Dealing With Difficult Stakeholders

Anything that involves humans is bound to come with its fair share of complexities. Whether it's working on a team project, managing a household, or even just navigating daily interactions, human behavior's unpredictability can throw unexpected challenges your way. In any project, product, or business, managing stakeholders isn't just a box to check off. It's the foundation of success. Your stakeholders' support can make or break your project. That doesn't mean that you have to say yes to everyone and make everyone happy all the time, which is impossible. However, whether you're a project manager, a team leader, or anyone leading a project, product, or business, knowing how to navigate difficult conversations, tackle challenging situations, and remove roadblocks is essential to keep things moving forward.

While I only had a brief module on stakeholder management during my PM studies, the real lessons came from years of hands-on experience, learning through trial and error. Over time, I discovered that building long-term, trustworthy relationships with stakeholders is not only key to success but also essential for effectively managing difficult situations. It's about knowing when to stand your ground, when to compromise, and always keeping the project's best interests at heart. Here are a few tips I've learned along the way.

1. Prioritize Stakeholders

When dealing with challenging stakeholders and potential issues, the first step is to map out all the stakeholders involved and understand their level of influence and interest in the project or product. This will help you identify at least one stakeholder who might pose challenges or have high demands throughout the project cycle. By being proactive and planning your communication, engagement, and information sharing strategies with these stakeholders, you can lower the chances of conflicts in the future and gain their early collaboration.

Remember that the intention here is not to categorize stakeholders as "good" or "bad." Instead, it is to identify potential risks of future conflicts that could cause project delays or obstacles. This method has always helped me identify all the relevant stakeholders, establish relationships positively and early on, and monitor them closely. It's all about building good relationships and ensuring everything runs smoothly.

2. Set Clear Expectations

You've probably heard the saying, "Prevention is better than cure." One of the best ways to prevent conflicts with stakeholders is by setting clear expectations from the start. By laying out what's expected and possible, you create a foundation for smoother collaboration, reducing misunderstandings and aligning everyone towards common goals.

At the beginning of every project, during the kickoff meeting, I take the time to clearly explain the goals, timelines, limitations, everyone’s role, and communication methods, including how often we'll check in. I make sure everyone understands and addresses any concerns right away. Also, whenever I set up meetings with stakeholders, I ensure that the agenda is clear, and the expected outcomes are communicated in advance. This approach has consistently helped get everyone on the same page from the start, avoiding surprises and minimizing misunderstandings down the road.

3. Constant Communication

James Clear wisely said, "It's generally better to over-communicate. Silence frustrates and confuses people. Better to communicate early and often." This is especially true when it comes to stakeholder management. Good communication is essential in any relationship, but great communication is what builds trust. It's not just about showing stakeholders that you're on top of things, reliable, and working in their best interest. It's also about keeping the lines of communication open for feedback, sharing information proactively, and trusting them to make informed decisions based on regular updates.

For example, imagine your client is expecting a feature release in the next quarter, something the management has promised. However, your team is concerned that they may not be able to deliver on time and might need to push the release to the following quarter. While it might be uncomfortable to share this news with the client, it's crucial that they're informed about the situation as early as possible. This way, they can make an educated decision and discuss alternative solutions, rather than waiting until the next quarter and facing disappointment and potential conflict when the feature isn't delivered as expected.

4. Be Kind, Empathetic, and Diplomatic

Dealing with difficult situations requires a lot of diplomacy and emotional intelligence. Most of the time, to a stakeholder's eyes, you're seen as the bouncer or the gatekeeper. But instead of closing doors, keep them open. Show them you're always ready to listen, collaborate, address their concerns, and fix issues. Melt them with kindness, and you'll find that even the most difficult stakeholders can become more cooperative and open to collaboration.

I once took over an internal project halfway through, relying on shared resources from another unit. These team members were crucial for meeting our deadline, but they couldn't allocate the necessary time because of their workload under their unit head. I've been trying to schedule a meeting with the unit head for weeks to discuss the issue, but he hasn't given me an opportunity. I also couldn't catch him for a casual chat because he's been avoiding me. After a few more deliberate attempts and with some help from another colleague, I was finally able to set up a meeting with him to discuss the issue.

At first, he was reluctant to be open and mentioned the workload and high priorities of his team, which I had already checked and knew were lower than he suggested. But after some back and forth conversation and actively listening to his concerns and reasoning, I realized the real issue. The team members had been assigned to my project without consulting him first, and he felt threatened by the loss of control over his team. I apologized for the oversight and promised to keep him informed about task timelines and priorities, ensuring he'd be involved in future resource-sharing discussions. This approach helped us solve the problem and strengthened our working relationship for the future.

5. Understand Their Needs and Listen Carefully

When dealing with difficult stakeholders, it's important to recognize that they're often pushing for something they deeply care about, whether it's their team's success, meeting specific targets, or ensuring the needs of end-users are met. Instead of looking at their demands as obstacles, listen carefully and try to understand the underlying reasons behind them. What pressures are they under? What are they trying to achieve?

