Same as for any important meeting: get a decent sleep, arrive on time, look appropriate, behave well, and (I guess you're doing this bit) have the content prepa

Same as for any important meeting: get a decent sleep, arrive on time, look appropriate, behave well, and (I guess you're doing this bit) have the content prepared. The advantages of meeting over a coffee are that it is quick, you're on roughly neutral territory, and there's an opportunity to feel things out enough to decide whether it's worth taking things to the next level both personally and technically. Being able to concisely describe what you've done in the past, what you'd like to do in future, and why you approached the firm should cover the bulk of the work content. Having an opinion on related technology issues is good, and I usually ask semi-random questions outside of work stuff too, just to get a feel for the person: nothing too controversial, but just conversational. Even if you're interested in a purely technology role, demonstrating that you can talk to strangers doesn't hurt. It could be a little as 15-20 minutes; it could last for hours. Be ready for either. CTOs are usually very busy people, so get to your points and don't waffle. Try to pay, but don't insist. Thank the person for their time. Send a followup thank-you email (and do anything else you said you would too). Good luck!