How To Grow Small Businesses With One-On-One Meetings

blog Nov 29, 2022

Way too many small businesses owners do not invest time and energy into One-on-One  meetings with their direct reports.

Depending on the number of people in the team, you may not be able to meet regularly with everyone, so make sure you meet with your own direct reports (the Managers), and ensure they meet with their direct reports.

These meetings improve engagement and help your team feel fully supported in their roles.

You also show that you CARE.

When you meet with team members individually, the subject must not be critical issues - rather, on than their work and their professional development.

Too many owners and managers in small businesses I’ve worked with clearly have blind spots when it comes to One-on-One’s. 

This tends to be due to very few businesses providing strong guidance or training for their managers about when and how to meet individually with their employees. 

My experience shows that managers who don’t invest in such conversations - who view them as a burden, hold them too infrequently or manage them poorly - risk leaving their team members disconnected, both functionally and emotionally.

The best managers in growing small businesses recognise that one-on-one’s are not an add-on to their role - they are foundational to it.

Those who fully embrace these meetings as the place where leadership happens can:

  • make their teams’ day-to-day output better and more efficient
  • build trust and psychological safety, and
  • improve employees’ experiences, motivation, and engagement. 

As the small business owner, your responsibilities are to ensure that:

  1. the meetings occur
  2. actively facilitate and / or promote them
  3. encourage genuine conversation
  4. ask good questions
  5. offer support, and 
  6. help each team member get what’s needed for optimal short-term performance and long-term growth.

The following are some ways to help you and your team:

1. Before the a One-on-One

Setting up your One-on-One’s should entail more than dropping invites into team members’ calendars.

You should lay the groundwork and process for your conversations, and plan the logistics to best fit everyone’s unique needs.

And be prepared - follow the 7 Ps:

Prior Preparation and Planning Prevents Piss-Poor Performance

That means, take notes during the week on feedback or topics you want to discuss with your direct report in their One-on-One.

Then be sure to review and organise these notes just before the One-on-One.

2. Communicate the initiative

Whether or not the practice of holding One-on-One’s is new to your team, announce it at a team meeting so everyone gets the message at the same time and no one feels singled out.

Tie the meetings to your business values (such as the importance of hearing employees’ voices) and to your personal values (such as striving to be a supportive leader). 

Also stress that these conversations are not meant to signal dissatisfaction with your team’s work and are not about micromanaging

Rather, they are opportunities for you and each direct report to get to know each other better, learn about their challenges and for you to give help when it’s needed. 

Your team members should drive the agenda with key priorities, being curious, being actively engaged, communicating candidly, thinking deeply about problems and solutions, and be willing to ask for help and act on feedback.

3. Determining cadence

Our strong advice, and that of the awesome Manager Tools podcast (the #1 downloaded business podcast), is to hold your One-on-One with each full-time direct report weekly. 

If they are part-time then do them fortnightly. 

Mark and Mike and Manager Tools have tested different cadences for full-time team members (fortnightly monthly and quarterly) and that data told them weekly is the most effective. 

Our Founder, Troy, did a great cast with Mark from Manager Tools - a podcast about small business and becoming a better manager and the management styles Mark recommends.

Each One-on-One should go for 30 minutes. 

That’s the optimal time. 

Sometimes they will go longer, sometimes shorter, and that’s OK. 

Now, I know you will groan when you read that.

“30 minutes, weekly! I don’t have time - with 6 direct reports, that’s three hours of my week!”

You will get that time back, boost productivity and increase employee retention. 

If the frequency is not weekly, building a trusting relationship can be difficult. 

And because more-recent events are easier to recall, the longer time lapse also means that you’re less likely to discuss any issues that arose several weeks prior to the meeting.

Importantly, avoid cancelling One-on-One’s.

The delay can hamper your directs’ progress, and make them feel they are low on your priority list. 

We strongly believe the right people are your most important asset, so why wouldn’t you make them a priority?

DISCIPLINE is needed!

Being busy is NOT a reason to cancel these meetings.

If you must cancel, reschedule the meeting right away, ideally for the same week. 

Another option is to reduce the length of the meeting, as better than none at all.

