When organizations begin a strategic planning process, the impulse is often to jump straight into defining goals, metrics, or drafting a shiny new document. But before any of that work can begin, it’s important to acknowledge what gaps you may have in your own knowledge and lived experience and, most importantly, who this planning will affect the most. Who should contribute to this work, and whose voice should shape this plan?
In our work, we’ve often seen leaders start a planning process by saying, “We don’t need to spend too much time on stakeholder engagement – I know what they’re going to say,” whether it be staff, board members, partners, or community members. However, more often than not, in-depth stakeholder engagement that truly centers stakeholder voices and experiences uncovers themes that might not have made it up to the leadership level but are still significant to those that the work affects. Without stakeholder voice, organizations often struggle to build buy-in, employees can disengage, and communities begin to view planning processes with skepticism. The process itself becomes a barrier instead of a bridge. At Trepwise, we emphasize that stakeholder engagement is much more than a box to check; it’s a foundational element for building effective strategy.
There are many approaches to stakeholder engagement, from broad listening sessions to more community-led processes (see our recent blog post on Community-Led Strategy and Planning to learn more about the different layers of community engagement). If you want your plan to succeed, you need to ensure the voices of those most affected are present, valued, and meaningfully incorporated from the start. Below are some of the lessons and behind-the-scenes realities we’ve learned about engaging stakeholders both effectively and responsibly.
1. Define Who Matters and Why
Every planning process begins with a simple but critical question: who needs to be heard?
Stakeholders can be internal (e.g. leadership, mid-level managers, staff, or the board) or external, such as partners, funders, clients, or community members. But it’s not enough to just list the “usual suspects.” Effective engagement also asks: Who will be most affected by this plan? Who carries influence? Who is often left out of these conversations?
For example, we worked with the seven state-designated Cultural Districts of Houston to shape a shared vision for arts & culture across the city. In order to do so effectively, we began by defining who needed to be at the table. We centered those most affected by the work – district leaders and staff, artists/creatives, and residents in each district’s neighborhoods – while also naming who carries influence (funders like Houston Endowment and city/regional partners) and who must be intentionally engaged to move the work: elected officials, business leaders, residents citywide, and the tourism/hospitality sector. This clarity on “who matters and why” guided an inclusive, year-long discovery process and later mobilized a network of ambassadors through HouArts in Action to keep those voices engaged in advocacy and implementation.
2. Clarify What You Want to Learn
Stakeholder fatigue is real. Communities and staff are often asked for input again and again, often with little clarity on why or what will be done with their words. This is where planning teams need discipline.
Before you send out a survey or schedule a focus group, pause to ask:
- What exactly do we want to learn from this group?
- What would success look like for them?
- What kind of “win” would they want to see from this process?
When speaking with staff members about organizational culture, for example, we’ll often ask: “When we leave here, what changes would you like to see in your workplace?” The answers occasionally surprise leadership, surfacing expectations they hadn’t considered – like improving communication and transparency, building in more intentional team building times, or implementing a new communication platform. When those ideas are surfaced early, they can become part of the plan instead of an afterthought.
3. Diversify Engagement Methods
Not every stakeholder wants – or is able – to show up in the same way. The most effective engagement processes offer a mix:
| Engagement Method | What It Offers | When To Use It |
|---|---|---|
| One-on-One Interviews | Depth, nuance, personal stories | When you need detailed perspectives from key stakeholders or those most impacted |
| Focus Groups | Dialogue, collective sense-making, shared themes | When you want participants to reflect together and surface group insights |
| Surveys (digital & paper) | Breadth, accessibility, quantitative data | When you need to reach many people, especially across diverse geographies/demographics |
| Informal listening sessions | Comfort, openness, inclusion of overlooked voices | When you want to hear from those less likely to join formal settings |
Meeting people where they are is key. For some communities, that means placing printed surveys in coffee shops or religious gathering spaces. For others, it’s offering a mix of virtual and in-person engagement to account for accessibility. When engaging staff members, you can ask yourself what whole-team meetings already exist that you can plug into (a bi-weekly all-hands meeting, for example) instead of adding another meeting to folks’ calendars. The objective is
4. Get the Logistics Right
An unglamorous truth of stakeholder engagement is that it’s a lot of project management. Without a strong process, even the most well-intentioned engagement can fall flat.
