With the right mindsets, soft skills and practical top tips you can turn them into valuable and collaborative sessions with immense impact.

I vividly remember my first one-on-one meeting with my boss at my first job. He opened up the meeting saying, “Mark, I think you have an attitude problem?” 

He was right by the way as I hated my job and I have never been very good at faking it! 

So I replied with a little bit of attitude, “So, have you got any examples of my attitude problem?”

Silence. He looked upwards, I think looking for inspiration and then what felt like an inordinate long time he came back with, “No, I can’t think of any examples.”

That was a useful conversation, not!

As a result for years I thought one-on-ones were a waste of time. It wasn’t until I experienced a really good one that I changed my mind. And now I am a big believer. As Adam Horowitz said in his book, The Hard Things About Hard Things, “people who think one-on-ones are a bad idea have been victims of poorly designed ones.”

In my first essay on one-on-ones I set out 9 benefits of having them.

In this essay, my second on the topic, I am going to dig into:

  1. The how:
    1. 11 key types of mindsets
    2. 3 soft skills 
  2. The what – 11 practical tips of running exceptional one-on-ones.

So let’s begin by looking at the mindsets that will make your one-on-one most effective. 

The How

11 key mindsets you should have in a one-on-one

When I coach founders on running successful one-on-ones I ask them to think about the coaching sessions I have with them and get them to replicate the mindset I bring into (or I try to!) each coaching session. 

There is little point in having a one-on-one unless as the leader you have the right mindset to make these coaching conversations meaningful and effective.

Here is a list of mindsets to help you have effective one-on-ones:

  1. Build rapport from beginning to end but like with any mindset you can overplay it. It shouldn’t stop you from having the tricky and crucial conversations
  2. Listening mode, full attention, no distractions
  3. Stay curious for longer, don’t jump in to fix the problem. Do not think that you must solve everyone’s problems for them. 
  4. Be supportive in the sense ‘I’ve got your back’ 
  5. Belief and respect. As a coach I must believe in the person I’m coaching and you must do the same with your team member. If you don’t find a way to respect them, it will seep out and adversely affect the meetings
  6. Non-judgemental. If you are going to sit there and judge your colleague they will soon stop opening up and start getting defensive, preventing any learning from taking place
  7. Empathic and holistic. Be sensitive to others’ feelings and comfortable talking about personal issues as well as professional challenges. I don’t think you can or should separate the personal and the professional
  8. Challenge your team member in the sense you believe open and honest feedback is necessary to help someone get better and that you really want them to succeed
  9. It is not just a cozy chat, it is very much results-orientated for the individual as well as the company as a whole
  10. Be their Thinking Partner to encourage them to do their best thinking. Questions are more powerful than answers
  11. Hold them to account and be their Accountability Partner 

Reading this list, you may think this is too much to think about. My advice is to practise one new mindset, one new habit at a time. 

3 soft skills you need to develop to have exceptional one-on-ones

Developing the right mindsets for one-on-ones is critical but you also need to have the skills to deliver on them. Here are three key soft skills you will need to learn in order to run exceptional one-on-ones.


Coaching helps someone bridge the gap between where they are today and where they would like to be without you telling them how to get there.

One-on-ones are more productive when leaders are coach-like and give support and guidance rather than instructions. 

A leader who is a skilled coach:

  • Helps their colleague define an ill-defined problem
  • Is aware enough to know when they don’t need to provide the answers
  • Can offer more value by asking the right questions,, listening attentively and supporting the team member to work out the best solution
  • Facilitates their development rather than dictating what needs to be done.

A leader who has mastered the art of coaching will impart knowledge as well as help their direct reports discover it for themselves. He or she will skillfully dance between the two. For example, when your team member is low in Task Relevant Maturity – i.e. not very experienced in their role – you may need to increase the level of imparted knowledge, and frequency of 1:1s.

Many leaders are put off by the thought of coaching because they tell themselves they don’t have time to coach others. But in many cases although it may take more time in the short term to coach a direct report, over the medium to long-term it will save you time as you empower and energise your colleague to solve their own problems and learn for themselves.

People don’t like being told what to do and telling people what to do very rarely results in sustained change.


Despite the fact that leaders spend up to 80% of their day listening, only 2% of them are trained to listen effectively according to Oscar Trimboli, the listening guru.

When was the last time someone actually listened to what you were saying? Paid you full attention, asked some open questions which helped clarify your thinking? For most people, it’s not anytime recently unless of course you have had a coaching session with me!! 

The benefits of great listening are profound – it helps you do your best thinking, to feel respected, to feel cared for. Great listening allows you to go faster as it reduces the need to repeat the conversation; it reduces the number of misunderstandings and mistakes. Great listening is key to creating powerful connections. Listening makes you feel special. It empowers you to go out there and be your best self.

