I love the sentiment of this post from Paul Jozefak.
We spend a lot of time thinking about how we can be a good partner to our portfolio companies but each different company and each different relationship has its own rhythm.
The one thing that I have found that works consistently well in relationships with founders is asking them to ask for what they want. The founders and CEOs that get the most out of me are the ones that do this directly.
Malcolm Cowley, CEO and Founder at www.performancehorizon.com was great at this. I led his Seed Round when I was at DN Capital and in the early days we would have a weekly call for him to run through his wish-list of input and introductions. Sometimes I could help, sometimes I couldn't. But I was never left wondering what he wanted. Eren Ozagir at Push Doctor is in the same mould and it is a great trait to have.
Get to the point! Your superiors, customers, VC's and whatnot usually don't have much time. Further, they've had all the niceties thrown at them. Just say what you want. There is always a fear of being too direct and potentially screwing something up. Trust me...you will never get in trouble asking for what you want. If the other party is offended that you didn't include enough niceties then you may need to rethink the relationship.