CaboPress, Returning to Work, Managing Change

Entrepreneurs are curious by nature. We seek to solve problems. We seek business opportunities in everything we do: no small hobby is safe when it pops into the mind of a creator.

So what happens when you put 45 of these individuals together for a week? What happens is change.

There’s an old saying that you can only rely on two constants in life: death and taxes. I propose we insert another item in this list: change.

If you are certain of nothing else in life, know that things will change. When you attend an event like CaboPress, know that your business mindset will change.

This isn’t a post about why the conference is such a rich experience. This isn’t a post about the amazing people I met, the deep conversations Jason and I had in the wee hours of the morning and night. This isn’t a post about the things I learned or the strategic decisions that felt a bit amorphous two weeks ago and are now taking shape.

This is a post about coming back from an event overflowing with ideas for change.

But when everything is important, nothing is.

  • So how do you create priority when everything feels urgent or worse yet, exciting?
  • How do you spoon feed change to an existing team without making decisions feel sudden and solely based on gut?
  • How do you keep up the momentum of the inspirational event without the risk that the wheels fall off your currently successful business?

Going Slow to Go Fast

I’m going to throw in another consultantese phrase here: “You have to go slow to go fast.” I tried to find one true person to attribute this quote to—there are several. (If you know the single person, please tell me.) Perhaps the best attribution comes from the Latin phrase Festina Lente, which translates to “make haste slowly”.

To me, this week and the next few weeks ahead are a curious time. I want to make haste. I want to put words into action. But first, I have to plan. I have to take an indeterminate amount of time to shape the thoughts and changes I’d like to implement.

Improving Our User Onboarding Sequence

I want to improve the user onboarding experience for our flagship product. We focus too much on people at the start of their journey with Paid Memberships Pro. I don’t even know where that assumption was made along the way.

  • As a free and open source membership product, I know that a large majority of our traffic and leads are drawn from
  • I also know that a large number of leads come from links in the admin of their own WordPress site.

These two reasons alone paint a much different picture of user onboarding. I have a good gut guess, but no solid data to support what percentage of new users joining (free or paid) already have our plugin installed and set up.

I don’t know at what stage they come to me for documentation, for business advice, for technical support, or for premium Add Ons.

But we designed an onboarding sequence that assumes everyone is at day zero. Huh.

Designing “Tell Me More” Automations

I also want to implement another sequence that Kronda of Karvel Digital refers to as a “Tell Me More” automation. Kronda’s talk hit me hard.

I began the session concerned that proactively reaching out to our users based on activity on our site would feel like a big brother is watching. In reality, that’s true.

But while “big brother” is inherently a negative concept, there’s also the framing that your “older sibling” is someone that is always looking out for you. 

And that’s all a matter of head checking your intentions. I want to help people get to the right pieces of content based on other interactions they’re having with our site. That means I have to do the hard work of creating those connections. I have to look at how people navigate my site and design a few flows that signify their use case, their stage in business, and how experienced they are as a developer.

Was this a new thing I learned? Not really. The best takeaway after this conference (for me) is affirmation. 

It is crazy powerful when experts share insights that affirm a path you had already seen for your business. And there was no bias here. I didn’t seek out the advice of someone that was of like mind. That kind of approach to personal validation is poisonous.

Instead, I showed up to an event, listened to a stranger, and nodded my head yes for 90 minutes.

There are other specific business things I take with me, and they all need shaping.

They all need time to marinate in my brain, in Jason‘s brain, and in time, as I let other people on our team into the conversation, these ideas will get shaped by their input as well.

A Time For Change

But as I said earlier, now is also a time to change. A time to remain confident in some decisions that I immediately know will help my business. So I need to prioritize the decisions and actions that we must make right now. This is me making haste. This is me as an owner taking a place of authority to say how our current workflow and work schedule might be redirected into other projects.

Did I mention I’m navigating all of this with my husband and cofounder who also came back from this event full of ideas?

If you attend an event like CaboPress with other people on your team, I’m here for you. I don’t have an exact formula for how to move forward, how to synthesize your thoughts and ideas with everyone else.

One thing we did was create a Google doc that we can both dump ideas into. We identify the things that are open questions, the things that we don’t have enough information to act on.

I already tabled one thing that Jason put on the list. It fits, and it’s awesome, but for now that idea is in the ‘Not now, not us,’ category.

Some things in that doc will fit into an early stage exploration category. These are the things that we have to make tiny movements on today.

  • Maybe we need to start asking different questions in our checkout and onboarding process.
  • Maybe we need to adjust a general process for something we’re already doing.
  • If we aren’t quite sure on the exact change, we need a process to gather new information to support decision making later.

Pitching Changes When You Aren’t the Founder

I’m writing all of this from the perspective of a business owner and founder.

If you attend CaboPress or any inspiring event and aren’t in a leadership role in your team, the work is even harder for you.

I would still encourage you to “make haste slowly.” And maybe slowly for you is a little slower than me. You want to go fast, but you need more information, more buy-in, and more support in your team.

  • In this case, share stories with your team, slowly.
  • Organize your thoughts strategically in a gigantic document.
  • Identify the changes you want to make that require more information. Find a way to start gathering that information to support changes you’d like to make.
  • Nominate your best ideas and highlight them in your sheet.
  • Take these ideas and move them to a separate sheet and build out the project into a one week or three week version.

Owners should like experimenting. Owners should support your need to test the waters. I firmly believe that companies should make reversible decisions quickly (that’s attributed to Jeff Bezos…). Unfortunately, that isn’t the culture of every business out there.

Change is scary, especially if you don’t know how you fit in the vision. 

I want to wrap up my thoughts on deeply inspiring conversations with a message to our team and anyone with a team returning from CaboPress.

Open your ears and mind and listen. Be a part of the experience your leadership is about to share with you.

You might need to put your life jacket on and ride the waves. It could be seen as a stressful period ahead: your leadership is very likely going to make changes that affect your day-to-day work.

I’ve been there—there are absolutely times where Jason has attended a solo event and come home with an energy I just can’t match.

But should I put a wet blanket on his enthusiasm? No.

Do I sometimes think of all the new work he’s making for me? Yes. Oh yes I do.

Is this an interestingly complex time to run a business in the world and the world economy? Yes.

So get excited about the changes. Involve yourself. Find a way to participate in the next few months of this journey.

Change is everything.