🤓 A Little User Manual for Matt MacInnis

Loosely based on this

About Me

Grew up in Canada, moved to the US for college. Studied engineering, worked at Apple for seven years, mostly in marketing. I lived in China twice, and speak Mandarin pretty well (still study it!). In 2009, I started a company called Inkling, and sold it in 2018. I joined Rippling in 2019 as COO because of the immense promise of this business. I have a husband and a daughter, both cute.

What I Expect of Myself and Others

Rigorous thinking and consistency of approach

  • I appreciate when people know their topic and hew strictly to the facts. I appreciate “I don’t know” as an answer. I appreciate when others call (my) bullshit.
  • I have a negative reaction to exaggeration, hand-wavy answers, and unsubstantiated assertions or assumptions.
  • I appreciate consistency and structured thought (“frameworks,” if you will).
  • I love working with people who have their own system. I will easily (gleefully!) adapt to your system if I understand it. It is a sign of clear thinking, which is what will help us all succeed together!

Reliability and grit

I love working with people who…

  • ... eat their management broccoli.
  • ... proactively deal with the boring, difficult, uncomfortable work.
  • ... only need to be told something once.

People like this absorb problems in the organization like activated charcoal; conversely, people who avoid the tough stuff spew problems into the space around them for these people to catch. I try to hold myself to these standards.

The humility to learn from others, especially when it’s inconvenient

I want to debate things, and I hope that we all take well-founded positions in our debates. However, it’s hugely important that pride and ego not blind us to new information, no matter how inconvenient. I try hard to keep an open mind about every possibility, and hope you will too.

The integrity to make and act on the right thing to do, especially when it’s inconvenient

Sometimes, it’s really painful to do the right thing, such as proactively notifying customers of an issue they may not otherwise notice, or giving someone difficult feedback when they’re already bruised. But I want everyone I work with to always do the right thing — no matter how painful. And I will try to be a force for good in that regard, too.

My Demons

Positive Feedback

I struggle to give positive feedback because it makes me feel a little uncomfortable. I recognize this, and I invite you to call me on it, especially if you don’t know where you stand. When I do give feedback, I try hard to make it useful.

Impatient Moods

When I am in get-stuff-done mode, I am sometimes impatient with friendly office banter. I forget to ask how you’re doing, and I bristle at attempts to ask me those questions. Usually, I like to jump into the matters at hand quickly and directly. If I do that, please don’t take it personally; it’s likely that care a lot about what you’re working on, and I want to get to the meat quickly.

To Be Direct on Hard Things, I Need to Prepare

I think a little more slowly and deeply than some people, which is a blessing and a curse. One side effect is that when I’m forced to think on the spot, I may end up postponing difficult but important conversations. I may brush things aside so that I can buy time to prepare my thoughts.

For conversations that are in my wheelhouse, I am quick to engage and respond. But for tough feedback conversations, for areas I’m not familiar with, or for areas where I lack context, I need to prepare. It is generally ineffective to surprise me with conversation topics, so providing me with context and time to think/process will help me be more effective.

Crassness

I sometimes use crass humor to deflect discomfort, or to build a sense of camaraderie. While humor in the office is generally good, if I say something stupid, please call me on it — or give me googly eyes to let me know I’m being foolish. One management framework calls this the “mischievous derailer,” and the name is appropriate.

Overthinking

I can be guilty of overthinking things. I can get caught up in process or approach, instead of staying focused on the quality of output. You can help me by saying, “Matt, you might be overthinking this. I think the answer is probably just X.”

How to Work With Me

Communication Channels

  • Email is for non-urgent matters. The success rate of reaching me via email is about 90%. Assume I will see your email within 24-48 hours, but rarely sooner.
  • SMS is for quick or urgent matters. My phone is 415-539-9111. I’ll generally respond right away. I use WhatsApp regularly, and it’s far better than SMS.
  • Slack is for conversational matters that aren’t urgent. Faster response time, but lower overall success rate of reaching me than email.

1:1s

  • For my direct reports, I default to biweekly, at a consistent time
  • Structured and purposeful, with a shared 1:1 Google Doc
  • Review progress, plans, and problems
  • My goal is to remove obstacles to your success
  • If we don’t need the time, cancel or end early

Planning

  • I like to say what we’re going to do
  • I like to do what we said we were going to do
  • I like to change what we said we were going to do as soon as we realize that it’s not the right thing to do (as many times as necessary until we find what is the right thing to do!)

Priorities

I am generally clear-minded and explicit about my priorities. My job is to achieve my priorities. Your job is to achieve your priorities. Our time together, in any context, is best spent at the intersection of our respective priorities. I therefore very much appreciate knowing what your priorities are when we talk.

Maker Time vs Manager Time

This is a fast-moving startup, which means I have a lot of stuff that I’m doing directly, i.e., I’m also a maker. If I have my time blocked as “No Meetings,” please do not schedule meetings. If you really, really need time with me during those windows, please ask — but the bar will be high. :)

Good Meetings

Please have only the meetings we need, and please ensure those meetings are productive. Always start with an answer to the question, “What are we trying to accomplish, and how will we know we got there?”

Mutual Development

If we work together, then I want to contribute to your growth. And I invite you to participate in mine. I won’t hold back, and welcome career and development conversations.

Keep Me Honest!

What’s missing above? Or where am I lying to myself and others? :) All feedback is welcome. The goal is to accelerate our collaboration and improve the effectiveness of our partnership.