Hey Operators ⚙️

Anyone else exceedingly busy this summer?

No complaints - it’s a good busy. I just find myself more grateful for the team we’ve built here at The Bottleneck every day.

We can all agree that, especially when building a business, you’re only as good as the team you assemble.

That lesson has been at the top of my mind lately, and I’ve been consuming a TON of resources on management and team-building.

So, naturally, I thought I’d bring out the best of those tips for you in today’s edition 🎁

⚙️ Here’s what we’ve got going on:

• A+ Org Charts for Your A+ Team → Can an org chart be beautiful?

• Optimize the One-On-One → No more meetings that could have been emails

• Team-Building That Doesn't Suck → Let’s skip the awkward silences

Ready? Let’s dive in 👇

PS: Want even more actionable content for operations professionals? Connect with us on Linkedin

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Operators Library

• Looking for ideas for an offsite activity? Here’s a Reddit thread packed with potential outings.

• “T-Shaped” operators are teammates that are broad in a bunch of different areas but very deeply skilled in a particular one. So how do we identify and hire them? Check out this essay from Andrew Chen.

• Develop your team into effective leaders using this practical rubric from Russ Laraway’s book, When They Win, You Win.

• Management isn’t always sunshine and rainbows. For those of us that need tips for the tougher conversations, here’s a guide to gracefully delivering bad news to your team.

• Leadership coach Dave Kline shares his three management non-negotiables.

I. An A+ Org Chart for Your A+ Team

Insight from Kate Eby

Putting together a great team requires a great hiring plan.

And, whether we like it or not, every hiring plan is going to require you to eventually build out an org chart.

Now, here at The Bottleneck we sweat the small stuff (I’ll unschedule a newsletter because it needs an oxford comma).

So when we make an org chart, especially if it’s going in a deck, we want it to be the best damn org chart our leadership team has ever seen.

But we also don’t want it to take that long 😅

So, without further ado, here’s your guide for a 7-minute org chart that will make you look like the company overachiever:

• Use a template: Canva makes things easy. We love easy, so we love Canva. They have a bunch of org chart templates that you can use to get things started quickly.

• Add photos: People love seeing people. It works in dating profiles, it works in advertising, and it will work in your slide deck. Add a little personality and watch your audience smile right back.
  

• Illustrate communication, not just reporting: Real collaborative teams don’t just talk to each other in hierarchies. Throw in some different-colored arrows (and a legend) to illustrate who talks to who day-to-day, giving a more helpful picture of how your org actually functions.
  

• Metrics, baby: This one will blow minds. Next to each role, note the key metrics/KPIs that that function is responsible for. You not only see the reporting structure, but how it works to deliver on the key business goals.

Learn more: How to create an org chart for your startup

II. Optimize the One-On-One

Insight from Harvard Business Review

We’re all guilty of it:

The awkward, 15-minute one-on-one that accomplishes… relatively nothing 👎

Something along the lines of:

1. “How’s your week going?”

2. “Anything I can unblock?”

3. Let me know if I can help out with anything else!

Both parties walk away thinking, “Welp, that could have been a Slack message.”

Now, if that sounds familiar (and it probably does), we’re here to help. Here are a few guiding frameworks that will level-up that weekly sync:

• Connect beforehand on an agenda: Take the time (even if it’s 5-10 minutes) to sketch out and send over an agenda for the topics you want to cover. This exercise forces us to give some thought to the conversation rather than winging it. Ask them to add items/sub-items as well, and watch how much more productive the conversation becomes.
  

• Make time to talk about career development: Where does your report want to be next year? Do they know what they need to accomplish to achieve a promotion or more responsibility? It’s easy for these meetings to index toward the reactionary. Show your report that you care about their career progression.
  

• DON’T CANCEL: This one is tough for busy operators, but it’s probably the most important in building a great team culture. Last minute cancellations/postponements tell your team that their one weekly opportunity to connect with you is less important than whatever else you’re dealing with. Treat that scheduled time as sacred. Be flexible with their circumstances, but inflexible with your own. Leadership, baby😎

Learn more: More secret sauce for effective 1:1 meetings

III. Team-Building That Doesn’t Suck

Insight from Jordan DiPietro

“So… uhhh… what does everyone have going on this weekend?”

Every. Single. Stand-Up Meeting.

There are better ways for your team to get to know each other.

Here’s a cool hack we came across:

3x5 Cards (points for anyone who can come up with a better name for this 😬).

Send out a survey to the team asking actually interesting questions (What’s the biggest adventure you’ve ever gone on? What’s something that you do in your spare time that no one would expect? What time period would you go back to if you had the chance?).

Keep their answers anonymous. 

Print each question and answer on a 3x5 card (can you guess where the name came from?), and have these on hand during team meetings.

The next time there’s an awkward lull during a stand-up with your team, that’s your chance to deploy your new secret weapon.

Pull a card from the deck, and have the team guess whose answer is whose.

“Who do you think secretly plays competitive trampoline dodgeball in their spare time?”

People’s first assumptions are usually wrong, which makes it even more fun. 

Meanwhile, the person who has the unexpected hobby is eagerly waiting for their moment to reveal it’s them. 

There’s guaranteed engagement, laughter, and connection, and it’s a much better off site activity than a trust fall. 

That’s a low bar, but you get the idea.

Learn more: 12 non-awkward team-building activities (even if your team's virtual)

Something Fun

You could follow all of the above tips, or…. you could be this guy….

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