How to Have the Career Development Conversations

Professional Development
12 followers
3 Video Views·May 22, 2025
Your people say that they want to learn and they want to grow. And the surveys that come back and the thing that people want the most is career development opportunities. Then you ask people, "How do you want to grow and develop?", and they say, "I don't know.".
In this video I am going to share how to have these conversations in such a way that allows individuals to take ownership of their own development.
Do your people say that they want to learn,
that they want to grow?
Do the surveys come back
and the thing that people want most
is career development opportunities?
But then you ask people,
how do you want to grow and develop?
And they go, I don't know.
On this video, I'm going to share
how to have a conversation in such a way
that empowers that individual
to take ownership of their own development.
Hi, I'm Chris Littlefield.
I'm the founder of a company called Beyond Thank You.
I'm a regular contributor to Harvard Business Review
and Forbes.
And what I do is I help leaders
have the most important conversations
that empower their people to do their best work.
Let's jump in.
According to a report by ExecuSearch,
86% of employees said that they would take a job
at another organization
and have had more career development opportunities.
Research by Gallup around engagement,
three of the 12 indicators
around people's growth and development.
Do I feel like someone cares about my development?
Do I, has someone talked to me about my progress?
Do I feel like I get to learn and grow every day?
So having these conversations is critical
to the engagement retention of our people.
But how do we have these conversations?
And how do we have them
when there may not be a position for them to advance into?
They may not have the skills needed to be able to get there
or the background needed to get those positions,
or they think that they should be a director already
and they're 22 years old
and nobody's had that reality conversation with them yet.
And even more commonly,
when we ask them how they want to grow and develop,
they don't know the answer to the question.
So let's tackle that last one first.
So you ask an employee how they want to grow and develop
and they go, I don't know.
Now, the mistake that many leaders make in this case
is they'll spend the next hour asking them questions
and trying to draw out how they want to grow and develop
and what they want to make happen in their life.
But in reality, you end up trying to do the work for them.
And this creates a dependency on you
when in reality what we want to do
is we want to put that responsibility back on them.
So here's something else you can do.
Say, hey, you need to take ownership
of your growth and development.
I can support you in it,
but if you don't know where you want to go,
I can't help you start working towards getting there.
So what I want you to do is over the next week
or the next two weeks,
I want you to think about
what are the things that you want to make happen
both personally and professionally in the next year
and the next five years.
I want you to think about the skills you want to develop,
the experiences you want to have,
the kind of people you'd like to be working with,
the topics you'd like to be working on.
And when you get a clear picture
of some of the things you'd like to have happen
either here at this organization
or at another organization, and that's okay,
I want you to reach out to me
and schedule a follow-up meeting.
But it's on you to be able to get clarity
about some of the things you'd like to do
and then schedule the meeting
and then we'll talk about how we can support you
to accomplish things here or somewhere else.
I just want to pause for a brief second here.
If you're enjoying this video,
it really makes a difference for me
if you hit that like and that subscribe button
and you share your thoughts in the comments below.
And also, if you're looking for scripts
and you're looking for training for your leaders,
please check out my programs
or reach out to me at beyondthankyou.com.
Okay, back to the video.
Now, there are two things
that are likely to happen at this point.
Now, one is they're gonna go off,
they do the work, they get clarity,
and they come back and they schedule that meeting
and then you can have a productive conversation
about the skills they want to develop,
the experience they want to have,
and you have something to work with.
And it also shows that this person
took a little ownership of this process.
You can connect them with other people
in your organization that have the skills
that they want to develop
or in the positions that they want to be in.
You can help them connect them to conferences
and books that they can read
and you have something to work with.
Now, the other thing that's likely to happen
if they weren't clear on what they want to do before
is they don't take the action.
They don't get clarity, they never schedule the meeting,
and then they get grumpier that no one's supporting them
because they were waiting for a Yoda,
a Mr. Miyagi, or a Dumbledore
that was gonna guide them through their life,
and they don't know that that doesn't exist.
So in that case, you wanna just keep on checking in.
Hey, did you do the work?
Did you explore what you wanted to do?
What are some of the things that you've been thinking about?
Ah, I haven't done it.
When are you gonna do it?
I can't do this work for you.
And keep on saying those signals
that you do remember that they want to grow and develop
and you're still pushing them to do the work.
And then you could also just go,
I'm giving you a deadline.
