The power of one-on-one meetings

30 June 2017 Reading Time: 5 minutes

Ever since Ben Horowitz wrote about one-on-one meetings in 2012, their popularity has increased and have been becoming a standard for many startups and small companies. Why? Because one-on-one meetings are a foundation for great companies. We know because we built our company on them. Here’s what we’ve learned.

What’s a one-on-one and what’s its objective?

Traditionally, it’s the CEO who does all the one-on-ones in a small to medium-sized company. The goal is to build a strong relationship with every individual in the company and grow from the inside, one employee at a time. But these meetings also serve to spot potential problems early on and avoid or tackle them as soon as possible. CEOs also use one-on-ones as a communication channel that brings transparency – they can communicate important decisions and answer any questions that people might have. The format of the meeting allows the employees to share their thoughts, even give feedback to the CEO directly. It should be a safe environment where anything can be discussed.

However, Horowitz wasn’t the first person to introduce me to this concept. It was David Coallier, who wrote about their objective and the impact on his company when he was a founder and CEO of Barricade (recently acquired). I was thrilled!

Why we started doing one-on-ones

When I started at Enhancv as the first Dublin employee in 2016, I flew to meet the rest of the team and join them for a Power Week. It’s something we do twice a year – to work, hang out, and triple our productivity and fun.

My goals for that week were:

  • To understand what worked and what didn’t in the company
  • To kick off some initiatives I had already identified were needed
  • To get to know everyone on the team

The one-on-ones were the perfect format to achieve those three goals. During that Power Week, I did 13 half an hour one-on-one meetings, one with each of the employees and the founders.

The meetings had an immediate impact on solving challenges pretty much on the spot. That’s why we decided to introduce them as a regular practice. First within the leadership, and soon after that across the whole organization.

How we do one-on-ones across the company

Enhancv The power of one-on-one meetings

When we introduced one-on-one meetings across the organization, we were soon to be 20 employees and it wouldn’t have been scalable if they were centered around the CEO. So instead, one-on-ones became a shared responsibility of the leadership team.

We all agreed on 2 key aspects of the meeting:

  • the employee dictates the agenda – it’s their meeting rather than the manager’s,
  • it’s a safe environment for the employee to share and ask anything  – that could be related to their personal and professional development, to the company, team, product, or a specific situation that they’d like input on.

And while we agree on those, we also have a lot of freedom to experiment with the agenda, approach, even the format, or frequency. Today, the one-on-ones at Enhancv reflect our own personal styles and their adoption as a regular practice came naturally.

We do three types of one-on-ones within Enhancv depending on the lead’s personal style:

  1. Solely focused on coaching & listening, in which we discuss the individual’s personal growth inside and outside of the company, including focus on self-discovery, and self-actualization
  2. Solely focused on advising when we give feedback, where we discuss more operational topics, specific challenges, and brainstorm together how to solve them
  3. A combination of listening, coaching, and advising

How one-on-ones help me as a CSO

Enhancv The power of one-on-one meetings

To help the person get the most of the one-on-one, I ask them to share with me the topics they’d like us to discuss prior to the meeting. I do them every couple of weeks.

I lead the one-on-ones with 4 people on the team

  • Georgi, co-founder & CEO
  • Volen, co-founder & COO & CMO
  • Dimitar, cofounder & CPO
  • Nikolay, customer success

As a CSO who brings the long-term strategy into life in the mid to short term of the company, I need a regular overview of the current state of every bit of the company. The one-on-ones with the cofounders help me align the leadership team, calibrate our understandings of certain challenges and solutions for them, as well as give us a platform to help each other and take actions quicker.

Our conversations with Niki from the Customer Success Department help me understand his challenges and support him in any way I can. For example,  will I advise him how to identify and overcome a challenge. We’ll brainstorm how to solve it together.

Some one-on-ones are focused on growth and pushing our limits. We dedicated one of the meetings to discuss Niki’s Top Strengths. We reviewed each one of them and discussed what he enjoys the most about his role. That also helped us shape the role of the second Customer Success person that we are going to hire in Dublin. Thus, their skills will be complementary to one another and they can help each other.

Questions I often ask during one-on-ones:

  • What do you want to talk about today?
  • What’s worrying you at the moment? That could be personal or professional. If it creates anxiety and the person wants to talk about it with me, we talk about it. When people don’t feel happy or successful in their personal lives, it’s unlikely that they will grow to their full potential professionally.
  • Why is that a problem? That helps me understand if we are looking at a symptom or the source of the problem so we can focus on what would make an impact rather than do a temporary fix on the surface.
  • How can we solve this problem? Once we have identified the problem, we analyze it together, even brainstorm how to approach it. Sometimes we talk a bit how I would approach it or have approached it. For example, frequently overcommitting results in an anxiety and in those cases, we sit down together, list all of the things on their mind, prioritize them, reprioritize them, and delegate or drop a few things.

When others lead one-on-ones with me

It’s not a coincidence that Volen – our co-founder & COO, and Denitsa – our Team & Operations both have one-on-ones with me.

Volen often helps me with various challenges. Sometimes these are anxieties related to working remotely. When working on your own, physically removed from anyone else on the team, it makes all the difference in the world to feel listened to, heard, and to hear “Okay, how can we fix it? No problem, we will solve this immediately”.

Conversations with Denitsa have a different purpose. I talk to her about my experiences as a remote employee. This allows us to be a more remote friendly company, from the onboarding we do for new employees and the benefits that we offer to the way company-wide meetings are structured.

What’s next?

Almost every one-on-one helps us identify current and potential challenges. We’ve tackled the majority of those on our own. But, we’ve also realized we occasionally need help with some of those personal and professional challenges.

We’re excited to share that Velina joined us as Talent & Leadership Catalyst, to help us with the personal and professional success of everyone at Enhancv. Currently, she’s working with the leadership team and gradually starting to work with the rest of the team.

How to balance one-on-ones and performance reviews?

This will be a follow-up article in the upcoming weeks, so keep an eye on the blog.

In the meantime, I would love to hear your thoughts on one-on-ones. Feel free to post them as comments or email me directly at

I’m based in Dublin, so shout out if you are around for a coffee. Also, I’m currently hiring here for a few roles:

Enhancv The power of one-on-one meetings

Vessy Tasheva

Career Industry Expert & Talent Scout at Enhancv. I help people succeed in their jobs & careers. In my free time, I do career coaching and write about it on

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