Having trouble influencing my boss first time round?

You can share and convey your ideas and/or recommendations through emails or discussion threads (depends on your organizational tools). Rationalizing those ideas and recommendations with additional context, information, benefits, etc., will aide in supporting your thoughts.

For instance, if an IT project, and you feel as though by doing things a different way will introduce increased scalability for future efforts, you have a clear recommendation with rationale that can be communicated to the stakeholders.