How to Lead Effective One-on-One Meetings

Jul 8, 2022 | Listen

How to Lead Effective One-on-One Meetings

Simon Sinek said it best: “Happy employees ensure happy customers. And happy customers ensure happy shareholders – in that order.”

Your employees are vital to the success of your growing business – especially when they are happy and productive.

And while there are tons of project management, chat, and time-tracking tools out there to help increase team productivity, these tools can’t do it alone. They need your help so your in-office and remote teams stay happy and productive in these challenging times.

One of the best ways to boost productivity is to hold regular one-on-one meetings with your employees.

You not only establish clear communications, but it’s an almost effort-free opportunity to improve internal processes, give corrections constructively, and connect with your employees with compassion.

So how do you structure one-on-meetings that don’t waste time and focus on feedback, performance, and personal connection?

In this episode of Help! My Business Is Growing, our guest Debbie Rosemont talks about one-on-one meetings and how they boost team productivity and your company’s success.

She shares practical and actionable tips on how you can structure them to ensure maximum productivity to benefit your growing business.

Timestamps for this week’s episode

  • 03:22 What do businesses struggle with the most regarding the productivity of their teams?

  • 11:09 Structuring productive one-on-one meetings with your team members.

  • 24:07 Easing the transition to regular, structured one-on-one meetings.

  • 31:01 Structuring one-on-one sessions with a large team.

  • 33:58 What is one actionable step business owners can take this week to get closer to implementing efficient and productive one-to-one meetings with their employees

What do businesses struggle with the most regarding the productivity of their teams?

The struggle many businesses face regarding team/employee productivity is not having measurable goals or objectives in place.

They don’t know what they’re working towards, what they want, to measure or what “done” looks like.

Productivity is achieving desired results, either as an individual or a team.

But you can’t measure your team’s productivity or if they are getting results if you have not clearly defined your objectives.

And, of course, hitting them is impossible if your team is not fully aware or has not been informed of what the company hopes to achieve.

The definition of productivity is achieving desired results. Whether we're talking about an individual or a team, we're productive when we're achieving desired results.

Structuring productive one-on-one meetings with your team members

  • Ensuring that there’s an objective that you’re working towards during the one-to-one.

Some examples include:

  • Build trust and strengthen relationships
  • Check their progress on the road to hitting their goals
  • Get employee input
  • Give feedback and constructive corrections

  • Determine how often you need to connect one-to-one.

Do you need a 30-minute or 1-hour weekly or monthly session? Even a 30-minute weekly meeting can be really effective if done correctly. Decide on what you feel is the right amount of time you need to focus on one person’s performance and experiences with the company.

  • Set an agenda
  • Having a meeting agenda is essential to be able to hit all the objectives you want.
  • You and your employee must also agree on the plan to guarantee a productive meeting.
  • Stick to the schedule as much as possible.
  • Stay open and flexible, allowing for the human element and natural conversation.
  • Set boundaries e.g. we won’t go longer than a half-hour in respect for everyone’s time or schedule another meeting if we find stumble into anything totally off the plan that we need to discuss

  • Suggested one-to-one meeting questions
  • To foster connections, build relationships, and get to know your employees, a great way to start a one-to-one is to invite them to share information. These can include
  • What’s a win since we last met?
  • What’s been the biggest challenge for you in the last week / where are you struggling – both off and at work?
  • What can I do to help you overcome this challenge?
  • Please give me a quick update on the three priorities we talked about last time, and where are you at?
  • Is there any place that you’re stuck in moving things forward?
  • Do you have any worries or concerns about meeting the objectives?

You can also include fun, icebreaker-type questions to get to know or understand them better, like: “If you were an animal, what animal would you be?”

A winning structure is:

Start with something positive or a win, then move on to the meat, give them constructive criticism or help them overcome challenges, and finally end with something light and cheerful.

“There are things that aren’t going to be appropriate for workplace conversation. Just because you’re behind a closed door, it doesn’t mean you can bring up things that you wouldn’t bring up if somebody else were in the room.” – Debbie Rosemont

Easing the transition to regular, structured one-on-one meetings

  • Discuss what your reasons are for making this shift.
  • Highlight your employees’ benefits from the regular, structured, one-to-one meeting. (e.g., increasing productivity, better feedback system, saving time).
  • Give advanced notice, don’t surprise them.
  • Consider making incremental changes instead of one significant change.
  • Put an agenda in place but still have some flexibility.
Structure and rigidity are two different things. Structure can help provide guidance and keep everybody on track. Rigidity is helpful when you need things to go a certain way and timeline to get an expected result. But it's not for building relationships.

Structuring one-on-one sessions with a large team

When your company’s workforce complement expands, holding one-to-one meetings might be very difficult for you.

You can then look at your employees and group them into logical teams. For example, they are all in the same department or do the same thing in various other departments across the organization.

Assign a team leader for each team. So, for example, if you have 50 employees broken down into groups of 10 employees per team, you’ll have 5 team leads, and you can meet with these leads.

“Consider each individual team member’s role, and come up with a couple of questions to ask in a one-on-one to get at that individual’s productivity, because that’s going to impact (overall) team productivity.” – Debbie Rosemont

Actionable Step

If you are struggling with team productivity and don’t hold one-to-one meetings, a practical, actionable tip is to start implementing them and set a short plan for your 1st sessions.

If you are already holding one-on-one meetings, something you can do in the next week is to consider each team member’s role in your organization and come up with a couple of questions you could ask in a one-on-one regarding productivity.


  • Not having measurable goals or objectives in place – or not informing employees about them is one of the biggest challenges businesses face regarding team productivity.
  • A successful one-to-one meeting structure includes: setting a meeting objective, deciding how often you’ll meet, setting an agenda, and asking a mix of fun, light icebreaker-type questions with informative inquiries about how your employee is doing and their wins and challenges, and more.
  • Help your employees by keeping the transition from not holding one-to-one meetings to suddenly having regular, structured one-to-one sessions by highlighting its benefits.
  • Holding one-to-one meetings when your company is growing and you have more employees is still possible by grouping employees into teams and assigning a team leader for each team. You can have one-to-one sessions with team leads to get a pulse of the employees they handle.
  • Start holding efficient and productive one-to-one meetings by going ahead to schedule them. Inform them early and prepare a short agenda for your 1st sessions. Think about each employee’s role and foster clear communication by asking them how they are doing and how you can help them succeed.


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About guest – Debbie Rosemont

Productivity Consultant, Trainer, and Founder

Simply Placed

Debbie is a sought-after Productivity Consultant, trainer, and the founder/CEO of Simply Placed, helping busy women who feel overwhelmed and overloaded prioritize what matters, plan their time, and produce valuable results with confidence and ease.

Debbie also helps clients implement strategies to work smarter, not harder, through her group It’s About Time – Virtual Productivity Program and her highly customized individual Six-Month Productivity Transformation package.

She is also the author of “Six-Word Lessons to Be More Productive” and co-author of “1 Habit for a Thriving Home Office”.

Website –

LinkedIn –

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Six-Word Lessons to Be More Productive by Debbie Rosemont

1 Habit for a Thriving Home Office by Debbie Rosemont and Steven Samblis

About host – Kathy Svetina

Kathy Svetina is a Fractional CFO for growing small businesses with $10M+ in annual revenue.

Clients hire her when they’re unsure about what’s going on in their finances, are stressed out by making financial decisions, or need to structure their finances to keep up with their growth.

She solves their nagging money mysteries and builds a financial structure with a tailored financial strategy. That way they can grow in a financially healthy and sustainable way.

Kathy is based in Chicago, IL and works with clients all over the US.

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