Future of Work

The power of one:ones – asking the big questions of your leaders

Kerry Swan

My husband and I run and operate three separate but integrated businesses employing more than 35 people. Our business growth has happened quickly, in the space of about five years. 

Across our businesses, the single most powerful thing that we do, to support our growth, is to hold regular one-to-ones with our key leadership team members. 

Our one-to-ones have helped us to shape our culture, drive the development of systems and grow revenue, but most importantly, they have helped us to build our people.

In our one-to-ones, we have the opportunity, within a predetermined agenda, to work through what’s happening at a business level, a team level and a personal level with our key leaders. 

The growth of the people around us, means that we can, personally, move away from the operational and technical issues, towards the things that will drive our businesses forward.

Do you have the skills for this?

As a business owner or leader, you are likely highly skilled in your own profession, trade or technical skill set.  

And, you might think that you don’t have the right coaching skills to tackle a deeply personal meeting like this.  Because, after all, what I am talking about is coaching and leading your team, at an individual level.

But humans want to talk about themselves and what they’re working on to make sure they matter.  A well organised, and regular, one-to-one will give your team members the time and the space to open up and orient themselves to the bigger picture.

There will be tough stuff

As you move through this work of a leader, you will come up against some tough stuff with people who might be experiencing mental ill health or deeply traumatic psychological issues.   But remember, you are not a psychologist. And, likely you might not have the skills to fix the big stuff. 

It’s your job, however, to unearth the issue. You can help your team members identify what is holding them back from their full potential. 

This is what a one-to-one is all about  – unearthing the deeper tensions that exist inside your team and your people so that you can help them to realise their full potential. 

Show grace and support to your team members, and help them connect to the relevant mental health professional that can support them through whatever’s going on. Then you can keep your role as a leader separate from their psychological process.

Schedule the important conversations

Schedule regular one-to-ones with each of your key leaders. Choose a regular time, place and timeframe, and put it in your diary. Set up an agenda, and work through it methodically.  The key questions that you’ll be asking your leaders will be:

  • What important work are you doing?
  • What important work have you finished?
  • Why is it important to you?
  • Why is it important to us?
  • What support do you need from me right now?
  • What is keeping you awake at night?

A one-to-one is the most critical leadership interaction that you can have with your team. You’ll need to build the trust slowly and gradually. As the trust between you and your key leader develops, you will go progressively deeper and deeper with them.

You will feel awkward 

As a leader, you might feel uncomfortable getting up close and personal with your team members. Do it slowly because they’ll feel a little awkward as well. 

Think about it from their perspective.  Imagine, the first time your boss asked you ‘what’s keeping you awake at night’?  Likely you would have been suspicious. Go at it gently.

Keep your professional barriers clear. Gradually build trust with your team members and then go deeper. 

The big questions 

In addition to your structured questions, you might also like to use some questions that help to expand your conversation.  Two of my favourites are ‘What did you learn from this experience?’ and ‘I’m curious to know what you think about this.’ 

These gentle questions allow the person to open up without you having to ask them straight out, ‘What’s going on for you?’

You might like to reacquaint yourself with some of the success questions we talked about back in principle 5.


Written by Kerry Swan.
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Kerry Swan
Kerry Swan, the author of Heartfelt Leadership (Publish Central $29.95), is a born-and-bred project manager. With more than 20 years of experience as a self-employed consultant, coach, and teacher, Kerry has worked with hundreds of leaders. These days Kerry works with her husband Craig across their diverse range of family businesses. With interests in real estate, earthmoving, and agribusiness and a team of 35 people, Kerry loves leadership.


Kerry Swan is an opinion columnist for the CEOWORLD magazine. You can follow her on LinkedIn. For more information, visit the author’s website.