One-on-one: The good the bad and the ugly (In the IT Industry)

Alberto Cubeddu
5 min readMay 8, 2018
“Two people sitting at a coffee shop table with a laptop, a tablet and a smartphone” by rawpixel on Unsplash

In the modern world of IT Industry, we usually hear a lot of buzzwords, one of them is “one-on-one”, regardless the popularity of this word is concerning how often people don’t know what’s the theory behind and the real benefit of having a one-on-one with your employee.

Consisting of or involving direct individual communication; person-to-person.

In the business world one-on-one is a meeting that provides an ongoing feedback strategy to keep both manager and the employee’s updated on their status. The sessions are private and focussed toward performance management, problems solving and process enhancement.

Why is so important to have one-on-one with your team members?

This meeting is the best way to connect, develop a strong relationship and ensure that employees feel like they’re working towards their main goals. This helps your business grow quickly having people with better skills, increase retention and creating an ideal work environment based on the feedback that they gave.

“You spend so much time finding great people, it’s worth it to help them grow to be the best they can be.”

JUSTIN ROSENSTEIN, (Co-Founder, Asana)

Your employee at the end of the day are the one doing the job, if you listen to them and craft processes based on their feedback not only you most probably increase the performance of all the team members, but you make people feel evaluated and part of something they created and they are proud to be part of!

Why is so important to know the employee’s status?

As a manager, your job is to deliver quality software on time with the best outcome, therefore, you are responsible to develop your team skills, not only giving the resources to learn but a strategy to embrace to help them achieve their best results in the most efficient way, nevertheless, it’s important to remember that is a sharing discussion where both employees and manager are aiming to improve.

The theory

I would say that for planning a one-on-one you need to consider 4 factors: Frequency, Expectations, Format and Goals. I want to say beforehand (and this is my personal opinion) that it doesn’t exist a perfect technique to run a one-on-one, it’s all about refining the process, listening to feedback and watching results. Sometimes you succeed, sometime you will fail, and if you do fail, don’t get demoralised just take it as an opportunity to learn from mistakes, it’s normal and common!

The good

Frequency is a must factor to respect, if you plan to have a one-on-one do it on a schedule base (every week, fortnightly or monthly) and be strict about it! Communication is the base for a good relationship and needs to occur as often as possible and in a scheduled routine.

Expectations need to be defined by the person in front of you, however asking them some standard questions will be helpful:

  • What or where would you like to improve?
  • What’s your challenge for the upcoming week/fortnightly/month?
  • Are you facing any difficulties or blocks?
  • Tell me about the achievement you made since we last spoke?

Always remember the one-on-one is based on your employee and is a place for coaching, mentorship, giving context or even venting. If you are getting stuck finding questions I will recommend this link:

Format: Is really important because marks the effort and the importance of this meeting. Having a discussion at the desk or having a walk makes such a difference, also remember to keep track of all the progress, this demonstrates to your employee that you really care and are committed to their professional development.

Goals: Successful one-on-one needs to be orientated toward the employee and be relationship-driven to achieve the best outcome and meet employee and business needs. The final goal is to keep employees happy, increase retention and performances among the team.

The bad and the Ugly

Leaders are not born but made, therefore, is most probably that you have not been managed in the best way.

Frequency is a key concept when a manager schedule time for you and then he cancels last minute this provoke a drop in confidence. If you ever need to cancel a one-on-one be sure to reschedule it as soon as possible and give a reason why the meeting was cancelled.

Expectations. It’s a busy world and not always is possible to achieve all the results, remember that your job is helping people, not to burn them out. If they had a bad week, try to make their life easier NEVER blame on them, NEVER use negative sentence ALWAYS cheers them up, ALWAYS listen to them and accept criticism to improve yourself and/or the workflow!

“The key challenge of the coach is to listen without a filter. A filter is a certain attitude or bias the listener takes on that inhibits his or her ability to be present with the authentic experience of the speaker.”


Format: Even if you are a wonderful speaker, having a format and respect it among all your employee is a good habit to make them feel all at the same level, also help yourself to collect metrics and produce statistics.

Goals are the final result of the one-on-one. If you are having bad results that’s mean that your employee never reach a goal and you should change your strategy. Remember you are a manager, you are here to serving your employee, not the reverse! If something is going wrong you are the only person to blame!

In conclusion

The best way to have a successful one-on-one session is based on a different factor such: improving yourself based on the feedback provided by your employee, listen without a filter, show statistics and most importantly celebrate results.

Your final goal as a manager is only one: keep people happy and motivated!

Photo by Ellyot on Unsplash



Alberto Cubeddu

Leadership || Management || Innovation - Technology Director & Former Head Of Engineering