Stay curious for longer

The goal in a one-on-one is not to be the smartest person in the room but to be the most curious. To empower your team member to talk about what is bothering them and to do the thinking and learning.

As Peter Drucker, the management guru, said the best leaders do not talk about their problems to their direct reports, they know how to get their team members to talk about theirs. And probably the best question to achieve that is simply, “What else?”. Ask the question and then shut up.

If your direct reports get into the habit of coming to you with their problems, they stop thinking for themselves leading to disempowerment and disengagement. And it leads to you getting overwhelmed as your days are filled with solving everyone else’s problems.

As Michael Bungay Stanier eloquently writes in his book The Advice Trap you need to tame your advice monster and change the way you lead forever.

The What

7 practical tips on how to run exceptional one-on-ones

We will now dig into the practical tips on how to make the most of these meetings.

  1. Who to have one-on-ones with?

At the start up phase you might be able to have one-on-ones with your whole team but once your team gets to 10 or more you should keep your number of direct reports to less than 10 and ideally to 5 or less.

As the CEO, the obvious one-on-one candidates will be your fellow c-suite team members but there may be others outside the c-suite who have a significant impact on the company and who would benefit materially from one-on-ones with you. 

  1. How often do you have one-on-ones?

I think it depends on a few factors. How experienced your team member is or as Andy Grove calls it their level of Task Relevant Maturity (“TRM”) i.e. in general the less experienced they are the more frequently you should have them. Maybe every week for someone with low TRM and every 2-4 weeks with someone with high TRM. 

Other factors to consider include the pace of change within your company e.g. more frequent meetings may be required in times of rapid change.

However regularly you decide to have them, make sure they are in the diary and everyone knows these meetings cannot be moved. It should be a recurring meeting. It is really vitally important that you do not cancel your one-on-ones. If you do, your team member will think you do not really care about them and the relationship. You want to demonstrate that this time with them is important.

  1. How long should one-on-ones be?

To some degree this will depend on the frequency of the meetings but I think to do it properly they should be an hour as a minimum. The important thing is that the direct report should feel they have enough time to raise tricky topics. If you only had 15-30 minutes this might restrict the conversation to more mundane matters which can be handled quickly.

  1. Where should one-on-ones take place?

Should it be in your office or your team member’s office? Ideally it should be in neither and in a third place where both of you feel comfortable and will not be distracted. If that is not possible it should not be in the leader’s office as it may feel too much like a normal meeting and not a safe place to open up.

  1. Who should prepare the agenda for your one-on-one?

If you have 10 direct reports (too many in my opinion) then it is unsustainable that you, the leader, should prepare the agenda for each meeting. But even if you have a more manageable amount of direct reports, a key point for a one-on-one is that it is your team member’s meeting.

Your team member should prepare an outline and share the agenda with you beforehand. This will give you the opportunity to give some input into the agenda. You do not want to take over the agenda but you do want to make sure topics are not missed off. Maybe you heard something mentioned earlier in the week by your direct report which you thought might be a good topic to talk about but has been left off the agenda. 

Also having the agenda set out beforehand gives you the opportunity to prep some questions, to get in the right mindset and read any material or information which has been sent along with the agenda. 

  1. What should be on the agenda of your one-on-one?

There is no one right list of agenda items to include in a one-on-one. Each one-on-one will have its own unique way of working. 

One framework that works is:

  • 50% direct report’s agenda
  • 15% your agenda
  • 15% how they are doing
  • 20% on their development plan

Be conscious of how much time you, the leader, is speaking. Anything more than 20% of the time and you are probably talking too much. Ideally you want your direct report to be talking 80% of the time.

Here are some suggested topics to talk about. You do not have to cover all areas in each meeting and you should experiment with what topic areas to include/exclude. Maybe plan out the topics you want to discuss over a quarter or 6/12 month period.

10 key areas:

