Stakeholder Engagement: When to Speak Up, When to Listen, and When to Escalate
Part 2 of the "Speaking with Confidence: Communication Mastery for Mid-Career Professionals" Series
"Where do you get more comfortable saying no? When and where do you meet halfway? How do you engage with points of contact that are not responsive? When do you go up the chain? When do you not? I'm concerned about losing force with external stakeholders."
These rapid-fire questions came from a client who was managing a multi-stakeholder project with tight deadlines, competing priorities, and several unresponsive team members. She knew what needed to happen but was struggling with the interpersonal dynamics of making it happen—especially when she wasn't sure about her authority to push, challenge, or escalate.
If you've ever found yourself wondering whether to speak up in a meeting, how hard to push an unresponsive colleague, or when a situation warrants involving higher-level leadership, you're navigating one of the most nuanced aspects of professional communication: stakeholder engagement.
As someone who coaches LGBTQIA+, minority, women professionals, veterans, and individuals with disabilities through these exact dilemmas, I've learned that confident stakeholder engagement isn't about having all the right answers—it's about developing the judgment to read situations accurately and respond appropriately while staying true to your values and goals.
The Unique Challenges for Marginalized Professionals
Let's acknowledge the additional complexity that comes with stakeholder engagement when you're from an underrepresented group:
Double standards where assertiveness is praised in some colleagues but criticized in you as "aggressive" or "difficult"
Credibility building that takes longer and requires more evidence than it does for majority colleagues
Code-switching fatigue from constantly adjusting your communication style for different stakeholders
Hypervigilance about how your advocacy, pushback, or escalation will be perceived
Representation pressure feeling like your communication style reflects on your entire community
Isolation when you're the only person with your background in stakeholder discussions
For veterans, there's often the challenge of translating direct military communication into civilian workplace diplomacy. For individuals with disabilities, there may be additional considerations around self-advocacy and ensuring accessibility needs are met. The key is learning to engage authentically while navigating these complex dynamics strategically.
Redefining Professional Assertiveness
The biggest shift I help clients make is moving from thinking assertiveness is about being aggressive or demanding to understanding it as clear, respectful communication about needs, boundaries, and expectations.
Healthy professional assertiveness includes:
Speaking up when you have valuable information or perspectives to share
Setting boundaries around unrealistic expectations or inappropriate requests
Advocating for resources, support, or changes that enable success
Addressing issues before they become bigger problems
Escalating when direct communication isn't resolving important issues
Listening actively to understand others' perspectives and constraints
This reframe is particularly important for professionals who've been socialized to be accommodating or who worry about being seen as "difficult."
The VOICE Framework for Strategic Stakeholder Engagement
Here's the framework I use with clients who need to navigate complex stakeholder relationships effectively:
V - Validate Before You Advocate
Before pushing for what you need, demonstrate that you understand others' perspectives:
Acknowledge their constraints: "I understand you're working with limited budget/time/resources..."
Recognize their priorities: "I know your main focus right now is [their priority]..."
Show you've considered their position: "From your perspective, this probably looks like..."
Find common ground: "We both want [shared goal]..."
O - Offer Solutions, Not Just Problems
When you need to speak up about issues, come prepared with constructive options:
Instead of: "This timeline is impossible." Try: "Given the current timeline, here are three options we could consider..."
Instead of: "They're not responding to my emails." Try: "I haven't been able to connect with X about Y. Here are some alternatives we could try..."
Instead of: "We don't have enough resources." Try: "To deliver quality results, we'd need either more time or additional support. What options do we have?"
I - Investigate Before You Escalate
Most issues can be resolved without involving higher-level authority if you approach them strategically:
Direct conversation first:
"I'm having trouble getting the information I need for this project. Can we talk about how to make this work?"
"I've noticed some challenges with our current process. What's your perspective on this?"
Peer consultation:
"I'm running into some obstacles with Project X. Have you dealt with anything similar?"
"What's worked for you when dealing with [specific challenge]?"
Resource exploration:
"What support is available for situations like this?"
"Who would be the best person to help us resolve this?"
C - Choose Your Battles Wisely
Not every issue requires advocacy or escalation. Develop judgment about what's worth addressing:
High Priority (Address Directly):
Issues affecting project quality, deadlines, or safety
Patterns of problematic behavior or communication
Resource needs that are preventing successful completion
Situations where your expertise could prevent bigger problems
Medium Priority (Monitor and Address if Pattern Develops):
Personality conflicts that don't affect work quality
One-off communication problems
Minor process inefficiencies
Preference differences that don't impact outcomes
Low Priority (Let Go):
Personal style differences that don't affect work
Historical grievances that can't be changed
Issues outside your sphere of influence or expertise
Situations where the cost of addressing exceeds the benefit
E - Escalate Strategically When Necessary
When direct approaches aren't working, escalation can be appropriate—if done thoughtfully:
When to Escalate:
Project success is at risk due to unresolved issues
Direct communication has been attempted multiple times without resolution
Policy violations or ethical concerns are involved
Resource conflicts can't be resolved at peer level
Safety or quality standards are being compromised
How to Escalate Effectively:
1. Document your efforts: "I've tried to resolve this directly through [specific attempts] but haven't been able to make progress."
