Episode 15

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Published on:

21st Feb 2025

Episode 15 How to Have a Career Conversation with Your Boss

In this episode, Sarah dives into a topic many professionals overlook: how to have a meaningful career conversation with your boss. Whether you’re seeking growth opportunities, more fulfilling projects, or simply clarity on your next steps, Sarah shares the benefits of these conversations and a step-by-step process to help you approach them with confidence.

What You'll Learn:

  • The difference between career conversations and performance reviews
  • Why regular career discussions are vital for your growth
  • Key benefits for both you and your organization
  • Challenges you might face and how to overcome them
  • A practical framework to prepare, initiate, and follow up effectively

Show Notes:

[00:00:00] Welcome to Unstuck and Unstoppable — Introduction to the podcast and Sarah's background.

[00:01:00] Episode Overview — The importance of career conversations and why they matter.

[00:02:00] What is a Career Conversation? — How it's different from appraisals, one-on-ones, and supervision sessions.

[00:03:00] Benefits for You and the Business — How these discussions support your growth and organizational goals.

[00:04:00] How Your Boss Can Help — The role of your manager in unlocking opportunities and providing guidance.

[00:05:00] Taking Ownership of Your Career — Why you need to be proactive and drive the conversation.

[00:06:00] Common Challenges — Addressing time constraints, lack of clarity, and fear of taking action.

[00:08:00] Identifying What You Need — Clarifying the support you seek: time, capacity, connections, visibility, or guidance.

[00:09:00] Turning Challenges into Opportunities — How to navigate uncertainty and use your boss as a sounding board.

[00:10:00] How to Prepare for the Conversation — Tips for getting clear on your goals and needs.

[00:11:00] Structuring the Conversation — From setting the scene to outlining your vision of success.

[00:12:00] Requesting Feedback — How to ask for constructive insights on your career path.

[00:13:00] Exploring Ideas and Agreeing on a Plan — Collaborating with your boss to identify opportunities and next steps.

[00:14:00] Building a Continuous Career Dialogue — Why regular follow-ups are key to sustained growth.

[00:15:00] What If Your Boss Isn’t Supportive? — Finding alternative mentors, sponsors, or career coaches.

[00:16:00] Closing Thoughts — Final reflections, resources, and an invitation to connect on LinkedIn.

Useful Links

Watch the LinkedIn Live

Sign up for Weekly Career Inspiration

Learn about Leadership & Advancement Coaching Programmes

Book a Free 121 Clarity Call

Join The Love What You Do Facebook Group

Connect with Sarah on LinkedIn

Rate & Review the Podcast

If you found this episode of Unstuck & Unstoppable helpful, please do rate and review it on Apple Podcasts or Spotify.

If you're kind enough to leave a review, please do let Sarah know so she can say thank you. You can always reach her at: sarah@careertreecoaching.co.uk

Your support means the world and helps more women unlock their extraordinary potential. Remember: Shine brightly, lead boldly, and be unstoppable!

Transcript
Speaker:

Welcome to Unstuck and Unstoppable,

the podcast for ambitious female

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leaders who want to create more impact,

income, and influence in their careers.

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feel connected to their passion

and purpose, but without

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selling out or burning out.

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I'm Sarah Archer, a leadership coach

and career strategist, helping women

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like you thrive in leadership roles

while staying true to your values.

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I'm the founder of CareerTree

Coaching and have over 15 years of

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coaching experience and significant HR

leadership experience to share with you.

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I know as a female leader it can

be hard to find time to focus

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on your career aspirations.

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The day job can be all consuming.

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Plus, no matter how senior you are,

there are always going to be times

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when you feel stuck, when you have

self doubt, or feel like an imposter.

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And that's where unstuck

and unstoppable comes in.

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Each week I'll be sharing practical

strategies, insightful interviews and

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inspiring stories to help you boost

your confidence, lead with purpose

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and achieve sustainable success.

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If you're ready to stop playing

small and unlock the incredible

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potential you have within you and feel

unstoppable, you're in the right place.

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Let's get started.

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Welcome to episode 15.

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I am so glad you're here.

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Today's episode is about how to

have a career conversation with

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your boss, which is something that

people don't often think about doing.

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And what I thought I'd do is

talk about the benefits of it and

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also a process that you can follow

if you're thinking about having a

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career conversation with your boss.

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Is this something you've done?

