How can the magic of one-on-ones change your leadership skills for the better

Forming meaningful relationships with colleagues is hard — especially now in the remote working world. Their quality can make or break an entire working experience. Years ago, when I was in my first manager role, I underestimated how critical regular one-on-one meetings are, particularly those with your direct reports.

Over time, I learned that investing time and energy into regular one-on-one conversations is invaluable as they allow us to understand people's aspirations, challenges and motivations on a deeper level. As I wish I had realized this sooner, I want to share my personal observations and lessons to help make your leadership transition smoother.
By Jan Takacs, 13th December 2021

Transitioning to leadership

There is a decisive chapter in the career of every aspirational leader that involves the transition from an individual contributor to a managerial role. Suddenly, you have to deliver outstanding work through other people instead of doing it yourself, and it's hard.

After this pivotal shift, it no longer matters that you could outperform people individually before, as it requires a wholly different set of skills and abilities. One of the critical components for the successful transition is the relationship-building ability with people in your team. Do it well; your team will shine — thus, you will shine. Do it poorly, and it all crumbles, quality of work suffers, and people leave in droves.

When I was a manager for the first time, one of the biggest mistakes I made was that I haven't been able to find enough time and dedication to do dutiful and regular one-on-one meetings with all my team members. As a result, I was selective and hopeful that my inherent social abilities would quickly build rapport.

Additionally, I underestimated the impact of the cultural difference between my European mindset and that of my Asian colleagues. I expected it would not matter that much, but it turned out to be an incredibly flawed assumption.

Managers have the most power to influence how engaged employees are at work. For the past 20 years, managers have accounted for at least 70% of the variance in employee engagement scores. (Source:

A rough start

During my first year in the role, I struggled to balance relationship building with all my team members and the continuous pressure of several deadlines at once. Fair to say that I did a semi-decent job with the portion of the team, but overall, it lacked the necessary dedication and time investment on my part.

Being extroverted, I mistakenly believed that many team events and social activities would do the job. Looking back, this was another faulty assumption as these were usually not the best situations to build strong interpersonal relationships to understand people on a deeper level at all. It might have worked for me in some ways, but it certainly didn't work for everyone around.

In my experience, finding enough time to talk and listen to your colleagues in a relaxed, personal setting is an essential part of leadership, which I previously underestimated. I realized that sometimes we need to slow down to move faster, especially when leading a diverse team of people with different cultural backgrounds and ways of thinking than ourselves.

From a practical perspective, I expected everyone to be proactive enough to schedule their one-on-one's themselves as I was doing it myself with my supervisors, but that turned out to be another mistake. Everyone is indeed unique, and it's inherently unfair to expect other people to behave as we do.
Finding enough time to talk and listen to your colleagues in a relaxed, personal setting is an essential part of leadership, which I previously underestimated.
As a leader, I learned that you can't expect people to proactively develop their careers and design their long-term strategies with you. Instead, you have to lead by example and demonstrate the value of a great piece of advice and mentorship.

In addition, a particular emphasis and energy need to be invested in people who are just starting their working lives to deliver genuine, long-lasting human impact.

Now I know better, and I do my diligence and schedule regular one-on-one meetings with everyone on my team actively myself, while making sure there is a substantial time investment and emphasis on short-term tactical goals and long-term career strategy.

Previous hard learnings taught me that it's practically impossible to be a good leader and understand what motivates, bothers, and excites people without being dedicated and continuously improving at this communication technique.

And yes, that includes even the basic, often tedious, work of finding suitable timing for everyone, synthesizing your findings continuously and listening to various issues and challenges patiently while providing the support people need.
Delivery services in Southeast Asia see spike in business because of COVID-19 (Source: Channel News Asia, Photo: Mediacorp)
Leading diverse teams When leading a diverse group of people with different cultural backgrounds and ways of thinking than ourselves, it's critical to find enough time to listen to your colleagues often and embrace new learnings and perspectives. Plenty of listening and observing bears fruit.

Why do one-on-ones matter so much

1) Getting the right insights from your team
Open and honest conversations allow us to learn about people's insights, true struggles and raw knowledge. Distilling these learnings is key to defining and driving key business objectives and highlighting specific issues and opportunities to the senior business leaders to make your mark on an organization.

2) Practising the art of a conversation
One-on-ones are a fantastic way to practice the art of a conversation and get the right insights from people within the given timeframe. But, as it is a practice, it's like with cooking; nobody becomes a master overnight, so it's unproductive to be too hard on yourself initially.

3) Small talk substitute for remote working
The loss of small-talk opportunities is one of the biggest victims of the remote working setup as it is a vital component of successful relationship building. Therefore, I concur with HBR's opinion of deliberately making space for the small-talk in your meetings and not sticking to the standard KPI-OKR craze, which makes a massive difference in the long-term culture building.

4) Help people think long-term
We are all on a long, arduous, but colourful career journey. Helping people make the right decisions by better understanding their talents and ambitions is, at least for me, a joyful part of leadership responsibilities. One of my biggest learnings is that even though some people rarely ask for such mentorship themselves, it's essential to take the initiative and help your colleagues shape their long-term career strategies.

5) Giving feedback matters (a lot)
Giving and receiving feedback is often a sensitive minefield. It matters to most people, even though we usually don't proactively ask for it for various reasons. Learning and becoming better at giving and communicating feedback is another piece of a puzzle that's essential to master. One-on-ones provide an excellent time for it as ultimately, when people become better, the business becomes better, too.
Grab operations span across 8 Southeast Asian countries (Source: Grab)
Our careers are long journeys  To deliver genuine, long-lasting human impact, it's necessary to address not only short-term tactical goals and challenges but also help people shape their long-term career strategy and vision.

In a nutshell

As it's more complicated than ever to connect and create meaningful relationships in the current remote working world, it's critical for a leader to invest time and energy into one-on-one conversations to understand people's aspirations, challenges and motivations on a deeper level.

I believe that regular one-on-one's are an essential tool in every leader's arsenal to create rapport, shape connections, talk about difficult topics that are hard to mention in group conversations, and venture away from simple status reports. Today's world requires that we sometimes slow down to go faster, and thus making space for genuine conversations is essential to deliver a long-lasting positive impact for people around us.

Do you need a direction on how to run one-on-ones? I recommend the following read:

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