It Doesn’t Hurt to Ask for Advice: Lessons from an Entrepreneur

It’s not what you know, it’s who you know.

We hear the cliche over and over again. But when you’re starting out, do you really know anyone?  And as you get going, do you really know anyone who matters?  And if you try to sit down with someone who does, will they really give you the time of day?

You’d be surprised.

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Perhaps the biggest surprise I encountered in my early days of 3Pillar was how many “successful” people were willing to give me time, advice, and assistance.  I was blown away by the entrepreneurs, CEOs, and executives that were willing to lend me a hand.

The reality is that most people are kind-hearted, if not flat-out generous. Almost anyone who has had any degree of success has been helped by others along the way; many of them want to pay it forward.

You’ll be amazed at how open and willing successful executives and entrepreneurs are. They have been given a lot and want to return the favor.  Simply ask, and I’d be willing to bet that you’ll be surprised how often you’ll make a new connection.

Here are three tips for getting the attention of a leader that you want to know:

Look for a connection.

With social media this is easier than it’s ever been. Almost too easy.

Does your Dad have a connection to the CEO you want to meet? How about your college roommate? Perhaps his dad was that lawyer’s partner early on in their career.

Find the connection and use it. Most people are more than happy to lend their Rolodex and busy leaders will respond best to a personal connection.

Respect their time.

Be clear and concise. Be upfront about what you’re looking for.

The 10-page email isn’t going to get answered. The 4-sentence email will.

Understand that your exec is busy. Respect their time.  Lay out what you’re seeking and be grateful for whatever they give.

Fifteen minutes just might be the beginning of a relationship with the person you want to get to know.

Be genuine.

One of the best ways to get to know an executive is to ask for advice.  People love to help but they also love to give advice and feel like they have something to give.

To some extent, you’re stroking their ego. But be genuine. Truly listen. There’s nothing worse than someone who says they’d like to learn from you but then knows all the answers. If you don’t mean it, don’t say it.

Oh, and don’t forget common courtesy. Follow up with a “Thank You” note. It’s a good way to grease the skids and make sure you get the follow up meeting your hoping for.

4 Comments Add yours

  1. Chris Mullen says:

    David, great advice. I know early in my career I was under the impression that if I asked for advice I would be seen as not being knowledgeable. I quickly learned this is not the case. People really do appreciate being asked for advice or meeting for 20 minutes over coffee to talk. If they don’t have the time they will tell you. It never hurts to ask!

    1. David DeWolf says:

      Isn’t it funny how we all (or so it seems) start out shy about asking for help – but all for different reasons? Some are afraid of being exposed, some of being inadequate, …whatever the reason, I’m not sure I’ve found what that has been well founded.

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