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issue #28 | date: 11/19/2025

Editors Note

Engineering wants to rebuild the entire platform. Product wants to ship fast and iterate. Sales wants custom features for their biggest deals. Finance wants to cut costs. Legal wants everything documented. Security wants to block everything until it met compliance.

And the CEO? She just wants to know why we aren’t moving faster.

Every meeting can feel like negotiating a hostage situation. You align three stakeholders, and two others will emerge with completely different priorities.

Now it’s 11 PM and you’re staring at your seventh conflicting Slack thread of the day.

What gives?

If you’re trying to make everyone happy, that's impossible.

What you need is a system—a way to prioritize, align, and manage expectations without becoming a full-time therapist for executives with competing agendas.

In this issue:

  • Why "keeping everyone happy" is a losing strategy

  • The stakeholder mapping framework that actually works

  • Tactical strategies for managing conflicting priorities

  • Jobs for people who can navigate complex stakeholder landscapes

Let's build the system.

Phedra Arthur Iruke

Editor in Chief

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Featured Job Listings

🏆 Top Picks of the Week (Hand-Picked, High-Impact Roles)

🔹 Head of Agile Development
Company: MSI (The Baldwin Group)
Location: Remote, US
Format: Full‑time (Remote)
Apply: Apply here
As a senior technology leader, you will build and scale a high‑performing Agile delivery organization across product engineering, platform and data teamsThe role defines and evolves the firm‑wide Agile operating model (team topology, cadences, metrics), establishes portfolio‑management governance, leads a team of agile coaches and program managers, and implements transparent delivery metrics while driving DevSecOps practices, CI/CD and automated testing. Requires 12+ years’ software‑delivery experience and 6+ years leading enterprise‑scale Agile transformations.

🔹 Director of Project Management
Company: FreedomPay
Location: Philadelphia, PA
Format: Full‑time (Hybrid)
Apply: Apply here
This leader oversees complex, high‑impact technical projects and manages a team of project managers, ensuring initiatives are delivered on time, within scope and Reporting to the AVP of Project Management, the role aligns technical execution with strategic objectives and is responsible for methodologies, resource allocation, risk management and continuous improvement of processes and team capabilities.

🔹 Director, Technical Program Management
Company: eBay
Location: Portland, OR
Format: Full‑time (Hybrid)
Apply: Apply here
At eBay, the Director of Technical Program Management drives strategic alignment and operational rigour across product and technology initiatives, partnering with executives to translate company objectives into actionable plans. Responsibilities include leading a portfolio of programs, building and managing a TPM/PMO team, establishing planning and reporting frameworks, and advising senior leaders while ensuring visibility, risk management, and cross‑functional execution. The role is based in Portland and designated as hybrid.

🔹 Transcend Director, Change Strategy
Company: Johnson & Johnson
Location: Titusville, NJ
Format: Full‑time (Hybrid)
Apply: Apply here
Part of Johnson & Johnson’s global ERP transformation programme, the Director of Change Strategy designs and implements change strategies to standardize processes and embed agility and continuous improvement. Duties include leading impact assessments, developing change plans, prioritizing initiatives, conducting readiness assessments, and partnering with senior leaders to cultivate a culture of transformation across Transcend. The role operates in a hybrid model based in Titusville, NJ.

🔹 Senior Director, Technical Program Management
Company: Walmart
Location: Sunnyvale, CA
Format: Full‑time (Hybrid)
Apply: Apply here
Walmart’s Senior Director leads enterprise‑wide AI and emerging‑technology programs that transform customer experiences. The role partners with senior leadership to define strategic vision, translates business goals into scalable programs, establishes frameworks for prioritization and success metrics, and drives cross‑functional collaboration across product, engineering, and business teams while overseeing large multi‑track initiatives and championing change management. Position is based at the Sunnyvale home office with hybrid flexibility.

🔹 Director, Implementation and Program Management
Company: Homebound
Location: Dallas, TX
Format: Full‑time (Hybrid)
Apply: Apply here
At Homebound—a tech‑enabled homebuilding platform—you’ll lead technology and AI implementations to improve the speed, quality, and cost of homebuilding operations. This highly visible role bridges product and operations, overseeing change management, process optimization, and cross‑functional program delivery while launching proprietary technology, aligning stakeholders, and driving platform adoption across field and central teams. Requires 8+ years in technical program management or operations strategy, strong change‑management skills, willingness to travel frequently (with regular field immersion in Texas), and the ability to translate between field needs, technical teams, and executive leadership.

