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The Simple Way I Strengthened My Personal Relationships (Without Leaving Work)

Feb 1, 2016 5 min readSelf-Improvement

A few years ago, my girlfriend proposed an interesting thought: How well do I really know my friends and family?

My initial thought was that of course I knew these people. We all get along and things are great. I’m friendly, they’re friendly. What more is there?

However, it wasn’t as simple as I thought. This simple question started a reflection over the past few years on how I really interact in my relationships.

Was I really curious and deeply invested in the people who I call my family and friends?

I came to realize that maybe my relationships weren’t as deep as I thought. However, I didn’t quite know how to improve this.

I knew in essence what needed to be done, but I felt vulnerable and scared to start going deeper in my relationships.


The solution to deeper personal relationships, counterintuitively, came to me through my work.

How one-on-ones helped me grow

Buffer is a fast-growing startup, and we’ve had interesting scaling challenges along the way.

One experiment was with a very flat structure, which made us drop our existing one-on-one coaching conversations.

A few months ago, we realized our mistake, and by this time our company had grown tremendously.

This meant that I got the opportunity to start being a mentor to two of our team members, Mike and Ivana.

The thought of leading one-on-ones, Buffer’s primary form of coaching, was super exciting for me, and yet at the same time an interesting challenge.

I knew that I wanted to balance the needs of the company with helping Mike and Ivana to find their best potential and create happiness in their job and life. I wanted to be their personal champion.

The first few one-on-ones were tricky as I learned, but eventually we created great relationships.

And this started having an impact on my personal relationships, too. I started asking better questions, opening myself more and aiming to invest my empathy wholly in the person I’m talking to.

How did this change happen? There are a few specific elements I’ve noticed that make a difference in developing a strong, deep relationship through one-on-one conversations.

Many of these same principles apply no matter if you’re speaking to a coworker, a partner or a close friend.

1. Setting the tone for digging deeper

In one-on-ones, the overall feeling is one of reflection and digging, asking questions like:

  • What challenges are you facing?
  • What went well last week?
  • How can I help with this?
  • What are your hopes and dreams?

The discourse helps to set the tone. However, the depth and impact of these discussions is also related to how well I am able to set the discourse.

If my questions were more superficial, the relationship might also remain superficial.

questions for digging deeper

Once you set the tone, the discourse setting becomes engrained. Once I start to dig deeper, the next time I jump on a one-on-one, the natural tendency is to dig into deeper challenges. It becomes the norm.

This made me realize that in my relationships, the discourse setting isn’t always so present.

If I’m sitting somewhere sipping a drink with a friend, maybe the natural tendency isn’t to chat deeply. It might feel odd, perhaps.

However, here, I could possibly start changing the discourse by being more vulnerable and asking deeper questions. It might be a slower change than in my work one-on-ones, but each step helps change the tone and expectation for future conversations.

So the next time I sit down for a drink, maybe the friend feels more comfortable to share more deeply. In the end, one can even transcend the setting, and the relationship becomes the discourse itself.

2. Flexing empathy

When I think about Mike and Ivana, I try and put myself in their shoes.

Are they feeling challenged enough in their work? Are they happy with their deadlines? How are challenges affecting them? How will a particular change in the company affect them?

If I want the best for our company, I need to have the best for them in mind. This involves a lot of flexing of empathy, which often means deeper questions and a lot reflection.

Empathy is not easy, and in my mind it’s something that needs to be practiced. Many times I’ve encountered talking about a challenge only to come to the wrong conclusion. Luckily, I get corrected, and this shows that I can become better at this.

With a deeper understanding of another person’s needs, a relationship can flourish and we can work together to address those needs—or in some cases, I can just listen (another skill of its own!).

In my personal relationships, I’ve really started to practice this more, to fully understand the person I’m talking to.

3. Practicing regularly

I have weekly one-on-ones. This has allowed me to consistently reflect on Mike and Ivana.

Our chats have a progression and continuity. Sometimes challenges can span weeks.

When I think about my personal relationships, having a deep chat once a month is probably not enough to really understand someone and build a deeper relationship.

I have to have them on top of my mind, and aim to interact regularly, if we can.

Regular practice has also helped me see the impact of how relationships can change if I start interacting more deeply.

4. Finding joy in listening

One-on-ones differ slightly from normal relationships in that they’re not 100% reciprocal. My goal is to listen as much as I can. This weekly hour is not about me, but about them.

Being good at listening is not only a great tool, but practicing listening so often has made me enjoy the action itself a lot more.

The reward is getting to know someone a bit better. Sure, sometimes the goal is also to help with challenges, but there’s also an inherent joy in simply knowing that this person chose to share this information with you.


One of my absolute favorite quotes on this comes from the movie Before Sunrise. The two main characters are sitting in alley talking about love when Celine shares this with Jesse:

“I believe if there’s any kind of God it wouldn’t be in any of us, not you or me, but just this little space in between. If there’s any kind of magic in this world, it must be in the attempt of understanding someone sharing something. I know, it’s almost impossible to succeed, but who cares really? The answer must be in the attempt.”

Listening more, and regularly, has solidified the gratitude that I feel when I can be a part of someone’s life.

What helps you build deeper relationships?

I feel like there’s a lot more to explore in one-on-ones as well as in my personal relationships. This feels like only the start of this journey.

I’m super grateful for what I’ve already learned, and I’m keen to keep growing.

How do you maintain and deepen your relationships, whether at work, at home or with friends? I’d love to hear your thoughts and suggestions in the comments!

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