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Have you had a specific career

conversation with your boss?

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Is it something you're thinking

about doing and maybe you're a

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little bit apprehensive about?

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Let's just think about what

is a career conversation.

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definitely something that's separate

to appraisal and performance review.

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It's separate to your one

to one catch ups.

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It's separate to your

supervision sessions.

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It is a dedicated conversation

to talk about your career.

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I would recommend you're having

these career conversations two or

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even three times a year, and that

they are separate to all those other

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types of meetings that you have.

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And there are opportunities to think

about where you are in your career

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and where you want to go and to engage

your boss, and through him or her, the

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organisation, in supporting your career

aspirations and helping you achieve them.

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And if your boss doesn't know about

what you want to achieve in your

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career, where you want to go to, how

you want to develop, then they're not

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going to be able to do the things that

they can do to enable that for you.

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It's really important to

have those conversations.

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If you're a leader yourself

as well, to have those career

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conversations with your staff.

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And I have gone into organizations and

run training sessions on How to have

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career conversations for both managers

and employees because those organizations

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have wanted to create a career culture

where those conversations are happening

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on a regular basis, because there's

lots of benefits for the organization

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of having those conversations.

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But those organizations can be rarer.

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So if it's something that's not in your

culture at the moment, it can feel a bit

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daunting to have those, which is why I

thought it would be good for us to do a

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session on having career conversations.

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Thinking about how your boss can help

you through having these conversations.

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One of the first things they can do is

give you perspective so they can give you

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their view on where you want to be, what

you want to achieve, and they can give

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you some useful insights and feedback.

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They can also be a door opener for you.

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They've probably got lots of connections

that could be helpful to you, and they

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can also enable opportunities for you.

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They've got a different view of what's

going on in the organisation, in the

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industry, and they can have you as top of

mind to position you for the opportunities

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that are going to give you what you need.

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There's lots of benefits from having

this conversation with your boss.

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And it's useful also to think about

well how's it helping the business for

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me to have a conversation about me?

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And it's useful for the business

because they can retain you when

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you think about how much it costs

to recruit a member of staff.

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It's quite considerable.

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So they can help retain you.

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They can develop you.

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They can enable you to have

more impact in the business.

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There's lots of advantages for

the business of this conversation.

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If that's been in your mind

about, can I ask for this?

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Is it going to be helpful to the business?

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There are, really valuable.

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Ripples from you having this conversation.

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It's good to position it in that way.

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But what I would say is, this is about

you driving this and being proactive.

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I say to all my clients, no

one's going to be as interested

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in your career as you are.

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Everyone's busy.

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So this is about you being proactive

and driving it and engaging

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your boss with your career.

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And I'm going to talk about

how you can do that today.

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You can use the conversation to

think about present and future.

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Sometimes when we're talking about

career conversations, you feel

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like it's always about advancement,

which it can definitely be.

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It can be, I'm here now and

this is where I want to be.

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I need help to get there.

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So that could be part

of that conversation.

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Or it could be, I'm here now and

I'm really enjoying where I am

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now, but I want to do X and Y now.

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How can you help me do that?

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It doesn't always have to be

about where you want to go.

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It can be making current,

more stimulating, more

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enjoyable, more challenging.

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So thinking about those two things

can be quite useful as well.

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But there are challenges to

having a career conversation.

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The first challenge is time, both yours

and your bosses, because when you're

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working as a senior leader, diaries

are often jam packed with meetings,

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and it can feel like, how can I?

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Find the time in my diary and in my

boss's diary for this conversation,

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but it's prioritizing you and, making

sure that you can find that time to

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have those conversations to enable

you to get from them what you need.

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It's about, okay, I've got to do this.

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I've got to find the time.

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Then the second challenge

could be around clarity.

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Feeling I've got to know the

answers to where I'm going to have

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that advancement conversation.

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And sometimes you do know where

you want to go, but sometimes it

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can feel a bit unclear, but your

boss could help you with that.

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Or it could be clarity around what

you need, because obviously The career

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conversation is about your boss coming up

with the answers for your career dilemma.

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It's about you being clear about

what you need from them and them then

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enabling that, because you don't want

to give more stuff to your boss to do

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because that's just not going to happen.

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It is about you getting clear about

what do I need from this conversation?

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And there could be different

aspects of what you need.

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It could be, I need time.

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I'm really overloaded at the moment,

but I need to prioritize my development,

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I need my boss to help me create time.

