#353 – October 08, 2026
it can feel mysterious and intimidating, but it is really just a skill anyone can learn
How strategy stopped intimidating me
3 minutes by Ryan Greenhall
Strategy can feel mysterious and intimidating, but it is really just a skill anyone can learn. A simple framework breaks it into three steps: understand what is actually happening, decide what choices to make, then act on those choices. This approach helped turn a blank document into a real business direction that worked.
Your startup's security policies are concerning
sponsored by Svix
Most startups put off security until a SOC 2 audit or an enterprise deal forces the issue, and by then bad habits are baked in. Tom shares the rules Svix runs on: no direct production access, time-boxed emergency access that alerts the team, and row-level security for customer data.
Hiring breakpoints
7 minutes by Stay SaaSy
Adding more people to a team does not always help and can sometimes make things worse. Some roles only need one great hire, while others benefit from a second person to create accountability. Managers struggle past about 10 direct reports, and teams above 150 people lose the tight coordination that smaller groups enjoy naturally. Staying lean and well-tooled for as long as possible tends to produce better results.
10 career traps (thoughtful people fall into)
13 minutes by John Cutler
Thoughtful people often fall into career traps because their strengths, like curiosity, empathy, and pattern recognition, quietly work against them. Volunteering to fix orphaned problems, defending misunderstood colleagues, or thinking out loud can all lead to being misread, sidelined, or burned out. Each trap has a saveable moment, a point where you can still pause and ask what is actually happening. The goal is not to stop caring, but to notice sooner.
Modeling software’s business impact
13 minutes by James Shore
Speeding up software delivery means nothing if teams build the wrong things. To understand real value, James suggests teams should create financial models forecasting outcomes like new sales, retention, and cost savings, using proxy metrics such as feature adoption rates for faster feedback. He argues that getting finance, sales, and customer success involved improves the models over time. Wrong priorities quietly sabotage company strategy, so treating prioritization as a serious discipline matters more than optimizing costs.
How do you deal with people who strongly disagree with your views?
4 minutes by Daniel Lemire
Daniel offers practical advice for handling strong disagreements. Start by listening carefully and asking genuine questions to understand the other person’s position. Find common ground, research the topic, and support your views with facts and clear language. Stories can make ideas more relatable. Most importantly, avoid personal attacks and calmly address disrespect when it occurs.
And the most popular article from the last issue was: