July 4, 2022

How Managers Can Embed Development Conversations in One-to-Ones (+ 5 Actionable Tips)

Melissa Malec

One-to-ones are a great time to gauge where your people are in their upskilling journeys. They're important conversations to have as a manager because they show your support for your team and allow you to align business goals with personal ones. 

But many managers don’t know how to bring development into the conversation in an effective and impactful way.

If you’re in the same boat, don’t worry. By the end of this guide, you will: 

✅ Be able to establish a better process for discussing development with your team

💪 Feel more empowered to have these conversations in a natural and effective way

🧠 Know the ins and outs of how these conversations can positively impact the business

Why Do So Many Managers Find It Difficult To Discuss Development?

If you find it difficult to communicate with your people then know that you’re not alone. 

In one survey, 69% of managers report feeling uncomfortable communicating with their employees and 37% find it challenging to give their people direct feedback.

Asking the right questions about career progression and creating personal development plans for each individual is challenging—especially if you have limited experience doing it. 

To get the most out of development conversations, you also need to ensure that your people feel comfortable discussing their careers and the skills that they want to improve with you.If you find that your people struggle to openly discuss their development, it could be for a variety of different reasons. 

It may be that your team members come from backgrounds where sharing this type of information wasn’t encouraged or safe to do. 

Or, it could be that the individual doesn’t feel comfortable being vulnerable for their own personal reasons.

This is why it’s important to evaluate whether it’s your company culture that’s to blame or the impact past cultures have had on your people. You may have to work on undoing damage and building psychological safety in your team.

If you don’t, you’ll struggle to feel comfortable having honest development conversations. 

Before You Begin: Establish Psychological Safety

Before you can have genuine development conversations with your people, you need to establish psychological safety.

This is when people don’t worry about criticism or judgement for making and admitting to their mistakes.

When psychological safety is embedded within your company’s culture, your people will: 

🧠 Feel comfortable sharing their goals with you during one-to-one meetings

🧠 Know that they are supported as they embark on their learning journey

🧠 Own their mistakes and feel empowered to learn from them 

Remember, Development Conversations Aren’t Performance Reviews

It’s easy to get confused between a development conversation and a performance review

A performance review focuses on evaluating a person’s workplace performance and how it affects the rest of the company. The employee’s self-evaluation is usually combined with wider feedback from their peers, as well as the manager’s evaluation of their performance. 

But the goal of a development conversation is to find practical ways to help an employee build on their existing skills and support them in achieving their goals.

If a direct report wants to develop new skills that help them progress in their roles, they can refer to their performance reviews or career development plans to guide them.

Another important difference is that personal development allows people to progress beyond workplace-related skills at their own pace. This could mean learning a new skill that’s not directly tied to their role at your company.

Tips for Embedding Development Conversations in One-To-Ones

Now that you know a bit more about how development conversations are used, we can get to the best part—looking at ways you can build them into one-to-ones. 

1. Start By Identifying Career and Development Goals

As a manager, one of your roles is to support, empower and develop your people. 

However, you can’t do that or help them find the right learning and development (L&D) resources if you don’t know what their personal or professional goals are. 

It’s important to remember that the best goals and development plans match the employee’s needs with that of the company. 

Once you understand what someone wants to achieve, you can create opportunities for them to get there, as well as brainstorm ways that the company can support them. 

The key to identifying a person’s development goals during a one-to-one conversation is to ask the right questions. 

At Learnerbly, we like to use the “GROW” model to guide our goal-setting conversations. 

Some of the questions we may ask within this model include: 

  • What would you like to accomplish? 
  • What could you be doing to reach your goals?
  • Where are you now in relation to the goals you want to achieve?
  • What do you think you need to do to achieve your ideal outcome?
  • Do you feel like you’re making progress toward your long-term goals here? Why or why not? 
  • What resources can help you reach your ideal outcome or goals?

By answering these questions, you’ll gain more clarity about what your direct report’s goals are so that you can create personal development plans (PDPs).

This will help set the course for your people’s growth and give them a better idea of what their development journey looks like.

2. Discuss Learning Focuses and Resources 

Once you know what your direct report’s goals are, you can steer the conversation towards discussing L&D resources that will help achieve them. 

While some people will know exactly what they want to learn and know how to pursue it independently, others might be unsure and benefit from guidance. 

This is where you come in. 

Set aside time during the one-to-one to help your people find and choose upskilling opportunities that are aligned with their professional development plan and goals.

3. Set Regular Progress Check-Ins 

One of the best ways for both you and your people to get the most out of development one-to-ones is to have them on a regular basis. 

This is a great way to see what progress your direct reports are making towards their career or learning goals and if the resources they’ve chosen are proving to be valuable. 

During these conversations, you can hold your team accountable with their L&D or help them find other resources and opportunities that will be more suited to their goals. 

Some people benefit more from mentors or networking as a form of growing in their role or by taking on a project where they can apply their learnings on-the-job.

There is no one size fits all approach to how often you should be having development conversations during your one-to-ones.

Some managers even schedule a monthly meeting dedicated entirely to development in addition to setting aside a few minutes of every one-to-one for career development conversations. If you have four one-to-ones a month, you could make the fourth one about career development without adding another meeting into your schedule.


