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Craig Kerstiens

Category: Philosophies

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.

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.

When to ship it, when to kill it

A few weeks ago at lunch I had the opportunity to catch up with a company in the current YC batch, building something very similar to dataclips. While we talked about a lot of things from what we’ve learned from dataclips, marketing, and other areas. One area we talked about was product and when to ship vs. when to kill things and I realized I hadn’t talked on my fairly simple but clear view on this publicly, so here it is.

A large credit to Adam Wiggins for giving this model early on in Heroku and his approach to shipping product.

Scaling Organizations - Scribing

In the process of growing a company there’s several hurdles based on the size of the company. What worked at 5 doesn’t work at 20, what works at 20 doesn’t work at 50, and what worked at 50 doesn’t work at 150. There’s a lot of talk about two pizza teams and scaling development teams out there. One thing I haven’t seen quite enough of is details around scribing and documenting things.