📌 IC & Manager Roles

Role

Company

Location (City, State)

Format

Apply (with direct link)

M&A Integration Lead

HubSpot

Remote, USA

Remote

Product Operations Manager

LinkedIn

Mountain View/Sunnyvale, CA; San Francisco, CA or New York, NY

Hybrid

Organizational Change Management Change Lead

GlobalFoundries

Offsite (Remote)

Remote

Field Labor Coordinator

Signal Energy, LLC

Mexia, TX

On‑site

Senior Project Manager

Critical Mass

Cupertino, CA

Hybrid (3 days/week in office)

Program Manager

BlueHalo

Albuquerque, NM

On‑site with hybrid flex schedule

Program Manager

TeenWorks Inc.

Fort Wayne, IN

Hybrid (office & work‑from‑home)

Implementation Manager

phData

Remote (USA)

Remote

Implementation Manager

EnsoData

Madison, WI

Hybrid

Manager, Implementation

Lightspeed DMS

South Jordan, UT

On‑site

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Bots Take the Wheel

🤖 Auto-Track Stakeholder Engagement & Sentiment

The Problem: You have 20+ stakeholders across different orgs. You can't remember who you last talked to, what their concerns are, or who's becoming a blocker.

The Fix: Automate stakeholder tracking so you always know who needs attention before they become a problem.

Real Use Cases:

  1. Gmail + Notion: Auto-Log Stakeholder Interactions

    • Logic: Every time you send/receive email with key stakeholders, auto-log it in a Notion "Stakeholder Database" with date, subject, and sentiment indicators

    • How: Gmail filter → Identify emails from stakeholder list → Zapier → Extract: sender, subject, date, body snippet → Create/update Notion database entry → Tag with project name

    • Impact: Creates interaction history. You can see at a glance: "Haven't talked to VP of Engineering in 3 weeks—need to check in."

  2. Slack + Airtable: Track Stakeholder Requests & Status

    • Logic: When stakeholders make requests in Slack (keywords: "need," "can you," "urgent"), auto-create tracking record with: who requested, what they need, status, due date

    • How: Slack → Monitor channels for request keywords → Zapier triggers → Create Airtable record with: Requestor, Request, Channel/Thread Link, Date, Status (Open/In Progress/Closed)

    • Impact: Nothing falls through cracks. You can report: "Here are all open stakeholder requests and their status."

  3. Calendar + Dashboard: Stakeholder Engagement Heatmap

    • Logic: Track meeting frequency with each stakeholder. Flag anyone you haven't met with in 3+ weeks (before they feel ignored)

    • How: Google Calendar API → Query meetings by attendee → Calculate days since last 1:1 with each stakeholder → If > 21 days, send alert: "Haven't connected with [Name] recently"

    • Impact: Proactive relationship maintenance. Prevents "Why haven't I heard from you?" escalations.

TL;DR: Stop managing stakeholders in your head. Build systems that track interactions, requests, and engagement frequency. When you have 20+ stakeholders, your memory isn't enough—you need data.

Visionary Voices

📝 Connie Chan, General Partner at Andreessen Horowitz

Quote: "From the way she answered every question to the way she had analyzed the firm to the poise she exhibited in the very way she sat in the chair, Connie was determined to be the best at everything she did." (Ben Horowitz on Connie Chan, Source: Andreessen Horowitz)

Connie Chan joined Andreessen Horowitz in 2011 as a deal partner and became a general partner in 2018—making history as the first person ever promoted to GP from within the firm. After 12 years at a16z, she stepped back in 2024 to pursue new ventures while maintaining her board seats.

But what makes Connie's story particularly relevant to stakeholder management? She built her career navigating some of the most complex stakeholder landscapes in venture capital.

On Managing Diverse Stakeholders:
Connie is well-known across Silicon Valley for her deep knowledge of the Chinese consumer technology landscape and is often tapped as an expert to translate how trends may move from Asia to the West. This unique position required her to constantly bridge cultural, geographic, and business model differences—managing expectations across founders, limited partners, Chinese tech companies, and Silicon Valley executives simultaneously.

Her first board seat as a newly promoted GP? KoBold Metals—a mining company. "After a career as a consumer tech investor, her first deal as GP was a mining company."Talk about navigating stakeholder skepticism.

