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
Sign up for Weekly Career Inspiration
Learn about Leadership & Advancement Coaching Programmes
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
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.