4 minute read

Last month, I attended calibratesf.com, a small single-day conference for new software engineering managers, held in San Francisco. I say “a small conference” because the organizers purposefully limit the conference size to 150 selected attendees. Each potential attendee must submit a small questionnaire explaining why they should be invited to attend. During the restive time between application and response, you wish the limit was far higher, but during the conference, you’re very thankful of the size. 150 people is a lot of people: more than you can meaningfully connect with during a single day. This year’s Calibrate conference was even better than last year’s. You can watch previous year’s talks on Youtube. The speakers prepared and delivered relevant and useful content for the target audience. While the speakers were great, the attendees were the real draw. I met some great managers with so much passion and energy for engineering leadership. I’ve already started developing these new relationships into mutually beneficial discussions and knowledge sharing. I’ll share my takeaways from each session.

The New Manager Death Spiral - Michael Lopp, VP of Engineering at Slack

The first responsibility of a manager is to delegate aggressively. Be okay with B performance and be ready to coach to an A. Focus on building trust with your team. A manager’s career growth is a result of growing your teammates. Encourage a healthy and passionate discourse to expose the best ideas. Identify what you’re weak at by asking someone. Some companies need strong technical leadership and not just people leadership. The measure of a director is the performance of their direct reports. Finally, let others change your mind. Be open to differing viewpoints.

Engineering management anti-patterns - Rod Begbie, Engineering Manager, Dropbox

Don’t treat people as clones of yourself. Don’t insert yourself as the decision-maker for your team because that doesn’t scale. You’re not buddies with your direct reports. Sometimes you need to give hard feedback to reports. Engineers need information and context to make the smartest decisions.

Daydream believer - Michael Ruggiero, Senior Engineering Manager, Twilio

How can you manage people not doing their best work? First, separate your story from theirs. People are different from you. Some people might not identify with their current role so find out. Give them a project to help them focus and give them constructive feedback. Don’t immediately reach for a performance improvement plan (PIP) unless their performance is toxic to the team. These situations are emotionally charged on both sides so get a second opinion. Discuss this scenario with a fellow manager while respecting the individual’s privacy. Radical Candor can help you communicate effectively.

The art of the pre-meeting - Karen Catlin, Advocate for women in tech

Pre-meetings are critical to influencing desired outcomes. Even without authority pre-meetings can allow influence. Pre-meetings happen before the big meeting. The primary mistake that dooms proposals is failing to socialize the idea ahead of time. Don’t assume stakeholders are too busy to have a pre-meeting. Don’t try to convince stakeholders instead make sure you hear their feedback. Don’t feel obligated to take all of their feedback. Don’t allow stakeholders to add to your proposal with the “while we’re at it” argument. Finally, senior leaders are context switching so frequently they forget the details so you should remind them. You should huddle with your pre-meeting stakeholders before the big meeting.

Tripling down without losing control - Nick Caldwell, VP of Engineering at Reddit

Reddit.com ranks 4th in the US and 8th in the world according to Alexa. Reddit boasts 325 million monthly active users. Those two stats are impressive but pale in comparison to Nick tripling Reddit’s engineering staff from 30 to 120 engineers in one year. When Nick joined Reddit a year ago, there were many tech leads but no managers. Nick defined tech leads as proto-managers that can either become architects or people managers. A few question can assess an individual’s preference for either architect or manager.


  • Be wary of your process because process becomes culture over time.
  • Urgency is discipline in disguise.

Winning at Growth Conversations - Marcy Swenson, Executive Coach

Listen with curiosity to people’s ambitions and goals. Explain how the world works to your direct reports. Promotions recognize business value. The most commonly coached skills are communication, emotional intelligence, and prioritization. Coach teammates on clear written and verbal communication. Emotional intelligence means intuiting the perspectives and emotions of others. Help your team learn to make priority decisions. Help them decide between individual contributor and management tracks. Ask what lense does the person see the world through? What books do they like to read? Tech or management. Do they possess the top 3 coached skills? Ask them to describe their colleagues. Do they focus on their skills or the person’s inner world?


I attended the Calibrate conference in 2016 and 2017. Both years had fantastic content. The professional connections I made will help me develop further as a leader. I highly recommend this conference to all engineering leaders regardless of experience level. Senior engineering leaders can mentor the next generation of leaders. Junior engineering leaders can build relationships that can guide them through common pitfalls and mistakes.