The Secret to Handling Stakeholders Early
Most stakeholder problems don’t appear out of nowhere. They grow in silence.
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In the last post, we talked about building confidence. Not the kind that appears out of nowhere, but the kind you develop slowly, by walking into uncertainty, taking responsibility, and learning as you go.
We explored how confidence isn’t something you wait to feel before you act.
It is something you grow into by showing up, by making decisions, and by handling whatever comes with honesty and effort.
If you’ve already started taking those steps, you’ve probably noticed something important.
One of the first things that tests your confidence in a real way is not a deadline or a tool. It is people. And often, it is the people who are not part of your team.
The ones who show up in meetings, ask tough questions, challenge decisions, or stay quiet but hold a lot of influence.
These are your stakeholders.
And learning how to handle them, especially early in a project, is one of the most important skills you can build.
This is not something most of us are taught in formal training. It doesn’t come with a checklist or a script. But it matters. A lot.
Because how you build trust and communication with stakeholders early on often shapes how the entire project goes.
So in this post, we’ll go deeper into that. We’ll talk about why early engagement matters, how to understand what stakeholders really want, and I’ll share a practical way to start these conversations without making it complicated.
And as we move through it, we’ll also connect this back to the kind of leader you’re becoming, one conversation at a time.
The First Myth About Stakeholders
There is this idea that stakeholder issues show up later in the project.
You’re moving along, everything looks fine, and then suddenly someone steps in with new priorities or objections.
Or worse, they disappear until the very end and then question everything you’ve built.
That does happen.
But here’s the thing most people miss: those problems don’t start in the middle of the project.
They start much earlier, but they stay hidden.
The real start of stakeholder trouble is often invisible. It begins with small assumptions.
One person thinks the goal is speed. Another assumes it is about cost savings. Someone else is worried about something they are not saying.
And because nobody talks about these things at the start, they grow. Quietly. Layer by layer.
Until the day when something important is blocked, and you realize that trust was never really built.
That is why waiting to “deal with” stakeholders until you need something from them is a mistake.
By that time, the relationship is already reactive.
It becomes about asking for help or defending decisions.
And that’s a much harder place to lead from.
Why Early Stakeholder Handling Matters
When you engage with your stakeholders early, before any tension shows up, everything becomes more manageable. Conversations are easier. People are more open. Y
ou get more space to understand their priorities and how they see the project.
And maybe most important of all, you build something that doesn’t show up in a report: trust.
Think of trust like a battery.
Every time you reach out early, share something clearly, or ask what someone is thinking before decisions are locked in, you’re adding value.
That trust battery fills slowly. And when challenges come, which they always do, you’ll be glad it is not empty.
You’ll be glad you already built something to rely on.
But if you skip this early connection, you’re stepping into the hardest parts of a project with no foundation.
And that is when even small issues feel heavy.
That is when delays feel personal.
That is when you spend more time repairing relationships than moving the work forward.
Later in this post, we’ll walk through exactly how to avoid that with a simple, honest approach.
What Stakeholders Really Want (And Are Afraid to Say)
Let’s slow down here…
Before we talk about how to approach stakeholders, we need to understand something deeper.
Stakeholders are not just titles or names in a document.
They are people.
And like any people, they come into a project with their own goals, their own stress, and sometimes even their own past disappointments.
Many stakeholders won’t say out loud what they really want, especially at the beginning.
But that doesn’t mean it’s not there.
Often, what they want is simple: They want to feel heard. Not just informed. Not just updated. Heard.
They want to feel included. Like their view matters, even if it doesn’t shape the final call.
They want to feel protected. Safe from surprises. Safe from being blamed. Safe from being on the wrong side of a failing project.
And here is the other side. Many stakeholders are quietly afraid. Afraid of wasting time. Afraid of being pulled into something they don’t fully understand. Afraid of being seen as a blocker. Afraid of being responsible for something they didn’t actually guide.
Once you see that, you can approach these conversations differently.
You don’t have to solve all their problems.
You just have to connect.
You just have to make space for honesty.
A First Conversation Framework
When you’re meeting a stakeholder for the first time, especially early in a project, you have a chance to set the tone for the entire relationship.
It’s about building a human connection and showing that you care about what matters to them.
This moment should feel natural, not mechanical.
So let’s walk through this conversation in more depth, step by step.
1. Ask about their role and perspective
Start by getting a sense of how they see their position in the project.
Even if you think you know their role based on the org chart, ask them to describe it.
You can say something like: "How does this project connect to what you're focusing on right now? What kind of involvement would be helpful or valuable for you?"
Why it matters: This helps you understand where they’re coming from, what pressure they might be under, and how much influence or responsibility they actually have, which is not always obvious from their job title.
2. Ask what success looks like from their side
Next, help them define what a great outcome would be.
Not in your language, but in theirs.
You might say: "When this project wraps up, what would need to happen for you to feel it was a win?"
Why it matters: Different stakeholders value different things. One might care about speed. Another might care about minimizing risk. Another might want visibility. If you don’t ask, you’ll assume, and you’ll probably get it wrong.
3. Ask what they’re concerned about
This is where you create space for honesty. Invite them to speak freely about what could go wrong.
Try saying: "What worries you about this project? Have you seen things like this go off track before?"
Why it matters: People are usually more open about risks at the beginning, before anything has happened. And if they’ve been burned in the past, this is your chance to avoid repeating those patterns.
4. Ask how they prefer to communicate
This step is simple but powerful.
Everyone has different rhythms. Some check email constantly. Others prefer chat or quick calls. Some want weekly updates. Others want a ping only when things shift.
Ask directly: "What’s the easiest way for us to stay connected? What kind of updates are most helpful for you?"
Why it matters: Good communication is not about frequency. It’s about clarity and comfort. When you align with their preferences, they feel respected, and that builds trust fast.
5. Ask what they’ve seen go wrong in similar projects
This is a powerful question that opens the door to valuable insight.
Say something like: "Thinking back on similar work you’ve seen before, what kinds of things tend to go off track?"
Why it matters: Stakeholders often have deep, experience-based knowledge of what derails projects. If you ask, they’ll share it. And when you show that you take their experience seriously, they become more willing to support your leadership.
Even if this conversation is short, taking these steps builds a foundation that helps you handle problems later.
You’re not just another project manager. You’re someone who listens, learns, and acts with care.
Five Common Stakeholder Mistakes (And How to Avoid Them)
Every project manager makes mistakes when dealing with stakeholders.
That is part of the learning curve, and honestly, you learn the most from the ones you wish you could go back and fix.
But some mistakes happen so often that it is worth slowing down to spot them early.
They are simple, they are human, and with a little attention, they can be handled before they cause real damage.
So let’s take it slowly here…
I will walk you through why they happen, why they hurt trust, and how you can stay ahead of them.
Mistake 1: Waiting too long to engage
What happens: You get busy setting up the project. There is so much to organize: schedules, deliverables, and resources. Stakeholders seem quiet, so you tell yourself, "I will update them when I have more to show." And before you know it, weeks pass without a real conversation.
Why it is a problem: By the time you finally reach out, the relationship feels transactional. They have no real investment in the work because you left them on the sidelines. Trust feels thinner. Every conversation becomes about negotiating or defending instead of collaborating.
How to avoid it: Engage early, when you still have nothing urgent to say. Reach out just to listen. Set a tone where they feel part of the story, not just observers of it. One simple call early on can save you hours of tension later.
Mistake 2: Treating every stakeholder the same
What happens: You create one big update email or one dashboard and send it to everyone, thinking, "This keeps it simple." No tailoring. No adjusting based on who cares about what.
Why it is a problem: When people get information that feels irrelevant to them, they stop paying attention. They tune out. Worse, they start thinking you do not really understand what matters to them, and trust erodes silently.
How to avoid it: Segment your stakeholders. Know who cares about delivery speed, who cares about quality, and who cares about visibility. Adjust your updates and conversations slightly to match. It is not about creating ten different reports. It is about acknowledging what matters to each person.
Mistake 3: Hiding risks to "protect" the relationship
What happens: A problem shows up. You tell yourself, "Let’s wait. Maybe it will resolve. I don’t want to worry people unnecessarily." So you delay sharing bad news.
