When is it Time to Pull the Trigger?

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Sometimes the universe sends us the perfectly timed message.

Other times it sends us frustrating contradictions. There are so many great proverbs that offer wisdom… and simultaneously contradict each other. For example:

  • “The early bird gets the worm” vs. “Haste makes waste.”
  • “Absence makes the heart grow fonder” vs. “Out of sight, out of mind.”
  • “Money makes the world go round” vs. “Money is the root of all evil.”
  • “You’re never too old to learn” vs. “You can’t teach an old dog new tricks.”

And my favorite:

  • “Look before you leap” vs. “He who hesitates is lost.”

This one is particularly frustrating to me, given how often I find myself wondering when it’s the right time to take action on something, e.g.:

  • How long should I wait before following up with someone if I haven’t heard back from them?
  • Should I launch a new program even though I’m really busy, or wait a while (as if I’ll be less busy in the future?)
  • When is it safe to quit my “day job” and be a full time independent consultant? (Fortunately I figured that one out a while ago!
  • How many people’s support/buy-in do I need (and whose?) before publicizing an event, project or opportunity?

That last one  is exactly the scenario we dove into in this week’s episode of Speaking to Influence. My guest, Jeff Orlando, the Chief Learning Officer for Bristol Myers Squibb, shares a powerful story about missing a key opportunity because he held back and waited for more support, instead of moving forward with a smaller group of influential leaders.


In this case, it became a question of quality of supporters and advocates over quantity.



Jeff and I spent a lot of time talking about risk-taking, ranging from how to decide what information to include vs. what to leave out of presentations intended for senior leaders and diverse audiences, to how to manage expectations when embarking on huge initiatives that will inevitably have major bumps along the way.

Here are just a few of the many gold nuggets you’ll find in this episode:


  • “(The key is) the importance of simplifying, the rule of three, and not trying to tell everything, but tell what's most important.”
  • “Present an executive summary of your topic, stop talking, and ask what questions they're most curious about; live in the room.”
  • “Senior leaders crave more of a real truth, real full story, which helps them make better decisions. And presenting in a bit more of a Q&A format gets closer to that.”
  • “If you can find a master of influence, call them up, buy them coffee, tell them your situation, tell them what support you have and get a sanity check from them. That will give you the clue you need on whether to move ahead or wait.”


Listen to the full conversation here or watch the video on YouTube here .

And speaking of “trying not to tell everything,” that's one of the biggest challenges I hear from everyone regarding how to give the perfect elevator pitch when meeting someone new.

We inevitably either give the other person a rundown of our daily task list (*snore!*) or we end up sounding like we swallowed a complete company brochure crafted by Chat GPT (*eye roll*).

Following the less-is-more approach is ALWAYS better in that context, but that brings us back to the question: What's the core info we should leave IN? 

And for that matter, how do we deliver it in a way that we actually sound like ourselves — natural, expert and engaging — instead of like we're lipsyncing to a chatbot?

Good news — on July 10th I'll be doing a special free workshop on exactly how to do both. Mark your calendars and stay tuned for more info coming soon!

And of course, sometimes we feel like there are so many things we should be working on, it's hard to know which to prioritize. Wouldn't it be nice to have the universe send a clear sign pointing to the right choice?

If that sounds familiar, take two minutes now to take my Leadership Communication and Influence self-assessment. It will serve like a bright yellow arrow pointing right to the areas that are your greatest strengths and the areas that you'd be smart to start working on today!

Who says the universe doesn't send signs right when you need them?

Don’t forget to rate the Speaking to Influence podcast on https://ratethispodcast.com/influence – thank you!

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