⏰ The regularity of these discussions will depend on the size of your team and what works best for each individual. 

⏰ Make sure that you schedule the development one-to-one as a regular calendar event for both you and your team members. 

If your company allows you to set personal learning budgets (PLBs) for your team, a regular check-in is also a good time to see if they are making the best out of it. 

You can use the one-to-one meeting to inspire your people to use their budgets more if need be and find out if it adequately supports their development. 

If it doesn’t, you can bring it up with your People team or Leadership team.

4. Use One-To-Ones to Carefully Consider Learning Requests

Many companies allow their teams to make learning requests that get sent to their managers for approval. 

As we’ve seen in this article, having regular developmental conversations with your people gives you a better understanding of what skills they want to develop. 

By combining that with wider company goals and PLBs, you can make informed decisions about which requests can be approved right away and what might need a quick catch up.

This is a great way to help your people ensure that they are engaging with resources that support their goals and where they may need a little help staying on track with their PDPs.

If your company uses learning requests, make sure that you carefully consider each one by asking yourself the following questions: 

🤔 Will the learning resource help them achieve their goals? 

🤔 Is it the best resource type for their goals?

🤔 Do multiple people have similar goals and does this create an opportunity for shared learning? 

5. Use Development Conversations to Lead by Example 

There’s little use in talking about development in one-to-ones without you championing the organisation’s learning culture. 

At Learnerbly, we’ve seen first-hand that the more engaged managers are with L&D—the more likely their teams are to follow suit. 

There are a few different ways that managers can lead by example: 

✔️ Share your 360 feedback with your team and highlight the areas that you’ve chosen to develop during one-to-ones. 

✔️ Suggest L&D resources that have helped you improve your skills during development conversations. 

✔️Open up about a time you applied something you learned at work and how it went

These are great ways to show your people that you take ownership of your development and speak about it openly with others. 

Hopefully, your attitude will trickle down to the rest of the team.

What Are the Benefits of Having Development Conversations? 

Sometimes knowing how to have the conversation isn’t enough to make sure you actually have it. So we want to make sure you know why it’s important to discuss development with your team members.

And quite frankly, there are many benefits companies and their managers can enjoy when they prioritise development conversations and support continuous learning.  

It Helps Keep Team Members Engaged

For many people, jobs are no longer just a means to an end. Alongside helping us pay our bills, a great job is one that inspires us to develop ourselves with the future in mind. 

No wonder research shows 82% of people would be more engaged if their managers had regular conversations with them. 

Having development conversations and encouraging your people to find opportunities to learn shows them you’re invested in their growth. And when that happens, they’ll feel more valued by you and more committed to the company. 

These conversations can also boost individual and team performance, ultimately maximising your teams contribution to the company which is in everyone’s best interest.

You’ll Develop Better Relationships With Direct Reports

Development conversations, when done right, will help you learn more about your direct reports on a personal level. 

Asking team members about their aspirations, interests and what they want to learn is a great way to show them you care about them.

As a manager, your job is to: 

⭐ Understand your people’s personal and professional goals 

⭐ Support direct reports in developing their skills

⭐ Help team members find projects and learning resources that will help them progress in their careers

By discussing and learning about these things, you’ll be able to build stronger relationships with your team and help them see you as a coach and mentor—instead of just a manager. 

You Can Help Your Team and Company Become Future-Proof

Although your team may have the talent around now to be successful, there’s a very good chance you’ll need additional skills in the future. 

Development conversations are a great time to explore potential needs within the context of your direct report’s future career goals. 

You can use one-to-ones to encourage your people to take active steps towards developing their skills so that they are equipped for any future job, industry requirements, or even to make their place at the company more secure. This is because ongoing learning helps companies and their people stay up-to-date with industry trends and even push ahead of them. 

When your team has the skills in-house that it needs to keep up with the ever-changing world of work, you’ll also save your company money on future hiring costs.

It Creates a Win-Win For Companies and Their People

The best managers:

💥 Find ways to get excellent performance from their teams while helping them grow 

💥 Use their people’s new and existing skills to create greater value for the company 

One-to-ones are the ideal time to find out what your people’s goals and learning aspirations are so that you can find ways to link this to the organisation’s key business goals. 

Doing this allows you to create sustainable career paths for your people within the company. 

It will also help you ensure that your company is able to stay agile and competitive in an ever-changing working environment. 

Development Conversations Help Boost Retention Rates

Many managers worry about investing time and resources into their people, only for them to leave the business in the future. 

But, investing in development is one of the best ways to retain existing talent

One survey found that 75% of people would be more likely to stay with their current employer if they had regular development conversations. 

When team members feel like their managers value and support their development, they are far less likely to seek job opportunities elsewhere. 

Having development conversations in one-to-ones also helps managers identify if one of their team members is unsatisfied earlier than if they hadn’t. This allows you to better support the individual and hold onto your team’s talent for longer. 

Now It’s Your Turn

Although having development conversations may seem overwhelming at first, the right process and questions will help you get the most out of them. 

Not only will they encourage your people to think about their career goals, but you’ll also be better equipped to help them find L&D resources to make those aspirations a reality. 

And development conversations can be made easier still. 

Take a look at this guide and discover how Learnerbly can enhance and support your development conversations.

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