the end) I get the team’s help to cluster similar ideas. If the board looks overwhelming, we’ll name each cluster and add a header Post-It.
  • Selection: Give each team member 3+ dot stickers and ask them to mark the Post-its containing the goal ideas that they’re most interested in focusing on for the quarter.
  • Discuss: Do we like the top choices?
  • Record: Once we reach a consensus, I record and organize the goals in a shared document. For the top goals, we collectively decide upon success criteria and an owner for each.(If the meeting feels too long, this can be done in a separate session.)

We follow up every two weeks, each time setting mini-goals and recording how we’re tracking. It’s ok not to meet the goal each week but it helps everyone to see progress, check-in and stay motivated. And of course, the goals can change along the way.

At the end of the quarter, we do a retrospective to guide how we would like the next quarter’s goals to go.

Example Team Goals

4. Retrospectives

To wrap up each week, we meet on Fridays for a team retrospective. I’ve grown to love Norm Kerth’s retrospectives (thanks to a tip from a great manager ;). Without this structure, things can sway a little sour.

  • What did we do well?
  • What did we learn?
  • What should we do differently next time?
  • What still puzzles us?

This is a time to air things out, not to fix things. However, sometimes I will ask the team at the end if it’s alright if I take action on something.

“Regardless of what we discover, we understand and truly believe that everyone did the best job he or she could, given what was known at the time, his or her skills and abilities, the resources available, and the situation at hand.”

— Norm Kerth, Project Retrospectives: A Handbook for Team Review

Retrospectives are most commonly used at the end of projects, but no need to wait! Adding a retro while something is still in progress gives you an opportunity to improve along the way.

Over the years, our team has tried out various additions. Things like selecting an item from the retro to focus on for the next week or using emojis and gifs to give the vibe of the week.

Example Weekly Team Retrospective

5. Change it Up

I’m continually learning and growing alongside my team. It’s important to remind myself of this. I’m not better or more important. I just have a different role that helps the group move forward.

I want the team’s feedback and I want us all to feel ownership. Too many meetings? Not enough collaboration? More hangout time? You never know until you ask!

Here are a few things we’ve tried over the years, and of course, not all at once. Most of these came out of our Goals sessions and stuck around for a quarter or two.

  • Design Days: A block of time to work on a design project as a team.
  • Design Critiques: One team member requests specific feedback from the group.
  • Teach-a-Skill: Each team member chooses something to teach the group.
  • Group Shadowing: If a team member is an expert in a tool, watch them use it.
  • Group Project: For example, creating a Design System over many months.
  • Take a Class: For example, IDEO’s Human Centered Design course.
  • Involvement in Design Community
  • Volunteer Projects
  • Team Potlucks

This is A Lot

I know what you’re going to say. This is a lot of work. Yes it is. And a lot of time. Sometimes it’s hard to make space to get “real work” done. At times I try to take on full projects as an individual contributor and beat myself up for not being able to follow through.

Things that help me… blocking off chunks of “busy” time, saying no and spreading out meetings when things get crazy. But to me, management is about supporting the team and the team’s work. If I’m able to squeeze in being an individual contributor here and there, that’s the icing on the cake. In the end, if the team is successful, I am successful… and valued… and worthy (and that’s a whole ‘nother rabbit hole).


The Startup

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Shea Sulkin

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The Startup

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