There are numerous ways we give each other advice in the technology company ecosystem. There are formal relationships like board members, formal advisors and professional service providers like myself and informal relationships such as industry mentors, investors and just old fashioned friends. This support network is sustained and nurtured by the satisfaction the advisor receives from giving advice that works out well. The advisor feels good about the benefits of her advice and the advisee has his fortunes improved.
Another side of that coin appears when the advice is not followed and negative consequences ensue. In these instances, the earnest advisee will often call to say “I should have listened to you.” In my view, this means that the advisor failed to do her job. On first blush, that might seem a harsh judgment. If a chef cooks up a fabulous meal, should she be blamed when the diner elects not to eat it? A good advisor, however, can both provide an answer that is substantively correct AND do so in a manner that will persuade the listener to follow such advice. “I should have listened to you” or ISHLTY indicates that only half of the job was done. That acronym looks remarkably like I SHITTY and I suspect that is because only a shitty advisor feels good when hearing this news.
How then to avoid being a shitty advisor?
First, know your audience. Some people prefer to work through an issue from first principle, rigorously stepping through the logic chain that leads to the ultimate advice. Others are heavily influenced by the way that industry luminaries have approached the same problem. Good advisors understand this dynamic and tailor their advice appropriately. Similarly, some people are snap decision makers, itching to resolve an issue as quickly as possible, while others are brooders who need time to process information. Before giving advice, think about the person to whom you are speaking. How can you discuss an issue in a manner that will best suit that person’s thinking patterns?
Second, use analogies, particularly when the issue is both complex and unfamiliar. In my occupation, I advise about venture capital financings and mergers and acquisitions, topics with which even the most sophisticated entrepreneurs have little experience. I rely on a series of trusted analogies involving: speed traps, pre-nuptial agreements, thunder and lightning, dog racing and the sexual proclivities of high school boys to bring these arcane subjects to life. These analogies translate issues into familiar concepts and give the listener an understandable framework to which they can relate back as the issue develops. Even if a perfect analogy is not at hand, an illustrative example is often better than a detailed explanation. This harkens back to the classic adage, “I’m sorry to have written you such a long letter. I’d have written you a shorter one but I didn’t have time.”
Perhaps the most critical issue about giving advice, however, has nothing to do with talking. In order to be effective at giving advice, one must actively listen and that’s not a particularly easy thing to do. Listening means more than just hearing the words that are being spoken; it involves reading between the spoken words to understand what the discussion is really about, looking for the non-verbal cues and trying to get to the heart of the matter at hand. I sometimes go overboard in this regard as I often disturb people by staring intently at them with a furrowed brow as they speak (frightening image of this phenomenon below).
Obtaining context is a vital part of active listening. I am sometimes asked to give advice on a very narrow topic without being given any context. That’s like asking a doctor to diagnose a patient without doing an examination! To get an accurate diagnosis, further investigation is required. Is this the first time this issue has arisen? What is the next best alternative? What have the conversations with the other party been like to date? Without understanding these types of parameters, it is difficult to give sage counsel.
It would be bad advice to advise that well-delivered advice is always followed, however, if you understand your audience, use analogies and actively listen, it will help you avoid ISHLTY and not be such a shitty advisor.
