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

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!

  • Michael Jenkins

    Empathy, in my opinion, is something that we as a culture are lacking. When did showing understanding and caring about someone become taboo? I love the fact that people and companies are trying to bring this back.

    I love the idea of Digging Deeper. I feel once you become honest with yourself you can accomplish more. The fact that you have your weekly one-on-ones helps people face themselves and to be more accountable. Plus it is a good time to reflect on your previous week and receive some tips that may make the next week better.

    The values and tools that Buffer is teaching are great to bring into your personal life. I continue to applaud them for this effort. Thanks for sharing your experiences. I truly enjoyed reading.

    • “When did showing understanding and caring about someone become taboo?” – amazing question. I don’t quite know the answer to this one. :) I’ve reflected on it though. My current thoughts revolve a lot around a capitalist/survival-of-the-fittest ideas that permeate western culture. A book I read recently that aimed to answer some of these questions is by one of my favorite philosophers & authors, Peter Singer. He wrote a book in the 90s called “How are we to live? Ethics in the age of self-interest”. Check it out here:

      It was bit of tricky read for newbie in philosophy like myself, but I came out with a better understanding in the history of self-interest, we feels sometimes feels at odds with altruism, caring, giving, empathy etc. :)

      Would love to hear if you’ve explore some of these concepts yourself Michael? Incredibly interested to learn from you.

      Thanks again for the great comment! :)

      • Michael Jenkins

        Niel, I agree with your thoughts to my question. I appreciate the feedback and book suggestion. I myself am a newbie to philosophy but have a deep appreciation for it.

        It has always been my belief that people have a tendency to follow the crowd and unfortunately it seems to be survival-of-the-fittest way of life.

        However, I do believe there are a lot who do not believe that way of life and live like I do. It is amazing when all you do is ask questions and listen to someone how you can change their day. I feel we all need to learn to listen more, it’s amazing what you will hear if you do.

        I will be looking into the book you recommended. It sounds very intriguing and I would like to learn more. If I have any questions while I am reading I’ll be sure to ask you ;-)

  • Yolcu

    I’m thinking to practice one-on-ones with my team. There is definitely a need for that. There isn’t any culture in that direction in the company (sadly) however there is a definitive need.

    There is also a video on how to approach the talk in a sensitive and constructive way.

    I’ll try the approach and let you know how it went!

    Thank you

  • Shantelle McDonald

    In my experience, deep relationships require a deep well of trust, so building relationships is an exercise in building trust. Getting to the hard, dark, or painful places in someone’s life means that they will have to expose themselves to potential judgment or condescension. It takes confidence that the other person will have empathy, showing love and acceptance, to bring your whole self from the shadows. As people learn to accept one another, they give each other permission to face the hard parts of their lives without shame or fear, freeing them to be the fullest version of themselves, not just the work self or the friend self. Coming alongside another human being and being present in whatever circumstances they are facing, without judgement or even necessarily advice, in my opinion, is deep and abiding friendship.

    • Wow. Amazing words there Shantelle!

      Do you perhaps have any tips, advice or experience in how to build this trust? Do you think there are ways to help develop this?

      For example, some people might take longer to open up than others. Super fascinating topic this!

      • Shantelle McDonald

        Thank you Neil! I find it totally fascinating as well. ? Of course, I’m a bit of a nerd and love digging into psychology and human systems so it’s not surprising. (This is a great site on human systems if you’re curious: This is actually a huge topic, so I took a little time to think about what would be most useful.

        Other than building personal and professional relationships, I used to work on a challenge course/ropes course (look at some pictures here if you’re not sure what I’m talking about: where assessing power dynamics, building trust and authority, and balancing those with a group quickly would influence their overall success and learning.

        I feel that the briefest answer I have is to be safe and make others feel safe. Beyond the straightforward actions of honesty, reliability, respect, and being genuine, I find that it’s helpful to be mindful of the power dynamic in the relationship (which is another big topic, so I won’t be digging into that here).

        Prove that information, feelings, requests, promises, fears, etc are not going to cause big reactions or whiplash judgement. That’s where being empathetic is really essential. Almost all challenges are relatable at least to a degree because we’ve all faced problems and made mistakes. When we start living as if things are relatively equal and quit building our own cosmic scorecard, we can connect with a much wider range of people.

        I have found that humility is also extremely useful in building trust. If I see my coworkers as people who have a deep well of knowledge and experience and invite them to share something that has relatively low stakes, I’ve started lines of communication that build trust. It’s important to remember that it isn’t differences of opinion that make people feel unsafe, but the reaction they receive (i.e. judgement). When you show interest, respect, and open mindedness toward someone who thinks differently, some safety is almost immediately established.

        You’re right, some people take longer to trust and all people have areas that take a long time to reach. Because trust is earned, there isn’t a shortcut. That’s what makes it valuable! My favorite analogy on this is the Trust Bucket: Trust is built one drop at a time, but it only takes one good luck to empty the bucket.

        I hope that helps! Let me know if there’s anything you would like me clarify or expand on, and good luck.

        • Wow Shantelle. This is beyond incredible. I feel so blessed that you shared all this. It’s got me thinking really deeply on this.

          The idea of safety is so crucial here. When I reflect on past times where I felt that I’ve lost trust in a relationship is when the other person shared which I assumed was confidential with other persons, or even change their behaviour based what we’ve talked about.

          “It’s important to remember that it isn’t differences of opinion that make people feel unsafe, but the reaction they receive (i.e. judgement)” – wow. That is so true. I’ll cherish this quote.

