Squiggly Shortcut: 3 Ways To Stand Out To Senior Stakeholders

30 Oct 2025 · 5 min · 5 chapters

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In short

How to stand out to senior stakeholders (managers or influential business leaders) to gain support, sponsorship, and learning opportunities.

Guest backgrounds

No guests mentioned; host Helen from the Squiggly Careers Podcast delivers the advice.

Key claims

Senior stakeholders can open doors to projects, roles, sponsorship, and experienced guidance. To stand out, (1) position yourself as a peer by reframing hierarchy and using curiosity-driven questions; (2) go further than a “thanks” follow-up by sharing value using their words (e.g., a quick presentation or AI-generated experiment); (3) build connections aligned to what they care about (e.g., young female leadership, performance/efficiency, AI).

Notable examples

Creating a presentation or AI output from their insight; bringing innovation-network connections into big companies to share insight.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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The Importance of Senior Stakeholders

1:35 to 2:17

Understanding the benefits of standing out to senior stakeholders in your career.

“So the first thing I guess to talk about is why?”

Positioning Yourself as a Peer

2:17 to 4:00

Learn how to engage senior stakeholders by reframing your mindset.

“So those people could potentially be the door openers for your development.”

Enhancing Your Follow-Up

4:00 to 4:49

Strategies to improve follow-up communications with senior stakeholders.

“Second idea for you is to go further with your follow-up.”

Building Valuable Connections

4:49 to 6:06

Discover the importance of connecting with people that matter to senior stakeholders.

“And last but not least, I would say build connections that they care about.”

Further Resources on the Topic

6:06 to 6:20

Information on finding additional episodes related to standing out to senior stakeholders.

“If this is a topic that you would like to learn a bit more about, we've done a much longer episode on it.”
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Transcript

Automatic transcript. May contain errors.

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1:17Learn more at schwab.com slash trading. Hi, it's Helen from the Squiggly Careers Podcast. and you're listening to one of our squiggly shortcuts. These are shorter episodes that we release every Thursday and they're focused on a very specific situation which we think can help you in your squiggly careers. And today I want to talk about how to stand out with senior stakeholders. This could be your manager, it might be somebody else in the business who has influence over your impact and there are some simple ways in which we can stand out more with these people that are going to have quite a significant impact on our career.

1:53So the first thing I guess to talk about is why? Why bother? Why do we need to put our effort into standing out with these people? Well, like it or not, people that tend to be more senior can offer us support. So they might have access to projects that we want to go on, or they might have influence over roles that we want to go into, as well as the support. So the experience we could get through them, they can also give us sponsorship. So those people could potentially be the door openers for your development. And also they've probably done some things that you might want to do. So senior stakeholders are probably more experienced than you and therefore they are brilliant people to learn from.

2:32So support, sponsorship and learning are kind of pretty powerful payoffs from building better relationships with these people. But how do we do it? How do we stand out with these people so that we can start building better relationships. I've got three ideas which I would love you to start thinking about what this might look like for you. So the first one is to position yourself as a peer. Now let me explain why I mean by this one. When you are talking to somebody who is more senior than you sometimes we kind of hold that hierarchy in our head and it affects how we talk to them because we might think that we are less them or not as important as them.

3:12And so from the outset, you're not engaging with them in a really kind of curious and conversational way. Whereas if you go into the conversation and you're not thinking, this is a senior person that I should be scared of. But if you're actually thinking, what would it look like if I was to position myself as a peer? What questions might I ask? How might this feel more conversational rather than I feel like I have to present and be perfect for this person? So whenever I'm doing this, and I have this all the time with people that come on the podcast, and do I think are, you know, they're really sort of senior stakeholders in the world of squiggly careers because of the research that they might have done, it's not really helpful for me to hold that in my head.

3:52So instead, I think position yourself as a peer. What questions do you ask? How do you demonstrate curiosity? How do you try and find points of connection? That's what works well for me. So that's the first one. Second idea for you is to go further with your follow-up. So you know with a senior person you might have some time with them and then you might send them an email afterwards and say you know thanks for your time, really appreciate it, found it really useful. That's a follow-up but if you want to stand out I'd recommend you go further with your follow-up. So think about what could you share that might be useful for them.

4:24Show that you've done some work with their words. So if you've had a chat with them and they've given you an idea or they've shared an insight think how could I turn that into something that could be more useful? Could I create a quick presentation? Or could I experiment with something in AI and show them what I've generated? That will make you stand up. So it's rather than just a thank you, it's sort of like the thank you and that we want to get used to doing with these particular people. And last but not least, I would say build connections that they care about. If you can find out what their particular priorities or passions might be, maybe they're really interested in young female leadership or maybe they're particularly interested in performance and efficiency or maybe they're a massive advocate for AI whatever it is they are passionate about or is a priority for them right now think about who you could connect with inside or especially outside of your company that could become useful for them so I would start to think about networks that you might want to spend time in I would start maybe connecting with people who do roles in those areas, but in other companies.

5:31And those connections can be really valuable to that senior stakeholder. I've done this several times with innovation networks, for example, when I was doing roles in big companies, I brought those connections into the companies to share insight. And it was a really unique value that I could add. So three different things that you can do to stand out to your senior stakeholders. First of all, position yourself as a peer. A lot of that is about your own reframing in those conversations. The second, go further with your follow-up. Make sure you're adding value. Think thank you and. And the third one, build some connections that they care about.

6:06If this is a topic that you would like to learn a bit more about, we've done a much longer episode on it. It's episode 334 of the Squiggly Careers podcast. So you can either just search for that on our website, amazingif.com, or we'll put the link in the show notes. Thanks a lot. We're back again soon.

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From the publisher

✨ Welcome to Squiggly Shortcuts— a series from the Squiggly Careers podcast, bringing you quick career tips in just 5 minutes, every Thursday. In this shortcut, Helen shares three practical ways to stand out with senior stakeholders — the people who can influence your impact, support your development, and open up new opportunities. Whether it’s your manager or another leader in your organisation, these ideas will help you build better relationships and be remembered for the right reasons.


Episode 507


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⏱️ Timestamps


00:00 Welcome to Squiggly Shortcuts

00:28 Why senior stakeholders matter

01:05 Idea 1 – Position yourself as a peer

02:10 Idea 2 – Go further with your follow-up

03:55 Idea 3 – Build connections they care about

05:10 Where to learn more


🎯 What You’ll Learn


- How to build confidence and connection with senior stakeholders

- Why going beyond “thank you” helps you stand out

- How to add value by linking people and priorities


🎧 Listen to Episode 334 to learn more: https://youtu.be/N_J9EySKxgg?si=6NRrcjFlDINWtVdp


For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com


More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join the Skills x AI Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

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