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Craig Kerstiens

Guidance for conducting offsites

Offsites an invaluable tool in getting a team aligned. I’ve been a part of organizations where offsites never happened, and then when they happened at a regular interval. Just because offsites happened it didn’t mean they had the same significant impact to alignment and ability to execute moving forward. What follows is a few key principles around conducting an impactful offsite.

The Engineering Manager/Product Manager Marriage

I’ve worked as a PM at a number of size companies for a few years now. At a startup and then as a part of a larger company once startups were acquired. I’ve been the first PM for a team as well as first for a company. I’ve written at times about product management, and today I’d like to drill into one aspect that doesn’t seem to get talked about enough and that is the pairing of product manager and engineering manager.

Come over for dinner

When I first moved to the Bay area I was fresh out of grad school. I was frequently heading out to dinner or to happy hour after work with colleagues. I was young and single, so why not of course. As time passed, marriage, kids, etc. the ability to go out for a quick drink or dinner was competing with various priorities. Dinner and drinks with co-workers was always a great time. It wasn’t just about hanging out, it built rapport and trust which I found made me a more effective teammate and product manager. It was about 8 years ago that I started to implement a variation of heading out for dinner and drinks.

I started inviting people over for dinner.

Talking on the phone: better communication

I interact with a lot of people in a given week, a few in person and far more on video and conference calls. I don’t claim to be a perfect person to talk to on the phone, but over the past several years I’ve noticed how painful some conference call experiences can be. As more and more work is conducted virtually and not face to face an ability to do communicate well on conference/voice calls is tied to what success you can deliver. It isn’t about having a fancy phone or high bandwidth video call–though that can at times be useful

Using email as an effective tool

I send way too many emails in a day. My inbox is very intermingled with my to do list and often represents some form of it. More relevant though is that email is a primary means of how I accomplish work. Being a PM I work cross functionally with other teams (from marketing, to engineering, to sales, to BD, to other product teams) and of course customers. Having to work so cross functionality I’ve found a lot of hacks I use to be able to better accomplish your goals with email, here is a collection of some of those.

Let me be clear, this is not another post about inbox 0, how I swapped to slack. This instead is how I use email to more effectively communicate and get people to engage. In other words it is about making emails more useful, not just getting through them faster. And onto those tips.

OKRs aren't going to fix your communication issues

Talking with a startup a few days ago they asked for my opinions on OKRs. I have slightly mixed opinions on them overall and started to disclose some of those. Though in sharing some of this I had a few immediate realizations that might be broadly applicable. The crux of his question was, at what stage should we put them in place. I’ve seen a few companies try to put in some form of OKR, and most were met with pretty mixed results. The reason is that OKRs need to change something about your behavior otherwise why put them in place… either change something about the goals you would otherwise have or the methods at which you went about achieving them.

Tips for your first tech conference

I make it to a lot of conferences these days. I often see colleagues, former colleagues, and friends at these conferences. Sometimes it is friends I haven’t seen in a few years, sometimes I just saw the same person in a different country the week before. Conferences now are much easier for me, in fact it is a bit hard to recall what the experience was like when I first started attending, but I’m at least going to try to give some input so others can have a smoother first experience.

Give me back my monolith

It feels like we’re starting to pass the peak of the hype cycle of microservices. It’s no longer multiple times a week we now see a blog post of “How I migrated my monolith to 150 services”. Now I often hear a bit more of the counter: “I don’t hate my monolith, I just care that things stay performant”. We’ve actually seen some migrations from micro-services back to a monolith. When you go from one large application to multiple smaller services there are a number of new things you have to tackle, here is a rundown of all the things that were simple that you now get to re-visit:

Why I love building developer products

For much of my career I’ve been focused on building out developer or data focused products with the customer in some form or fashion being a developer on the other end. I fully realize now that I’m destined to spend the rest of my career in that space, either that or trying my hand at wine making. There are a few things that I personally find rewarding about the space that I’ve shared with a number of people individually lately and thought I would share more broadly.

How can I help? East coast vs. West coast mentalities

Often times when I’m traveling on the east coast, whether it is NYC area or back home down south I try to spend some time to catch up with various people. In catching up we’ll spend some time talking about what we’re both up to, thoughts on tech or in general, and at the end I typically ask “Is there anything in particular I can help with?” More often than not the answer to this question isn’t super substantial, which is fine.