You need to do this by Friday,
and then you just schedule that meeting with me,
but you need to do it.
And that shows that person that you still care about them,
you care about their development,
and you haven't forgot about it.
Now, what do we do when an employee
is actually an excellent employee,
they've got amazing skills,
and they really could probably do your job,
but you're not planning on leaving,
and there's no other position for them to move into?
Well, if this is the case,
then what we wanna do is we wanna talk to that person.
Hey, what are the skills that we can help you develop
and work on while you're here?
What are the experiences you wanna have?
What are some of your ideas of how you could grow
and expand in the position that you're in?
And then also have the reality check.
Hey, there isn't a position for you here,
but maybe we need to start exploring a position for you
in another department or even another organization,
because I get that you wanna grow and develop.
And many people don't wanna have these conversations
because we're supposed to retain our people.
We don't wanna let them go.
But in reality, if we try to hold them
in a position that's too small for them,
eventually they're gonna get resentful.
So the best thing we can do is help promote them
into a position, maybe in another organization.
And when an opportunity does open up,
then they'll most likely come back,
and they'll always remember you as a manager
being a person who cared for them.
Now let's talk about the third scenario
where the person wants to advance.
There may be a position available,
but they don't have either the interpersonal skills
or the technical skills to be in that role yet.
And so here are two separate conversations we need to have.
So if it's the technical skills that they're missing,
then you wanna work with them to identify
what those skills are and talk about
what are some of the ways that they can develop those.
Maybe it's shadowing somebody.
Maybe it's taking a course at a local university.
Maybe it's taking an online course.
Or maybe it's just putting them on a project
where they're working with somebody who has expertise,
and they can learn that on the job.
And once you identify those things,
you wanna make that part of each one of your one-on-one.
And you check in, hey, how's this going?
How are you developing this?
And then talking about some of the things
that you wanna be able to see them being able to handle
before that they can apply for that next position.
Now if it's interpersonal skills,
that's a little more challenging to navigate.
And I recommend you checking out my video,
Three Feedback Mistakes and How to Avoid Them.
And that will give you a whole framework
to be able to prepare to have this conversation.
And it'll give you details of how to identify the behavior
that you wanna give them feedback on,
the details you need to include when you do,
and what you'd like to see instead.
And all the things you wanna avoid
to make sure that conversation goes well,
which can be useful regardless
if it's around career development
or just something you're dealing with on the job.
But you need to help that person see
the changes that you need them to make.
And if they're a person who frustrates people on other teams,
who's difficult to work with,
who's constantly gossiping and showing drama
and not showing that they can be
in that leadership position or that next level position,
you need to make them aware of that.
And that's many times a tough conversation,
but we forget that those tough conversations
are many times the biggest gifts that we get
in the advancement of our careers.
Now the last and probably most important distinction
around development conversations
is they need to be built into everything we do.
Now many employees think that development means
that when they get a promotion,
when they attend a training,
they work with a coach or they go to a conference.
Yet most of our skill development advancement
happens on the job doing the work.
But we don't tend to see the progress we're making
when we constantly have that next milestone
we're trying to hit,
that next challenge we're trying to navigate.
And so as a leader,
you wanna be facilitating conversations
in your one-on-ones and in your team meetings
to help people get present to the progress they're making.
You can do this by asking,
hey, what's a skill that you developed or you improved?
What's some sort of challenge
that we've navigated as a team
and how are we able to do it?
What are the things that you're proud of?
What are the things that you can do better today
than you could six months ago?
And by doing that, you're gonna shift their attention
not to where they're not,
but to the skills, the abilities that they've developed
at their time with your organization and with your company.
Having development conversations
is one of the most important things we can do
for the engagement and retention of our people.
And they're not always easy to have
because people don't have clarity
on how they wanna develop.
There may not be opportunities for them in the organization
or they may not have the skills needed to advance.
But if we take the time, the 15 minutes, the 20 minutes,
the half an hour to engage in a conversation
and dialogue with our people,
that really lets them know that we care.
And that caring for people is what has them stick around,
do their best work and nurture that culture
where people feel valued every day.
Once again, I'm Chris Littlefield.
I hope you found this video helpful.
If you did, hit that like and subscribe button,
share your thoughts in the comments below
and share at least one other person
who you know make a difference for,
and together, build cultures
where people feel valued every day.
Take care.
