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What Does Good Look Like?

What Does Good Look Like?

During my time at HubSpot, I worked closely with one of those leaders that instilled a productive kind of fear in people.

Not fear in the sense of danger, but fear in the sense of tension – if you went to a meeting with him and were unprepared, you would feel the pain instantly.

He never raised his voice, was always calm, never belittled you or made you look foolish in front of others, but he had a gentle-but-firm way of letting you know that you were far below his expectations. A bad meeting with him made you want to crawl under a blanket and hide for the rest of the day.

I've had the misfortune of being one of his bad meetings (thankfully, it was only once.) I've also had the fortune of being a participant in many of his meetings as a stakeholder, so I could watch from a distance and understand how he did it.

I noticed that whenever someone pitched him an idea, made an ask, or was telling him about some initiative that was underway, he would inevitably ask these three questions:

  1. What does a bad outcome look like?
  2. What does a good outcome look like?
  3. What's a reasonable timeframe for this to happen?

It was always shocking to me how often it was that most people didn't have clear answers to these very reasonable questions.

It was just as shocking how he could improve almost every project just by asking these questions, as it forced people to zoom out and think in terms of outcomes, not project checklists. Oftentimes, when we are enthusiastic about something, we dive in headfirst without thinking about these things – which opens us to all sorts of bias when judging our performance.

Ask these 3 questions for your most important projects. And definitely before you start something new.

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If you liked this, you'll enjoy my summary of one of my favorite leadership books, The Score Takes Care of Itself.