Swinging the Sword

Eddard Stark famously said, “The man who passes the sentence should swing the sword.” It’s often one of the worst parts of the job, yet I believe it is imperative for any self-respecting leader. You might be surprised to realize that there are a bunch of scenarios where you might be (unawares?) passing the buck. […]

Gedanken Experiment: Your Purpose

I love making my clients go through thought experiments to help them better assess a certain scenario and also as a way to accelerate decision-making. I’ve shared before about one for making your day-to-day more productive by holding the vacation thought experiment. This time, let’s consider one you can do today to better flesh out […]

Startup Hyper Paralysis

I recently had chats with a bunch of founders of early-stage startups, and they all happened to ask me the same question: What problems do I repeatedly see in my work with startups their size? While I listed a handful, I thought that hyper-paralysis is an interesting one to delve into. It sounds like an […]

Conversation Catalysts: Embracing Shibboleths

My previous | articles touched on the subject of cultivating a better communication culture in your organization. As part of that, I mentioned shibboleths as an agreed-upon way to fast-track certain scenarios. Given that I got a few questions about this, let’s consider some examples. Hint, you’ve probably just seen one in use recently when […]

Spotty Connections

Don’t you hate it when you say something and the other party doesn’t answer? You’re left wondering if they didn’t hear you well and repeat the request, wait in silence, or just give up. Oh, I’m not talking about choppy Zoom calls. This is just how badly too many leaders seem to be communicating nowadays. […]

High-Density Conversations

Some of the most precious moments in our work are those we spend communicating with others in meetings. They’ve become even more valuable, given the increased rarity in the hybrid/remote age. That’s why it’s mind-boggling to watch how many teams have a conversation culture that essentially wastes these moments with lots of fluff and a […]

Gilding Guilds

Things always operate in trends, and if my clients are any indication, it seems like “guilds” are back in vogue. Nevertheless, many teams waste countless hours on guilds that provide little value or even turn out to be detrimental. Therefore, one has to be mindful of the common pitfalls and best practices for setting up […]

Pathological Anxiety

Anxiety, like an uninvited guest, often overstays its welcome in the minds of leaders. It whispers in our ears everything that could go wrong. Some executives go through years bracing for an incoming storm, even when the skies are clear. When anxiety becomes your default viewpoint, it’s like trying to lead while carrying a weight […]

Evaluating Leadership: Beyond the Basics

In the high-speed tech world, hiring senior talent often feels like trying to assemble a puzzle while riding a horse-drawn carriage on cobblestones. We tend to focus on the familiar pieces – experience, technical acumen, and perhaps even charisma. Yet, as our industry continually reshapes itself in response to new trends, regulations, and societal shifts, […]

Startup Rollercoasters: Communication for Leaders

We’ve all heard about the “rollercoaster” of startups, and it seems like these rides were upgraded to be a bit more… loopy in the past couple of years. For some leaders, this is a constant point of worry and discomfort with their teams. How much should they say? How direct should they be? But what […]