2. Focus on impact, not personalities: "The project timeline is at risk because..." rather than "X person isn't cooperating..."
3. Come with recommendations: "Here's what I think might help resolve this situation..."
4. Suggest minimal intervention: "Could you help by [specific small action] rather than taking over the whole situation?"
5. Frame it as seeking guidance: "I want to make sure I'm handling this appropriately. What would you recommend?"
The Art of Strategic "No"
Learning to decline requests appropriately while maintaining relationships is crucial for sustainable stakeholder engagement:
When to Say No:
Capacity reasons: "I want to do quality work on this, and given my current commitments, I couldn't give it the attention it deserves in that timeframe."
Scope reasons: "This falls outside my area of expertise/responsibility. [Alternative person] would be better positioned to help with this."
Resource reasons: "To take this on effectively, I'd need [specific resources]. Without those, I don't think I could deliver what you're looking for."
Priority reasons: "Based on our earlier conversation about priorities, this would mean delaying [agreed-upon priority]. How would you like me to balance these?"
How to Say No While Offering Alternatives:
Partial assistance: "I can't take on the full project, but I could help with [specific portion]."
Timeline negotiation: "I can't deliver this by Friday, but I could have it ready by the following Tuesday."
Resource suggestion: "I can't do this personally, but I know [person/resource] who might be able to help."
Scope adjustment: "I can't address all of these requirements, but I could focus on [most critical elements]."
Managing Unresponsive Stakeholders
One of the most frustrating stakeholder challenges is dealing with people who don't respond to communications:
Before Escalating, Try:
1. Vary your communication approach:
Different channels: email, phone, text, in-person
Different timing: morning vs. afternoon, different days of the week
Different format: brief vs. detailed, formal vs. casual
2. Make it easy to respond:
Specific, closed-ended questions
Multiple choice options when appropriate
Clear deadlines with explanation of why they matter
All necessary context included
3. Add value in your communications:
Share information they might find useful
Connect your request to their priorities
Offer assistance with their projects
4. Address potential obstacles:
"I know you're incredibly busy..."
"If this isn't the right time, when would work better?"
"Is there someone else I should be working with on this?"
When to Escalate Unresponsiveness:
Project impact: When lack of response is affecting deliverables or deadlines Pattern behavior: When this is a recurring issue, not a one-time occurrence
Time-sensitive: When delays create cascading problems for other stakeholders Resource waste: When teams are blocked from making progress
Building Your Stakeholder Engagement Confidence
Daily Practices:
Practice direct communication in low-stakes situations
Ask clarifying questions instead of making assumptions
Document agreements and follow up on commitments
Express appreciation for stakeholder cooperation and support
Weekly Practices:
Review stakeholder relationships and identify any issues needing attention
Assess communication effectiveness and adjust approaches as needed
Plan strategic conversations for the upcoming week
Celebrate successful stakeholder interactions and analyze what worked
Monthly Practices:
Map your stakeholder network and identify relationship priorities
Evaluate escalation decisions and learn from outcomes
Seek feedback on your communication and engagement style
Identify patterns in stakeholder challenges and develop preventive strategies
Your Stakeholder Engagement Edge
If you're working on improving your stakeholder engagement skills, here are three strategic questions:
Which stakeholder relationships are most critical to my success, and where do I need to be more strategic about speaking up, listening, or setting boundaries?
What patterns do I notice in my escalation decisions, and how can I improve my judgment about when and how to escalate issues?
How can I use my unique background and perspective to bring value to stakeholder discussions while advocating effectively for what I need?
Remember: effective stakeholder engagement is about building mutually beneficial relationships, not about winning or losing individual interactions.
Ready to Master Strategic Stakeholder Engagement?
Developing confident stakeholder engagement skills while navigating the unique challenges faced by marginalized professionals requires both strategic thinking and authentic communication. It's especially complex when you're building relationships across different levels, departments, and organizational cultures.
Through my practice, Hourglass Coaching, I work with mid-career professionals—particularly LGBTQIA+, minority, women, veterans, and individuals with disabilities—who want to engage more effectively with diverse stakeholders while staying true to their values and communication style. Together, we'll develop your advocacy skills, practice difficult conversations, and build strategies for navigating complex organizational dynamics.
I'm offering a complimentary 30-minute coaching session to readers who want to strengthen their stakeholder engagement and advocacy abilities. This isn't a sales call—it's an opportunity to explore your specific engagement challenges and develop approaches that feel authentic and effective for your situation.
If you're ready to stop second-guessing yourself in stakeholder interactions and start building the communication confidence you need to create positive change, email me directly. Let's explore how to transform stakeholder engagement from a source of stress into a strategic advantage.
Previously in This Series:
Part 1: "Briefing with Confidence: Tailoring Your Message to Every Audience"
Coming Next in This Series:
Part 3: "The Art of Simple Communication: Making Complex Ideas Accessible"
Part 4: "Building Your Professional Voice: From Anxiety to Authority"
