Facilitate Career Conversations

Learning Objectives

After completing this unit, you’ll be able to:

  • Conduct effective career conversations.
  • Answer tough career questions.
  • Help your team members build an action plan.

Facilitating Career Conversations

Great career conversations...

  • Great career conversations help you understand what your team members want,
  • give you the chance to provide feedback,
  • are the perfect time to make the plan to help your employees grow their careers, and
  • happen both formally and informally throughout the year

No two career conversations are the same.

A career conversation takes planning BEFORE, great facilitation DURING, and follow through AFTER.

Before During After
  • Ask your employees to come prepared to talk about their career interests, strengths, and passions. Encourage them to take workshops to learn more about themselves.
  • Think about your employees strengths and opportunities for improvement and what feedback you want to give.
  • Reflect on what you already know about their career goals.
  • Write down some questions you can ask to facilitate the conversation.
  • Ask questions to help your employees think about their career interests.
  • Listen carefully and clarify what you are hearing.
  • Provide coaching and candid feedback on their strengths and development areas.
  • Help your employees identify career options and the direction they are interested in.
  • Build or review the action plan.
  • Determine when to meet again to check in.
  • Check in with your employees on how they’re doing toward their career goals.
  • Have regular career conversations.
  • Provide frequent feedback.
  • Connect employees with others in the organization to learn more.
  • Readjust the action plan as needed.
  • Encourage your employees to take on new experiences to grow and develop.

Let’s break it down.

Before the Conversation

Take time to plan! There’s no better way to have a great career conversation than to plan for it in advance. Think about what you know about your employees and encourage them to get to know themselves better. Get a sample Career Conversation Planning Tool from the Coaching & Feedback pack.

Do you know their:

  • Strengths
  • Areas for improvement
  • Career direction
  • Interests and passions
  • Options they are interested in

Did you discover as you were planning your conversation that your team member has no idea about what he or she wants from a career? Help employees take advantage of workshops and tools you have in your organization to learn more about themselves.


At Salesforce, we offer the webinar “Navigating Your Career.” It includes a self-assessment tool to help employees reflect on what career direction they want to head in and helps them make it happen by creating goals, getting feedback from others, and asking for support.

During the Conversation

It’s important to help employees feel comfortable about having a career conversation. They could be unsure about how to ask for your help and unsure of what it takes to get started. Set a positive tone. Go have coffee, take a walk, talk over lunch. Don’t make it feel too formal. Having a conversation at least once a quarter helps keep the dialogue going.

Career conversations can go in many directions. If your employees don’t have a clue about what they want, you can help them figure it out. If they know where they’re headed, your conversation can focus more on what actions they can take to get there.

Let’s look at two different directions your conversation could head in.

Career interests aren’t clear Career interests and goals are clear

“Let’s explore what interests you in your career. You don’t need to have the answers. I’m here to listen and help you think through what you find most interesting and why.”


  • What are you most passionate about?
  • What are your strengths?
  • What do you want to improve? Why?
  • Which new skills do you want to learn?
  • What do you enjoy doing that you’d like to do more of?
  • Which recent assignments have been more satisfying or interesting? Which haven’t?
  • How can I help you think through your career goals?

“It sounds like you know what interests you, and your career goals are clear. Help me understand your goals, and let’s focus on how we can work together to help you get there.”


  • What are your career goals?
  • Where do you see yourself in one year? Three years?
  • Which roles, departments, or opportunities are you most interested in? Why?
  • What does it take to be successful in the role you’re interested in?
  • What are your next steps to get there?
  • What support do you need from me?

Ready to help your Mountain Climbers reach the summit? And your Adventure Seekers get that next thrill? And your Deep Divers reach the depths? Try these ideas to get started.

Give it a try!

Mountain Climber Adventure Seeker Deep Diver
  • Manage expectations by explaining what it takes to be promoted—it’s the match between a business need and the right person at the right time.
  • Provide clear feedback about the necessary skills, experiences, and capabilities to be considered for a higher role in general.
  • Build an action plan with timing and clear steps to prepare for a higher level position so that the individual is ready when the time comes.
  • Encourage networking and informational interviewing with people on other teams.
  • Connect the employee with others across the company who have had varied career paths.
  • Help the person think out of the box about career options.
  • Be a champion as other opportunities are explored.
  • Keep your ears and eyes open for opportunities that could be a good match.
  • Help the employee take on stretch assignments to learn more.
  • Identify new experiences that require the person to deepen his or her skills.
  • Assign new projects or tasks to help build new skills.
  • Match the employee with a mentor in the department or encourage getting a peer coach to gain insight along the way.

Interested in more? Use the Career Conversation Tips guide in the Coaching & Feedback pack.

Answering Tough Career Questions

What about those really tough questions?

Let’s take a look at how to answer a few tough questions you could run into.

Tough Career Question Try Saying
What does it take to get promoted? “I understand a promotion is important to you. There are limited promotion opportunities, and we need to find the right opportunity at the right time. I’m committed to helping you. Let’s talk about the skills and experiences you need and what your current strengths and improvement areas are. Let’s put a plan together and get you ready.”
How do I get a new opportunity here? It seems impossible! “It’s not impossible. My job is to support you, help you identify the options, and work with you to put actions in place to get there. Something we can do right now is look at what you’d like to do more of in your current job. Let’s find some exciting opportunities right here as we get you ready for something else.”
Why isn’t it more clear what’s next for me? “With so much change in the company and the speed of our business, there’s no one ‘right next step.’ The good news is that there are many options within our team, on other teams, and across the company. It makes it more exciting, and it also takes more work to decide what options are a good fit for you. Let’s talk about it!”
How can I get the experience to move my career forward? “Help me understand what you want and what skills and experiences you already have. When you have an idea of where you’re headed, we can make a plan to get you there. There are lots of ways to get new experiences in your current job. Let’s figure out what you want and build the plan to get there.”
How am I supposed to spend time thinking about my career? I’m too busy! “We all face this challenge. Too much to do, and no time to slow down to think about things like our career. Let’s take some time in our one-on-one meetings to have these conversations. There are also great ways to think about your career every day as you notice what you love to do and want to do more of.”

