The dread of One-on-Ones

Sean Robinson
6 min readMay 17, 2018


There are few words that seem to furnish us with quite so much dread as the sentence “Time for our one-on-one”. Through decades of poorly handled or abused sessions, we have come to see this time as a frustrating waste in the best case, or fear inducing managerial bureaucracy at worst.

This is an appalling shame, as properly facilitated one-on-one (O3) meetings can be one of the most powerful and useful ways of spending our time. I was first introduced to the power of this meeting through a boss early on in my career. He was successful, but retained a strong humanist approach that inspired confidence and loyalty. My own journey started there, but grew through my experience with more formalised performance coaching. The underlying format I present is strongly inspired by the early sessions I had with the aforementioned leader.

A properly facilitated O3 should provide validation to the employee, give a sync point for duplex feedback and form the basis of a strong coaching platform.

Buy bother?

It’s important to remember that O3s are primarily for the coachee. This is an opportunity to provide:

  • Validation
  • Coaching
  • Mentoring
  • Career development
  • Synchronisation on non-critical issues

But what about the coach or business?

  • Validation
  • Coaching
  • Mentoring
  • Career development
  • Synchronisation on non-critical issues

Yep, exactly the same benefits. By providing this opportunity, the business is able to ensure a happier and more performant workforce, with all the well documented benefits that it brings.

It doesn’t work!

I hear the above regularly when I start to introduce O3s, it seems a common theme that they are often not run with the coachee in mind.

One-on-Ones are driven by the coachee

If nothing else, take with you the knowledge that O3s are not for you as a coach, they are primarily for the benefit to the coachee.

If you encounter some of these concerns, try some reframing.

Often, these subtle psychologic shifts for yourself and the coachee can be enough to start the ball rolling. Remember, you are a servant leader.

Getting Started

Broadly speaking, we want to start by looking at longer term goals and then focus on more imminent steps that contribute towards the longer-term vision. I think that it’s important for the coachee to notarise as you progress. If you are the one taking notes, then you have removed some degree of ownership immediately. By taking their own notes, the coachee is implicitly committing to themselves.

Initial O3 Flow

Long Term Vision

This helps to set the context around the ongoing sessions. As a coach, you will focus on aiding the coachee in discovering their own vision. A coaching background will help here, but you could start by looking into Socratic questioning or the GROW method by Passmore. At this stage, you may want to help the coachee identify a vision that aligns with the business objectives. This shouldn’t necessarily result in KPI style goals, but they will have a much easier time realising their goal if the business is already committed to achieving something similar.

Next Month’s Objectives

With the longer vision established, it’s now prudent to move immediately on to concrete actions that can be taken over the next iteration. The time scale could vary, but I will assume a monthly cadence.

The activities identified here should represent objective steps towards achieving the vision. These should be focussed more directly on the individual instead of the business.

Issues and Resolutions

It’s important to provide a safe space for issues to be raised here. These will not likely be critical problems as these should be raised when they become apparent. If you find that these meetings are dominated by serious issues then it’s worth ensuring that the coachee feels comfortable coming to you outside of the protected time. Again, ensure that all of this captured by the coachee.

For a first O3, this is a good start. For subsequent ones, we’ll change it up a little.

Subsequent O3s

Once we’ve established a baseline, we can then refocus our meetings around those initial discussions.

Subsequent O3 Flow

Previous Objectives

We should start off by discussing the previous month’s objectives, there should be a written record kept by the coachee. The coach’s role here is not that of interrogator demanding to know why something was or was not complete, it’s closer to a facilitative sounding board, a non-judgemental guide as the subject is explored.


One of the most long-lasting impressions I retain from those early discussions was the focus on the positive. We see Gratitude based Mindfulness becoming more and more prevalent recently, as research shows that focussing on the positive aspects in ones life leads to a physiological change in brain composition, leaving us with a naturally more positive outlook. The same is true here, by ensuring that we capture at least one thing that someone is proud of, we further solidify the feeling of ‘safe space’, and provide a historical record of the good things to look back on.

Issues with Me

This is more relevant when you are coaching a direct report. It might take some getting used to, but buy encouraging the coachee to discuss issues that they may have with you as a line manger, you can really start to strengthen the trust between you both. The coachee gets to feel comfortable discussing difficult topics, and you get some free and open feedback.

Issues and Resolutions

As with the previous flow.

Long Term Goals

I flip-flop on the placement of this item, for now I’m including it here. This is the opportunity for the coachee to discuss their longer term vision. It’s perfectly natural for us to reframe our view of the future, so make sure to provide some space to discuss this should they require it. The coachee may be satisfied with their current vision, in which case you can safely move on.

Next Months Objectives

As with the initial flow. The coachee may want to include incomplete things from the previous iteration, or move onto something completely different. As always, facilitate their exploration instead of passing judgement.


How often should I do this?

It varies, but aim for once every 2 to 4 weeks.

How long should it take?

As long as it takes, but 15–30 minutes per week is a good rough guide.

Who should I go through this with?

I would strongly suggest that you provide every one of your direct reports with this opportunity.

Can I skip an O3 if I’m busy?

Never. This is protected time devoted to the development of your charge, skipping this meeting could be significant harm to the trust you’ve built. If you do need to cancel, then immediately rearrange for the closest opportunity.

It’s important that you tailor this process to something that works for you and for your relationship with the coachee. Not many things work off the shelf for long.


So there you go, hopefully this can enable you to reflect on your own O3 practices going forward. If you want a template for running these meetings, you can download a free-form mind-map here.

Here are some closing reflections:

The Good

  • Validates and empowers coachee
  • Provides tight feedback
  • Encourages openness
  • Builds trust
  • Builds careers
  • Encourages long-term partnerships

The Bad

  • Extra time in meetings!
  • Lifetimes of misconceptions to break
  • Learning curve for managers
  • Possibly some initial apathy from coachees

The Debatable

  • Heavy focus on employee instead of business

Good luck!