In this episode, Sarah dives into the art of challenging upwards — how to voice your concerns or alternative views to senior leaders without damaging your career or key relationships. Whether it’s pushing back on a strategy, highlighting risks, or setting boundaries, she shares practical strategies to navigate these tricky conversations with confidence and empathy.

Timestamps:

[00:00:00] Welcome to Unstuck and Unstoppable — intro to the podcast and today’s topic

[00:02:00] Why challenging upwards can feel difficult — the fear of damaging relationships or careers

[00:03:00] Real-life examples: My leadership experience at Amnesty International and recent client stories

[00:05:00] The importance of positioning — it’s not about disrespect, but offering an alternative view

[00:06:00] Connecting with your values and choosing your battles wisely

[00:07:00] Building strong relationships with senior leaders to create trust and credibility

[00:08:00] Developing cognitive flexibility — seeing different perspectives as a leadership skill

[00:09:00] Understanding your unconscious needs — are you driven by the need to be right or liked?

[00:10:00] Recognizing emotional triggers and giving yourself time to respond thoughtfully

[00:11:00] Crafting your message — using facts, logic, and data to resonate with senior decision-makers

[00:12:00] Language matters — why “and” is more powerful than “but”

[00:13:00] The importance of bravery — standing firm as a leader while remaining professional

[00:14:00] Quick recap of strategies for challenging upwards

[00:15:00] How I can support you with leadership coaching — connect with me on LinkedIn or my website

Useful Links

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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

Remember, you are capable of more than you know. Shine brightly, lead boldly, and unlock your extraordinary potential. Be unstoppable.

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 20.

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I am so glad you're here.

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Today's session is all about how

to challenge upwards successfully

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without it damaging your career or

your relationship with your boss.

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When can this happen?

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It could be that you disagree with

an approach or a strategy that your

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boss or a member of the senior team

is taking, or maybe you need to make

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them aware of the risks for decision

that you don't necessarily agree with.

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Or it might be around setting

some boundaries around.

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your work, or your department team's

work, or saying no to something.

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And as I've referenced, it could be

your boss that you're challenging, it

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could be a member of the senior team,

or the senior team itself, or the board,

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or it could be senior stakeholders.

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in the organization.

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And it can feel quite scary to do this.

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And I think some of this is a

hangover from conditioning, probably

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when we're at school, that you

don't challenge people in authority.

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And sometimes this can be a hangover

that we take into the workplace and

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feel that, within the hierarchy,

there are levels that we can

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challenge and levels that we can't.

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But it's also, perhaps a worry that you

might damage that relationship you have

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with that individual or individuals,

or that it could damage your career in

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some way, particularly if those decision

makers can have influence over your

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promotional prospects or, internal

opportunities or even externally.

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They might influence it.

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And also you might want to feel

like you protect your reputation.

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So you don't want to be seen as a

rebel or a troublemaker or a challenger

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and you don't want to be labeled

as difficult or even aggressive,

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so all of that can play into us.

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not wanting to challenge upwards.

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I can think of examples of this

from my own experience, but also

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from clients that I've worked with.

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When I was in my first leadership

role, when I worked for Amnesty

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International I had to challenge some

of the members of the senior team or

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my boss, they were they were directors.

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I was an HR manager.

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And because it was a campaigning

organization, it attracted people who

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had strong views, strong opinions,

strong voices, both internally and

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externally in order to be successful.

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And I was establishing the HR function.

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So I was having to introduce a

lot of HR initiatives that weren't

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their priorities necessarily.

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And I had to learn.

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possibly the hard way, how to influence

and challenge upwards successfully.

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And I'm going to share some of those

experiences today in this session.

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Also I've worked with a couple of

clients recently who are at direct level.

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One of them was relatively new in post

and had to do a restructure for her.

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department, one of her first objectives.

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And she and the chief exec had very

different views about that restructure.

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And so she had to be able to

challenge and influence upwards.

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We worked on her strategy for

doing that in some of the sessions.

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And I also had another

leadership client where.

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She was working for a scale up business

and there was lots of change, lots

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of growth and her boss was addicted

to change and there was constant

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change coming through and she had

to be able to challenge some of that

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change to protect her team in terms of

capacity and pace and so we looked at

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strategies for her to be able to do that

effectively within the context of a very

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fast paced and growing organization.

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I'm going to, share some of

those strategies today with you.

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The first thing to think about is

that you are not challenging their

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authority or disrespecting them by

putting forward an alternative view.

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Positioning it for you, that you

are putting forward this alternative

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view, it's not about doing

something that is disrespectful.

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in terms of their authority

or their position.

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So that's the first thing

in terms of positioning.

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The second thing which is important

is to connect with your values and your

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why, because this is your strength.

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And this will really help you think

through how you want to position it, but

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also what you want to challenge about.

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So it's that choosing your challenges

because you might work in a organization

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where there's perhaps lots of things

that you don't necessarily agree with

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and if that is the case then you

might want to think about whether it's

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the right organization for you but

obviously there are going to be lots

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of things that perhaps you want to

have a different approach on so it's

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choosing which ones you want to actively

challenge and you can use your values

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and your why to help you with that.

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The third thing to think about is the

relationship that you have with the

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person or people that you are going to be

challenging and hopefully you will have

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built a good relationship with them and

that they trust you because that's going

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to be an easier position for you to be

able to challenge them from so think

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about do I need to do more relationship

building before I start to think about

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challenging people who are senior to me

and in that You want to be demonstrating

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that you understand their goals, their

needs, and what it's like for them.