It’s impossible to prepare for all the tough questions that can come your way, but here are some guidelines to help you approach answering tough career questions.

  • Learn more about your employees' career aspirations.
  • Let employees know you are committed to their success.
  • Provide candid feedback about their performance.
  • Manage expectations and help them be realistic given the business.
  • Help them plan for the future.

Ready to play Career Conversation Challenge? Watch below.

Building an Action Plan

Lights, camera, action! We’ve arrived at the most important part of the conversation: Action planning. It’s time to focus on the specific experiences and skills that can help employees reach their goals.

Check out how this works at your company. It might be called “Development Planning” or “Career Planning.” Even if there’s no formal process or form, figure out the best way to keep what you talk about—you’ll use it, so don’t lose it!

Get an action plan started by asking questions.


  • What steps could you take?
  • What experiences would help you learn more?
  • Who could you connect with?
  • What could help you make progress?
  • What ideas do you have?
  • How can I help?

Now it’s time to identify the actions that make sense to help your employees reach their goals. Think about how you’ve progressed in your own career. You probably learned from experiences on the job, from others, and from training or formal education. Keeping these points in mind, here’s a helpful rule to follow when you are action planning. It’s called the 70/20/10 rule.

The 70/20/10 rule is a helpful rule to follow when action planning. 70% on the job, 20% from others, and 10% from training.70% experience—Research shows that the best way for people to learn is through on-the-job experiences. When you’re coming up with actions to help employees with their careers, focus 70% of the actions on things they can do on the job.

20% exposure—People learn from others. Focus 20% of the actions you identify on sharing skills and information.

10% education—What about training? Yes, people learn through training, but it’s been shown to be the third most effective way to learn. Think about it. Unless you have an immediate chance to put the skills you learned in training into practice on the job, it just doesn’t stick. Consider including training or other educational opportunities, but your plan shouldn’t just be all about training.

Experience—Learn on the job (70%) Exposure—Learn from others (20%) Education—Learn from training (10%)
  • New assignments, special projects, increased responsibilities
  • Designing or building something new, solving a problem, refining a process, turning a project around
  • Team leadership experience, including project and cross-functional teams
  • Filling in for someone
  • Expanded job responsibilities
  • Mentoring
  • Peer coaching
  • Job shadowing
  • Networking
  • Social learning
  • Participating on a committee
  • Classroom, online, and other courses
  • Web resources, webinars, podcasts
  • Company education assistance programs
  • Books and articles

Two actions that can be part of most plans are stretch assignments and job shadowing.

What’s a stretch assignment? It’s when you make a change in a role to increase the scope of your employees’ responsibilities. It might stretch them out of their comfort zone. A great way to learn! You could give them an opportunity to lead important projects or initiatives, work across multiple teams, or influence others across the organization in a way they didn’t have a chance to before.

Job shadowing lets employees spend time with someone in another role or department to get the inside scoop in an area that interests them. It can be a 10-minute conversation or half a day together with their job shadow “host” to give them a realistic view of what another job, role, or area of expertise is all about.


At Salesforce, our employees can connect with others to participate in job shadowing through our mobile Connectr App. It takes only minutes for them to connect with an available job shadow host in a department they are interested in.

There are many ways to help others. Check out the Top 20 Ideas for Developing Others guide in the Coaching & Feedback pack.

Let’s look at an example of what’s on Ally Adventure’s action plan. She wanted to move into marketing in six months from a role in sales. One skill that she needs to build is product messaging, and she’s identified three actions to help her get there.

Sample Career Action Plan

Ally Adventure's career action plan to move from a Sales Associate into a Marketing role within 6 months.

Skill to Build Actions Time Frame Progress
Product Messaging Experience:
  • Incorporate the key messages developed by marketing into my sales pitch with key accounts and track the response.
  • Develop and deliver a presentation that reflects my unique pitch and get input on it from a marketing team member.
Exposure (others):
  • Spend two days shadowing a marketing team member to learn more about the process of developing product messaging
  • Attend a conference to see marketing messages in action.
  • Take an online course on product messaging.
  • Over the next quarter (for five accounts)
  • In 30 days (by January 31)
Update this space during regular meetings to capture progress made.

Make sure your actions are S.M.A.R.T.

Specific—Do the actions identified support the career goals?

Measurable—Can the results of these actions be measured?

Actionable—Will the actions make a difference in helping the employee meet career goals?

Relevant—Are the actions relevant to achieving the career goals?

Time Bound—Is there a clear time frame to complete these actions?

The best plans have two to three key skills identified with a couple of actions for each. Don’t let employees overdo it with dozens of actions to take. Keep it realistic and achievable!

Following Through

Now what? What do you do after the conversation?

It’s time to follow through and do the following.

  • Set aside time to have ongoing informal career conversations at least quarterly. It’s helpful to set up time separate from your regular one-on-one meetings.
  • Continue to help employees explore their career interests and options.
  • Set aside time to check in on how the action plan is going.
  • Give ongoing feedback and update the plan when needed.
  • Focus on coaching, instead of giving career advice.

In a nutshell, career conversations are just that, conversations. The pressure is off—it’s not about you knowing the future and having all the answers. It’s about asking the right questions. Sound familiar? It’s about helping others take the steering wheel, with you there to help navigate when needed.

Now that you’re all set, try it out!


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