Know What You Want Before You Walk In

by Kerry Siggins | Jul 9, 2026 | Accountability, Challenge Yourself, Communication, Feedback, Growth, Talk with Trust

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A few weeks ago, during a leadership team meeting, one of my team members made a comment that caught me off guard. It seemed small, just something he said while making a point, but the way he said it felt more like a jab than support. Right there in the room, I started telling myself a story about what he meant, but I chose not to react, as it would have derailed the meeting, and I would have done it from a place of defensiveness rather than curiosity. So I kept my cool, and we moved on.

For the rest of that week, I noticed I felt a bit tense around him. During our usual check-ins, I kept thinking about his comment and realized I was not over it yet. I wondered if it was worth bringing up. Was I making too big a deal out of it? Did his intentions matter enough to talk about? I decided it was not worth it and tried to move on.

But I didn’t really let it go. I just stopped talking about it, which is not the same thing. So I decided I needed to say something about it.

Getting Clear Before I Opened My Mouth

Before our next weekly meeting, I paused to consider what I truly wanted from the conversation. I thought not only about what I wanted to say, but also about what I hoped would be different by the end.

I wanted to let him know how his comment made me feel. I also wanted to hear his side and hoped our relationship would come out stronger, not weaker. I didn’t want it to sound like I was giving feedback or asking him to change. I just wanted to be honest about my feelings and explain that his words affected me, not because he caused it, but so he could understand me better.

During our walking meeting, I brought it up near the end. Before I spoke, I imagined how things might go if I started by saying, “That comment in our executive team meetings felt like a dig, and I would appreciate it if you did not do that in front of the team.”

That approach would have been honest, since that’s how I felt in the meeting, but it probably wouldn’t have helped. It might have made him defensive or made him feel he had to explain or apologize. Worse, we could have ended up more guarded with each other. So I stuck with my plan and told him I wanted to share how something affected me and hear his perspective.

He knew exactly which moment I meant before I even finished my first sentence. It turned out he meant almost the opposite of what I thought. He wasn’t criticizing me; he was actually agreeing with me and trying to support me in the meeting. I realized I had made up a story about something that wasn’t even true.

If I had led with my first reaction, based on how his comment hurt, I probably would have just gotten an apology instead of the real story. I wouldn’t have learned what he really meant, and that would have been a missed chance. The good news is I got what I wanted: I spoke honestly, understood his perspective, and strengthened our relationship.

The Second Conversation

A few days later, I sat down for a session in a hypnotherapy program I had started.

For years, I had an inner voice telling me I was not enough. It said I had to perform, prove myself, and take care of everyone to be successful, and that if people did not see me as a good leader, then I wasn’t one. Recently, I decided I didn’t want to live with this negative pattern anymore. I wanted to change “I am not enough” to “I am worthy the way I am.” Basically, I didn’t want to feel like I was failing just by being myself. I told my hypnotherapy coach exactly what I wanted to work on.

It was hard in two ways. Part of me didn’t want to admit certain things to myself and preferred to keep them vague. Another part was afraid of what my coach would think if I said them out loud, worried he might judge me. But I kept focusing on the outcome I wanted: breaking the pattern of feeling like I had always to perform and prove. And I knew that if I tried to protect myself from judgment, both his and my own, I would never get there. So I said the uncomfortable things anyway, every time, no matter what.

I can say that this experience has been unequivocally life-changing. Hypnotherapy works. And I doubt I would have had such transformative results if I hadn’t been really clear about what I wanted from this work.

Know What You Want Before You Walk In

Before almost anything, such as important meetings, tough conversations, and high-stakes decisions, I ask myself: What outcomes am I looking for? Not what I am supposed to want or what would look good, but what do I actually want? Why? Because every time I have skipped this step, the results have been less than stellar.

If you know what you want before something begins, you are much more likely to get it. Specifying my ideal outcome is not just a theory for me. It is why my conversation with my direct report led to the truth instead of just an apology. It is also why ten tough hypothetical sessions actually changed me. Deciding what you want first might be one of the most powerful choices you can make.

Before your next tough conversation, decision, or doing anything that matters to you, take 30 seconds to ask yourself what you really want. You retain so much more ownership when you go in already knowing.

Specifying the outcome is the first step in the SHARES model, which I cover in my upcoming book, Talk With Trust, now available for preorder. This week’s episode of the Kerry Siggins Podcast explores this topic in more detail. If you are interested in how this could work for your own team, I would be happy to talk with you. Book a time to meet with me here or reach out to me at kerry@kerrysiggins.com

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