Long ago when I worked for a big tech company I spent a great deal of time traveling in big city airports around North America, often with my boss, and often we ran into celebrities.

My boss, who I’ll call Phil, was a huge Apocalypse Now fan, as am I. Phil would often tell me of his hero – lead actor in the movie Martin Sheen – and all the things he would say to Mr. Sheen should they ever meet. How much he loved the movie, how Sheen’s role inspired him given he had a heart attack and almost died making the film and was found lying in ditch but still managed to recover to finish the movie, how Phil had followed every step in his career for over 20 years.

Suffice to say it was a bro-mance, a male love affair that was probably never going to see the light of day.

One night in early 2000 as Phil and I dropped off our rental car at the Vancouver airport and we trudged into the terminal to catch a late flight. We were tired, hungry and a little pissed off at a bad meeting we had been a part of earlier in the day. As we approached the door I noticed a well dressed gentleman heading our way and I knew right away who it was. It was unmistakable, and I immediately leaned over to Phil and whispered “Phil…..it’s Martin Freakin Sheen……”

Phil was stunned and he knew I was right. As his pace slowed and we got closer to Martin (to confirm it was in fact him) Phil stopped, face beet red, heart pounding and palms sweaty. He looked Sheen dead in the eye as they both stopped in greeting and stuttered…..

“….Martin Sheen………..ummm, ahhh, I love you man….”

That was it. The moment was over. Phil was in fact speechless … all Sheen could awkwardly reply was…“umm Thanks” as he move quickly along to get his rental car.

Phil was devastated. He had missed his one chance to have a private face to face conversation with and idol. Instead, all he got a was a quick and embarrassing pass-by.

In the years since I’ve thought a lot about that chance encounter, especially how it related to meeting that “big lead” that I or others like me were trying to land. Chance encounters happen a lot more than we think, especially in the business world where as we all know –  industries – no matter what industry it is, are very very small. So we should plan for chance encounters – in fact: be as prepared as a Navy Seal would be if they were about to jump from a helicopter into enemy territory.

Phil’s reaction on meeting his idol was actually quite predictable, and it’s one I’m sure everyone has experienced at one time.

The – Oh, My, God, what do I say now without sounding like an idiot, (that actually makes us sound and feel just like an idiot).

All of preparation we should have done, the research we wished we had acquired, and the questions we should have ready to ask but don’t create a stress in us that changes us physically and effect our physiology. It make us bumbling idiots.

One of the things I have done to effectively combat this problem is to follow these three simple steps:

  • Make your hit list – the names of the top 5-10 people you want to work for or with. The people you admire that are your “big fish”. Then set a date that you want to have met them by. This is similar to making a SMART Goal with regards to the structure.
  • Do some research as to where these individuals spend their off work time. Clubs they belong to, memberships they have, groups, concerts, etc they regularly attend. All of these generally can be found via Linked-in, Facebook or Twitter. Then plan to be at some during the periods you have set.
  • Last but not least, create an Opportunity One Sheet for each person. This is NOT an elevator pitch. This is a strategic document that outlines the following:
  • The goal you have with this individual, their product or company – why do you want to meet them? This HAS to be crystal clear, and it is this clarity that will provide the backbone of the confidence you will have.
  • The Summary – what are the facts about this individual that has lead them to be on your list and why you are positioned right now to have this conversation. Again if you notice this information is more about giving you solid ground than it is providing a manufactured script. We don’t want to become a blubbering Phil right!
  • Calibrated Questions – a tactic used by Chris Voss – formally one of the world’s top FBI hostage negotiators – designed to engage your target. Get their interest through your questions to them, not by answering their questions to you – which they won’t even ask because they don’t know anything about YOU. Ask questions based on the information in your summary – things like – “I know your company has been searching for way to combat the market pressure your getting from company xyz – I’ve got a few ideas – could I ask you a couple of questions to see if my ideas might be on point?”
  • Finally, and another bit of Chris Voss magic, from his best selling book Never Split The Difference – ask a question that will get them to say no. Not yes. No.  This sounds like: “Jim, thanks, I have three things that I’m sure will make a difference to your company based on what you just said, would it be crazy to think we could have a 20 minute meeting so I can outline them?” Again, because the logical answer to this is probably no – it’s not crazy (make sure your ask is relatively easy to do) – they will probably answer no – and you can quickly arrange a meeting.


The big thing to remember here is:

Doubt Kills More Dreams Than Failure
and doubt comes from being unprepared.

Create some opportunity one sheets and have them ready for those “unexpected” encounters you expect to have.

~ Kevin Simpson – ActionEdge Business Coaching