The reality of being a VP of Engineering

What does being a VP of Engineering actually involve? Honeycomb’s Emily Nakashima breaks it down.

What does a typical day in the life of a Vice President of Engineering look like? It might be an impossible question to answer. 

Unlike a software engineering role, which often has strong daily and weekly rhythms, the VP of engineering role operates on a longer cadence. The most important cycles are typically quarterly and annual, instead of daily, weekly, or monthly. Instead of stand-ups, sprint planning, and retrospective meetings as the recurring touch points, quarterly OKR planning, board meetings, annual budgeting, and planning processes become some of the most important calendar milestones. Regular 1:1s and sync meetings bring some rhythm to the week, but in general, one day is rarely like the next. 

When compared with other engineering management roles, the VP role is much more about high-level strategy and long-term direction than the day-to-day business of engineering.

Director of engineering vs. VP of engineering

I made the transition from a director of engineering to Honeycomb’s first-ever VP of engineering in 2020, after three years at the company. As a startup of approximately 100 people, there wasn’t a clear need for a CTO, director, and VP of engineering. This made it challenging to understand exactly what might need to change about my responsibilities as I made the shift.

Honeycomb’s CTO Charity Majors provided me with a crisp description of the difference in a single, aspirational sentence: “Directors run the company.” Her point was that, although it’s both my job and my directors’ job to run the engineering department well, the directors should ideally be empowered to run the day-to-day operations of the company in most circumstances. This frees up the VP tier to focus on strategy and longer-term planning, making sure the ship always ends up pointed in the right direction, despite the daily twists and turns. 

This high-level focus doesn’t materialize 100% of the time in practice. As a growing company, there are always gaps appearing in a company’s management coverage, and I often become closely involved in running day-to-day operations. This is especially true in times of change when we’re making adjustments to our management structure or team practices. For example, this comes into play when hiring for new types of roles, reorganizing the team, or rolling out a new roadmapping or planning process. In these moments, I often spend time immersed in conversations with senior individual contributors (ICs), engineering managers, and directors, understanding what is and isn’t working and collaboratively crafting how we’ll evolve.

This more tactical work is important and valuable partly because it provides a chance to work closely with your engineers to build connective tissue for the future. However, it’s just important to resist the temptation to let this workload balloon into filling up the entire calendar and distracting from the important but not urgent strategy and planning parts of the job.

Working horizontally vs. vertically

All engineering management roles have aspects of working both vertically, where you work with your manager, your direct reports, and their reporting chains; and horizontally, which involves collaborating cross-functionally with other company leaders. However, I’ve found that in those roles, the ratio of this type of collaboration was more or less fixed. In the VP role, attention can shift from horizontal to vertical based on current needs. Knowing when to make this shift is part of the art of the role. 

Legendary point guard Sue Bird played college basketball for UConn, where she spent most of her first year injured. As she got back on the court and started to figure out her role, her coach, Geno Auriemma, told her, “Everything that happens on court, it’s your fault. I don’t care if [your teammate] Asjha Jones makes a bad pass to Swin Cash, it’s your fault.” She was initially put off by the advice, but it later began to make sense. Her ultimate goal wasn’t just to perform well as an individual, it was to win as a team. She could use her skills, presence, and guidance to make the whole team more successful. Just because she wasn’t holding the ball, that didn’t mean her responsibilities as a leader ended.

As a new member of a startup executive team, I wanted to bring that mentality to my relationships with my executive team peers. I quickly learned that nobody appreciated the exec team member who got their own house in order and then sat back waiting for everyone else to do the same. Our job is to build an enduring, successful, valuable business, and a healthy, thriving workplace for our employees. If something is standing in the way of that, it doesn’t really matter to me whether that problem is within engineering or not, I’m going to find a way to help out or try to lend my support.

This means that if the best thing I can do to help the company is to spend my week working with other execs on company strategy, refining messaging with members of our go-to-market teams, working the booth at a conference to support our marketing team, or spending time at a sales offsite sharing my perspective as a proxy for our prospects’ budget holders, I’ll often make the call to prioritize those things over working on initiatives within engineering when our house is mostly in order.

Alignment, evolution, focus

What does it mean to have your house in order though? Like a director, it’s about having a well-run engineering department, with three key additional responsibilities: alignment, evolution, and focus.

Getting alignment is the most important deliverable that I owe to the teams within engineering. If you have ever worked at a company where everything feels broken but you don’t know why, that’s probably due to a lack of alignment. 

Without executive-level alignment on the state of the world and key priorities, teams will constantly be at odds. To avoid this and quickly make progress as a company, the executive team must have a shared picture of where the company is going, crisp agreement on priorities, and a lot of shared context about how the current state stacks up against where you want to be. As a VP, your job is to work with those executives to reach alignment, so that teams aren’t stuck wasting time and effort re-litigating the same questions over and over again. 

If alignment is mostly about what you are doing now, evolution is about where you’re going in the future. 

How do we need to evolve the department and the company? Where do we need to be two, three, or five years down the road, and what do we need to put into place today to get there? Are we missing key skills or expertise that we’ll need to build up within our teams? Are there important changes to our technology or organizational structure that necessarily will be years in the making? 

Knowing how to answer these questions and evolve the department is one of the most critical, yet daunting aspects of the VP role. Teams that don’t proactively evolve their practices and configuration toward a planned future state tend to stagnate and fall behind.  

Finally, a VP should enable their teams to focus. On any engineering team, the ratio of things you’d like to build to those you actually have time to build is at least ten to one. Teams and individuals have to constantly say no to requests that are genuinely neat ideas, but are not the most important things for the business. Each no is painful and takes time and explanation. 

Engineering leaders can sometimes become distant from this and start to add their own wishes to the pile. However, it’s much more effective to be a shield for all these distractions, and say the hard no’s to distracting requests further up the chain so that your teams don’t have to fight off these requests themselves. A VP “no” can go a long way and make a lot of space for all the things your teams genuinely do need to say yes to. 

How to prepare for the role

The number of VP of engineering roles at a company is typically much smaller than the number of director roles, and it can take years to find a suitable role that aligns with your strengths and successfully navigate the hiring process to land it. Before that, there are a number of ways to build the requisite skills while in a director or manager-of-managers role.

One of the most valuable sets of skills needed for a VP role is crafting and refining strategy. As an engineering manager or director, you’ll likely see lots of strategy documents, and potentially even write some of your own. Taking time to ask questions about these documents – or even challenging some of what you see –  can be a great way to build this skill. If you like management books, Richard Rumelt’s Good Strategy Bad Strategy: The Difference and Why it Matters and The Crux are great introductions to the problem of writing good strategy.

Finally, if you aspire to be promoted to a VP role at your current company, it’s easy to underestimate the importance of building great relationships up, down, and sideways. The same people who might interview an external candidate for the role are likely the ones who can exert their influence in support of making an internal hire. Being the kind of coworker who is generous with their time and expertise and is already sought out for advice and cross-team perspectives can go a long way toward showing other senior leaders at the company that you could navigate the social transition into this sort of role.

It can take a while to find and land a VP of engineering role, but happily, all of these skills can be force multipliers in other roles around engineering teams. Just as all VPs were something else before they became VP, most VPs don’t stay in the role forever. Many successfully occupied the role and then went on to pursue other challenges of different shapes at new companies. 

The job title can feel special and coveted just because it’s relatively rare, but at the end of the day, you’re still just one more player on the court helping the whole team succeed.