          This reminds me of a book called Nonviolent Communication ( where it really changed my thinking on how easily utterances are some kind judgment, even if they are implicit.

          Thanks again for the awesome comment! If you perhaps have a blog/Medium, I’d love to read & digest more.

          • Shantelle McDonald

            Thank you Neil. I’m honored by your praise and overjoyed to be an influence in your reflection on this subject!

            That’s a great book suggestion; I’ll definitely look into it.

            I don’t yet have a blog, but I’ve started compiling some content and I’ll be sure to let you know when it’s up and running.

  • felicia.cristofaro


    I feel that I’ve made this comment before, but I truly admire the way Buffer structures one-on-ones. The linear structure is fantastic, it results in providing everyone the chance to be both a mentor and mentee, and learn what it means to be more compassionate and be willing to take on different perspectives. The principles you’ve identified certainly set the stage for a deep and meaningful relationship. These principles are a simple way to ensure that you keep your relationships healthy, and continue to help them grow. Super important for a company like Buffer!

    Similar to what you’ve said, I’ve found that what has helped me most in building deeper relationships is listening. One hundred percent, fully undivided attention listening. I feel that it helps people subconsciously feel that you care about what they’re saying, encouraging them to delve more into their issue or talk. Thanks for sharing!

    • Thanks for the kind words Felicia! I’m so curious to see how 1:1s grow at Buffer. I’m six months into this journey (being both a mentor & mentee) and it’s feeling really amazing so far.

      Listening is such a key thing. Sometimes, and I’m definitely culprit in this too, people find it tricky to chat or even fully understand the full concept of their topic or challenge, that listening as a mentor & asking the right questions is so valuable to bring out the true feelings & thoughts. I’ve often, in my 1:1s with Sunil (him being the mentor) only realized my true thoughts while talking about a challenge. It becomes crystallized when I try and explain it to someone. When the mentor asks deeper questions, perhaps for them to understand it better themselves, you help yourself get a clearer picture too. :)

  • Sylvia

    Niel, thanks so much for writing this. I totally track with you~ As I’ve started to do more informal one-on-ones with a growing team, I love that you get to know someone outside of a normal basic work capacity and get to even be friends. I’m most curious about what you said earlier about being their personal champion. I have an idea of what that might mean, but can you help explain that a bit more?

    • Hi Sylvia,

      exciting start to your journey! Great question that. I see it as a way to really embrace this person fully in the team and champion for their best outcome in their journey at Buffer. For example, sometimes we have to make decisions at Buffer which might be challenging for the person I’m mentoring, and I have to try be mindful of their experience and find a way to still provide the best outcome for them and for Buffer.

      Here’s an example that I could perhaps share that happened with Ivana. She’s an amazing engineer. Since she started at Buffer, she’s been hopping around many different areas, Buffer for Business, Onboarding, Dashboard, Journey/Jobs pages etc. Truly astounded at her ability to pick up new code and gain momentum quickly.

      When Buffer acquired, we were thinking which engineers might best be suited to join the area. Ivana felt like a really great fit, however she has shared to me before that she really enjoys gaining a bit more momentum in an area and hopping around to new areas so frequently felt a bit challenging at times. Even though I know she’ll do an incredible job at it (and she did! :D), my first instinct when the decision was made about Respond was to reach out to Ivana immediately to hear how this felt. How will this decision impact her in the short term and how can we work together to find a great outcome for both Buffer & her. So any decisions that get made, I aim to have empathy with the people I’m mentoring to imagine how these might feel. Even if I’m totally off-base on my feelings, reaching out and touching base feels key to helping each team member thrive.

      I almost see a personal champion role by answering the question, “Who looks out for this person in the company?”. I want to be that person for them.

      I hope that helps clear things up Sylvia? :) Happy to answer any more questions you have.

      • Sylvia

        Niel, you are wicked quick! Thank you! The example of Ivana does help. What if the person you reach out to wants to go in a different direction? If Ivana really wanted to stay put what might have happened there? I’m not exactly sure how decisions are made at Buffer regarding changing roles, but would you then advocate or mediate a conversation with stakeholders to come to a mutual agreement? P.S. You sound like a great person to have backing her up.

        • That’s a good one. I think we’ve been quite lucky to have not reached impasses like that.

          I think in general, decisions like those, for example, where people are moved from different areas, it’s really key to explain the full context. For example, we really felt that Ivana is the best candidate to work there (because she is so darn amazing at what she does). Describing that and any other contexts is great. If decisions are made in a vacuum, it becomes more tricky for people to visualize & embrace the change.

          However, in a hypothetical situation, if an impasse does come about, all stakeholders would probably get together to figure out a plan. I think in cases like this, a mentor’s value would be even more, if the decision doesn’t quite feel 100% in line with mentee’s choice. It’d be a great challenge to help guide & figure out how we can work together in this new scenario. Being honest & transparent here about how each person feels, coming back to building deeper relationships, helps with sustaining this relationship.

          Hope that answers your question Sylvia? :)

          • Sylvia

            Niel, yes, it does! Thanks so much for taking time and putting a lot of thought into replying to me. This definitely helps and encourage me to be a better mentor in my own team.

  • @NielDLR:disqus Great reflection and introspection. Thanks for sharing this! It’s always great to take relationships to a deeper level. A great reminder to do this!

  • Nda-jiya

    This reminds me of this new app that finds context driven ways to help you keep contact with those you want to keep close.

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