That means tracking who you’ve reached out to, when you last connected, and what follow-up is needed. It means being realistic about scheduling – external stakeholders are busy, and getting calls on the calendar almost always takes longer than expected. At Trepwise, we have a pretty structured internal tracking system to keep all the important information in one place, like who we’re reaching out to, how we’re engaging them, what we want to learn, and when we communicated with them. Without it, too much key information can slip through the cracks and negatively affect your ultimate planning outcomes.
5. Respect Time and Provide Incentives when Possible
Engagement is an investment of people’s time and expertise. Respecting that sometimes means providing compensation, especially for those directly affected but not formally involved in organizational leadership.
For example, when developing a long-range plan for the New Orleans Jazz & Heritage Festival Foundation, we engaged dozens of culture bearers who make JazzFest – and New Orleans – such a successful cultural oasis. We leveraged several different engagement and incentive strategies, including an in-person focus group for musicians so they could connect with one another and prepaid gift cards to compensate interview and focus group participants for their time, which we provided digitally or physically, depending on the individual’s needs. Incentivizing engagement and lowering barriers to participation ultimately encouraged participation and signaled how much we valued their knowledge and insights.
6. Ground in Culture and Context
Stakeholder engagement doesn’t happen in a vacuum. It is always shaped by what’s happening in the organization and in the world around it. Effective and responsible engagement creates space for what might be influencing your stakeholder’s current environment. When engaging an organization’s staff, there may be recent leadership transitions, survey fatigue, or layoffs. Externally, communities may be experiencing elections, natural disasters, or cultural milestones. Being attuned to context shows empathy, respect, and humanity, and will often result in more genuine, in-depth insights.
Living in New Orleans has given us a particular taste of this – between Mardi Gras season, when it’s nearly impossible to get on people’s parade-packed calendars; hurricane season, where we need to be prepared to pivot responsively and gracefully at a moment’s notice; or football season, when the vibe of a Monday focus group can really depend on the results of Sunday’s Saints game. Show sensitivity and authenticity for your stakeholders’ circumstances by being intentional about your energy, questions, and timing before you engage.
7. Acknowledge Power and History
Engagement doesn’t always start with a blank slate. Many communities and employees carry the memory of being asked for input without seeing results. Ignoring that history undermines trust and can cause disengagement pretty early on.
Naming it, on the other hand, creates more credibility and transparency. Beginning a session with, “We know you’ve been asked for feedback before and haven’t always seen change,” can disarm skepticism and create space for more honest dialogue, especially when followed with what you plan on doing with their feedback and how they can follow along for updates.
Stakeholder engagement isn’t only about who’s in the room; it’s also about recognizing who historically hasn’t been, and addressing that imbalance with intention.
8. Synthesize Themes Thoroughly
Listening is only half the work. At the end of stakeholder engagement, your role shifts: now it’s about faithfully conveying what you’ve heard and becoming an advocate for the experiences of those you heard from.
This is your opportunity to honor the time and energy stakeholders gave you. It means:
- Naming themes that emerged repeatedly.
- Acknowledging one-off experiences without letting them dominate the conversation.
- Recognizing that different groups may have very different experiences of the same organization.
Distinguishing between what should be viewed as a weakness, a threat, or an opportunity to build upon strength, momentum, and interest.
For instance, in one organization’s stakeholder conversations, staff consistently described a lack of career pathways. That was a weakness – an internal challenge that leadership needed to address. At the same time, external partners noted increasing competition for talent across the sector – a threat outside of the organization’s control but still shaping its environment. Yet the fact that staff were voicing a desire for more professional development so clearly was also an opportunity: it revealed energy and appetite for growth that the organization could harness to build new development programs.
Remember to stay true to what stakeholders said. You are a steward of their input, not just a filter. How you synthesize and present their voices will shape the trust they place in the rest of the process and help you build a plan that aligns with reality.
9. Close the Loop
When you wrap up your findings report, be sure to connect back with the stakeholders you engaged. Thank them again for their time, share the results with them as appropriate, and/or let them know how they can follow along to see the final outcomes of the report or plan. The way you close the loop determines whether people feel their time and insights truly mattered (or whether they’ll approach the next process with skepticism).
Conclusion
Stakeholder engagement isn’t about checking a box, collecting the most survey responses, or holding the most listening sessions. It’s about clarity, respect, and fidelity to what you’ve heard.
Done well, engagement lays the groundwork for strategy that is lived, not shelved. It creates plans that reflect real experiences and build genuine buy-in.
Ask yourself: If you were a stakeholder in your own planning process, would you feel heard, respected, and represented in the outcomes?
If you’d like support building a successful planning process grounded in stakeholder engagement, reach out to us today.