Why it is a problem: Silence builds suspicion. Even if the risk is small, if stakeholders find out late, they wonder what else you have been hiding. Trust drops fast when people feel you are not being transparent.
How to avoid it: Treat risks like weather reports, not personal failures. Share them early, clearly, without drama. Say, "Here’s something we are watching. It may not become an issue, but I wanted you to know." Stakeholders prefer early visibility over late surprises, even if the news is uncomfortable.
Mistake 4: Getting defensive when challenged
What happens: A stakeholder questions your plan or criticizes a decision. Instinct kicks in. You explain. You defend. You talk more to prove you have thought it through.
Why it is a problem: Defensiveness shuts down dialogue. It signals that you care more about being right than about listening. And often, challenges carry useful information you miss when you react instead of listening.
How to avoid it: Pause. Take a breath. Instead of explaining, ask questions. Try saying, "Tell me more about what concerns you." Or, "What would you approach differently?" You might discover a better idea. Or at least, you will show respect for their perspective, even if you disagree.
Mistake 5: Overlooking the quiet stakeholders
What happens: You focus your energy on the loud voices. The ones who email you back fast. The ones who jump into every meeting. Meanwhile, the quiet stakeholders barely speak, so you assume everything is fine.
Why it is a problem: Silence does not always mean agreement. Some of the most powerful stakeholders say the least. If you ignore them, you risk missing concerns that surface late, when they are harder to fix.
How to avoid it: Proactively check in with everyone, not just the noisy ones. A simple "Just wanted to check if you have any feedback or thoughts you have not shared yet" can make a big difference. You show respect. You surface quiet concerns early. You build trust across the whole landscape, not just with the vocal few.
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Stakeholder Management Is a Trust Game
It is tempting to think that managing stakeholders is mostly about strategy.
About using the right templates, sending the right updates, and booking the right meetings.
And yes, those things help.
But at its core, stakeholder management is not about tools. It is about trust.
And trust, you will see, is not built in one big moment.
It is built quietly, almost invisibly, through a hundred small moments. It grows when you reach out before there is a problem. It grows when you show you are listening, not just reporting. It grows when you tell the truth, even when it is uncomfortable.
When trust is there, everything else becomes easier. Feedback comes faster. Problems are shared earlier. Decisions get made without endless battles. But when trust is missing, even small misunderstandings turn into major roadblocks. Meetings feel heavier. Progress slows down. The work feels harder than it needs to be.
This is why stakeholder management cannot be something you think about only when things go wrong.
It has to start early. It has to be nurtured over time. It has to be something you build not just with your words, but with your actions.
And it does not take anything fancy.
It just takes showing up with presence, with respect, and with consistency.
One Step You Can Take Today
This might feel like a lot. Maybe you are thinking about all the stakeholders you have on your current project, wondering where to start.
That is normal. But you do not need a perfect plan right now. You just need one step.
Here is something simple you can do today.
Think of one stakeholder. Maybe someone you have not talked to much yet. Maybe someone who has stayed quiet. Maybe someone you are not sure really feels connected to the work.
Reach out to them. Send a short, honest message. It can be as simple as:
"Hi [Name], I would love to hear how this project looks from your side. If you have a few minutes, I would love to understand what is most important to you and what you are seeing that I might not be."
That is it. No heavy agenda. No formal meeting invite. Just a human reaching out to another human.
And when you talk, really listen. Ask open questions. Let silence be part of the conversation if needed. Show them that you are someone who values their perspective, not just their approval.
That single action can change the whole way your next few months go.
Have you ever had a moment where connecting early with a stakeholder made a real difference?
Or maybe a moment where missing that early connection made everything harder later?
I would love to hear your story. Feel free to leave a comment or reply.
Sometimes the small lessons we learn — the ones that do not show up in formal training — are the ones that help others most.
And who knows? Your story might be exactly what another leader needs to hear today to make their next project a little better, a little smoother, a little more human.
We are all learning to lead better, one conversation at a time.
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✅ Strategic questions to align teams and stakeholders
✅ Feedback prompts to handle issues early
✅ A clear step-by-step conversation roadmap for project success