4. Set a location

Ideally, you should meet in-person at a location where you and your direct report will feel at ease, present and free of distractions. 

Sometimes outside locations, such as coffee shops, or taking a walk near the office works. 

Talk to your team members to gauge where they feel most comfortable.

5. Create an agenda

Many managers assume that One-on-One’s are too informal to require an agenda.

But my experience indicates that having one is a strong predictor of the effectiveness of the meeting, whether it was created in advance (which is ideal) or at the meeting itself (if necessary).

The structure we recommend is:

The first question

You should ask “how are you going?”

This very open question allows them to immediately talk about any issues on their mind, even personal ones. 

First 10 minutes

Is for the direct to raise any questions, challenges or update you on their role, projects and KPIs.

Second 10 minutes

Is for you to provide any feedback or coaching (if is short, otherwise book another time for a specific coaching session). 

Every second week, pull out their Job Description and projects list and run through it with them.

Here are some questions you could ask;

  • What would you like to talk about today?
  • How are things going with you and your team?
  • What are your current priorities, and are there any problems or concerns you would like to talk through?
  • Is there anything I can help you with or anywhere I can better support you? 

Even include some personal questions to help get to know them better.

You must avoid immediate tactical issues and fires to be put out. 

Ideally, include longer-horizon topics such as career planning and development opportunities.

Final 10 minutes

Discuss their professional development - the one thing they need to increase their knowledge and / or skill in this quarter, and the resources you both agreed they should consume to attain that.

6. At the meetings

Once you’ve prepared for a meeting, a good discussion will depend on your ability to create a setting in which your team members feel comfortable. 

A valuable One-on-One addresses both the practical needs and the personal needs, so they feel respected, heard, valued, trusted and included. 

To ensure that a meeting does so:

Set the tone - be present!

Turn off email alerts, put your phone away, and silence text notifications. 

Remind yourself as the meeting begins that it is about your directs’ needs, performance and engagement.

As you go into the meeting, check your emotional state. 

The mood you bring to a meeting can have a contagion effect so start out with energy and optimism. 

Reiterate your goals and hopes for the meeting and then move to some non-work-related topics, rapport building, wins or appreciation to generate momentum and foster feelings of psychological safety. 

You must ensure your team members do not see One-on-One’s as merely another task on their already long list.

This can impact on how you listen, how you collaborate, and how engaged you are.

Listen more than you talk

The biggest predictor of a One-on-One’s success is your direct’s active participation, as measured by the amount of time that person talks during the meeting.

Listen actively to fully understand your direct, before you speak. 

Display genuine interest without judgement, and acknowledge your direct’s viewpoint - even if you disagree with it. 

Ask questions that clarify and constructively challenge that viewpoint. 

Encourage your team members to provide thoughts on the matters at hand, and potential solutions to problems. 

Add your perspective

A One-on-One provides an excellent opportunity for you to give honest and specific feedback on your direc’s performance. 

It is also a good place for you to engage in collaborative problem solving by truly understanding whatever issue is at hand, identifying root causes and creating a solution that both parties feel good about.

A great initiative to create more commitment is running with a team member’s solution if viable - even if it’s not better than your own. 

Be flexible

As you work through your established agenda, allow the conversation to move organically as needed to help provide value. 

Focus on the items that are most critical. 

If some items go unaddressed, move them to the following One-on-One. 

Let your team member know at the start that changes can be made to the agenda if a critical item emerges.

Also, to best connect with each direct report, consider that person’s preferences regarding communication, collaboration, and so forth, and adjust your leadership approach accordingly. 

That will increase engagement and inclusion, deepen the relationship, and importantly create TRUST.

End well

Clarify takeaways and action items for both parties, including how you will support next steps. 

When both the manager and the direct document these, chances are better that the actions will be carried out. 

It also builds continuity between meetings and allows for needed follow-up.

Software can be useful for efficiency, like

Finally, show gratitude and appreciation for your team members' time.

Show this by starting and stopping on time.

6. Improve over time

Ideally, both parties should leave the conversation feeling valued, respected, and well-informed, with clarity about next steps on projects, solutions to problems and the commitments that each of them has made. 

However, the most important metric for success is whether your employee found the meeting both valuable tactically and fulfilling personally.