Announcing Plucky’s 1:1 Starter Pack!

tldr; I just released Plucky’s first product, a tool for managers to elevate the conversations happening in 1:1s. You can check out the 1:1 starter pack here.

I was teaching a workshop to leaders last year. One of the questions I have the attendees answer during introductions is this: What did you want to be when you were 8 years old? Do you ever feel like that’s even a tiny part of your job today?

The conversation in the room exploded. People were laughing, eyes wide, recognizing that, yes! They do feel like marine biologists some days as a Senior UX strategist! How strange and illuminating!

As I wrapped up the conversation to move onto the next thing, I told them to take that question back to their reports, to use it in the next round of 1:1s.

“I feel weird asking stuff like that,” a manager told me. “I think my reports will think I’m trying to be Oprah.”

And here we have it. A problem with identity. A manager who has just seen that a powerful question can open up fascinating metaphors and be reapplied to work, career path and more cannot authentically find a way to ask it. So her 1:1s will remain stagnant.

I observe this so often from managers, though I admit it’s not my problem. Anyone who has ever met me knows I am totally comfortable asking big questions. (It’s my day job!) I started to wonder how that facility could be passed on. Can you teach vulnerability? Can you teach identity shift?

Last summer I flipped through 14 notebooks filled with notes from 4 years of coaching sessions to find the powerful questions recorded there. See, when the conversation goes deep in a session, I draw a margin and record the question that prompted it. Like this:

I collected about 50 questions and started looking for patterns. Slowly I recategorized them into 8 main categories:

Leadership, Organizational Culture, Career Planning, Productivity, Work-Life Balance, Communication, Decision Making and Innovation.

I started wondering how I could get these questions to managers. An app? A service? I had some old index cards laying around so I made myself a little project one afternoon. It looked like this:

Then I messaged my friend Greg Storey, who does much of the design work for Plucky. I wondered if he was interested in doing some print work for me, this time a product idea. He was game.

The first time I saw his designs, I felt like a new mom. THE CARDS WERE ALIVE! We went back and forth for weeks; I swapped out questions, I went through many drafts of how they should work.

Finally, I realized that they were more than a deck of cards. The cards were a tool, a tangible piece of social proof. Feel weird asking the question? Blame the card. As long as you’re able to say “hey, I got this new tool to try out” with your report, the rest is possible — because the card made you say it.

I wanted to take it a step further. The cards give you permission to ask the question, but how will a manager know how to tie it in with work? Secondary topics were born; on the bottom of each card, I listed two concepts that I felt the question was really driving at. Regardless of how clunky the conversation is, those secondary topics are my chance to whisper in the manager’s ear.

Psst! You’re really asking about these concepts! Listen closely!

I brought them to the San Francisco So Now You’re a Manager in October. Everyone went bonkers. Can we have these?! How do we order them?!

I texted Storey. Let’s print these!, I said. But he had other ideas.

Storey believed the cards would be better if they were larger than a deck of cards, that they would convey a sense of authority and seriousness that the tiny versions didn’t.

So we ordered the big versions. Only 3 boxes to start, to make sure they felt good in practice. I asked a talented friend, Tegan Mierle, if she would help me photograph them the following weekend for the shop. She agreed!

AND THEN. The factory shipped the cards without the boxes. I was so mad. Livid! Tegan was ready to go… but I didn’t have the boxes. Look at this crap:

Tegan persevered because she is boss. She told me to buy giant rolls of colored paper that match colors in my style guide. Then she went to town:

A few weeks later, the cards WITH their boxes arrived. And they. were. beautiful.

At that point, the holidays were here. I was pissed that we had missed the opportunity to market for the holidays but Storey talked me off the ledge. (It is amazing how often in this creative project I got to FINE NEVER MIND UNIVERSE, I AM TAKING MY CARDS AND GOING HOME.)

In late December, 100 starter packs arrived. Look at this amazingness:

When I look at these boxes stacked in our bedroom, here is what I think: so many great connections are going to be made because of these cards. So many new ideas, deeper understanding, authentic truths will be communicated. Even just sharing that you are a manager who experiments with tools like this communicates something of great value to your report: I am a manager and I am learning, too.

I believe these cards will change relationships. And those bettered relationships will change teams. And those bettered teams will change companies. And those bettered companies will change the world.

I really think that. And I think you will too.

Now go buy a pack! Change the world today!

P.S. I am also indebted to many other folks along the way, including Chris Free who answered my random phone call about wrapping paper for the cards from an aisle in Walgreens, all of the early adopters who bought packs this month and the many encouragers along the way. And, of course, my husband. Chris Dary built out Plucky’s Shopify, helped me update the .com and always helps me figure out marketing emails. I am grateful to them all!




Recovering perfectionist. Likes humans. Brain tumor survivor and a mom. Founder of

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Jennifer Dary

Jennifer Dary

Recovering perfectionist. Likes humans. Brain tumor survivor and a mom. Founder of

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