Ultimate Guide to Perfect One-on-One Meetings

Our 37 Point Guide Enables Managers To Build A Highly Motivated Team & Team Members To Build Skills, Achieve Goals & Overcome Challenges

This Guide Will Help Managers Build A Highly Motivated Team & Help Employees Show Their Professionalism & Promotability. Together, You Can Achieve Greatness.

Holding a great one-on-one meeting means you will have a highly motivated and energized employee. Repeat the process repeatedly with your employees to have a high-performing team.

The humble “One on One” meeting is actually the cornerstone of high performing teams and organizations.

Why Are One-on-One Meetings Important?

A One-on-One meeting is a way for a manager or team leader to stay connected to a team member and stay aligned with projects and goals. If the team member is struggling to overcome challenges, the manager can assist. It is also an excellent way for the team members to stay connected to their manager to understand their business priorities and decision-making processes. One-on-one sessions are motivational for the employee and important for the supervisor to stay up-to-date.

An average or poor manager will neglect regular one-on-one meetings because they are “too busy” or have more pressing priorities, negatively impacting the team.

If you want to be an average leader of an average team, then ignore One on One meetings at your peril

The often neglected personal one-on-one meeting is important because it enables you to connect on a level with that person you cannot do in a team meeting environment.

Great teams are built from great one-on-ones, then great team meetings, and then proving that you can deliver astounding results as a team.

The Purpose of One-on-One Meetings

The aged business textbooks, business schools, and average managers will tell you that the one-on-one meeting is the best way to chase your employees and ensure they are doing the work they should in the way you want them to do it. But that could not be further from the truth.

The goal of any great leader is to build a strong confident team, who can perform to the highest levels and make great decisions, knowing they have your support

Having a team that performs at its best means you have more time to focus on strategy and future planning, and the team focuses on delivering the results.

10 Benefits of One-on-One Meetings With StaffThe Manager

Whether you are a manager, director, vice president, or CEO of a company, you cannot and should not skip your meetings with your direct staff. If you do, you will miss out on a wealth of information and your opportunity to develop motivated employees and the next generation of leaders.

It all starts with a conversation.

1. The opportunity to speak directly with the employee.

If your only contact with a staff member is on the office floor or in the team meeting, you are missing out on the level of conversation and interaction you need to form a relationship. I am not talking about a deep and meaningful personal relationship; I am talking about a professional relationship with respect for the individual. Some topics cannot and should not be discussed in a multi-person setting.

2. You can connect on a personal level.

Never underestimate the importance of personal connection. You do not need to know what the person ate for breakfast, nor do you want to know how they contracted that sexually transmitted disease; somewhere in between is ideal. Too personal, and everyone thinks you are their best friend; too impersonal, everyone will not feel comfortable with you. Strike the right balance and personal connection, and you can build trust.

Never start a one on one meeting with business, ask them genuinely “how they are and how is the family?”  they are human too.

3. Get a feel for the current conflicts within the team.

Talking in a secure environment allows team members to express whether they are experiencing harassment or negative political infighting within the team. This can enable you to establish plans to start eradicating unprofessional behavior in the group.

4. You can get regular updates on their work.

You should ask for an update on their work but allow them to prioritize what they talk about. The question “What would you like to discuss?” is open-ended enough to allow them to go through their updates. In your mind or on paper, you should know the critical activities they are working on, so if they have not covered them, ensure that you make time at the end of the meeting.

5. You can ask them to take on new challenges.set targets take on new challenges

Rather than force work upon someone in a team meeting, the respectful way is to talk about it one-on-one. You may think a particular employee is the right person with the right skills to take on a new challenge, but they may disagree. They might feel insecure or feel they do not have the right skills or even think someone on the team could do a better job.

6. You can ask them to help other struggling team members.

A great way to foster a winning team is to ask your high achievers to help other team members struggling with a task. It is almost like a mini promotion because the person feels they can help others succeed; it makes them feel needed and highly motivational.

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7. You can iron out conflict in a private setting.

Not everyone stays happy and motivated all the time. Some people are downright miserable unless everything is going their way. One of the most exceptional people I have ever hired is a cantankerous Hungarian from Slovakia. He has a pinpoint intellect and wants to challenge every decision he disagrees with. In fact, that was the reason I hired him; I knew he would test my direction and always provide an alternative view. I knew I was on the right path if I won him over. Sometimes, we agreed to disagree, but if we disagreed strongly, the one-on-one meeting was the place to talk it out and resolve the issue.

8. You get to congratulate them on their successes.Ultimate Guide to Perfect One-on-One Meetings Leadership & Management Guides

Despite the number of times team members have told me of what they have overcome and the goal they have achieved, it never gets old. I love it. The fact I get to hear it from them personally enables me to congratulate them and enjoy their glow. The additional bonus is that I can mention it in the team meetings and congratulate them in a group setting, which is highly motivating for the employee and the team alike.

9. You can help them through any issues they have.

Almost nobody operates at top performance levels all the time. Some of your best people can struggle with specific issues they would never discuss in public, but it all comes out in a one-to-one. I worked with an exceptionally intellectually gifted person at Hewlett-Packard. He was so smart that he had to educate me for a couple of months to understand what he was talking about.

Ultimate Guide to Perfect One-on-One Meetings Leadership & Management Guides

His issue was talking in simple terms to simple people (like me and the rest of the planet). After spending so much time with him in one-on-one meetings, I finally started to understand what he said. This person, let’s call him Stephen, started a movement that led to a transformation in our outsourcing business worth over $300 million in savings, productivity improvement, and innovative thinking. I acted as his translator and management advocate and defended him against senior management detractors, and together, we changed an organization of over 25,000 people.

10. You can coach them to success.

Some people need to know they are on the right track. Coaching is not telling people what to do and how to do it; it is the art of helping people draw their own conclusions and giving them constructive feedback on how to reach that conclusion. Giving people the time and helpful guidance to come to the right conclusion feeds their self-confidence. Also, by helping them during the decision-making and problem-solving process, you instill your personal and professional values in them. Always be respectful and help them get to that decision. Learn more about managing remote teams.

If you do it right, they will follow you and be your supporter. Why?  Because they know you support them, and you want them to be successful.

5 Reasons Why One-on-One Meetings With Your Boss Are Important

As an employee, a “one-on-one session” is vital for many reasons, from personal connection to strategic alignment and guidance.

1. Time with your boss is quality time.

If your manager is a great manager, you will believe that your time with him will help you succeed in your job. Fundamentally, you want to progress and be successful at your work. That gives you meaning in what you do; it even gives you a reason to get out of bed in the morning—apart from the money. If you have a great boss, his job is to help you be great, too.

2. Establish a personal relationship.building a personal relationship with your boss

The best people I have worked for always spent a little time getting to know me. I was never someone to expose my deepest personal secrets, like my stag party in Amsterdam, but I was willing to share my hobbies, interests, and family stories. And frankly, that is enough. Your boss is not interested in the argument you had with your partner; they should be interested in your general well-being. Your manager is not your best friend; they should be a trusted colleague and professional confidant.

3. Direct input from your boss.

If you are struggling with a customer situation or your work colleagues are giving you hell, you should feel free to discuss it with your manager. If you are in a position that requires you to make many decisions and you are unsure of the right direction, you should take your time to walk through the decision-making process with them. It will allow you to see how they think and enable you to make more confident decisions in the future.

4. Demonstrate sound decision-making and work ethic.

demonstrate good decision making with your boss

As you make better decisions in line with your manager’s direction and vision (if they even have a vision), you demonstrate your ability to operate with more independence and empowerment. This means you move away from micro-management or being overly supervised to be a trusted staff member.

Being highly trusted in a team and organization paves the way to creature comforts like working from home a few days a week or even being a backup for your boss when he is on holiday. Being your manager’s stand-in is the first step to promotion.

5. You get to challenge your manager’s decisionsopportunity to challenge decisions

The best place to challenge a decision or direction is in a one-to-one. There is no point in being an aggressive leader of the resistance in a team meeting and being a pussy in a one-to-one. Hammer out your disagreements in private and be positive in a public setting, and you will be moving in the right direction.

Establishing the Perfect One-On-One Meeting

I have literally conducted thousands of one-on-one meetings with the thousands of people I have managed over the 25 years I have been in the corporate world.

Make the one to one meeting about the employee, not about you.

If you want to achieve your goals, every team member needs to achieve their goals. So, it is not about you; it is about them.

How Long Should A One On One Meeting Be?Ultimate Guide to Perfect One-on-One Meetings Leadership & Management Guides

The perfect One on One meeting is 30 minutes. You can extend it if required, especially if there is so much of high importance to discuss. But you have to adhere to the maths. If you have a small team of 20 people and have a weekly one-to-one meeting, 10 hours of your week are gone. If that one-to-one is one hour long, you are spending literally 50% of your time on it; that is too much.

Your default needs to be 30 minutes twice per month. The only exception is struggling employees, who may get 30 minutes weekly for a short duration to help them get back on track.

