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In a perfect world, we'd have perfect professional chemistry with all of our colleagues. But alas, it's not a perfect world—not even close. Fortunately, even if there are certain stakeholders you mesh with less than others, it's almost always possible to overcome personality clash and find a way forward.

Here are the tips I've found to be most helpful for working with, not against, your most difficult teammates.

Orient Your Team To Their North Star Early And Often

I’m not here to tell you exactly what your North Star should be made of, but I am here to tell you that you need one. If your team doesn’t have a clearly defined aspirational picture, purpose, or reason to be, they’ll suffer from disorientation.

Without a North Star, teams will find themselves having to constantly recalibrate and reorient, spending precious energy that could be put toward charting the course ahead and building something new.

Your North Star helps your team align, build momentum, and foster collaboration. These exercises can help point the proverbial telescope in the right direction.

Make it visual 

Once you’ve got a North Star defined, be sure it is captured in a document of some kind (any kind!) that your team can refer to frequently. Visuals create shared understanding when words alone fall short.

Create a document to represent the North Star your team is striving for. This could be a design crafted by a designer to inspire the team, or a storyboard illustrating how your target customer's life will be transformed as a result of your work. If you don't have visuals yet but have a vision statement, OKRs, KPIs, or any other way of orienting your team towards a shared understanding of the future, include them in a document that is simple and visual.

Remind your team to look up

Just like we can get caught up in the weeds of our day-to-day lives and forget to look up at the magic of the sky, your team can get absorbed in their work and lose sight of their purpose.

Lack of orientation is one of the primary reasons why teams end up with people pulling in different directions or stalled out without progress toward a shared common goal. So, how can you keep people oriented? Start meetings with a review of your North Star.

By consistently beginning planning and review meetings with a reminder of your North Star, your team will maintain a shared picture of where they’re headed. This also contributes to a shared sense of purpose, bringing energy and reason to the work ahead. Additionally, reminding teams of their north star can help redirect derailing questions and conversations, allowing you quickly refocus on the mission at hand.

In a recent workshop, I was able to address a leader’s potentially derailing question by reminding her of the problem statement and success criteria the group created together (which was conveniently written up on the board for all to see). I acknowledged that her question was valid, but was able to refocus her attention on the work to be done and remind her of the agreed upon direction that the team was working toward. 

When you keep the group oriented around your North Star, it’s a lot easier to keep the team on-track.

Define Roles And Routines 

I have had the opportunity to work with a variety of companies and their teams, ranging from large, established organizations to small, newly-formed startups. Regardless of size or age, my goal is always the same: to help teams work together more efficiently and effectively. A common desire I have observed is that most people wish for a magic formula or a ready-to-use way of working (a silver bullet).

And who doesn't occasionally long for that in life? We are all guilty of seeking quick fixes for our problems.

However, the reality is that every team I have worked with has had to develop their own approach based on their unique and evolving needs.

The challenge with this reality is that defining the right approach for your team requires effort: determining roles, responsibilities, and routines. Failing to do this work results in confusion, inefficiency, frustration, and resentment.

So, how can you define a way of working that suits your team? 

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Invest time

Although it may feel inconvenient to spend valuable time defining how you will work when you simply want to dive into the work itself, putting in the effort will yield better results and a more positive work experience for your team. I have noticed that startups and early-stage companies are particularly prone to wanting to jump in without clearly defining roles, and while this approach may work initially, it is not sustainable in the long run. I have partnered with teams struggling to transition from startup to scale. The most crucial work at this stage? Clarity about roles and establishing effective routines. The result? Less pain and frustration in day-to-day work, and a smoother path to growth.

Build on what works

If you have a process that has worked well in the past, start with that. Identify what is effective and areas that could be improved. If there are individuals whose roles are clear, document them.

Address pain points

Just as we identify pain points for our customers, we need to address the challenges we face as a team.

Some potential issues may include:

  • Meeting deadlines
  • Streamlining the QA process
  • Managing input from rogue leaders
  • Avoiding duplicative work

Collaborate to improve

Engage your team in defining solutions and finding ways to improve current practices. Similar to a co-creative design session, collaborate to design the optimal approach to working together. I firmly believe that teams who define what works for them are more likely to succeed than those who are dictated an approach.

Put it in writing

Once you have made decisions, document them. Create an org chart that outlines roles and responsibilities for team members. If there are gaps that need to be filled, clearly indicate that. Document the routines you will follow and specify who will lead regular meetings or communications to the team.

Regularly revisit

Revisit your approach on an ongoing basis (I recommend quarterly) and hold sessions with the team to refine it based on what is happening.

