(Business) Retreat, (Business) Retreat!

(Business) Retreat, (Business) Retreat!

I ran into a colleague the other day – we will call him Alonzo – and it was a beautiful early morning. We both found ourselves fortunate enough to be able to take a half hour and walk together, so we set off toward Portland’s beautiful working waterfront. It’s very common in my life that a discussion with friends or colleagues leads to discussion of some sort of business problem or issue that one of us is dealing with. I love a good brainstorm as much as I love solving problems.

On our walk, my colleague presented his own frustrating position: over the past few months, it had become clear that Alonzo and his business partner had some nagging stylistic differences in how they worked, managed, and delegated, and I sensed that it may be the beginning of a wedge. Some recent personnel changes at his company had heightened nerves of the owners, and their administrative staff was squeezed. Throw COVID in there, and you could easily be dealing with a pressure-cooker situation. Not good. Heightened anxiety leads us naturally to seek solid ground, to seek control. It is those states that we naturally become more rigid, more defensive of your current position, and generally less calm and flexible. In a partner situation, because this is happening to both people possibly at the same time, things that are not working can explode really quickly.

It’s an opportunity to get away and forget all your work “in the business”, and direct your full attention to your work “on the business”.

Well, my friend was not really asking for advice, but, after empathizing and ensuring that he was heard, I suggested the idea of a “retreat” with his partner. This is obviously not a novel idea, but I feel that tiny organizations (2-4 people) do not prioritize such an annual event, when they are so healthy from a number of perspectives. It’s an opportunity to get away and forget all your work “in the business”, and direct your full attention to your work “on the business”.* Most importantly, it’s a process through which you work with your business partners to develop business practices that work for everyone, make the business better, and which seek to achieve your shared goals and vision (and fundamentally, certainly to confirm that you actually have a shared vision and goals!). The retreat is a great way to both discover those things about your partner, but also to develop strategies to bring them in line. Another great part of the retreat – if a meaningful relationship is desired – is the planning of cocktail hour, game night, walks, or other non-work times to, at the very least, make sure you guys actually like one another!

This extremely odd time in our lives – the never-ending period between when the threat of another big outbreak of the pandemic is very real, and the time when 95% of Americans are vaccinated – could be a really great time to slow it down and plan your retreat. Short-term rental and hotel bookings are low, so scoring a great place for two nights is easy, and testing for COVID is fairly readily available in Maine, so you could test, short quarantine while you await results, and then head out when you’re all cleared, so you can “pod up” for the weekend.

Slow down, calmly identify the issue objectively and together, and co-design a solution that works for you and the team.

At a higher level, this conversation reminded me that in times in high stress – yes the entire COVID period counts – that people (including you!) need more calmness, love, and empathy, and less anxiety and pressure. So, when a course of dealing with a business partner (or any meaningful relationship, really) is becoming heated, punchy, and frustrating, instead of stepping up, maybe you should instead retreat! Slow down, calmly identify the issue objectively and together, and co-design a solution that works for you and the team.

Here’s some basic suggestions about what to do on your retreat. Remember, the aim is to establish common ground, evaluate the past and current, and make a plan for the future.

Retreat Roadmap

In addition to the common roadmaps of a retreat, which include sessions like:

  1. Establishing core values, a mission statement, and goals for the company and each partner
  2. Business Track Mapping:
    1. How did we get to where we are now?
    2. Where do we want to go? What is our vision of success?
    3. What is going to get in our way? What do we need to be aware of?
    4. What do we need to get there?
  3. Basic SWOT analysis
  4. Landscape analysis (competition, partners, influencers)
  5. KPI analysis

Questions To Consider

I’d suggest you ask yourself and your partner some high-level questions about the way you want to work and live, such as:

    1. Each partner should do the following assessment for themselves, and then for the other partner:
      1. What are my/your best attributes? What skills set me/you apart?
      2. What are my/your biggest challenge areas? What do I/you really struggle with?
  1. How does each partner actually measure success? To put it another way, what does true success mean to each of you? (For some, it’s measured in money, for others it’s free time, and others it’s new and creative work opportunities.) No judgment here, just get it out there so you guys have an understanding.
  2. What is the one thing we dislike the most about running our business? And how can we eliminate that dreaded task/issue?
    1. Follow up: What tasks do we currently take on that we could hire out (invoicing, marketing, client follow up, etc)? And are we hiring anything out now that we don’t really need (i.e. are we wasting money anywhere)?
  3. If we could bring on one employee (or new partner) what would their ideal skill set and contribution to the company be?
  4. What systems are we using, and are they working? How could they be improved? What in our business needs a system that doesn’t currently have one?

Final Thoughts

Obviously, it’s up to you to take or leave anything here. The point is to generate ideas and invoke discussion. The retreat is for you and no one else, so make it your own.

I hope this post has been helpful in some way, and has provided some inspiration to address a block that is getting in the way of you creating the life you want as an entrepreneur, whether it is to go on a physical retreat, and take a retreat of another kind. 

Be well, be safe, and be kind to one another.


*These concepts were first coined by Michael E. Gerber in the E-Myth.

Zeke Callanan

Zeke founded Opticliff Law in 2012. He thrives on new ideas and brainstorming with clients about thinking bigger, and growing mere ideas to sustainable business plans. He works with startups, growing companies, and evolving relationships through entity formation and strategy, everyday business contracts, and complex fundraising compliance work. Zeke is very involved in his community, and supports local growth and progress through his network.