The "5 Whys" technique can help answer these questions and uncover the root cause. Often, the initial conversation only scratches the surface, and stakeholders may not immediately reveal what they want and why they're resistant or unhappy. Sometimes, they might need help understanding the root cause themselves. It's your job to ask, "Why do you think that is?" or "Why do you feel that way?" after each response, digging deeper to uncover the real demand or issue. By seeing the situation from their perspective and getting to the heart of the matter, you can find common ground and work towards a solution that benefits everyone.

6. Address the Root Cause

Suppose you don't address the root causes of the issues as early as possible. In that case, you'll find yourself constantly dealing with and negotiating with stakeholders, which may become increasingly difficult over time. Stakeholders won't trust you just because you're diplomatic, kind, and easy to work with. They'll trust you when you resolve their issues and get the work done. So, it's crucial to identify root causes, find solutions, plan fixes, and communicate clearly with your stakeholders about when those issues will be resolved.

I once had a team member who was disengaged during our retrospective meetings. I tried adding some fun activities to encourage participation, but it didn't work. During a one-on-one meeting, he explained that he didn't see the point of retrospectives if we weren't actually having serious conversations and implementing the solutions we discussed. In his previous teams, retrospectives had become just a routine of noting down things without real action.

This feedback gave me a new perspective. It made me realize the importance of addressing concerns and root causes immediately. After this conversation, we made retrospectives a time to celebrate wins, truly solve the team's issues, and find ways to improve rather than just going through the motions. By focusing on real solutions and meaningful conversations, we were able to create a more productive, trustworthy, and engaged environment.

7. Negotiate and Find Common Ground

Managing difficult stakeholders is not so different from negotiating with a lawyer. They're meticulous, relentless, and always looking for the slightest advantage. You need to be well-prepared, stay calm under pressure, and be ready to find common ground without giving up too much. But remember, it isn't about winning. It's about finding a solution that works for everyone involved. When working with difficult stakeholders, start by looking for areas where your goals align with theirs. Focus on these commonalities to build a foundation for collaboration, ensuring that both sides feel heard and valued.

However, there will be times when you can't get everything you want. In these situations, being ready to compromise is key. Flexibility shows that you're committed to finding a solution that benefits everyone, even if it means adjusting your own expectations. By finding a middle ground, you can resolve conflicts and keep the project on track, all while maintaining strong, cooperative relationships with your stakeholders.

8. Don’t Take Things Personally

If you take criticism and closed-off reactions personally, you're setting yourself up for a rough ride throughout your projects. The work is never about you. Stakeholders often have reasons for disagreements and conflicts, and while it's easy to internalize that as something personal, it's important to recognize that it's usually not the case.

This doesn't mean you have to put up with rude behavior or discrimination (handling that deserves a post of its own). In my previous experience, that unit head kept rejecting my meeting requests and avoiding me altogether, and it would have been easy to assume he had something against me personally. But the reality was, he didn't even know me, and his frustration was rooted entirely in something else. The real issue was that his team members were being reassigned without his approval.

In situations like these, it's important to step back and consider why someone is acting the way they are. By not jumping to conclusions and taking things personally, you can begin to understand the real issue at hand.

9. Saying 'No' the Right Way

Steve Jobs once said, "Focusing is about saying no." But let's be honest, saying "no" is easier said than done. It's even harder to do it without burning bridges or coming across as rude. Yet, pushing back in certain situations is necessary, and being assertive without being rude is not always easy.

When working on projects, you're often faced with requests, ideas, or demands that may not align with the project's goals, and saying "no" becomes essential to maintaining focus and ensuring the project's success. The goal is to be assertive without coming across as harsh. Start by understanding the request thoroughly and gathering any necessary data or research to support your decision. When you push back, explain your reasoning clearly, showing that it's not a personal rejection but a decision based on the project's best interests.

Always choose the right communication channels, and back up your reasoning with solid research, data, and information. I highly recommend setting up a meeting or video call instead of explaining things over email. Text is a one-way communication, and your message can easily be misinterpreted. But when you're face-to-face, whether in person or via video, you have the chance to explain your decision, counter with data, and ultimately gain stakeholder buy-in without burning bridges in the process.

The Bottom Line

When it comes to managing stakeholders, teams, or clients, there’s no one-size-fits-all approach. Every person, relationship, and situation is different, and that’s what makes human interactions both challenging and rewarding. Instead of rigid instructions, we rely on guidelines, best practices, and shared experiences to navigate these complexities. Success in these situations lies in your ability to understand the unique dynamics at play and adapt your approach to match them, build trust, and foster an environment where collaboration can thrive, even when things get tough.

Every experience brings new lessons, and we all have our own ways of navigating tough stakeholder relationships. What’s worked for you? Share your advice and experiences in the comments!

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