The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

Before shooting a blasé email to a new client or pinging a colleague about a problem on Slack, consider the following: Is this a one-way share of information or is it conversational? Email is a great way of blasting off information for people to consider on their own schedule; they can respond whenever they like, and you are likewise not pressured to reply until you’ve gathered your thoughts. As casual as it can sometimes feel, however, emails are not conversational: They lump all of your thoughts together rather than allowing two people (or more) to spar point to point. This means they also come with a high chance of misunderstanding. Email is an effective way to inform people of something, but if you’re aiming to influence others and generate a deep understanding, choose a conversational format instead, like back-and-forth messaging, picking up the phone, or an in-person conversation. Is the topic collegial or is it sensitive and potentially controversial? Whether it is via Slack, Facebook Messenger, WhatsApp, iMessage, or whatever your preferred texting service, casual conversations best take place over a real-time messaging system. However, the bite-size quality of this form of messaging means it’s not well suited to discussing complex matters. Its text-based nature also strips away the tonal nuances of voice and the inaudible visual cues of discomfort. If your topic is sensitive, push yourself toward a more intimate medium—especially if you find yourself preferring te...