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Working out what can I not do, or how

can I do things differently to create

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that time to get the development

exposure, whatever it is I need,

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or it could be about capacity.

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I really want to work on this

particular area of work because I

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want to have impact in this area.

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But with the resources I currently have,

I don't have the capacity to do that.

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But there's real business

benefits of me doing that capacity

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work or that impactful work.

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How could I?

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increase my capacity

to be able to do that.

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And your boss can help

you think that through.

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It could be around connections.

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As I mentioned, your boss is

probably well plugged into the

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industry, to the organization.

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It could be being able to put

you in touch with people who can.

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Help you in some way it could be

visibility, if I want to be keynote

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speaker at this conference or I want

to be a thought leader on this, your

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boss is going to have some great

ideas about how you can access that.

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Or it could be guidance, noticing

what are the gaps for you in

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terms of where you want to go.

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They can give you some guidance

about how you can plug those gaps.

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It could be job information, maybe

your boss has walked the route that

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you want to take and they can give

you information about what's the

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reality of this next role for me?

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What the challenge is, what the Highs,

what do I need to be looking out for?

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Being clear about what you need from

them, and you're not necessarily going

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to ask for all of these things, but it

can help you use that time wisely and

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get from them what you really need.

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It can feel challenging

to get that clarity.

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But it might be saying to your

boss, I need clarity, I need this

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career conversation to help me

work out what it is I really need.

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And they can just be that

sounding board for you.

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And then there could be a challenge

around taking action, I'm going to

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have this conversation, but then

I'm going to have to take action.

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I just don't have time to do that.

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But, it is important to be able to

move things forward by having these

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conversations and recognizing actually.

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It's being proactive in your career and

you're prioritizing your career, which is

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as important as prioritizing your work.

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So noticing the challenges, but

still deciding, yes, this is

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something I really want to do.

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It's going to be valuable to me

to have this career conversation.

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Let's think about then how

you make it happen and how you

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utilize that time really well.

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The first thing I would

say to you is prepare.

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Getting clear, am I talking

to my boss about future?

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Am I talking to them about present?

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And thinking about what you need and

what you want, but not feeling like

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you've got to have all the answers,

but certainly you're not just going to

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go into that conversation unprepared

because that's going to be a waste

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of time for you and for your boss.

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Then you want to establish this dedicated

meeting, so you want to be clear that

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you want to talk to your boss about your

career, that it is a career conversation.

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So they're not going

to have any surprises.

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They're not going to think they're

going to be talking to you about, the

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project you're running at the moment

or whatever, they know that you want to

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have a career conversation with them.

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And then in the actual meeting, you

want to start on a positive note.

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Cause imagine if one of your direct

reports books in a career conversation

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with you, you might be thinking,

Oh God, are they going to resign?

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Are they going to be

asking for a pay rise?

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You're going to be maybe anticipating.

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The worst.

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So you want to open that conversation

on a positive note and setting the

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scene, reassuring them maybe that you're

not, you're not going to be leaving.

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You're committed to your current

role, to the organization, you will

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value their insight into your career.

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You're setting the scene for them.

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They're not going to have to be

on their guard because they think.

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You're going to want a pay rise

or a a negotiation around, the

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fact that you might be leaving.

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You might want to then

discuss your journey so far.

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You might want to remind them

of what you've done already,

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where you are in your career.

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It depends perhaps what your relationship

is like, how distant they are from

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your your previous career or how long

ago it was that you were interviewed

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by them, but you might want to remind

them about your journey so far.

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And then you probably want to outline

what your vision of success looks

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like, whether that's advancement in

terms of where you want to move to.

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And your time scale for that, or

whether it's about your current needs

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to make your current career even better,

your current job more fulfilling.

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And then you might want to ask them

for some feedback around what do they

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see as maybe some gaps for you or

some things that you could do more

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of, things you could do less of.

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those kind of conversations, getting some

really useful feedback on your career.

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Remember, it's not performance

review, you're not asking them for

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performance feedback, you're asking

them for feedback around your career

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aspirations because, you're wanting

their guidance in terms of your career.

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And then it's doing some

exploration about what are their

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ideas, what are their thoughts

about how you could approach this.

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Because you might have come up with

some ideas about what you want them

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to help you with, but they might

have other perspectives as well,

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which are going to be useful.

