Calibrate San Francisco


Jonathan Wong / October 02, 2017

6 min read––– views

Calibrate Conference in San Francisco, CA

When my boss was first getting to know me in our 1:1 meetings, he explained the typical Software Engineering career ladder containing two different tracks. It looks something like this depending on your company and its size.

IC (Individual Contributor)

  1. Junior Software Engineer
  2. Senior Software Engineer
  3. Principal Software Engineer
  4. Architect, CTO


  1. Junior Software Engineer
  2. Senior Software Engineer
  3. Engineering Manager
  4. Senior Engineering Manager
  5. Director, VP of Engineering, CEO

He understood it was still early in my career but wanted to know which side of the fence I fell on. I've always felt comfortable leading others and it had been my plan to transition into management. I expressed my future ambitions and he ensured me he would do his best to get me there.

Going to California ✈️#

Over the past six months I've been managing and mentoring a newly hired intern on our team. By title, I'm still a Junior Software Engineer, but this has given me a trial run to see if I enjoyed the work required for a manager and if I could develop and grow my report. I've been working hard to help him achieve his goals, but there's always room for improvement.

Workiva invests a lot of time and money into training and developing their employees and one of the most common avenues for career development are conferences. I've attented more engineering focused conferences in the past, but I'd never considered one more suited for managers. After some researching, I stumbled onto Calibrate.

Calibrate is a 1-day leadership conference in San Francisco for new engineering leaders hosted by seasoned engineering leaders. Their goal is to focus specifically on engineers who have transitioned into mangagement from an IC role. The conference boasted a variety of speakers from reputable companies across the valley such as Slack, Lyft, Evernote, Reddit, and more. It was the perfect fit for me.

The Conference 💡#

Calibrate is a not-for-profit conference and attendees have to apply and be selected to attend. The founders truly care about the experience and purposely limit the size to 150 people ensuring quality discussion and interaction. Along with monitoring the size, they also intentionally hand pick a diverse field from all locations, ages, races, genders, and personalities.

I really wanted to push my boundaries and challenge myself to network extensively. The conference is designed with longer breaks, lunches, and a happy hour to give the attendees a chance to share their backgrounds with each other and network organically. After talking with a variety of people, I realized I was the only attendee from Iowa. The two most common questions I got were:

  • Iowa? Why Iowa?
  • What is Workiva? (Hint: You can find the answer here)

I'm proud to say I accomplished my networking challenge, advocated for Workiva, and even reminded a few people that Iowa is a state in the Midwest.

Key Takeaways 📝#

Calibrate was packed full of excellent content and it would be impossible to summarize everything into one short blog post. I did write down some of my favorite bits of knowledge and would like to share them with you. My favorite speaker was Michael Lopp, the Vice President of Engineering at Slack. His talk was titled the New Manager Death Spiral and told a tale of hard-earned advice he's learned over the years.

“Your job isn’t to get things done, it’s to get them done at scale.”

Lopp explained how new managers sometimes feel they need to constantly prove their worth, signing up for all the things and becoming overwhelmed. One valuable tip he shared was that you need to aggressively delegate your work. It's not a loss of power and it gives others the opportunity to shine. Remember, you can't do it all yourself.

Let's say you're struggling with delegating your work because you think you will do a better job of completing the task than the others. Lopp explained how this can become problematic. If the work is delegated to so-called "B players", it gives you the opportunity to coach them to an A. This instills confidence in your reports and trickles down, making the overall team and organization more effective. High trust teams are high velocity teams. Simply put, they get stuff done.

“Management is not a promotion.”

One common theme between a few talks was about the transition into management. A lot of engineers view this as a progrssion step on their career ladder. If you’re going into management for the first time, it’s a career restart. It requires a completely different set of skills that don't directly transfer over from a previous engineering role. That's why there's difference between leaders (e.g. a technical lead) and managers (e.g. directly managing people).

Another common theme was around diversity in tech. One way to augment your obvious and non-obvious weaknesses is with a diverse team. It's very easy to choose the path of least resistance when building your team by choosing people who agree with you. However, ideas don't get better with agreement. Let others speak their opinion and change your mind. There are many more of them than you, so they will probably think of something that you missed.

"We should grant trust to those who lead us, but we still need to earn that trust as a leader."

My final takeaway from Calibrate was about 1:1 meetings with your reports. During these meetings, they should be talking most and not you. Talk less - listen more. If they're not talking, try asking more open-ended questions like "What frustrates you?" or "If you had the opportunity to work on anything here, what would it be?". It's important to foster personal connections during this time. It helps to establish trust with them.

One strategy for improving the quality of the meetings is ask them to rate the 1:1 at the conclusion of the meeting. Then, you should also give a rating from your point of view. If they are different, explain why. Get construstive feedback to make the meetings more valuable for both of you. We’re inherintely conflict adverse (we don’t want to make people feel bad) but honest, critical feedback will go a long way here.

Conclusion 🍻#

After an extended weekend in San Francisco, I'm now on a flight back to Des Moines to continue with my regularly scheduled programming. I plan on applying the knowledge and strategies discussed in this blog to develop as an individual and as a manager.

See you again soon, San Francisco.

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