This week, Michael Lopp, a.k.a. @rands or "Slack's VP Engineering", was in Toronto and he was kind enough to meet with us and share some of the more common don'ts and do's that he encountered in his experience thus far.

[…] walk us through a story where a new manager successfully performs every single common mistake in their new role. The New Manager Death Spiral is a cautionary tale full of good advice.

Meta

• You might also know @rands as the author of Managing Humans, Being Geek or randsinrepose.com
• Upon a quick raise of hands, he assesed the room to be ~60% full of introverts.
• His disclaimer: this hypothetical story is a worst case scenario.
• My disclaimer: following is a log of my personal notes; sometimes out of context, sometimes missunderstood.

The New Managers Death Spiral (or the insightful part)

Affirmation #1: "I can do it. I'm the Boss"

• You think you've been promoted!
• First, you sign-up for all the things.
  • Hey, it worked for you as an IC.
• You are instinctually reluctant to delegate to others.
  • Feels like giving away power.
• Your first failure mode
  • The quality of your work drops.

Affirmation #2: "I can do it all myself. I'm in control because I'm the Boss."

• The ineptitude of fake delegation.
  • Lacking context, goals etc.
  • "Go figure it out… or else."
  • Your job is to aggressively delegate.
  • You are not listening
    • So the team starts to talk amongst themselves.
    • You did not build trust.
    • Opinions become facts.
    • Poor communication
  • They think they have failed.
    • Irreparably harmed the relationship with your team.
    • "Hey Rob, your team is saying this thing about you."
    • And it hurts, it's toxic.

Affirmation #3: "This is not me."

• Teacup pigs. :o)
• Management is not a promotion.
• It's a totally different game/role.
• Management is career restart.

Lesson #1: Let others shape your thinking

• People disagree with you. That's great!
• Augment your obvious and non-obvious weakness with a diverse team.
• The first 30% of a project lifecycle.
  • "I surround myself with people that design […]"

Lesson #3: Delegate more than is comfortable.

• A vote of confidence in their ability.
• You build yourself by building others.
• Trust.
• The burden is on you to prove that you deserve.
• Start small.
• Am I building or am I erroding trust with this action that I'm about to take?

AMA (or the juicy part…)

• How do you identify early signs of "management" in engineers?

  • Empathy
  • Ability to read the room

• Managing up

  • The same rules apply
  • Clear communication
  • Constant communication
  • What do you worry about most as a compay grows? Politics.

• Biggest management mistake, in the last year?

  • I (Marius) chose to leave this out; if you're interested, ask @rands personally. ;o)

• Giving critical feedback

  • 1-1: every week, 30 minutes.
  • Feedback
    • You did this great,
    • This less great,
    • This is how I would do it.
  • Listen
    • Is this what you meant?
    • Paraphrase it.
    • Build trust.
  • Djoume: How can I be a better lead / manager for you?

• New managers, with friends on the team.

  • It's a difficult situation: void it, as much as possible.
  • Manager hat, friend hat.
  • "Speaking as your manager now […]"
  • Be deliberate about the role in the relationship.

• Managing up:

  • What makes for a "good" 1-1?
  • What are some quick wins on improving them?

• Key characteristics

  • Vision
    • Can you describe a compelling future?
  • Strategy
    • How are we getting there?
    • Can you build the roads and the roadsigns?
  • Tactics
    • Can you describe the growth path for all your direct reports?
    • Feedback for every 6 months
    • Judgement
    • Experience
  • Communication
    • Can you build the roadsigns
    • Can you read the roadsigns?

• Formal training is lacking. Where to get it?

  • External
    • Harrison Metal — Leadership training
  • How are we training the managers at Slack?
    • Internal talks
    • Mentorship circles

• Judgement

  • How do you interview for judgement?
  • How do you judge for judgement?
  • Look for a non-obvious judgement call, and the ability to explain it.
  • Can you walk me through your thinking?
  • Can you tell me why? Or was it just a coin flip?

• Self-management renders managers obsolete?

  • Holocracy?
    • Did it work at Zappos?
    • Did it work at Medium?
    • Managers are a force multiplication factor.
    • Information conduits.

• Coaching in a distributed team.

  • Biased towards face to face interactions
    • Lightspeed.
    • Read the room.
  • A lot of traveling.
  • Different cultures, being aware of that.
  • Remote people can be made to feel like second class citizens.

• Growth paths? It depends.

  • CEO
    • Move outside of engineering
    • Experience other facets of the business
  • VP engineering
    • People, process, etc.
  • CTO
    • Still coding
    • "Bringing the app back to life"
  • Chief Architect
    • Coding as well.
    • No direct reports?

• Failing…

  • …is where you can learn.
  • Managers fail just as much as everyone else.
  • Fail faster, feel safe.
  • "You screwed up, but I got you: we'll fix this."

• Delegation

  • Rework, book by Jason Fried
  • Do you triple down on their strengths?
  • Or delegate it to Julia who's going to get a B on this?
  • Try to work towards a growth mindset.

• Being able to read the room: how do I improve? A

  • A lot of introverts run companies…
  • Listen, get people to talk to you.
  • Conversation about how to get better.

• Quitting my job

  • Every 3 years.
  • The moment I get bored… deathly afraid of becoming irrelevant in this industry.

Disclaimer: Remember that you have been forewarned: this was just a log of my personal notes; sometimes out of context, sometimes missunderstood.

Now, if you've read this far, what are your thoughts?