Modern One-on-One Meetings: Common Mistakes & Best Practices

Mark Lewis
September 23, 2019
min read
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One-on-One Meetings

One-on-one meetings are an essential part of modern leadership. A regular, informal but structured, forward looking conversation. One-on-one’s done right build a trusted employee-manager relationship, save time and increase productivity.

We all want instant results, but employee performance is a work-in-progress. Regular one-on-one meetings help keep your definition of progress on the same page as theirs. One-on-one meetings focus on an employee’s immediate needs and allows them the opportunity to voice their concerns on what is constraining their progress in real-time.

The two-way dialogue helps them feel engaged, productive and valued - characteristics found to result in higher retention rates for employers. Managers will boost the effectiveness of their leadership, and subsequently allow team members to take greater ownership of their own development.

This ultimately builds a modern culture of performance . It’s an ‘everyone wins’ scenario!

On the surface, productive 1-on-1’s seem like something that would be easy to achieve. However, it’s easy to fall into the trap of a backward-looking ‘status update’ style of meeting. The status update usually means a one-way flow to the manager with almost zero value for employees.

Putting some simple tips into action can avoid this trap and make one-on-one meetings your best friend. By shifting the focus from a backward looking review to forward looking coaching, you’ll give employees a much greater chance to reach their full potential.

While some managers may view one-on-one meetings as something they don’t have time for, this is a common myth, as in their absence you will find a flood of distracting emails, desk chats or instant messages. With regular one-on-one meetings employees become more planned about the work they’re doing, which also leads to less fires that need to be extinguished later.

Regular one-on-one meetings are not simply increasing the number of performance management cycles, it’s actually an altogether different conversation that builds trust and performance from the ground up .

Your employees probably want regular one-on-one meetings. We have create a range of 1-on-1 templates to support your employees and managers have positive conversations.

What your employees really want

It’s time for a reality check - we’ve researched thousands of employees, and what we’ve seen as the most common performance concern is that an annual meeting model just doesn’t achieve the results it was designed to achieve.

The modern workplace has been excessively bogged down with rigid performance processes, backward looking reviews, box-ticking exercises and KPI’s.

Employees are feeling disconnected and undervalued; the human element of the employee is being missed. Not only is this a terrible experience for employees, it’s also bad for business.


So, what’s the good news? You already know how to fix the problem.

Just like your other relationships, those you develop with your employees need cultivating and nurturing. Frequent check-ins, ongoing dialogue, and coaching conversations placed at the center of the manager-employee relationship is a key way to achieve the great performance and leadership every business strives for.

Crewmojo helps foster these great relationships for your business, replacing those once-a-year backward-looking appraisals that most employees feel uncomfortable with. See how to encourage and implement forward-looking one-on-one meetings that bring out the best in everyone.

Keep reading to learn more of what modern one-on-one meetings look like, why they’re a useful performance tool, what kind of results they’ve been driving in the real-world, and how you can implement regular one-on-ones in your business.

1. The Basics of One-on-One Meetings

Keep Agendas Flexible

Flexible means the agenda is not the same every meeting and you have the freedom to talk about the most important things that are happening right now. But don’t fall into the trap of thinking flexible means unprepared. With Crewmojo you can easily capture ‘talking points’ or add an ‘activity’ to the agenda and the other person gets notified - so when you meet you’ll already be on the same page.

It might be daunting creating an agenda for the first time, so some of the areas you may want to discuss could include:

  • What’s working well for the employee.
  • Reviewing progress after previous feedback.
  • Challenges with current goals.
  • Next steps for learning and development.
  • Any problems keeping the team member from performing well.

If you default to a concrete agenda, you may risk having a repetitive meeting which covers the same ground. Not only will this frustrate your team member, you’ll both get little value and soon lose interest. Let’s face it, we don’t need to have a career conversation every 2 weeks!

Keep in mind that your employees will all have areas they want to discuss in the meeting. Once you both become accustomed to regular meetings, encourage them plan some talking points? You won’t have to rely on your mind-reading abilities and they will be able to get more out of the experience.