How to Address Difficult Issues

Let's say you have a North Star, clear roles and routines, and yet disruptive behavior persists. It is important to remember that people are complex and imperfect. No matter how well-defined your team's operating model is, there will be instances of disruption, derailment, and discomfort.

As a product leader, it is your responsibility (for the sake of the work and the team) to address issues that hinder effective collaboration and have the courage to address difficult topics.

Common scenarios: 

The Derailing Questioner

Resistance can manifest as derailing questions ("Why are we here?" "What are we even doing?"). You can confront this directly by reminding the person of the group's prior agreement. 

The Disengaged Stakeholder

Disengagement can manifest as not fully participating, showing up distracted, or as physically present but mentally absent. When a team member is disengaged, use your judgment to determine if you can address this issue publicly or if a private conversation would be more appropriate. Their energy may shift if you simply ask them to recommit to the work and the team. If they are on a device or visibly distracted, inquire if there is something they need to attend to and if they can fully engage once it is resolved. They may need to express grievances or share frustrations. If that is the case, listen to what they have to say and then see if they are willing to re-engage. Sometimes, just being heard can go a long way.

The Unpredictable Contributor

Whether it’s a leader, creative individual, salesperson, or anyone else, those who show up and are unpredictable contributors can be highly disruptive, as they can divert the team's attention.

Addressing this behavior can be challenging because the contributor may assert their rank or claim that their idea will generate significant sales and revenue. They’re typically excited, eager and may show up with lots of ideas or something seemingly out of left field. During these moments, acknowledge their suggestions and enthusiasm but communicate that the current focus is different. Use a whiteboard to create a "parking lot" for ideas that come up during meetings, or maintain an idea backlog in your shared collaboration tool to capture these contributions.

Prepare for difficult conversations

Check yourself

If you anticipate a difficult conversation or the presence of a disruptive team member in a meeting, take a moment to assess your own energy. It is harder to navigate a challenging conversation when you are feeling negative. Prioritize grounding yourself beforehand; a few deep breaths alone or a short walk to get fresh air can greatly help you show up in a well-prepared and composed manner.

Consider your objective

What is the purpose of addressing difficult issues and working through challenges with this team? This is where your North Star comes into play again. You are on a mission together, and the objective is not for any individual to win or be right, but to collaborate and build something remarkable. Remembering this can foster a healthy detachment from what might otherwise feel like a difficult interaction.

Do not take it personally

Although challenging in practice, this mindset makes a significant difference. When someone acts out, it is rarely about you. They may be frustrated that their idea is not gaining traction or resistant to participating in the meeting or workshop you have organized. Instead of becoming defensive or reactive, try to diffuse tense situations by asking questions and showing empathy.

The "Cliff’s Notes"

Working with challenging stakeholders as a product manager requires a combination of clear communication, defined roles and routines, and the ability to address difficult issues.

  • First and foremost, it's crucial to orient your team to a shared North Star. This means having a clear vision or purpose that everyone can rally behind. By doing so, you'll create alignment, build momentum, and foster collaboration.
  • Secondly, define roles and routines within your team. Taking the time to establish clear responsibilities and ways of working will prevent confusion, inefficiency, and frustration. It's all about finding what works best for your unique team and continuously improving upon it.
  • Third, it's important to address difficult issues head-on. No team is immune to disruptive behavior. Whether it's dealing with derailing questions, disengaged team members, or unpredictable contributors, having the courage to address these challenges is crucial for effective collaboration. When it comes to having those tough conversations, it's essential to check your own energy and mindset. Take a moment to ground yourself and remember that the objective is not about winning or being right, but about collaborating and building something remarkable together. And most importantly, try not to take disruptive behavior personally. It's rarely about you, so diffuse tense situations by asking questions and showing empathy.

By implementing these strategies, you'll be better equipped to navigate challenges and work more effectively with your stakeholders. So go ahead, foster that effective collaboration, and build something amazing!

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By Jackie Colburn

Jackie has deep expertise in technology and digital product, and is passionate about helping teams design experiences that improve people’s lives. Her customized workshops provide the structure required to quickly align and accelerate a plan or idea, whether working with startups or Fortune 50 clients. Before launching her Facilitation and Strategy practice in 2017, she spent ten years in product leadership at two digital product firms, guiding groups through the development of new business ideas and bringing them to market. She’s also a speaker, coach, and the co-author of the Remote Design Sprint Guide. Her work has been featured in Inc. Magazine and recent client work includes projects with organizations such as Target, Allina Health, and Marquette University.