As technical leaders, our job is very often to convince others of something. Maybe convince your team to adopt a new campaign. Maybe convince another executive to accept your recommendation. Likely to convince your boss that you are doing a good job. As you consider these goals, it is important to evaluate your actions through the lens of those you want to convince.

I recall a time when I was putting together a strategy for product development. I wanted my boss to have confidence, so I worked to flesh out the details and be sure the logic was sound and compelling. When I presented the strategy, my boss spent almost no time on my detail and instead asked how my team felt about it. It struck me as the wrong question to ask; but I realized if I wanted his confidence it was the question I would have to answer.

As senior technology executives, it is not unusual for us to have very different default behaviors than our bosses. Especially if you are the senior most executive, your boss may be from sales or other parts of the organization that rewards fast-paced, people-oriented behavior styles. As you consider how you will engender confidence, remember that that works for you may not work for her.

I recall a time when I arrived prepared to discuss the addition of a new position on my team with another executive. I was asking for more budget, and I knew that it would not be given easily. When I shared a one-page summary of the role and the benefit, I was shocked that the response from my colleague was dismay that I had wasted time preparing a document for the conversation. He clearly valued action and activity over plans and preparation, to a point where my preparing a plan was a negative reflection on how effective he thought I used my time. I never made that mistake with him again.

Your boss may value the opinion of others more than you do. She may look for action rather than a detailed plan. She may want high level vision rather than details and numbers. Ask yourself what resonates with your boss when you want to make an impact, especially if there are signs that your boss sees things differently than you do.

As we consider what we are seeking to achieve, it is important to understand the lens through which the listener views us. When we blindly pursue a style that works for us, we may stumble when we find the listener sees our argument very differently.