The engineering manager's guide to a pain-free reorg

In many technology companies, the biggest engineering challenge isn’t a killer app or an incredible database. Instead, it’s building and organizing a team that’s optimized to achieve company goals.

For a fast-growing startup—where the engineering team is often growing rapidly—those goals can change from quarter to quarter (or, in some cases, week to week). Occasional reorgs are a necessary reality for every engineering organization -- but they don’t have to be a painful reality.

As a technical leader with more than a few reorgs under my belt, I’ve put together these four principles to make the process pain free.

Principle one: Create a communication plan, and hold everyone to it

Engineers are process-driven by nature.  It’s really easy to get caught up in laying out the org structure, seating plans, and workflows and fail to remember that the impact of a reorg is felt by individuals. Your plan can be perfect on paper but if you’re not communicating carefully you could end up with an organizational catastrophe. 

So, how to prevent that particular problem? Enter the Communication Plan. Make a list of everyone in the organization, including critical information about each of them: Who their current manager is, who the new manager will be, and some notes about their work. Use this as a checklist for making sure that every person on the team has a 1:1 conversation with both their current manager and their new manager. Then, set target dates for managers to have each of those conversations. Ask each manager to hold a meeting by those dates and update the plan as they have conversations. 

You’d be shocked at how often engineering orgs fail to ensure that managers are talking to teams throughout the process. Sometimes you get told you'll be on a new team and the new manager doesn't talk to you until it happens. Other times, information is conveyed in a group meeting. This can be discouraging to those looking for an opportunity to bring up concerns and questions they wouldn’t necessarily want to have in a group setting. 

The advantage of 1:1 meetings isn’t just for team members. Leadership can learn so much by opening themselves to organizational pushback a manager wouldn’t have considered. The power of the communication plan is that it isn’t just one way -- feedback can be taken into consideration and teams can be adjusted accordingly.

Principle two:  Give everyone a True North

Ideally, you have company goals you can tie everyone’s work into.  Of course, if you’re working at a startup, that may not be the case.  Part of your job as a leader is to push for those, and if they don’t exist, to create them for your own team.  In order to maximize team performance,  there should be a set of initiatives or key focuses the team will have for the next 6 months to a year. 

While conducting a recent reorg in my current role at Flyhomes, we looked for natural divisions to help shape the organization against company goals, making a much smoother organizational structure. We divided the org into three teams.  The first supports the value proposition of Flyhomes -- that is, that we bring every part of the homebuying process under one roof. 

The Vertical Integration team tackles projects such as internal CRMs and other tools that keep the business running smoothly.  The other two teams are all about our main customers: Homebuyers.  One of those teams is called Acquisition, and they partner with marketing, for example, on driving leads and maximizing conversion on our website. After the customer has signed up, the Vertical Customer Experience takes over, working on the customer-facing websites and apps. Clearly articulating the names and responsibilities of each team creates a clear decision-making lens for projects.

Principal three: Make and empower better managers

Research shows that people work for bosses, not companies. However, when we promote people because they have excellent engineering skills, we don’t always think about how to prepare them to be a manager. This is never more critical than it is during a reorg.

With each manager on a team, it’s important to understand their level of experience and confidence leading up to an organizational change. I have a series of questions I ask: Have you led a reorg before? What worked? What didn’t work? What are you worried about?

Make the time to coach them through tough conversations. Encourage them to think about how they’re delivering messages to their teams. Leading up to a re-org, put investment into making sure your engineering managers know their job isn't just cranking out products; it's also, critically, growing people on the team. 

Principle four: Your most powerful tools are your ears and your voice

The real lesson I’ve learned over the years is that a reorg isn’t done once you’ve moved everyone’s seats and changed their reporting structure in your payroll software. In fact, the biggest job in leadership is continuing to keep your finger on the pulse of the org, so you can quickly correct what isn’t working and signal boost the things that are working.

Your main tool is going to be talking and listening. I maintain weekly 1:1s with each of my managers and rely upon them to have 1:1s with their teams. Each week we have an agenda item to talk about what we’re observing on the team. People don’t always communicate conflicts, and instead will leave an organization or team if they’re stuck, frustrated or bored.

When you create a culture of trust, you will be rewarded by having the opportunity to fix those problems and retain your team. I always want my teams to know that there is room to create challenging, exciting work for them as long as they communicate.