On Building Influence Without Traditional Credentials:
When a16z announced Chan's promotion to GP, it broke the firm's nine-year tradition of only hiring general partners who had been CEOs or founders. She didn't have the "traditional" operating experience that a16z typically required.

What she did have:

  • The ability to identify and support talented founders, credited with a16z's investment in Pinterest when it was valued at $200M (now valued at $12B+)

  • Deep expertise in an area the firm desperately needed (China consumer tech)

  • A track record of delivering results that spoke louder than her resume

On Strategic Relationship Building:
Ben Horowitz described her investment style as "very different than our other partners," noting that "Connie approached investments in a very different way". She didn't just follow consensus—she built conviction through deep research and brought stakeholders along through compelling narratives.

Founders who worked with her consistently cite her unique strengths:

  • Product intuition rare for investors

  • Strategic thinking that crosses domains

  • The ability to see future trends before they become obvious

On Managing Up:
Connie credits Jeff Jordan as "the one and only" who "taught me how to evaluate ideas even before they're launched. He modeled how to work with integrity, competitiveness, curiosity and humility". She also learned communication from Margit Wennmachers, "the queen of marketing herself, who alongside her team helped me find my voice and gave me the courage to use it".

She understood that building relationships with senior stakeholders wasn't about politics—it was about learning from the best and delivering results consistently.

What You Can Learn From Her:

  1. Build expertise that's uniquely valuable – Connie became the go-to expert on China consumer tech, creating demand for her insights.

  2. Results overcome credential gaps – She got promoted to GP without CEO experience because her deal track record was undeniable.

  3. Bridge worlds – Her ability to translate between Chinese and American tech ecosystems made her indispensable.

Where to Learn More:

Why She Matters to Delivery Professionals:
Delivery leaders constantly navigate stakeholder complexity—engineering vs. product, short-term vs. long-term, execution vs. innovation. Connie's career demonstrates how to build influence across diverse, sometimes conflicting stakeholders by:

  • Developing unique expertise that others need

  • Delivering consistent results that build trust

  • Bridging different worlds and translating between them

  • Building relationships based on adding value, not politics

If you've ever felt like you don't fit the "traditional" mold for leadership, Connie's story proves that results and relationships matter more than checking boxes.

Final Word:
Connie Chan's career shows that stakeholder management isn't about having the perfect resume—it's about building trust through expertise, delivering results consistently, and becoming the person everyone turns to for insights they can't get anywhere else.

Gif by nickatnite on Giphy

Weekly Recommendations

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Former Marine reveals the 5 habits that separate naturally great leaders from everyone else.

This CEO's approach to workplace resilience completely transformed how her team handles crisis situations.

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Professional Development

📚 Stakeholder Management That Actually Works

You cannot make all stakeholders happy. If you try, you'll burn out, deliver mediocre results, and satisfy no one.

Effective stakeholder management isn't about pleasing everyone. It's about:

  • Knowing who matters most

  • Understanding what they care about

  • Managing expectations strategically

  • Building influence systematically

Let's break it down.

1. The Stakeholder Mapping Framework

The Problem:
Most people treat all stakeholders equally. That's impossible and ineffective.

The Solution:
Map your stakeholders by power and interest, then tailor your strategy accordingly.

The Matrix:

High Power, High Interest → MANAGE CLOSELY
High Power, Low Interest → KEEP SATISFIED  
Low Power, High Interest → KEEP INFORMED
Low Power, Low Interest → MONITOR

How to Use It:

Step 1: List all your stakeholders

Step 2: Rate each on two dimensions:

  • Power: Can they block or significantly influence your project? (1-10)

  • Interest: How invested are they in this project's success? (1-10)

Step 3: Plot them on the matrix

Step 4: Develop strategies for each quadrant

Quadrant 1: Manage Closely (High Power, High Interest)

These are your critical stakeholders. They care deeply AND can make or break your project.

Strategy:

  • Weekly or bi-weekly 1:1s

  • Involve them in key decisions

  • Proactive communication (don't wait for them to ask)

  • Understand their personal goals and constraints

Example:
VP of Engineering who's accountable for the platform you're building on. High power (can kill the project). High interest (their team's roadmap depends on it).

Tactics:

  • Weekly sync: "Here's where we are, here are risks, what do you need from me?"

  • Early visibility into problems

  • Credit them publicly when things go well

Quadrant 2: Keep Satisfied (High Power, Low Interest)

They have the power to impact your project but don't care deeply about day-to-day details.