Our 1-on-1 templates are a good place to start. We've included the exact weekly check-in that we use here at Crewmojo just in case you are curious about how we approach this.

As time goes by, you won’t need to spend as much time preparing.

It’s All About Time

With everything else going on, one-on-one meetings can seem like an unnecessary luxury. It’s way too easy for managers to use their authority to skip or postpone one-on-one’s. But doing this sends a message that your team member is not a priority for you.

One-on-one’s are always clunky to begin with but after a few months, our customers tell us, it is some of the most productive and valued time spent by managers and employees alike. Set aside time to meet with employees and be consistent about it. You’ll want at least 30-60 minutes to ensure you get to the heart of any challenges and work out a plan forward.

As for frequency, there’s no golden rule. The research tells us weekly is most effective but in practice we see most teams electing for fortnightly or even monthly. Every team is different and in the first instance it’s about finding what works.

You might want to start with monthly one-on-one’s to achieve a sense of success in the new process. Then increase the cadence if you find your notes are overflowing with talking points. A lot can happen in a month!

With Crewmojo, you can easily adjust the cadence and we help make the process employee owned by sending nudges to employees when they need to be booking a one-on-one with their manager. After all, the new process is designed to avoid an administrative burden for managers.


Ensure that you agree on the cadence with your employees so they’re prepared. Don’t let the days turn into weeks, and the weeks turn into months.

You’ll save a lot of time in the long run as your team become more planned and deliberate in their work. Not only does this prevent fires later on, but you’ll be more in tune with what’s actually going on.

Getting Employees on Board

If you’ve never tried regular one-on-one meetings before, it may cause uncertainty or misunderstanding among some employees because their previous experience of meeting directly with their manager may well have been a negative performance experience.

First, run the idea past them and be upfront about what you’re aiming to achieve. Say something along the lines of “I’d like to start focusing more on team development. It will help me to help you achieve your goals and objectives. I think we will all benefit from regular one-on-one meetings”.

A good tip is to start one-on-one meetings with casual conversation. That’s right, put away that laptop or notepad, you’ll build greater levels of trust by taking the time to genuinely and authentically connect at a more social level.

This is not to be treated as a ‘management technique’. Quite simply, if it’s not genuine and authentic, your team member will quickly smell a rat and trust will drop through the floor.


Employee First

We’ve already explored the benefits for employees of creating an agenda once they’ve settled into regular meetings. This will help them to self-review their own progress and think about any issues which might have arisen before seeing you.

Think about it this way: your meetings should be 80% about your employee, and the remaining 10-20% about news from you.

Let’s break that down. 80% of the time should be helping the employee’s development. Managers should ask ‘how can I help you achieve your goals?’ rather than ‘have you achieved your goals?’

The last 10-20% should be focused around news from you. This isn’t a time to share all news from the business, only the most crucial or relevant to the employee.

2. Dealing with the ‘f’ Word

It’s the word that strikes fear into employees and leaves employers frustrated. Yes, it’s feedback.

For many of us, hearing the words “I’ve got feedback for you…” are enough to give us sweaty palms and a dry mouth. We envision the worst case scenario and our brain starts to respond with fight or flight decisions, shutting down our ability to respond rationally and objectively… actually making it difficult to even recall the discussion after it’s passed.

More Feedback

We’ve become accustomed to fearing feedback due to the impersonal nature of annual reviews. Yet at the same time we’re often told by customers that employees have requested more feedback. How are we meant to get past this divide?

The answer is more subtle than you might think. It turns out that when we request feedback, we are opening ourselves up and are receptive to the conversation. Because it’s invited, it also makes it easier for the person delivering the feedback, plus there’s less anxiety wondering how said feedback is received.


That being said, the way feedback is given can heavily influence how it is received. No matter how carefully delivered, negative feedback can often create space between both parties.

Rather than the typical ‘positive’ and ‘negative’ feedback, change to a mix of positive praise and considerations for improvement. This change can work wonders for team morale and minimizes potential animosity.

