Managing High-Performing Teams at Start-ups Through Frequent Org Changes

Tina Pastelero
Gusto Insights and Operations
4 min readAug 13, 2019
Photo by rawpixel.com from Pexels

One of the biggest surprises for me transitioning from working at large established companies to startup life here at Gusto was the speed and volume of organization changes. I was used to a world where any org change could take weeks to months to get implemented given the approvals required and complex processes in place. It was a big change of pace for me to experience how things were done at a startup where org changes could literally happen after a discussion and handshake. Whatever was needed to meet the needs of our business (and customers) came first, so if we needed to restructure a team or move people around, it was implemented quickly.

When I returned to work after parental leave late last year, I was asked to help run our Sales Insights & Operations team on an interim basis, in addition to my day job running the Marketing I&O team. It was a daunting task. I had to figure out how to adjust to returning from parental leave, onboard three new hires at our Denver office (while working out of our San Francisco office), and learn about the ins and outs of Gusto sales. After a few months of working at a breakneck pace, we hired a permanent head of Sales I&O, and I was able to get back to Marketing I&O full-time.

This was a huge learning experience for me, so I wanted to share some of the tips and tricks I’ve learned about managing high performing teams through frequent org changes.

1. Communicate early, often, and via the appropriate medium

To prevent members on your team from feeling blindsided about sudden org changes, communicate upcoming changes (and the rationale behind them) as early as possible. It’s also key that you update your teams and cross-functional partners about who will be responsible for what moving forward. Something that worked well for me was creating a simple “Who’s doing what” document that I shared broadly referred to frequently.

Finally, use the appropriate medium. If upcoming changes may be met with anything but enthusiasm, make sure to broach those topics in person (or via video chat), not with Slack or email. It may be tempting to fire off a detailed paragraph and let the chips fall where they may, but the ability to express your tone and answer questions in real-time makes in-person communication the way to go.

2. Write an “About Me” user manual

When I first encountered the “About Me” document at Gusto, I found it a little strange to write out things about myself that would normally be part of the natural discovery process of working with someone. However, when I was thrown into the world of Sales I&O with a new team to manage, I understood the value of having a short one-pager for my team to quickly learn about me and understand the best ways to work together. Among the details I included were:

  • Times I like to work and when I am available across platforms
  • How I prefer people to communicate with me
  • How I prefer to receive feedback
  • The path that led me to my current role
  • Conditions under which I find myself doing my best work
  • What motivates me, what frustrates me

3. Give frequent feedback

We have formal performance review cycles at Gusto every six months. Even though this is more frequent than the annual review cycles I was used to in previous workplaces, the rapid growth at Gusto has taught me the value of eliciting and delivering direct feedback even more frequently. Regular feedback that is delivered with care for others and a genuine desire to see people develop is invaluable. Feedback helps you see your blind spots, develop your skills, and grow successfully. There’s a big temptation to punt feedback to the future (especially those tough conversations), but at a startup, you don’t have the luxury of time to wait for formal review cycles to come around. Plus, if you flex your feedback muscle frequently, it becomes less awkward and more productive for everyone involved.

4. Handle manager transitions with care and thoughtfulness

It can be jarring to have frequent manager changes. When I started as the interim lead of Sales I&O, someone on the team told me they had experienced four different managers in a span of two years. With that pace of change, it can be hard to keep up, and even harder to know what’s expected of you.

It’s important to set expectations upfront about how transitions with a new manager will go. This includes things like how long 1x1 meetings will keep going with the previous manager and who will be responsible for writing and delivering performance reviews. I also did formal “manager transition” meetings with each person on my team and their new manager to ensure I was transparent about what I was telling their new manager about their strengths, areas of development, and career goals. The conversations can seem a little awkward at the time, but they are much appreciated after the fact, as everyone is on the same page moving forward.

5. Embrace change

Org changes are a fundamental piece of startup life. As you strive to adapt to the needs of your customers and the competitive landscape, you may have to pivot and transition roles quickly. This can lead to friction if not done thoughtfully. Hopefully adding these tips and tricks to your toolbox will help ease any friction and create the best transitions possible for your team.

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