tl;dr:“Giving the right amount of context helps teams move faster. Too much context? Your manager can’t tell what’s important. They’ll need to wade through details, trying to sort information into a pile of what’s important vs what to ignore. Too little context? Your manager has to follow up and pull information out of you that you should have mentioned proactively. There is such a thing as being too concise.”
tl;dr:“Signposting is using key words, phrases, or an overall structure in your writing to signal what the rest of your post is about. This helps your reader quickly get grounded, so their brain doesn’t waste cycles wondering where you’re taking them.” Wes shares how to implement this when writing about complex ideas.
tl;dr:“If you share information that’s not obviously positive or negative, you must proactively tell people how they should feel. Give context to the information, data, or fact. If there’s even a slight chance your audience might benefit from the extra clues, I would consider using signposting. It’s super fast for you, and super helpful for them.” Wes shares examples.
tl;dr:Wes developed the framework below when explaining projects to direct reports, dotted-line reports, vendors, agencies, contractors, recruiters, and anyone she’s managing formally or informally. Here are five areas to cover: (1) Increase comprehension: Am I explaining in a way that’s easy to understand? (2) Increase buy-in: Am I getting the person excited? (3) Derisk: Am I addressing obvious risks? (4) Confirm alignment: Am I giving them a chance to speak up? (5) Feedback loop: Am I creating the shortest feedback loop possible?
tl;dr:Wes developed the framework below when explaining projects to direct reports, dotted-line reports, vendors, agencies, contractors, recruiters, and anyone she’s managing formally or informally. Here are five areas to cover: (1) Increase comprehension: Am I explaining in a way that’s easy to understand? (2) Increase buy-in: Am I getting the person excited? (3) Derisk: Am I addressing obvious risks? (4) Confirm alignment: Am I giving them a chance to speak up? (5) Feedback loop: Am I creating the shortest feedback loop possible?
tl;dr:Principles on how to feel more confident sharing your point of view: (1) The more controversial the idea, the higher the burden of proof. (2) Update your assumptions about how you add value. (3) Share where your hunch is coming from—because it’s coming from somewhere. (4) Describe why the problem matters, so people understand why you’re speaking up. (5) Don’t rely on your credentials. Your idea should make sense on its own. (6) Use language that accurately reflects your level of certainty.
tl;dr:Wes gives phrases of how to verbalize each: (1) Embrace managing up. (2) Focus on the punchline. (3) Show your thought process. (4) Flag potential issues. (5) Bring solutions, not complaints. (6) Use information hierarchy. (7) Keep your manager in the loop. (8) Are you being micromanaged, or do you need to communicate better? (9) Over-communication might be the right amount. (10) Proactively assert what to do. (11) Don’t only ask questions. Share your point of view too. (12) Anticipate questions. (13) Know when to get out. (14) Be explicit about what you need. (15) Expect to manage up forever.
tl;dr:Wes gives phrases of how to verbalize each: (1) Embrace managing up. (2) Focus on the punchline. (3) Show your thought process. (4) Flag potential issues. (5) Bring solutions, not complaints. (6) Use information hierarchy. (7) Keep your manager in the loop. (8) Are you being micromanaged, or do you need to communicate better? (9) Over-communication might be the right amount. (10) Proactively assert what to do. (11) Don’t only ask questions. Share your point of view too. (12) Anticipate questions. (13) Know when to get out. (14) Be explicit about what you need. (15) Expect to manage up forever.
tl;dr:"If you appear hesitant, doubtful, or desperate… The other person picks up on it. You get more nervous. They start doubting you." Before you hit send, ask yourself: (1) Could this be interpreted as sounding defensive? (2) Am I overcompensating or overexplaining? (3) How would I respond on my best day? (4) Would I say this if I felt secure?
tl;dr:For both managers and direct reports. For managers: (1) Encourage your team to be honest about timing, especially high performers. (2) Temporarily “over-correct” to convince your team it’s safe to push back, celebrate their behavior when they do so. When they feel comfortable, become tactical. For reports: (3) Speak up at the first sign that you might miss a deadline. (4) Wes shares scripts of what to say. (5) Suffering in silence is not useful.