Squiggly Shortcut: 3 Ways To Stand Out To Senior Stakeholders

Podcast: Squiggly Careers
Host: Helen Tupper
Episode Date: October 30, 2025

Episode Overview

In this Squiggly Shortcut episode, host Helen Tupper addresses a crucial topic for career development: how to stand out to senior stakeholders. With her trademark practical approach, Helen outlines three actionable strategies that listeners can implement immediately to build better relationships and advance their careers. The episode is concise, focused, and packed with tips to help professionals connect meaningfully with those in positions of influence.

Key Discussion Points & Insights

1. Why Stand Out to Senior Stakeholders?

(01:17 - 02:06)

• Importance: Senior stakeholders offer three major benefits—support, sponsorship, and learning opportunities.
  • "People that tend to be more senior can offer us support, so they might have access to projects that we want... They can also give us sponsorship, so those people could potentially be the door openers for your development." – Helen [01:17]
  • They are also sources of knowledge and experience.

2. Three Strategies to Stand Out

(02:06 - 10:00)

1. Position Yourself as a Peer

(02:30 - 04:22)

• Reframing Mindset: Arrange your thinking so you engage with senior people as peers, not subordinates.
  • "Sometimes we kind of hold that hierarchy in our head... you're not engaging with them in a really kind of curious and conversational way." – Helen [02:43]
• Practical Tips:
  • Enter conversations with curiosity.
  • Seek connection points rather than striving for perfection.
  • Consider what questions you’d ask if you saw them as an equal.

2. Go Further with Your Follow-Up

(04:22 - 06:20)

• Beyond the Basic Thank You: Don’t just send a courteous message after a meeting; add tangible value by sharing something useful.
  • "If you want to stand out, I'd recommend you go further with your follow up... Could I create a quick presentation or could I experiment with something in AI and show them what I've generated?" – Helen [05:09]
• Suggestions:
  • Share relevant resources, ideas, or a quick experiment based on their advice.
  • Demonstrate that you’ve actively worked with their feedback.

3. Build Connections They Care About

(06:20 - 09:15)

• Understand Their Priorities: Find out what excites or matters to them—be it diversity, performance, innovation, or tech trends like AI.
  • "If you can find out what their particular priorities or passions might be... think about who you could connect with inside or especially outside of your company that could become useful for them." – Helen [06:40]
• How to Deliver Value:
  • Build a network in areas of their interest.
  • Connect those resources or networks back to your senior stakeholder.
  • Example: Helen mentions bringing external innovation network contacts into her company, providing unique insights senior leaders valued.

Notable Quotes & Memorable Moments

• On Reframing Relationships:
  "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?" – Helen [03:08]

• On Adding Value through Action:
  "Show that you've done some work with their words... that will make you stand out. 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." – Helen [05:22]

• On Creating Unique Impact:
  "Those connections can be really valuable to that senior stakeholder... it was a really unique value that I could add." – Helen [08:22]

Important Timestamps

| Time | Segment | |-----------|----------------------------------------------| | 01:17 | Why Stand Out to Senior Stakeholders | | 02:30 | Strategy 1: Position Yourself as a Peer | | 04:22 | Strategy 2: Go Further with Your Follow-Up | | 06:20 | Strategy 3: Build Connections They Care About| | 09:50 | Reference to Longer Episode #334 |

Further Learning

For those looking to dive deeper, Helen recommends Squiggly Careers Episode 334, dedicated to "How to Stand Out at Work." Find it on amazingif.com or in the show notes.

This episode provides a practical, encouraging roadmap for navigating relationships with senior stakeholders—equipping listeners with clear tactics and the confidence to act.