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The Anatomy of a Great One-on-One

In last week's article, I talked about why you need to love one-on-ones.  They really are such a powerful trust and connection building tool with your direct reports.

This week I want to dissect what a great one-on-one looks like.

In my opinion, one-on-one's are really about your direct reports and what they need.  It's not so much about project updates.  Instead, it's their time to get unstuck, ask questions and feel connected to you.  

Is this important?  

It's critical.

Research by Gallup found that the relationship between an employee and their manager determined how long an employee will stay in a company and their level of productivity.  Managers are catalysts. They help speed up employee's skills to meet current business needs.

But not only that, with many employees working remotely, one-on-one's are crucial to helping people feel as though they are still in the loop.

Make sure you attend one-on-ones with the intent to be of service to each of your direct reports.  This way you reduce the interpersonal fear that gets so many people fretting that their boss doesn't like them.  

According to neuroscience, we need three things to feel safe in our environment - safety, connection and future. The Integrated Trust Building System, from the book, Trusted to Thrive: How leaders create connected and accountable teams (get your free chapter here) provides leaders with a helpful framework to run a one-on-one.

Our brain is regularly scanning the external environment to make sure we are safe asking questions subconsciously such as: Is it safe to be myself? Do I belong here? Whats my future with these people?  Can I trust these people to look out for me?  Safety, connection and future are important for our brain to trust.


When these questions are answered affirmatively, it provides employees with the comfort they need to contribute and create rather than withdraw and self-protect.

If people dont subconsciously receive these assurances from their team leader (or each other), they hold back opinions, information and working with others.  Behaviours their limbic brain feels will keep them safe.  They stay invisible, procrastinate and feel unworthy.

A great one-on-one ensures people feel safe, connected and that they have a meaningful future in the company.  They feel that they are part of something bigger than themselves. Let's go through how to do this.

1. Pre-Work

As Abraham Lincoln once said If I only had an hour to chop down a tree, I would spend the first 45 minutes sharpening my axe.” 

Before you jump into doing one-on-ones, you want to do a little bit of preparation beforehand to set you and your direct report up for success  Creating a one-on-one routine will save you both valuable time and ensure your discussions are focused on the right things.

This involves consulting with your direct report on the nuts and bolts of your regular get togethers.  This is important as you want to co-create your one-on-ones with each individual on your team to get their maximum buy-in.  

Start with:

  • The importance of regular one-on-ones.  Explain the reasons for why you want to do one-on-ones.  Sometimes people resist one-on-one's due to poor past experiences.  Clearly outlining why you are doing them and discussing mutual expectations will pave the way to making them beneficial to both of you.
  • Decide how frequently to do a one-on-one.  Typically, best practice for one-on-ones is weekly.  But it really does depend on the context - how closely you work together, how fast projects are moving, team size, and availability.  A good rule of thumb is to have them weekly with new starters and then move to fortnightly once you get comfortable with one another and there are no surprises in performance or job tasks.  Either way, you want to mutually agree on the cadence.
  • Scheduling a regular time on the calendar. Ideally, you both get out your calendars and block out your one-on-one meetings in advance.  Choosing the same day and time where you know you won't be distracted  Allot the right amount of time - 30 minutes for weekly meetings or an hour every other week.  Make this time sacrosanct, so that you both know that cancelling or rescheduling is only done in emergencies.  I've seen a lot of managers unnecessarily create distrust because they cancel too frequently (a telltale sign of under-management).  Of course, if you both agree that you have nothing to talk about, then it's okay to cancel.  Just make sure you focus on rescheduling, so they still feel valued.  And whatever, you do, don't make cancelling a habit.
  • Create an agenda in advance.  If you want to get buy-in with your direct report you want to co-create the agenda together.  It only needs to be modified if circumstances change - such as they've been promoted, on a new project or it needs to centre around a difficult conversation.  Create a master digital document that you can use as your guide to create agendas for all of the individuals on your team.  Then, create a copy for each individual and make it their responsibility to update/customise their agenda.  While the majority of the content will remain the same, put the onus on them to add 3-5 new questions they want to ask you each week.  You can also add your questions to the online document.  An example of an agenda is:
    • Check in. Ideally, this is a friendly chat to build rapport.  Ask questions on life outside of work.  Get them to share personal updates on hobbies or their family.  And make sure you share as well.  This is a chance to be vulnerable and authentic. (5 minutes)
    • Employee feedback.  Employee discusses where they're at and asks questions to unblock performance. (10 minutes) 
    • Manager feedback.  Where you find out what you need to know and create alignment.  This includes updates, what they have learnt, what's working or not and how you can lead them better. (10 minutes)
    • Wrap up (5 minutes)
  • Write notes.  Choose your preferred format to write notes about your regular conversations.  Best practice is online - because you can refer to your notes anywhere.  But for those of you who love writing in journals, you might want to get a different coloured writing book for each direct report.  Don't omit writing notes as it visibly sends a powerful message that you care about your direct report's progress and wellbeing.

Running the One-on-One

Once the personal preamble is done, empower your employee to lead.  

Below are some questions that work towards forming a closer bond with your direct report.  I recommend choosing 2-3 questions under each sub-heading which you can use in the Manager feedback section of the agenda.  And here are tips for asking questions.

1. Foster Safety

Creating safety involves reducing people's innate fear of interpersonal risk.  Start by asking questions that show that you value them as a human being who has a life outside of work.  Then, go into questions that foster learning and demonstrate you support them.  Some good questions include:

  1. How is life outside work?
  2. How are you feeling?
  3. What has been the highlight and lowlight of your past week?

2. Create Connection

Creating connection in a workplace is a multi-faceted process that is a bit like a jigsaw puzzle.  Your role is to help connect the dots for people.”  Its not just about connecting people to people, but also explaining how all of the different parts fit together within the broader landscape.  From projects, products, platforms, priorities right through to all of the people that make everything happen.  This works towards providing shared consciousness - a quality of high performing teams.  It requires linking people to how their work impacts others - both within and outside of your team.

  1. What are you doing to ensure your work is making an impact for clients?
  2. What is the most meaningful part of your job?
  3. How do you feel about the progress you are making on your goals?  Are you on track? Are there any blockers I can help with?

3. Stepping into a Meaningful Future

In a workplace, feeling that there is some sort of future for us is important for our productivity and wellbeing.  To perform at our best, we need to know that we have a meaningful future in our organisation.

And it's on two different levels. The first one is clarity on the big vision for the organisation and where the leader plans to take the organisation. While the second is how each person fits into that and what capabilities are required.

One-on-one meetings are a great opportunity to ensure employees feel more comfortable talking to you about their career.  Use them to discuss career development and to ask how they are going with the company's vision.  Questions to use include:

  1. What do you think of this goal we’re pursuing? What’s the best way to meet it? What are your top three priorities in helping us get there?'
  2. Here’s where I see you going as an individual with the new vision.  Where do you feel your skills match?  Which skills or behaviours you feel you need to strengthen?”
  3. What questions do you have about the future operating plan?  Do you have any concerns?

Wrap-Up and Next Steps

Finish the meeting by reiterating the key takeaways from the discussion and the 2-3 actions you will both work on.  And make sure you follow up and take action.  Anything less and it will quickly break trust.

A great one-on-one ensures people feel safe, connected and that they have a meaningful future in the company. 

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