I still remember the moment I asked my good friend Heidi if she’d consider joining Outsourcing Angel.
We were already great friends, and a little voice in my head said, “Linh, are you sure? What if this ruins the friendship?” At the same time, I knew that Heidi was someone I trusted with my life, someone who shared my values and work ethic.
I had this gut feeling that if we set the right boundaries and communicated openly, we could make it work.
Looking back now, I’m so glad I followed that instinct. Working with Heidi hasn’t just strengthened our business; it has deepened our friendship in ways I never expected. She has now been working with me for over 5 years and we’ve never had any conflict or awkward moments.
In this blog, I want to share the key lessons I’ve learned from our journey together so that you can see how working with friends can actually work beautifully, if done right.
1. Respect Each Other’s Roles
One of the biggest things that has worked for Heidi and me is respect.
When we’re at work, we both wear our “business hats”. I might be the founder and technically the boss, but I never treat Heidi like an employee who just has to follow orders.
I value her opinion and trust her to lead her own area
Heidi mentioned that having those clear boundaries, me respecting her role in sales and her respecting my leadership, has been crucial.
I’ve learned that when you give people the freedom to own their space, they show up with more passion and pride.
2. Communicate Honestly and Openly
We’ve never had a friendship blow-up or a work-related conflict. Why? Because we talk. Really talk.
If something doesn’t feel right, Heidi will let me know, and I do the same.
There’s no bottling things up or letting resentment build. This is so important because I’ve seen relationships, both personal and professional, fall apart when people don’t express how they feel.
Being honest might feel uncomfortable at first, but it’s the key to maintaining both friendship and business harmony.
3. Set Clear Expectations
One thing I’ve learned as a leader (and a friend) is that you cannot assume people know what you expect from them.
With friends, it’s even trickier, because we naturally want to give each other the benefit of the doubt.
But I’ve realised that friendship doesn’t mean you skip accountability. Heidi and I have clear KPIs and quarterly goals. We hold each other responsible for results.
Friendship or not, if someone isn’t performing, it can affect the whole business.
This was a big takeaway from our chat:
Friendship doesn’t mean avoiding tough conversations, it means having them with love and respect.
4. Separate Work and Play
One thing we’ve done really well is finding balance. During our morning huddles, it’s all about business, numbers, tasks, goals. Once that’s done, we switch off and have a laugh or talk about life.
This separation helps us maintain both our professional and personal relationship. It’s like flipping a switch between “work mode” and “friend mode”, and it’s something I highly recommend if you’re considering working with mates.
5. Try Before You Commit
Heidi made such a great point in our interview: don’t dive head-first into working with friends. Test the waters first.
We started with smaller projects and slowly built up. This “trial period” gave us a chance to see if our dynamic worked in a professional setting. It also ensured that if things didn’t work out, we could step back without damaging the friendship.
6. Transparency Builds Trust
One thing I love about working with Heidi (and Annie too) is that we share everything, our wins, struggles, and even personal plans. Heidi doesn’t feel like she has to hide life updates, like planning for a family, and I feel comfortable sharing what’s going on with me too.
This transparency makes it easier to support each other and plan for the future. It’s one of the unexpected gifts of working with friends, you’re not just building a business, you’re building life together.
My Takeaways
Talking to Heidi reminded me that working with friends isn’t about luck, it’s about intention. It works because we:
- Respect each other’s skills and boundaries.
- Communicate openly.
- Hold each other accountable.
- And most importantly, we never take our friendship for granted.
If you’re thinking about working with a friend, start small, set clear expectations, and commit to being honest no matter what.
Done right, it can be the best of both worlds, you get to build something meaningful while sharing the journey with people you truly care about.
What About You?
Have you ever thought about working with one of your friends?
Or maybe you’ve tried it and it didn’t work out?
I’d love to hear your experiences.
Think about the friends in your life who inspire you, who share your vision and values. What would it look like to build something amazing together.
If this is on your heart, take it slow, test the waters and have those open conversations about boundaries and expectations. Who knows, it might just become one of the best decisions you ever make, like it was for me and Heidi.
