5 Lessons for Starting Strong at a Self-Managing Organization

Joining a self-managing team is no small feat, particularly for someone like me who’s spent a decade working in hierarchical organizations. So, hitting my 90-day mark at August was a big deal. To mark the passage, I decided to write a letter to myself on my first day with a few pieces of advice for starting strong.

Hey Karina!

Welcome to August! You’re about to dive into a self-managing organization for the first time. Get ready for a fun, intense and challenging first 90-days.

In the spirit of shared learning (and time travel?), here’s a few hard won lessons that I wish I’d been able to share with you on your first day. Better late than never, right?

  1. Have patience. With yourself, first and foremost. You’re too hard on yourself and it’s going to hold you back. In particular, let go of your need to be seen as competent. Please, I beg you. I know this hard — you’ve staked your professional identity on being the most competent person in the room. In your first 90-days, allow yourself space for learning — it’s a luxury that won’t last long at this fast moving org. Take time to sense the system, dive deep into the practices, ask all the questions of your onboarding buddy, and embrace that feeling of being a little lost — all that learning will pay off as you get more reps at August.
  2. Lean into vulnerability. You already know two things about yourself: you’re private and vulnerability is exhausting for you. This is going to make your first 90 days tough at a radically transparent organization. Heck, it’s going to make embracing the #futureofwork tough. You’ll spend a lot of time wondering whether to ask a question in Slack or turn to the person sitting next to you. You’ll hate CCing the whole team on every email. You’ll feel like crap when everyone can watch your to do list on Trello and it becomes apparent when you’re avoiding a hard task. You’re used to hiding your failures and learning in private. Get used to allowing others to work alongside you, even when it violates every perfectionist bone in your body. You came to August because the organization practices what it preaches — so get into it. Vulnerability is a super power.
  3. Trust your intuition. You’ve been doing this a while, but you’ll lose your confidence for a hot minute and think your pals at August know something you don’t. They’re awesome and they’ll open your mind to new frames for understanding the theory and practice you embraced at your previous gig and they’ll introduce you to new practices. Sure, they’ve spent more time working with corporate enterprises, but when you’re in a meeting and you’re having a gut reaction, instead of asking yourself “What am I not getting here?” ask yourself instead “What might be right about the intuition I’m having?” Your wisdom is powerful — learn to listen deeply to yourself and channel your tensions into useful action.
  4. Give yourself permission (because no one else will). It’s one thing to have power distributed to you, it’s another thing to take hold of this power and turn it into action. You’ll find this surprisingly hard after a decade spent in hierarchical organizations. You’re used to someone directing and protecting you. You’ll spend a lot of time trying to understand the rules only to learn that they don’t exist. You’ll go looking for “right answers” only to get the response “what do you think is the right answer?” This will piss you off because it’s obvious that more tenured ‘Gustos have more wisdom than you, particularly about client work. But you’ll eventually realize that too much time spent trying to figure out the rules is a waste of energy. Do stuff and see what happens. The organization will evolve with you and around you.
  5. Play hard. You’ve spent the last five years as an advisor to other organizations. This has been satisfying work. But when you get to August, you’ll have the hard realization that you’ve gotten comfortable playing from the sidelines. You’ll default to the role of coach and resist jumping on the field. When you do jump in, you’ll get bruised a few times. But, you’ll soon figure out that it’s much more satisfying to play than to sit out.

And lastly, for your next 90-days, one more piece of advice: delete Slack during your Parental Leave. Seriously. It’s ok. It’s weird to join an organization and go on Parental Leave as soon as your 90-days are up. But my wife and I are expecting our first child and that’s got my attention for the next 16 weeks. While I’m changing diapers, staring at my baby, and going all in as a 50/50 parent, I’m fortunate to have my colleague Alix as my Parental Leave Advocate. She’ll make sure my voice is heard at the organization and help me reach my goals when I return, which means I’ll be deleting Slack from my phone. After 90-days of working in the open, I’ll admit it — I love Slack — and I’ll have a touch of FOMO. But I’ve got more important things to do for now.

Onward.

- Karina