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And then you want to agree a plan, so

if you're asking them for, you want

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them to look out for opportunities

for you to engage more with a.

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with the C suite or maybe you're asking

them to look out for opportunities for

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you to speak on behalf of your department

or in your industry or, whatever it

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is you've identified you'd really like

their support on, you're going to agree.

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Those things with them, and then you're

going to book in the next meeting,

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because you want to have these career

conversations on a regular ish basis.

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It might be saying, I found this really

valuable, can I book in another career

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conversation with you in six months?

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Thinking about, what time

frame is going to work for you.

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But getting that in the diary, again,

is going to help you stay focused.

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I've had this conversation, I

need to, move progress forward.

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So in six months I'm not having

the same conversation with them.

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And also they're then again

committing to supporting you

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within your career aspirations.

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And then you might want to, after

the meeting, do a follow up.

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Confirming what you've agreed

or summarising the conversation,

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which would be helpful for

you, but also for them to know.

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What you're looking for from them.

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Again, you're going to be

a senior manager yourself.

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So thinking about what's helpful to you.

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If you've had that conversation with

your direct report, is it helpful to

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know point by point or just overview

what's going to be most useful.

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And again, you can also think about.

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In terms of preparing for that

meeting, what your boss is like in

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terms of how they communicate, how

they take in information, are they

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really big picture and less granular?

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Are they quite granular about stuff?

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Thinking about How to get the best

out of that conversation, is it

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better to do the big picture with

them and then you do the more detail

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and get them just to agree to it?

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Or are they good at coming up

with solutions and generating

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ideas or, are they somebody who

likes preparation in advance?

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Do you need to send them a bit

of an agenda about what you

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want to talk through with them?

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So being strategic about how you're going

to get the best out of this time with them

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is going to mean that you're going to meet

what you need from it, but also they're

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going to find it a useful experience

and they're going to be open to having

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another career conversation with you.

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And the final point to say is if you

feel like you don't have this kind of

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relationship with your boss that you could

have this type of conversation because

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let's face it, sometimes our relationship

with our line manager can be challenging.

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If that's Something you don't feel

you can do with your current boss.

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And it's looking for somebody

else that you could have this

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career conversation with.

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That might be somebody else

in the organization that you

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have a good relationship with.

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It could be a previous boss who

you value their insights in.

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It could be that you have a mentor that

you could have this conversation with.

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Or it could be that you feel

actually maybe a career coach

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would be somebody that I would

need to have this conversation with

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because I don't have access to it.

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internally or externally.

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But, knowing that actually there's a lot

of value you can get from having other

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people's perspective around where you want

to take your career or how you want to

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make your current role more fulfilling,

more stretching it's very valuable.

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I hope you felt inspired to

have a career conversation.

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And I would love, to know from

you, if you do go on and book

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some time with your boss and.

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Follow that kind of loose ish structure

around having a career conversation.

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I'd love to know how you got on.

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This episode is also available

as a LinkedIn Live and I'll put

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a link for you in the show notes.

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And while you're over on LinkedIn, please

do connect with me if we're not already

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Thank you so much for listening

to this episode of the Unstuck

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and Unstoppable podcast.

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I have lots of free resources you

can access on my website, ww.career

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tree coaching.co

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uk, and I'll also put

links in the show notes.

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If you found this episode

helpful, then please subscribe

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so you don't miss the next one.

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And please do share it with a

friend and leave me a review

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and I will personally thank you.

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Remember, you're capable of more

than you know, shine brightly.

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Lead boldly and unlock the

extraordinary potential within you.

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Be unstoppable.

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About the Podcast

Unstuck & Unstoppable
Career Talk For Ambitious Women
Unstuck & Unstoppable is the go-to podcast for ambitious female leaders ready to amplify their impact, boost their income, and achieve career success on their own terms—without burning out or compromising their values. Hosted by Sarah Archer, a leadership coach and career strategist dedicated to empowering women in leadership, this show provides the tools, strategies, and inspiration you need to thrive in your career.
Whether you’re looking to overcome imposter syndrome, enhance your leadership skills, or create a sustainable path to success, each episode will offer actionable insights, expert interviews, and real-life stories to help you take your career to the next level.
It’s time to stop playing small, unlock your full potential, and create the impact you’re destined for. Tune in weekly to discover how you can lead boldly, live fully, and succeed with confidence and integrity.

About your host

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Sarah Archer