Writing Annual Reviews In Ten Minutes

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Reviews are critical to employee, manager and corporate health. A lack of regular feedback can create misunderstandings when it comes time for annual reviews, it can lead to compensation or promotion shocks and a lack of strategic delivery on products. Hiring is a big part of what I do. So is keeping people aligned and keeping them happy. Here’s how I do that.

I’ve been managing people for going on 15 years. When I ran my private investigation agency, I focused on bringing money in the door, finding the best contractors and letting them do the actual work. You learn a lot about managing people when a rush call comes in to staff a 24-hour surveillance for 10 straight days, no one wants the cops involved and our subject is threatening to shoot the client. One of my favorite large projects was a months-long asset search of everyone in the Bernie Madoff scandal where I knew the hedge fund manager client would wager tens of millions of dollars on our findings. Staffing the former project was all retired cops. The latter was all former newspaper reporters. Despite their differences, they all liked to be managed the same way. The same went for a lawyer who worked full time for me too.

A lot of my people management actually started with my son. I was a mostly-stay-at-home dad for the first three years of his life. The best piece of parenting advice anyone gave me was from his first pediatrician: Little kids thrive with clear rules/expectations. Predictability makes them feel comfortable. Give them feedback right away if they need correction. Always treat them six months older than their present age because that’s what they’re capable of. That worked well with a toddler and it’s how I like to be managed myself. Clear expectations, rapid feedback and assume I’m more than capable. It was essentially what I’d learned from reading Ray Dalio’s Principles around the same time when I was a hedge fund consultant.

Annual performance reviews are a standard… but a 365-day feedback loop is too long for me and the people who report to me. I can’t remember what I did last month, let alone 11 months ago. So I developed an annual review process that ties into quarterly calibrations that tie into weekly 1:1s. Aside from helping me, a side benefit is that annual reviews are essentially done when the time comes around. Here’s how I structure both of those.

Quarterly Calibrations

Every IC who reports to me is given a shared document their first week titled Quarterly Calibration. I’ve tried multiple apps/tools/software for this and just find a shared doc simpler. It features the following five sections, each quarter feeds into the next and we copy/paste a fresh five bullets at the top for the current quarter. We’ll use Q1 as an example.

  • Personal Summary of Q1: This is their personal summary of how their previous 90 days went.
  • Vacation Days during Q1: Regular time off is important for employee health, it forces the manager to create systems of redundancy, and the company avoids relying on heroes.
  • Manager Summary of Q1: This is my summary of their previous 90 days. I make sure it’s about three paragraphs. The first is a quick summary, the second covers my assessment of their performance goals (established in Q4) and the third covers their professional development (established in Q4). I might add a fourth paragraph if needed.
  • Next Quarter (Q2) Performance Goals: The IC and I work together on this. We talk about their level (example is the CircleCI Competency Matrix) and whether they are performing at their job level and whether they are interested in moving up. (Not everyone is.) We talk about our team’s OKRs for the coming quarter and write down how they will contribute to them. That helps them feel like their work is meaningful, helps me deliver on my goals and the company has all its security engineers pulling in the right direction.
  • Next Quarter (Q2) Professional Development Plans: Professional development is my favorite part of this process. If the company is a good fit for them, what they are burning to learn should be in harmony with what we need here. It could be learning to code in a different language. It could be setting up a honeypot on the internet. It might be learning to lead a conference or how to present at an all-company meeting. Whatever it is, we probably need it. And if I’m helping them learn the things they want to learn, that’s an employee benefit that goes beyond cash and free lunch.

Like clockwork, we update these every 90 days without fail. This makes sure there are no surprises on their end and it gives me confidence people are delivering what we need.

Weekly 1:1s

I try to never miss weekly 1:1s with my individual contributors. For each one, I have a document with the following five items. Every week, I copy/paste a new section and bump the date so there should be 12 in a quarter. (I don’t do this for skip-level meetings. Those are just me listening.)

  • Quarterly Professional Goals: Copied from their Quarterly Calibration document so I’m reminded of what we agreed to focus on. I always want to know going into the 1:1 what they’re main objective is professionally.
  • Quarterly Personal Goals: Copied from their Quarterly Calibration document so I’m reminded of what they’re trying to learn for fun.
  • This week, I’d like to talk about: Specific items of praise, feedback or questions that have come up since the previous week. Not all feedback for ICs should go in a public Jira ticket. When I have it over the course of a week, I jot it down here.
  • Notes on the talk: I try to write a few sentences summarizing the 1:1 each week. How they doing? Are they happy? Is there anything of concern? These are the notes that I base my quarterly manager summary on.
  • Actions we agree to take: Any action items for me to help them get unblocked or get more resources.


When it comes time for writing the annual reviews, ICs copy/paste their four quarterly summaries into a single document, stitch them together and that’s that. I copy/paste my four manager summaries, stitch them together and that’s that. The annual review takes less than 10 minutes to write, there are no surprises and it allows us an opportunity to spend time reflecting on themes.

I don’t just keep these quarterly and weekly notes for people who report to me. I do one for myself and share it with the person I report to. I eat my own dog food because it’s good for me.

Is this perfect? Probably not. Even this blog post is subject to change:) But the frequency of these Quarterly Calibrations and 1:1s ensure that we (IC and manager) will quickly surface what’s not working so we can make improvements quickly. The lack of surprises and steady predictability is good for them, good for me and good for the company. What worked well for a toddler, cops, journalists and me translates straight across to all the engineers I know or manage.



Security, Builder, Dad

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