Many of my coachees bring a similar concern into our sessions. They want to raise an issue with their boss, but they anticipate resistance. They worry about how the conversation will go, whether they will be heard, or whether it will quickly turn into a back-and-forth of objections.
So we slow down and do an exercise. Before thinking about what they want to say, I ask them to step into their boss’s perspective.
The Exercise: Objections First, Alignment Next
We start by asking these key questions:
What might their boss be concerned about?
What pressures are they under?
What might they push back on?
And just as importantly, where is there alignment?
By mapping this out, you’re not just anticipating pushback; you’re finding common ground in advance.
And this creates a shift. They are no longer walking into the conversation hoping their boss will see things their way. They are preparing to meet them where they are.
When you demonstrate that you understand your boss’s priorities and concerns, you shift how you are perceived. You are no longer just raising an issue, you are showing up as an ally and a strategic partner focused on moving things forward.
Why This Works
This is the same principle that top sales professionals use. They don’t start by ignoring objections. They address them early and show they understand the other person’s needs.
A Collaborative Approach
Once you’ve signaled alignment, the conversation shifts. You’re not just presenting an issue, you’re inviting your boss to solve it with you. Just like a collaborative sales call, you position the discussion as a joint effort toward a shared goal.
From Resistance to Partnership
Next time you’re preparing for that tough conversation, take a page from both coaching and sales. Start with what you know they care about, address the concerns upfront, and watch how partnership grows where resistance once stood.
What’s one conversation you’ve been putting off because of expected pushback? How might starting with alignment change how you approach it?