Strategy:

  • Monthly high-level updates

  • Only escalate when decisions are needed

  • Keep communication crisp and executive-level

  • Don't overwhelm with details

Example:
CFO who controls budget but isn't invested in technical details.

Tactics:

  • Quarterly business review: "Here's ROI, here's spend, here's risk"

  • Flag budget issues early (never surprise them)

  • Frame everything in business terms (revenue, cost, efficiency)

Quadrant 3: Keep Informed (Low Power, High Interest)

They care deeply but don't have decision-making authority.

Strategy:

  • Regular updates via email or Slack

  • Include them in planning discussions (they often have valuable context)

  • Leverage their enthusiasm (they can be advocates)

Example:
Product Manager who's passionate about the feature but isn't the decision-maker.

Tactics:

  • Include in planning sessions

  • Share docs and prototypes for feedback

  • Keep them in the loop so they feel heard

Quadrant 4: Monitor (Low Power, Low Interest)

They're affected but neither care deeply nor have much influence.

Strategy:

  • Minimal communication

  • Include in broad updates (team all-hands, newsletters)

  • Don't invest significant time here

Example:
Tangentially related team that might integrate later.

Tactics:

  • Add to the email distribution list

  • Invite to demos (but don't chase if they don't attend)

Pro Tip:
Stakeholders move between quadrants. Re-map quarterly.

Example:
A low-interest stakeholder suddenly becomes high-interest when their project depends on yours. Adjust your strategy.

2. Understanding What Stakeholders Really Care About

The Problem:
Most people think they understand stakeholders but only know surface-level goals.

The Solution:
Dig deeper. Understand:

  • What they're measured on (OKRs, performance reviews)

  • What keeps them up at night (fears, risks)

  • What they care about personally (career goals, reputation)

How to Uncover This:

A. Ask Directly (In 1:1s)

"What are your top 3 priorities this quarter?"
"What's your biggest concern about this project?"
"How does this project's success or failure impact you personally?"

B. Observe

  • What do they talk about most in meetings?

  • What questions do they ask repeatedly?

  • Who do they defer to or push back against?

C. Research

  • Read their internal docs, Slack channels, or team pages

  • Check their LinkedIn for career trajectory and expertise

  • Ask peers: "What does [Stakeholder] care most about?"

Example:

Surface-level: "The VP of Sales wants this feature shipped."

Deeper: "The VP of Sales is measured on Q2 pipeline. They have a board meeting in 6 weeks where they need to show progress. This feature unlocks a $5M deal they've been working for 9 months. If it doesn't ship, they look bad to the CEO."

Now you understand the urgency—and can manage expectations better.

3. Managing Conflicting Stakeholders

The Reality:
Stakeholders will have competing priorities. That's not a bug—it's a feature of complex organizations.

Your job isn't to eliminate conflict. It's to navigate it.

Framework: The Conflict Resolution Playbook

Scenario 1: Two Stakeholders Want Opposite Things

Example:
Engineering wants to rebuild the platform (6 months).
Sales wants to ship features now (can't wait 6 months).

Strategy:

Step 1: Find the shared goal "We both want to win more customers and scale the business."

Step 2: Present the tradeoff clearly "Option A: Rebuild now, slower short-term wins, faster long-term.
Option B: Ship features now, faster short-term wins, technical debt compounds."

Step 3: Escalate to the decision-maker "This is a strategic tradeoff between short-term revenue and long-term scalability. [CEO/COO], what's the priority?"

What NOT to do:

  • Try to please both by half-rebuilding and half-shipping features (you'll do both badly)

  • Make the decision yourself if you don't have authority

  • Let it fester without resolution

Scenario 2: Stakeholder Keeps Changing Requirements

Example:
Product keeps adding "just one more thing" to scope.

Strategy:

Step 1: Name the pattern "I'm noticing scope has expanded three times in the last month. That's impacting timeline and team morale."

Step 2: Propose a process "Let's agree: No new scope this sprint. We'll create a backlog and prioritize for next sprint."

Step 3: Enforce boundaries When they ask for "one more thing": "I hear you. Let's add it to the backlog and discuss priority in next week's planning."

What NOT to do:

  • Keep saying yes (you'll never ship)

  • Get frustrated and push back emotionally

Scenario 3: Stakeholder Is Undermining You

Example:
A stakeholder is going around you directly to your team or bad-mouthing the project to others.

Strategy:

Step 1: Address it directly (in private) "I've noticed you've been reaching out directly to my team on [issue]. Can we talk about what's driving that?"