More on feedback here - How to Make Feedback your Secret Leadership Weapon

Keep it Two-Way

Like any good relationship, communication happens both ways. As a manager, you also need to encourage feedback during one-on-one meetings. By modeling the behavior and asking for feedback you demonstrating that it’s safe to ask for feedback in this team.

For more honest feedback, make sure to set the right tone and choose your questions wisely. Some questions you may want to use include:

  • What have you liked about my leadership? Is there anything you dislike?
  • Are you satisfied with my involvement in your daily tasks? Would you like more or less?
  • How can I support you better?
  • What is something I can improve on?

3. Best Practices for Modern One-on-One Meetings

A Change of Scenery

Sometimes it helps just to escape the hustle and bustle of the office by mixing up where you hold one-on-one meetings with employees. Maybe it’s the overly formal nature of the conference room, or the concern of being overheard, removing some of these factors can really help employees open up for a more authentic conversation.

In fact, it’s been found that there are a number of advantages to having a one-on-one meeting out of the office. As well as helping both parties feel more comfortable sharing, out of office one-on-one’s help to improve focus through greater stimulation to the brain, improving engagement. This also allows for more creativity, rather than being at the same desk where many hours have been spent. You may also find there’s greater camaraderie.

Go for a walk or a nearby café. Wherever it is, ensure the space is quiet enough for conversation and enough of a break to your routine.

Be an Active Listener

We all want to be understood, and that’s why active listening shouldn’t be ignored with one-on-ones. There are a number of ways you can ensure you’re actively listening to your team member:

  • Asking questions to clarify what has been said: “Let me know if I’ve got this right. Do you mean that you would like more flexibility at work?”
  • Paraphrasing: “so you are saying that I should allow for greater work from home to assist with family commitments.”
  • Acknowledging how they feel, “I understand your strong feeling for having a better work-life balance”

On the other hand, what if an employee only gives short or general answers? If this happens, it’s an indicator to ask some more specific questions to gain the information you want.

For example, instead of asking, “are there any roadblocks you’re experiencing at the moment?” a manager might say, “tell me about the most challenging project you are attempting at the moment and why that is.”

It’s important that silence sometimes happens. Employees might need that time to process the question. Remember, they haven’t been thinking about it for nearly as long as you have. It’s completely fine to let the silence hang rather than rephrasing a question.


Lost for Words?

You glance at the clock. There’s 15 minutes left, but you’ve covered everything. Maybe your employee is lost for inspiration. What do you do now?

This is the one exception where it’s perfectly fine to talk about you in a one-on-one meeting. It could be a problem you are currently encountering, or a story from a similar situation your employee is in. Who knows, maybe your employee will deliver a nugget of wisdom?

It can also be a good chance to grow the relationship with your team member.

Freedom in a framework

One-on-one templates can be a great tool for teams who are just getting started with regular 1-on-1 meetings. These templates provide a structured framework that can help guide the conversation and ensure that important topics are covered. Many people fear that these meetings will become boring.

Having 1-on-1 meeting templates on different topics can give teams the freedom they need to have more focused and productive meetings. By providing a structured framework, the templates can help team members stay on track and ensure that all important topics are covered.

However, having templates on different topics also allows teams to choose the focus of their meeting based on their current priorities and needs. For example, if the team is currently working on a specific project, they can use a template that includes sections on project status updates and potential roadblocks. Alternatively, if the team is focusing on professional development, they can use a template that includes sections on skill-building and career goals.

Here are a few that might interest you;

Having different templates to choose from gives teams the flexibility to tailor their meetings to their specific needs and goals. This can help to make the meetings more engaging and relevant for team members, which in turn can lead to more meaningful conversations and better outcomes.

Additionally, using different templates can help to keep the meetings fresh and prevent them from becoming monotonous or predictable. By changing up the focus and format of the meetings, team members are more likely to stay engaged and motivated.

4. The Benefits of Adopting Regular One-on-One Meetings into Your Business

You Save Time

You would think increasing the amount of time spent in meetings is unproductive, right? In fact, it’s the complete opposite. With regular one-on-one meetings you’ll reduce the amount of time spent sending sporadic emails and having desk side chats.

