Hey Reader,

This week, I want to take you back to a time in one of my previous roles where everyone in the office had labelled a certain developer as “difficult.”

Now, you know me, I’m not one to let someone else’s opinion determine how I treat someone.

So instead of going through the “office whisperer” everyone else relied on, I decided to just treat that colleague like I would any new team member. I made it a point to be straightforward in my communication, focus on how I could support them, and find small, human ways to connect.

One of those moments was a simple chat over lunch in the office kitchen. Nothing deep, just two people talking about life outside of work.

From that small conversation, a genuine working relationship started to form. It didn’t happen overnight, but by showing respect and not letting other people’s opinions colour my approach, I found that this “difficult” stakeholder was really just someone who needed a bit of directness and a human touch.

In most cases, it’s down to misunderstanding or miscommunication.

But once in a while, you’ll come across someone who’s actually being difficult or disrespectful.

I want you to be prepared for both. Here’s what I’ve learned over the years:

Observe before reacting

• Look for patterns, not moments.
  • Is this person unresponsive with everyone, or just you?
  • Are they inconsistent, or consistently hostile?
  • Are deadlines slipping because of confusion or avoidance?
  • Is the client relationship being impacted by this person?

Don’t jump to conclusions - assess before you act.

Start with a direct, human conversation

• Sometimes a calm chat can cut through tension faster than a dozen emails.
• Be specific and neutral: “I’ve noticed we’ve been missing a few handoffs lately. I want to make sure we’re on the same page - is there something I can adjust on my end?”
• Tone matters more than words. You’re not confronting, you’re clarifying.

If the behaviour continues, document professionally

• Keep a neutral record: dates, incidents, who was present, and what was said.
• Not because you’re trying to build a case immediately, but because it’s your insurance if things escalate.

Choose the escalation route carefully

• If it’s a work blocker: loop in your line manager or project lead for alignment.
• If it’s personal, toxic, or discriminatory: take it to HR, and bring your evidence.
• If it’s a misunderstanding with a senior stakeholder: send a clear, factual email summarising your understanding, no emotion, no blame, just be clear.

Keep your composure

• No matter how justified you feel, emotion clouds perception.
• You want to be remembered as the person who stayed calm, fair, and professional - even under pressure.

So here’s the takeaway: when you’re managing a tough stakeholder, whether it’s a team member or a client, remember they’re human.

Before you label them “difficult,” ask whether it’s really a misunderstanding or just a different communication style. If it’s something more serious, handle it firmly but professionally - with clarity, documentation, and respect.

And hey, if you have your own story about handling tricky stakeholder situations, share it in our Skool community. (We now have a free tier!)

It’s always great to learn from each other’s experiences.

Until next time,

Yomi

​​​