How to Work with a Hard-to-Read Leader

It's not about me.

Early in my career, I had to work with a leader who was... hard to read. He avoided eye contact, seemed a bit nervous, and wasn’t one for small talk. Meetings with him were all business, no fluff, and there wasn’t much room for laughter. Honestly, I struggled. I kept thinking, Is he not interested in what I’m saying? or Does he not like me?

But over time, I realized something important: his behaviour wasn’t about me.

It was just his way of communicating. Once I figured that out, I relaxed. I stopped taking his reserved style personally and started adjusting how I worked with him. Have you ever worked with a leader who’s tough to read? Their words are few, their expressions neutral, and their feedback either cryptic or nonexistent. It’s like trying to make sense of a map without a legend.

If you’ve been there, you know how uncertain and even frustrating it can feel. But here’s the thing: working with a hard-to-read leader doesn’t have to be a constant guessing game. There are practical ways to create clarity and connection.

Why Some Leaders Are Hard to Read

There’s more than one reason why a leader might be hard to read. Some leaders are naturally introverted, others prefer to focus on tasks over relationships, and some may not realize how their communication style impacts their team.

But as a trauma-informed executive coach, I’ve also learned that sometimes there’s more below the surface. Leaders may be hard to read because of past experiences that shape how they show up at work. They could be:

• Guarded due to a fear of being judged or misunderstood.
• Focused on maintaining a “wall of strength” to avoid appearing vulnerable.
• Overwhelmed by their own challenges, making them seem distant.

Understanding this adds depth to the picture. A hard-to-read leader isn’t necessarily disengaged or uncaring. Their behaviour might stem from something below the surface.

5 Ways to Work with a Hard-to-Read Leader

1. Silence Doesn’t Always Mean Disapproval: If they don’t share much feedback, it doesn’t automatically mean they’re unhappy with you. Instead of filling the silence with worry, try asking specific, open-ended questions like: 'What’s your perspective on this?' or 'How do you see this aligning with our priorities?' This invites them to share their thoughts without feeling pressured, and gives you insight into their point of view.
2. Adapt to Their Communication Style: Every leader has a preferred way of communicating. Some might lean on quick emails over face-to-face discussions. Others might appreciate concise updates instead of detailed explanations. Pay attention to what works for them, and adjust your approach.
3. Pay Attention to Nonverbal Signals: Hard-to-read leaders often communicate in subtle ways. Look for shifts in their tone, body language, or even the pace of their responses. These small cues can reveal what’s going on beneath the surface.
4. Build Trust Through Consistency: A leader who’s hard to read might take time to open up. Show them they can count on you by delivering consistent, high-quality work. Over time, your reliability can create a stronger connection. You might be surprised.
5. Be Specific When Seeking Feedback: Asking broad questions like “What do you think?” might not get you far. Instead, focus on specifics:“How do you feel about the direction of this project?” or “Are there any areas where you think I can improve my approach?” This will help them provide more targeted and actionable feedback.

Working with a hard-to-read leader isn’t always a challenge—it’s a call to adapt your approach.

Over time, I realized that my leader’s reserved nature wasn’t about me; it was shaped by his past. One day, out of the blue, he opened up and told me that his dad wasn’t one to show emotion, and that’s something he carried with him. In that moment, all my judgments about him just melted away. It was a powerful reminder that we can’t always judge someone based on how they act on the surface. Whether they had a tough childhood or not, the real lesson is this: don’t make assumptions—take the time to understand where they’re coming from.