According to research by Gallup , holding regular one-on-one meetings between managers and employees leads to staff being 3 times more engaged and 21% more productive.

A few months after annual reviews, key performance indicators are often made redundant due to a change in direction, yet the pressure remains to meet them by the next review.

Not so with regular one-on-one meetings. By regularly checking in on objectives, you can clearly align progress with the next actions to achieve goals. It’ll allow you to check any performance issues before they get serious.

You Raise Morale

All employers want high staff morale, but achieving it is another thing. Regular one-on-one meetings give you the chance to really grasp the motivation levels of your team members. A motivated team is not only happier, but more likely to raise profitability.

You Build Loyalty

Being able to get help with challenges or share progress with an employer is a huge motivator for employees. It’s also a way to build loyalty between both parties, which is crucial in a healthy workplace.

It’s hard to build loyalty through a few emails and desk side chats. It takes consistent effort, but the positives far outweigh the negatives.

“We’ve had this tradition, in the last eight years or so that we’ve worked together, where every week we start the week and end the week just meeting one-on-one together, and going over everything that’s going on, and reflect on what’s going on, giving each other feedback.” - Mark Zuckerberg talking about his one-on-one’s with Sheryl Sandberg

5. Final Thought: How to Get Started with One-on-One Meetings

One-on-ones can be a very useful development tool for managers and employees. They also form a key way of strengthening workplace relationships, and who wouldn’t want to know the people they’re working with better?

Asking the right questions can improve performance, boost employee satisfaction and reduce turnover rates.

While there are many benefits of conducting one-on-one meetings, it might seem like a substantial investment in time to make the switch to regular one-on-one’s, especially if you have a well-oiled annual appraisal process up and running.

But here’s the thing: You don’t need to take an all or nothing approach.

While some of our customers have made the decision to scrap the annual process entirely, that doesn’t mean you have to. In order to get started with one-on-one meetings, you can keep everything exactly the same, and simply add one-on-one meetings to the mix.

You can think of it as making time for ‘performance development ’, only this is real-time, and is powered by meetings which keep both the manager and employee engaged.

At Crewmojo we’ve developed a quick and easy way to request and manage your one-on-one meetings. With just a few clicks, you can request a one-on-one, choose a time and place (get an entry directly into your calendars), select an activity (e.g. go for coffee) and add any talking points.

It’s a simple way to keep track of upcoming meetings while keeping things flexible.


Ultimately, by making the switch to regular one-on-one meetings, you’re separating performance improvement from assessment… giving your employees an environment for growth and allowing your business to grow through their success.

You’ll have better leadership, better relationships, and better performance. And everyone will find their mojo!

Ready to learn more about Crewmojo? Request a demo now.

6. Bonus: 27 Coaching Questions for your One-on-One Meetings?

What are you most excited about?
What are you most worried about?
What’s your pie chart of what you are working on? What do you want it to be?
How can I help you to be more successful?
What are your strengths?
What tasks do you really enjoy or happily volunteer for?
What has gone well in your progress toward your goals?
What has blocked your progress, and what changes do you need to make in the rest of the quarter to achieve your goals?
What is one company value you want to work on?
What have you learnt from this quarter that will help you next quarter?
What’s on your mind this week?
Last time we spoke you said X was a challenge for you, how is that going?
Do you have any questions about the recent change involving X?
How confident do you feel with where the company is going?
How aligned do you feel with where the company is going?
What has energized you in your role over the last month?
What has challenged you over the last month?
What’s one thing you have learned this week?
Do you feel confident in how you/your team are progressing?
How is everything going with people you work with/on your team?
Any interactions you’d like to discuss?
What feedback do you have for me?
When you think about yourself in two years time, what comes to mind?
How are you progressing towards your bigger life goals?
What are you committing to between now and the next time we meet?
What can I help you with between now and the next time we meet?
Is there anything we didn’t cover that you’d like to discuss next time?

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