Step 2: Understand their concern Often undermining comes from feeling unheard or uninformed.

Step 3: Re-establish communication norms "Going forward, can we agree that if you have concerns, you'll bring them to me first? I want to make sure you're getting what you need."

Step 4: If it continues, escalate "I've tried to address this directly, but it's still happening. I need your help."

What NOT to do:

  • Ignore it (it'll get worse)

  • Retaliate (makes you look petty)

4. The Art of Managing Up

The Problem:
Senior stakeholders are busy, impatient, and don't have time for your 40-slide deck.

The Solution:
Communicate like an executive.

Framework: The Executive Communication Formula

1. Start with the decision or the ask (15 seconds)

Bad: "So, we've been working on this project for three months, and we've made good progress, but there are some challenges..."

Good: "I need a decision on whether to delay launch by 2 weeks or cut scope. Here's the context."

2. Provide 3 key points of context (60 seconds)

Bad: "Well, there are a lot of factors..."

Good:
"Three things you need to know:

  1. Engineering found a security issue that needs fixing

  2. Fixing it takes 2 weeks OR we cut the admin dashboard

  3. Customer A (our biggest deal) doesn't need admin dashboard at launch"

3. End with your recommendation (15 seconds)

Bad: "So what do you think we should do?"

Good: "I recommend we cut the admin dashboard and ship on time. We can add it in v2 next month."

Total time: 90 seconds.

Senior stakeholders will love you for this.

Other Managing Up Tactics:

A. Send Pre-Reads Before Meetings

Don't make execs sit through context they could have read.

"Here's a 2-page brief. Come with questions."

B. Bring Solutions, Not Just Problems

Bad: "We have a problem."

Good: "We have a problem. Here are three options. I recommend option 2. Here's why."

C. Respect Their Time

  • Start meetings on time

  • End early if you can

  • Don't schedule 60-minute meetings when 30 will do

D. Make Them Look Good

When they ask for status in front of their boss: "We're on track. [Your Boss] unblocked us on the budget issue last week, which kept us moving."

Why: You just made them look good in front of their boss. They'll remember.

5. Building Influence Without Authority

The Reality:
Most stakeholder management happens without formal authority. You can't tell them what to do.

The Solution:
Build influence through:

A. Competence
Be so good at your job that people seek you out.

Tactics:

  • Deliver consistently

  • Solve hard problems

  • Share frameworks and insights

B. Reliability
Do what you say you'll do, every time.

Tactics:

  • Never overpromise

  • If you commit, deliver

  • Communicate proactively if something slips

C. Generosity
Help stakeholders succeed—even when it doesn't directly benefit you.

Tactics:

  • Share useful info ("Thought you'd find this interesting...")

  • Make introductions

  • Offer to help with their problems

D. Strategic Visibility
Make sure the right people know about your impact.

Tactics:

  • Share wins in team channels

  • Present at all-hands or strategy meetings

  • Write docs that get shared widely

The Result:
Over time, stakeholders come to you—not because they have to, but because they want to.

6. The Stakeholder Management Checklist

Use this weekly:

Weekly Stakeholder Audit:

  • Have I talked to my "Manage Closely" stakeholders this week?

  • Are any stakeholders moving quadrants (priority shifts)?

  • Do I have any unresolved stakeholder conflicts?

  • Have I proactively communicated project status?

  • Is anyone feeling surprised or uninformed?

  • Have I helped a stakeholder succeed this week (beyond my project)?

  • Am I spending too much time on low-priority stakeholders?

Monthly Stakeholder Review:

  • Re-map stakeholders (Power/Interest matrix)

  • Identify relationship gaps (who haven't I connected with?)

  • Review conflicts (what's still unresolved?)

  • Assess influence (am I more or less influential than last month?)

TL;DR: Stop trying to make all stakeholders happy—it's impossible. Map stakeholders by power and interest, then tailor your strategy: Manage closely (high power/interest), Keep satisfied (high power/low interest), Keep informed (low power/high interest), Monitor (low power/low interest). Understand what stakeholders are really measured on—not just what they say they want. When stakeholders conflict, find shared goals, present tradeoffs clearly, and escalate to decision-makers. Build influence through competence, reliability, generosity, and strategic visibility. Communicate like an executive: lead with the decision, provide 3 points of context, end with a recommendation.

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Until next time,

The Business of Delivery

Quiet moves. Bold Careers.

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