Insights, tips, and strategies for modern recruitment and career development
Startup Leadership Series - #5
Why do we struggle to find the right words?
We know the conversation needs to happen. We can see the issue, we can feel the tension, and we understand that avoiding it is not helping. But when it comes to actually speaking, we hesitate. We overthink how it will be received. We worry about saying the wrong thing, sounding too harsh, or damaging the relationship. So we delay, or we soften the message to the point where it loses its meaning. And the result is often the same: the issue remains unclear, and nothing really changes.
What makes a difficult conversation effective?
The goal of a difficult conversation is not to be perfect; it is to be clear.
What makes these conversations effective is not the choice of sophisticated words, but the ability to separate facts from interpretation, and observations from judgement. This means grounding the conversation in something concrete: what happened, what impact it had, and why it matters.
When conversations stay vague, they create confusion. When they become personal, they create defensiveness. But when they stay anchored in observable reality, they create clarity.
How do you structure what to say?
Here's the shift: instead of trying to “get it right”, focus on making it clear.
You can structure the conversation in three simple parts: First start with the situation, describe what you’ve observed, without interpretation. Then explain the impact, what this has caused, for you, the team, or the work. Finally, clarify the expectation, what needs to change moving forward.
For example, instead of saying “you’re not proactive enough”, you might say: “in the last few weeks, I’ve noticed that deadlines have been missed without updates. This creates uncertainty for the team and affects planning. Going forward, I’d like us to find a way to communicate earlier when something is at risk.”
This is not about being harsh; it’s about being specific. Because in startups, where speed and alignment matter, clarity is what allows people to adjust, improve, and move forward. And often, the most helpful conversations are not the most comfortable ones; they are the ones that make things clearer for everyone involved.