  1. Things that have gone well. I believe every meeting should start and end with a positive reflection. It helps bring the person into the room and get their mindset in a creative and calm mode. It’s also an opportunity to identify your direct reports’ strengths and talents and to develop roles which play to their strengths. Questions you might ask: “In the past week, what have you been happy about?” or “What has gone well?” or “What has your team done well?”
  2. Top of your mind. This may be related to the main agenda topics but it might not. It is worth asking more than one question on this as you may uncover something impactful which may change the agenda – that’s ok. Questions you may ask: “What’s on your mind?” or “What’s been dominating your thoughts this week?” or “How are you feeling?”
  3. Follow up from the previous meeting. One of my clients always asks these two questions at the end of each one-on-one and then checks in with the follow-up in the next session. Remember one-on-ones are not therapy sessions they are productive, action-orientated conversations:
    1. “What can I hold you accountable for next time we talk?”
    2. “What can I be accountable to you for the next time we talk?”
  4. Learning. Progress is key for everyone. Use your meetings to identify what your team member wants to learn. A check-in on the recent learnings is a good way for both of you to reflect on the level of progress being achieved. Questions you might ask: “What is the most impactful thing you have learnt this week?” or “What can I and or the company do to help accelerate your growth and learning?”
  5. Priorities and goals. The temptation may be to only focus on the immediate goals. It is important to have your direct report’s short-term goals as well as their long-term goals front of mind. Questions you might ask: “Is there anything blocking you from getting your work done?” or “What does success look like in the next month/quarter?” or “What is one thing we could do today to help you with your long-term goals?”
  6. Challenges and concerns. You want to make sure in your one-on-one you don’t neglect the personal. You want to encourage your direct report to reflect on their work and life challenges. You want to try and identify the root cause of any issues and to refrain from jumping in to solve the symptom. You want to tease out issues early. Question you might ask: “What do you enjoy most about working here? What’s not fun about working here?”  or “What would make you leave this job for another?” or “How do you feel your energy levels are right now: strong and motivated, ok, or feeling run down or burnt out?
  7. Team performance and dynamics. You want to hear about how well the direct report’s team is performing and how effectively they are working together. Questions you may ask: “Who on your team is performing really well? What have they done? What is one way we can improve your team’s operations? Is anyone on your team not pulling their weight?” or “Who on the team do you have most difficulty working with? Why?”
  8. Giving and receiving feedback. The one-on-one is a perfect place to give each other feedback to help both parties improve their performance. Questions you may ask: “Can I give you some feedback on X (a performance issue you’ve noticed)?” or “Can you give some feedback on my management style specifically related to my listening skills?”
  9. Career development. The number one perk (according to research from Gallup, Deloitte and Google) is career growth. And when people are looking for new job opportunities, career advancement is number one priority according to PwC research. Questions you might ask: “What do you think are the key skills for your role? How would you rate yourself for each of them?” or “What skills would you like to work on right now?” or “What do you want to be doing in one year, 5 years or 10 years?” or “What do you want to be doing at the pinnacle of your career?”
  10. Company and cultural improvement. One surprising benefit of your one-on-ones is their flexibility and it can be a great time to talk about how to improve your company and/or culture. In a relaxed, safe environment of a one-on-one you may get priceless insights into what’s working and what isn’t and how to make things better. Questions you might ask: “What’s the company not doing today that we should do better to compete in the market?” or “Which company values do you relate to the most? Which the least? And why?”

The end of the meeting should end with time for reflection. I like to use the 4 L’s retrospective – what did you like, what did you learn, what did it lack and what did you long for. 

And right at the end, as you began, end on note of positivity. A note of appreciation and gratitude is sufficient. “I appreciate and value what you’re doing.”

7. What documentation should you use in your one-on-ones?

It is critical that you create momentum with your one-on-ones and that there is continuity from one meeting to the next. Isolated conversations will be much less effective and you will waste a lot of time reminding yourselves of previous conversations. 

I recommend you have a shared document where the agendas, the meeting notes and action points are kept up to date. Consistent documentation has many benefits:

  • Easier to track follow-up items
  • Helps show progress over time
  • Demonstrates to the direct report they are being heard
  • Creates a record of performance successes and issues
  • Makes the annual performance review more meaningful as you have a record of actual examples over time rather than relying on fading memories

The meeting notes should include feedback given and received, the content of any learning, coaching or development plan progress, positive recognition and celebration.

Another advantage of having an accessible shared document is that in-between sessions you can easily add things to the agenda that you would like to discuss in the meeting rather than in the heat of the moment. 

During the session both parties should take notes although not to such a degree that adversely affects the free flow of conversation. 

Mastering the one-on-one is essential

You may say to yourself you don’t have time or we are all adults who can handle their own problems.

You might think that one-on-ones are something to check off, a waste of time or an unforgettable experience. 

The chances are if that is the case you are not running them effectively. It is up to you, the leader, to make them work. 

There are many demands on your time. As a scale up leader investing in your people is one of if not the key priority for you. And one-on-ones should be a key part of your ‘investment in people’ tool box.

One-on-ones are the opportunity to create a happy motivated team. To have conversations you never get round to. To make your team members feel heard.

They are an opportunity to create a bond of trust which makes for honest and open communication and meaningful collaboration. 

It is never too late to get started. As the Chinese proverb says:

“The best time to plant a tree is 20 years ago. The second best time is today.”

Do you need help improving the effectiveness of your one-on-ones? Reach out and let’s discuss how we can help you.

Mark Farrer-Brown
Founder and CEO Coach, Entrepreneur, Business Builder and Angel Investor

Mark Farrer-Brown

Mark is known for his scale up expertise having been part of multiple successful exits over the last 25 years as a founder, business builder, coach, mentor and investor.

Follow Mark on LinkedIn.

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