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Musings as a manager

2024 September

Last August upon my return to Ramp, I was tasked with hiring for Procurement. At the time, the engineering team was comprised of myself, Kevin (one of my co-founders from Venue), and PaulS on FE.

My scope has expanded since, and as of the time of writing, I lead the Procure-to-Pay org comprised of three teams – Procurement, Vendor Management, and Bill Pay. I currently manage a team of 12 backend engineers.

All managers were once first-time managers, but the start of the management journey is especially challenging. Many smaller companies, including Ramp, avoid hiring for external people managers (a subject we'll leave out of scope here). At these companies, the main pre-requisite to having a report success as an IC. However, unsurprisingly, being a good manager requires a completely separate skillset from being a strong IC.

Prior to taking on reports, I solicited advice from more experienced people managers at Ramp, and a consistent recommendation was The Manager's Path. I recommend this book to most engineers who ask for advice, since it covers all stages of an engineer's career from IC → manager → engineering leader.

With all of that said, we can get into an assortment of subjects below.

An unreasonable ideal

In a perfect world, your management career would be filled with ideal reports. These reports would be self-sufficient, be receptive to feedback, surface how they're doing proactively, crush it at their jobs, and make your life simple as a manager.

In practice however, most of your time is spent coaching and working with others, approaching but never fully reaching the ideals above. Frankly, I think management is the ultimate "journey before destination" job. The joy derived as a manager is from the slow and steady growth you help others achieve.

Guiding principles

I had a manager at Facebook who summarized their management philosophy as prioritizing "you (the report) first, then the team, then the company". My manager even explicitly mentioned that if I wanted to leave either the team or the company, they would do their best to support me on that path.

I generally agree with the philosophy above – as a people manager, your responsibility is to help your report grow and achieve their career goals, while balancing them with the company's goals as much as possible. Although it may seem counterintuitive, I strongly believe that prioritizing in the order above leads to better outcomes for both the report and the company.

Notes and 1:1s

Have regular 1:1s. This is the simplest thing you can do to ensure your report feels supported and has a place to voice their feedback.

Take notes in the tool of your choice (at Ramp, we use Google Docs or Lattice). These notes should be date-stamped, contain an agenda of topics discussed, and have enough substance to recall what was discussed. These are crucial when you inevitably reckon with performance problems, and is also good to keep for your own sake.

Feedback, aka being honest

The crux of being a manager is giving feedback to help your reports grow. If you don't give feedback, your reports don't know where they're doing well vs. where they can improve. Giving feedback on what's going well is easier but still important – for me, it's an exercise in paying attention and remembering to share it regularly. Giving constructive feedback is the real challenge.

A strongly held belief I have is that establishing transparency with your reports lead to much better outcomes. This is cultivated by regularly soliciting feedback on yourself, consistently checking in on how they're doing, remembering to follow up on any requests they have, and being there for them whenever tricky situations arise.

Assuming you & your report feel comfortable being transparent, sharing constructive feedback is much easier. Delivery of feedback is equally as critical as the message itself, but if I had to choose, the latter is more important. One mistake I made early on was overly softening critical feedback – this caused the severity to be misjudged, leading to misalignment on both sides. One way to sanity check this is to ask reports to summarize the feedback after delivery, to make sure nothing has been lost.

From what I've seen, a manager's inability to deliver constructive feedback is the most common reason for departures from a company. The most common failure mode here is falsely promising promotions (root cause: avoiding hard conversations), leading to extreme loss of faith afterwards.

In terms of how to deliver constructive feedback, always do the due diligence. Solicit supporting feedback from others and have specific examples in mind. You should never feel that you're having to make up examples on the spot – it's obvious to everyone if you haven't done your homework.

To summarize - be honest. Put in the work to have the hard conversations. They never get easier, but you're doing your report a disservice by avoiding them.

Performance management

All people managers have to performance manage at some point. As mentioned above, the best preparation is consistently taking notes. These should also include any feedback shared above (Lattice has both shared & private notes, and I keep track of feedback delivery & reception in the private notes).

Ravi Gupta has a great article on this subject that I wholeheartedly agree with, and we'll be using this as the starting point for the rest of this section.

First, I think the above is something to aspire towards, more than something we can all immediately put in practice. There's plenty of reasons why we wouldn't enthusiastically rehire someone, but also continue to work with them because the company is a better place with with them there.

In my experience, most companies tend to be too lenient with performance management, which can lead to unnecessary layoffs and your most talented members feeling frustrated. Amp it up goes into detail on how companies are sports teams, not families. Great people want to work with great people, and when you don't hold the standard, it's easy to fall into mediocrity.

Assuming you're giving regular feedback, haven't been avoiding the hard conversations, and you've been taking notes, you're already on the right path. One piece of management advice that resonated with me was that most of your time, your gut instinct is right. When someone's underperforming, you probably know, but you avoid the signs because of the implications: performance management has a lot of friction, necessitates extremely hard conversations, and can reflect poorly on the manager. Despite this, it's important to follow through and help the people you work with grow.

Poor performance shouldn't be a surprise for your report. As a manager, avoid the pitfall of observing behavior and either not delivering the feedback or not giving your report time to improve.

Hiring

First, I would recommend understanding the entire hiring pipeline end-to-end. How many candidates are getting hired on a monthly/quarterly basis, who's involved in the interview process, and how do prospective hires get assigned to teams?

Bad hires are incredibly expensive for a company, but even more so for the manager who needs to performance manage the report. Unfortunately, hiring is incredibly subjective, and it's more of an art than a science.

Here's some general advice I have:

  • In my experience, communication is the least coachable attribute. I've never worked with someone who went from a poor communicator to a mediocre one. The ability to effectively communicate ideas is foundational to being successful, and being misunderstood (from poor communication) can lead to all kinds of downstream problems.
  • Hire for slope over intercept. Regardless of seniority, willingness to grow is directly connected with open-mindedness. This can take many shapes – those willing to put in extra hours, those who want new challenges, or those who are always open to new suggestions to improve.
  • Keep archetypes in mind. Part of good hiring is recognizing the gaps in your team. This isn't always about leveling – it can be engineering archetypes as well. Although most companies don't think about this until IC6, you should consider the trajectories/archetypes of the members on your team when determining who to hire.

Everything else & resources

This is by no means an exhaustive list, and there's far more that goes into management. Here's some resources that I've found helpful: