How To Have More Effective 1-On-1 Employee Coaching Sessions

One of the cornerstones of the work I do with managers, is helping them improve their relationships with the folks they manage. Key to that success is 1-on-1 employee coaching sessions.

To be clear, we aren’t talking status updates where you are being filled in on their workload and progress. I mean intentional and purposeful times where the conversation rises above their to-do list.

In order to have more effective 1-on-1s, there are a few parameters that are helpful for managers to know and abide by. It helps first to differentiate between 1-on-1 employee coaching and group coaching wherein you might be meeting with your whole team to give insights and guidance around performance and department success.

What is 1-on-1 coaching?

Simply defined, when you are meeting with one employee with the goal of sharing insights and feedback to help improve their performance, we’d call that 1-on-1 coaching.

Whether you are doing this in on-the-spot micro-moments or a sit-down scheduled meeting, the goal of 1-on-1 coaching doesn’t change. Coaching is the approach a good manager takes to help improve the skills and abilities of the people on their team.

Can a team exist without coaching? Sure, in the same way a professional sports team could. Players could play the game, but without a coach, the plays and execution at some point would break down.

There’s a difference between being in a 1-on-1 setting than being in a group setting, and certainly a time and a place for each. In a group, you can discuss general process changes or broad performance improvements and you still have the opportunity for the group as a whole to improve. In a 1-on-1 session, a manager can get more specific and more personal with the employee at hand.  

What constitutes successful 1-on-1 coaching?

Success in coaching an employee isn’t as obvious as turning on a light switch. Off one minute then shining brightly the next. Success is more subtle and individual than that. To help determine when coaching has been successful, a manager can use a few gauges – ones where an employee shows, knows and grows as a result of the coaching conversation:

Outward signs of improvement

This is when an employee SHOWS a shift in their behaviors. We can observe that a change has happened, and the employee has taken steps to show up in a more productive way. For example, if an employee is coached about their tendency to show up late to important meetings, an outward sign of improvement would be arriving on-time (or early!) for the foreseeable future.

Internalization of topics discussed

This is when an employee KNOWS more about the skills or situation around which they have been coached. Their level of knowledge has increased, and they are better equipped to communicate, collaborate, and deliver in their jobs. For example, if an employee is coached about being more self-aware, an internalization of that management training topic might mean they are more reflective about their words and actions and think differently about how they act and impact others at work.

Growth in their job and career

This is when an employee GROWS because of the coaching they’ve received. It’s one thing to shift your behavior because you’ve been coaching is entirely another thing if you use the advice to grow in your career. For example, if an employee is coached about being a better listener because their co-workers didn’t feel heard, growth in their job and career stems from taking this advice and making listening a top focus by practicing it, role-modeling it, teaching the skill to others and really immersing themselves into that skill with the goal of long-term effectiveness (vs. short-term improvement).

Strategies for successful coaching

Good coaching requires a few ingredients: planning, timing and accountability. When rushed to solve a problem or stop an unproductive behavior, a lot of managers miss these three steps in the speed of the moment. Being intentional about your approach as a manager who does well with 1-on1-coaching sessions is the key for success.

It takes a plan.

Planning for a 1-on-1 coaching session doesn’t have to be difficult or time-intensive. It may just mean you are armed with a few prepared questions to ask. It may mean you take 5 minutes to think through the situation and possible outcomes. Think of planning like a speed bump in the road, designed to slow you down in a meaningful way vs. stopping you in your tracks.

When I coach managers on how to have more successful 1-on-1 coaching sessions, I have them start with drafting out a 3-question plan for the conversation.

First, what exactly is going on? It’s so important to put thought into why you need to coach them in the first place.

Did they do or say something inappropriate? Is there a skill that is lacking or needs improvement? Are their teammates who are getting along? By being very clear on the topic of the coaching conversation, it sets the tone for how the rest of the talk might go. Without clarity, the potential of misunderstanding, or digression runs high.

Second, think about the impact of the behavior or situation you are looking to rectify. What is the impact and who else / what else is it affecting?

For example, an employee who is habitually late may not fully understand the impact their behavior has on the rest of the team. Being late all the time means their co-workers start to feel let down by the lack of respect for everyone’s time, they may feel frustrated because important meetings start late or need to be rescheduled, and trust between the employee and their teammates may slowly start to erode.

There is a larger impact on the team as a whole that the late employee might not consider.

Last, as part of having a plan for a more effective 1-on-1 coaching session, think about the ideal outcome. After having this conversation, what outcome would you like to see?

Of course, we want the situation or behavior to improve but on the whole, we need the employee to buy into the solution. Mandating a change doesn’t mean it will happen without the person feeling like they’ve been a part of crafting the solution.

Going back to our tardy friend, we may ask a question aimed at getting buy-in that sounds like, “What is something on your end that you can do or shift to allow you to arrive on time?”

The employee may have details about their home life that impact their ability to get to work on time that a manager isn’t aware of. This is where discussion, flexibility and a bit of compromise might need to happen in order to improve the situation.

It requires right timing.

Not every moment is a coaching moment and a good manager knows that the timing of a 1-on-1 coaching conversation is key to its success.

Is walking into an important client meeting the right time to coach your employee on their presentation skills? Probably not. Is riding up on the elevator to your floor the right time to coach on being a team player? Maybe, maybe not.

There aren’t hard and fast rules on timing and location YET timing must be considered. Put some thought into where and when you’ll be having a coaching conversation. Is it private? Is it quiet? Is it appropriate? 

A client of mine shared a story that his boss called from their car on a Saturday to deliver an annual performance review while saying they had just about 10 minutes until they had to run into the store. Yikes!

Timing is crucial because the digestion and understanding of your words can only happen if the person is ready and willing to receive your coaching. Anxiety, noise, or wrong timing don’t help.

It requires a level of accountability.

Imagine coaching like a pitcher throwing a baseball, if there isn’t a catcher on the other end, it doesn’t really do any good for the game. Coaching your employees is only part of it, accountability and helping them say on a course for improvement is the other half.  

Being accountable means the manager has set the expectation for the improved performance and together, the manager and employee, have agreed to how things will operate moving forward and, also together, they monitor the improved behavior until its resolved. 

Without accountability, an employee might not have the guidance to stay on the right path of improvement. A good 1-on-1 coaching session gives accountability an important place in the conversation.

Steps to take in 1-on-1 coaching

Once planning, timing and accountability have been thought through, a manager is now ready to step into the 1-on-1 coaching conversation. The steps to take in the conversation don’t have to be complex and really are designed to help keep the conversation on track.

>  Step 1: Have a gentle lead-in to set the tone for the conversation. My go-to is, “My goal is to coach you to your best self. In order to do that, I’d like to talk about ________.”

>  Step 2: Have questions at the ready. The goal is to involve the employee in the conversation, especially with the goal of learning more. Questions like, “Tell me your thoughts on what happened yesterday,” or “What is your view on how things are going with ________?”

>  Step 3: Tune into the conversation dynamic. A lot of what’s said in a coaching conversation may be non-verbal. Pay attention to body language, especially if the employee starts to shut down, gets quiet or closes off. I keep a few questions as the ready if I sense shut down, like, “You look like you have something to say, what are you thinking?” or “What are your thoughts on what we’ve been discussing so far?”

>  Step 4: Remember the human in front of you. At the end of the day, a 1-on1- coaching session is designed to build an employee up and grow them into a better and more effective person. Have compassion and empathy for their feelings and what might be hard for them to hear.

>  Step 5: Make a plan to follow-up. No one likes to be ghosted. If the conversation is important enough to have in the first place, it’s important enough to keep it on your radar. Decide in the conversation when and how the two of you will follow up – on what day, with what action to happen in the meantime and so on.

Sample questions to ask during 1-on-1 coaching sessions

The quality of any coaching conversation can be determined by the quality of the questions managers ask during them. The goal is to go beyond the obvious or irrelevant and have conversations that build relationships, trust and communication and we can do that by having a list of good questions in hand.

Here are a few samples you can try in your next 1-on-1:

  • Question 1 : What is the number one challenge for you here?

  • Question 2 : What have you tried already to solve this?

  • Question 3 : How else might you look at this situation?

  • Question 4 : What of this situation or challenge is yours to own?

  • Question 5 : What needs to happen for this issue to be resolved for you?

The final takeaway on effective 1-on-1 coaching sessions

As good managers, there is a responsibility to develop employees to their best ability -  development that is often contingent on effective 1-on-1 coaching sessions. But we all know that workload, clients, and deadlines get in the way of even the best intentions when it comes to having the time and focus to coach individual employees. This is where the importance of structured training of managers becomes evident.

Teaching managers the importance of regular, authentic, intentional 1-on-1s is an integral lesson in Manager Boot Camp, our virtual leadership training and In-Person Training course for managers. It’s not enough to say these 1-on-1s are important then never give managers training or tools to conduct them.

In our online course, we give managers specific conversation lead-ins to initiate a leadership coaching conversation, we teach them how and why feedback conversations typically go awry and what to do about it, plus we provide a list of coaching questions to use in future 1-on-1s.

Through the lessons and advice shared above, access to our Manager Boot Camp course, and the efforts of every manager to deliver quality 1-on-1s, all employees have an opportunity to learn, grow and fulfill their greater potential.




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About The Author

For the past two decades, Cecilia Gorman has helped advertising agencies and other creatively-minded companies fix costly communication and productivity issues by teaching managers how to become better connectors, motivators, and leaders. Cecilia is the author of Always Believe In Better, creator of the digital learning course for managers—Manager Boot Camp, and co-founder of the global training and support community for working women—Empowership.

Interested in growing your skills as a manager? Check out how Manager Boot Camp might help.

Cecilia Gorman2022Comment