the paperfinger guide : to company retreats

As you may know, Paperfinger believes in company retreats. I've been doing it every year, even the years when it was just me, talking out loud to myself for a few days. I so believe in the practice that I'm sharing this year's agenda with you to encourage you to retreat as well, be it for your own small business, or maybe your own personal vision quest. It's incredibly difficult to carve out time for something seemingly non-essential. But I am always hugely rewarded by the effort.

Here are some quick tips as well as an outline that we used this year. Plus some activity pointers and worksheets that you may enjoy consulting. Let me know your other ideas for making sacred time like this or if you found any of this beneficial! Would love to hear back.

Retreat supplies:

  • Easel paper with sticky backing (big thinking requires big paper)
  • Pens and paper you love to write with and lots of blank sheets
  • Some sort of agenda. You don't want to design the process on the fly.

Random pointers:

  • If acceptable and appropriate, getting tipsy with colleagues is always wonderful for long-term bonding. I mean it.
  • Don't try to go for long stretches. Lots of short breaks is a huge help since these kind of mental exercises can be draining after too long. Get up and move around, even a short walk.
  • When you need to, allow yourselves to space out for a minute and take breaks from talking.
  • Group brainstorming should not be the only method. Make lots of time for quiet solo reflection and thinking. You can then come back together to share thoughts and grow the ideas from there.
  • Working, playing and thinking outside of your normal work spaces really helps with focus and mind-opening.
  • Being near a large body of water is a very good influence on this process. When you can, ask the ocean a few questions.
  • If you can, make some time to meet with other people who inspire you and thrive in their own work. Even if it's a completely different businesses, it's really helpful to get out of your own head and hear about another person's process.
  • You can TOTALLY do all of this by yourself and it will still be awesome.

A Sample 2-Day Agenda:

Retreat Goals (in no particular order):

  • Answering questions we never make time to ask
  • Re-energizing and re-focusing break from our daily routine
  • Set clear priorities and initial plans for executing first steps
  • Open conversation
  • Build a vision that helps clarify decision making process on goals and priorities


How are we? Today's Goal: Unpack and reflect on how we are each doing individually in our roles as well as how the business is doing in general. A solid check-in.

Meditation, 15 min. Let go of all the to-do lists, and daily work annoyances and let yourself be free and relaxed in this new retreat space. All you need to do is be here.

How are we? The feelings: Silent reflection, 1.25 hrs Try this worksheet of questions and brainstorming stimulants. Questions focus on the individual and the business in general.

Walk/Break, 15 min

Discussion, 1.25 hrs Discuss the How are we? answers, sharing and exploring

Lunch Break/Activity

How are we? The data: Time, 30 min How have we been spending our time? What takes up the majority of our energy, what time is profitable time, what is overhead time?

How are we? The data: Business reports, 30 min Overall business P&L summary review and discussion; draw conclusions, identify questions


How are we? The data: Project reports, 45 min Specific projects P&L review and discussion, how are we doing on different types of projects, draw conclusions, identify questions


How are we? Conclusions, 1 hour Make three easel pads with these three headings:

Happy face stuff is going really well. Sad face is not. Straight face is going okay but we want a lot of improvement. Write the main themes that showed up both on individual reflection, business reflection and in the data. Don't get too specific, focus on the general categories that cover the issues discussed.

Toast the end of a good day!



HOW DO WE WANT TO BE? Today's Goal: Think big and open up to ideas of what the real company vision is and what our priorities are. Factor in all that was revealed when answering How are we? and use it to define goals and directions for moving forward.

Meditation, 15 min

How do we want to be? Silent Brainstorm, 30 min Use the vision worksheet to brainstorm on your own.

How do we want to be? Share & Discuss, 45 min Share ideas and answers, discuss, review any pre-existing vision statement, share additions, changes and new ideas, compile ideas

Lunch/Activity Break

Vision Refinement, 1 hour With all the ideas gathered this morning, draft a new and improved vision statement for the business. It can be a bulleted list, a concise paragraph, a solid powerful sentence, whatever feels right and comfortable. The idea is that this vision will help guide all decision now and ongoing and will serve as a grounding reference always.

How do we want to be? Goal and Idea Dump, 30 min Brainstorm together all the different ideas and goals for where the business will go next. These can be long-term, immediate term, whatever. Release all the ideas you carry around or be open to new ones. Put them all down. When you've finished, organize them by broader categories. For example, we ended up with about six broad categories with 6-8 goals within each. One category was simply "Improve around time issues" and that included individual goals such as 1) refine our estimates process; 2) batch more tasks each week; and 3) decrease our general internal/admin time overall. Don't worry about answering how you're going to achieve these goals, focus on what you want to accomplish, change or continue.


How do we want to be? Goal Evaluation, 30 min Use this chart and for each individual idea and goal, evaluate it on these categories:

  1. $
  2. Joy
  3. A good fit for the brand
  4. In line with the vision
  5. Is it an area of strength?

This exercise helps you see what might be your best ideas or goals, but it shouldn't be a matter of scoring high on all categories. Some goals are worth pursing if they are a huge source of joy and just an okay source of revenue. It's just a matter of being conscious of what you're choosing to pursue and why.

Set immediate and mid-term goals, 45 min Identify three goal categories that are your top priority for the next three months. Ours are Product, Brand and Time. For the next six months after that, what are your top three goal categories? Narrow your focus. There are lots of different areas we want to grow in, but we start with a manageable list and time frame.

Then we made a chart for the next three months:

In each month, we want to take a few actions towards the three goal priority areas. List no more than five tasks associated with each goal that you will complete in that given month. In the last month, add a task to meet again and plan the three months to follow. Of course, if you have time to plan and goal set further out, go for it! But we are satisfied with a clear picture of what's right ahead, knowing that it all fits within the high-level vision of where we're going.

Call it a day Enjoy a celebratory toast for all the good, important work you've done.


There's always more to do, but two days like this is already so much more than we ever make time for. Do it, go for it and hope this helps!

*P.S. I find lots of good inspiration in the book The Big Enough Company, check it out!

*P.P.S. I could go on and on about this take this for what it is and trust that I'll continue to share my evolving ideas and framework for thinking it all through!