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Starting with them rather than you, when

you're thinking about positioning your

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challenge, because you want to be able

to show empathy for their situation and

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show that you are aware of the bigger

perspective because the higher up you

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are in the organization, the more you

have to take into account how those

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decisions impact the wider organization,

not just the team or the department.

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And having that understanding that

your boss or other senior people in the

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organization are coming at it from a

wider perspective and having empathy for

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that, that it's maybe hard for them to

make these decisions can be helpful.

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And it can also help you develop something

called cognitive flexibility, which all

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leaders, great leaders need to have.

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And that is that ability to

understand that there are different

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perspectives than your own.

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and be able to see those different

sides before making a decision.

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So you can use this as a way

to develop a great leadership

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capability of cognitive flexibility.

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And then we want to think about other

things that might be going on for you.

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Understanding your unconscious needs,

being aware of your unconscious

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needs, and how they might be playing

into this desire to challenge.

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So it's good to check in with yourself

and those unconscious needs could

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be things like, I need to be right.

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I need to look good.

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I need to be liked, I need to be

safe, and I need to be in control.

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Understanding, are those coming into play

when you're having your response to that

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particular decision, or that approach,

or that strategy, or that request of you?

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Because it's really helpful to know

that, and also to be aware of what might

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trigger you, because when you're triggered

by something what happens is that for

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the first 90 seconds, you're going to

be flooded with particular hormones,

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and you don't want to be responding

to anything in those 90 seconds.

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You want to be able to be aware

that you're being triggered, and

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you will know that because you might

get a surge of anger or frustration

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or resentment or panic or fear.

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And you want to be able to step

away and then think about how you

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want to respond when you're not

experiencing that surge of emotion.

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It's absolutely fine to be

able to respond and say.

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I've got some thoughts about that.

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I'd like to come back to you on that.

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Not feel like you have to respond

straight away because you're not

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going to give your best challenge

when you're being triggered.

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Recognizing that and also then being

aware of our unconscious needs that I

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have playing into my desire to challenge.

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Which also goes back to that, choosing

which things you want to challenge on.

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And then when you are clear about,

yes I'm going to challenge this

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decision or this strategy you want

to think about how you can get them

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to hear what you want to say to them.

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And of course, with any challenge,

you're going to be coming with

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solutions with alternative approaches.

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You're not just going to be challenging

with, I don't like this, you're going

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to be coming up with suggestions.

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To give you an example of this kind

of positioning so they can hear it,

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when I worked at Amnesty I am in the

Myers Briggs personality preferences.

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I am a feeling decision maker, which

means I'm always driven by what the

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impact on people is going to be.

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So having that strong empathy about

how people are going to be affected by

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that decision, probably why I was in HR.

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And what was interesting is that

within the senior team, the majority

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of the senior team were thinking

decision makers, which their primary

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decision making was around facts.

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Logic analysis.

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That decision making approach.

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When I started out trying to challenge

upwards, I would be coming at it

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from this is the right thing to do.

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People are going to respond

negatively to this, or this is not

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going to land well because X, Y, Z.

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And they couldn't hear that because

it wasn't important to them.

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And I had to understand that to get

them to buy into whatever it was I was

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trying to propose as an alternative, I

needed to position it in language they

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would respond well to, which was about

facts, information, logic, data, and so

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therefore once I started to do that they

began to respond more positively to the

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things I was trying to challenge around.

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Also, it's very important to think

about language, because if you go

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in with a but, they are immediately

going to be on the defensive.

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Whereas if you go in with and, Can I

propose an alternative solution for this?

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Could we discuss the pros and

cons of this particular decision?

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They're going to be much

more responsive to you.

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And it's also looking for language

that can be tempting to use,

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but really doesn't help you.

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When I was at Amnesty, it was a

unionised environment, and what I

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noticed in the union negotiations is

that they would always start with,

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when they were challenging something

with the greatest respect, which

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immediately translated into I don't

respect you at all in this situation.

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And, it wasn't helpful.

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So sometimes it can be tempting to

use these kind of languages, which

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are not they're not really going to

get you the outcome that you want.

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Thinking through definitely your

positioning, which means that.

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stepping away and coming back to

the conversation is really helpful.

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And finally, it's about being brave.

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Because, challenging does mean

getting out of your comfort zone.

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And you are paid.

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to be a leader, to be a manager, to

bring your expertise to the organization.

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And sometimes that will mean having

to let people know what that

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means in terms of a decision.

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Being able to say to senior stakeholders,

the board, whoever it might be, Let me

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just explain some of the impact that this

decision is going to have if you choose

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to take this particular route, rather

than not saying anything because you feel

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they're not going to change their minds.

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You are paid to do that.

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It means standing up and

actually being brave.

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And it's going to be a skill as a

leader that you're going to need

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over and over again as you progress

through your leadership career.

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To quickly recap, to remind

yourself, you're not challenging

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their authority or disrespecting them.

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You're presenting an alternative

view building your relationship and

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increasing the trust is going to be key.

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Showing that you've got that cognitive

flexibility that you can think about.

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See different perspectives and have

empathy for those senior stakeholders.

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Thinking about your unconscious needs,

being aware of them, thinking about

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what might triggering you and being

able to step away, thinking about

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how you can present information so

they can hear it, thinking about

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the language you choose to use and.

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being brave and knowing that

this is something you are going

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to do in your leadership career.

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If this is something that you do

find difficult, and let's face it,

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most of us do, and you would like

some leadership coaching around this

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particular area or other areas of

leadership, then please do get in touch

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Send me a direct message on LinkedIn or

via my website and we can have an initial

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conversation about how I can support you.

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with these leadership challenges.

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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 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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Have a great rest of the week, enjoy the

weekend, and I will see you next week.