How Often Should You Have A One On One Meeting?

The regularity of one-on-one meetings should be weekly. If you want to maintain a strong working relationship with your team, one-on-one meetings come in only two formats: Weekly and Bi-Weekly. The duration of the one-on-one sessions depends on the staff member’s experience and challenges.

The experience of the team member.

If the person is new and relatively inexperienced, they may need a more regular one-on-one meeting. It is undoubtedly worth assigning someone a mentor or guardian within the team to help them acclimatize to the work, but they will still gain great value from time spent with you. You may need to conduct weekly one-on-ones with them to ensure they are on the right path.

If the person is highly experienced and a trusted operator, I would suggest a one-on-one every two weeks. You could make it every month, but honestly, that is not regular enough. With a 30-minute one-on-one, you may only speak to someone for 6 hours per year. Even for your best employees, that is not enough.

The challenges the person faces.

When the horse manure hits the fan, and you are lucky enough to have a highly experienced operator on your team to delegate that crisis to, you should think about turning your bi-weekly one-on-one into a weekly one or even more often, as they may need your support.

Low-performing employees require more One-to-ones.

Despite all your efforts, there will always be a few employees who have stopped caring. Despite how much you try to help, coach, and guide, they seem not to respond and not deliver. This is usually because they have their eyes on another prize. A move to another company where the grass is greener, or even they are close to retirement and have stopped caring. When this is the case, sometimes you have to give up the ghost.

If they are young, strongly encourage them to find another job (preferably outside your company). If they are retiring, grant them the dignity they deserve, wish them luck, and even ask them to coach other team members so that you can relieve them of their pressured day-to-day duties. Learn more about managing remote teams.

The One-on-One Meeting Agenda

During my decades of management, I never had a written agenda for the 121 meetings. But over time, it developed into a reasonably stable structure that worked perfectly every time.

  1. A few minutes of Small Talk: Ask them how they are, and be genuine
  2. Ask them for a summary of what they would like to discuss.
  3. Tell them what you would like to discuss.
  4. Jump into the critical issues and provide guidance.
  5. Discuss the most important points and provide guidance.
  6. Note any critical actions for the next one-to-one or announcements for the team meeting.
  7. Closeout and thank them for their work or remind them what they need to do to improve.

What To Ask Your Manager During A One On One?

As an employee, I will give you one critical piece of advice.

Your manager’s time is important, they have 20 other employees like you, so you want to be able to demonstrate your professionalism and respect for their attention.

1. Be Prepared!Ultimate Guide to Perfect One-on-One Meetings Leadership & Management Guides

Prepare for your one-to-one meeting at least 30 minutes in advance, and take the time to have all your questions written down.

If you are truly professional, you will have a notebook or Excel sheet ready to take notes throughout your working week about decisions you need your manager to make or input you require.

2. Provide Clear Updates On Your Actions

You will have a list of short-term actions and yearly goals if you are well organized. Be ready to update your boss on all of your outstanding activities.

2. Be Clear On The Actions You Need Your Manager To Take.

If they need to send an announcement or call to action on your behalf, send them the draft before the meeting and ask them to take action during the meeting.

4. Share Your Successes?

Have a list of the decisions or actions they need to take and the opportunity to share your wins or challenges. Usually, your manager is your manager because they are older, wiser, or have more experience. Use them to improve your performance and help you succeed on your path to a “Great Work Life.”

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5. Share Your Challenges

We all have challenges in business, and hiding them will not help you to achieve your goals, which means you are not helping your manager to achieve her business goals. Be open and honest; you will be appreciated for that.

6. Discuss Your Personal Development Needs.

If you are mindful of your day-to-day work, you will soon realize that you could have handled certain situations better if you had developed certain skills. From negotiating sales contracts to calculating complex equations in Excel, we can all improve.

Think about what skills you would like to develop, find a solution, and pitch it to your manager. Then, all your boss needs to do is say yes.

7. Share Your Career Aspirations

Believe me, if you want to progress in your career, your manager will want to know about it. The measure of a great leader is that they produce great leaders. So, if you have a passion for growing and progressing your career, let your manager know. A good manager will be happy to give you more responsibility and promote your progression through the ranks, providing you have the skills, of course.

Barry D. Moore
Barry's 25 years of experience with Silicon Valley Corporations such as IBM, Compaq, Hewlett Packard, Hewlett Packard Enterprise & DXC Technology enables him to share his knowledge of succeeding in today's professional corporate environments and develop a great work life for yourself.


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