5 Things I Learned From Working With Friends

Building Business Without Sacrificing Relationships

Joe Schuberth
I Fired My Boss
5 min readJun 20, 2022

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Photo by DISRUPTIVO on Unsplash

As a community-driven entrepreneur, I love the idea of working with friends. What could be better than taking over the world with the people you love?

However, working with friends can be a balancing act. On the one hand, you have people you know you can rely on, brainstorm with, and keep you accountable. On the other hand, there is a genuine risk of things going sour if your relationships aren’t managed well.

Here are the five things I have learned from my experience working with friends.

Set Clear Expectations

Whether starting up a garage band or a startup in your garage, expectation management will be the first crack to be exposed in any venture.

Defining clear expectations for a project from the beginning allows you and your friends to have a sense of accountability around how much time and energy each person contributes. You each know what you need to do and what you don’t need to do, allowing each member to focus on the areas of their strength rather than feeling like they need to be able to contribute to every facet.

Part of this expectation management can come through defining clear and SMART (Specific, Measurable, Actionable, Relevant, Time-bound) goals. These thoughts can feel daunting, especially when a passion project turns into a 5-year plan, but what feels more overwhelming is being a year into a commitment and not knowing what direction it’s taking.

Embrace Conflict

As a naturally conflict-avoidant person, dual relationships are hard to manage. Working with friends made it difficult to raise concerns, disagree with proposals, or even share my frustrations.

But conflict is not only unavoidable; it’s necessary.

One book that was a turning point for me in conflict management was Patrick Lencioni’s 5 Dysfunctions of a Team. In his book, Lencioni notes that avoiding conflict only leads to artificial harmony.

So share your concerns, thoughts, and disagreements openly, frequently, and promptly. This habit is a muscle many of us will need to build over time, but welcoming necessary conflict can save your friendships and your business.

Support Independent Projects

Another layer that isn’t spoken about enough in entrepreneurial circles is supporting your friends’ independent projects. No matter how successful your collaboration becomes, your friends may still desire to have solo projects or partnerships with other people.

Your business will never meet all the needs that your friends have.

When colleagues feel free to pursue energizing side projects and partnerships with others, they will feel safer with you. This doesn’t mean that accountability to your commitment disappears. If anything, this is where accountability matters.

If you feel like a new passion project is distracting them from your commitment, don’t avoid conflict; ask questions. If you’re worried they will use their best ideas elsewhere, check your relational trust.

This concept is why major corporations such as Google and Apple not only encourage but budget time for their employees to work on creative projects.

Establish Boundaries

Establishing boundaries may feel formal, but it is the foundation for protecting yourself and your friends.

This is less about setting hard and fast rules about joking during working hours and more about deciding that you won’t work during joking hours.

I have been a part of enough work-related friendships to know that once work starts popping up in places other than work, your relationships begin to feel weighed down.

Perhaps you can even come up with a middle ground. If inspiration sparks and you want to share your thoughts, maybe you and your friends agree that a quick text or chat over coffee is fair game, but an ad hoc zoom meeting or immediate 30-minute call to iron out the details is not.

Two great tools that I used in friends-based work groups were Slack and Google Docs. When a “second brain” can be referred to by everyone, team members can write notes in proper channels, living documents, or messages designated for work-related purposes.

Getting a Slack message shouldn’t feel urgent during non-work hours. Seeing one of your coworkers online should not pressure you to go online. Trust the process of setting boundaries to increase productivity and creativity.

Know When to Take a Break

Why would you need to take a break? Perhaps your life outside of the business is changing, you don’t feel the same excitement as you once did, or you would rather guard your friendship than managing the tension you feel within the project.

Taking a break can mean slowing the pace after a long push for a product launch, building in company time-off policies, or reassessing your business goals.

Taking a step back from a friend-based project can be one of the hardest things you may have to do. But, building an exit strategy before taking your first step may save you some pain. Ask the hard questions:

What happens if one of us leaves?

What happens if one of us isn’t performing to standards anymore?

What happens if one of us wants to do more?

If these conversations frighten you, it may be time to have them. Sometimes you need to save your friendships from your business. You’re not going to regret putting people first.

Final Thoughts

I have had incredible experiences working alongside friends, and I’ll never forget the lessons I’ve learned. As you get excited about building a better world with your best friends, consider the cost of working with people you love.

If you need to take your time to iron out some of these points, your business will be better for it. And remember, you can always start small and scale up as resources and commitment become more available. It’s much harder to slow down once you’ve built something big.

Focus on your friends’ strengths; consider bringing in people who can complement your competencies and shine where you can’t. And, at the end of the day, you don’t have to work with friends. Your friendships are more important than anything you could ever build.

Joe Schuberth is a writer, coach, and lifelong learner who is passionate about collaboration within creative communities.

Joe can be found on Facebook, Twitter, and Instagram and is always interested in networking with community-minded entrepreneurs — so feel free to shoot him a message, or reach out by email at joe.schuberth@gmail.com

In addition to contributing to I Fired My Boss, Joe also writes about food and literature at [RE] Composition.

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