How to Pick Someone's Brain Without Looking Like an Ask-hole

How to Pick Someone’s Brain Without Looking Like an Ask-hole

Picking someone’s brain.

We’ve all asked this of someone before or, at the very least, considered it.

Whether you’re venturing into uncharted territory and looking for guidance, or seeking validation on your current business model, there’s always that one industry leader’s opinion you would kill for.

You want to reach out to them, but you don’t want to be one of those ask-holes (get it? I’m witty!) who comes screaming out of the woodwork demanding their time and attention.

The people we look up to most also tend to be the busiest. They have commitments and their own businesses to run. While they are often more than happy to mentor the less experienced, there is an etiquette to follow.

Step One: Infiltrate their network

I’m pretty considerate, but let’s be real, giving my time to complete strangers isn’t something I like to do.

Human nature dictates that we are more likely to help those who we feel connected to, even if that connection is as loose as being Facebook friends.

If you want to reach out to an industry leader, start by getting on their radar. Follow their social platforms, reach out to them on LinkedIn, or send them a shout out complimenting one of their recent successes or perhaps their latest blog post.

You can even ask a mutual friend to introduce you. Shared connections will help you bridge the gap between being a complete and total stranger to acquaintance.

Step Two: Think long and hard about what you want to learn from them

Before you even think about making the ask, think about what you truly want to learn from this individual.

I love plenty of people’s work, but I would only reach out to a few of them for advice. Why? Because not everyone we dig is aligned with our own business vision.

I wouldn’t ask my favorite crime drama author to give me advice on my email marketing business. Though we are both essentially writers, our areas of expertise are nowhere near the same. While J.D. Robb can throw down a mean tale of love, lust and murder (don’t judge me!), she probably wouldn’t have much to say on my email based sales funnel.

So, sit down and think about what this potential industry leader does and how their particular area of expertise could be of value to you.

Step Three: Hammer down ONE question you would like to ask

Let’s not get greedy, y’all. If you are going to ask for someone’s time and expertise you better have one particular question you would like advice or direction on.

The reason for doing this is simple, you want to make it easy for them to help you. Yes, YOU want to make it EASY for THEM. The clearer you are on what you’re asking, the higher the value they will be able to share with you.

One quick note —  if you are chatting with an expert in your industry, and ask them to divulge their exact strategy for XYZ, don’t be offended if they say no. Be realistic about what you are asking. Successful business owners deserve to have a few secrets when it comes to how they got so successful.

Step Four: Make the ask

The final step is to make the ask. There are a few ways to go about this, but essentially, you want to be direct. Explain why you’re reaching out, share why you think they would be great to get advice from, and let them know that if they agree you will respect their time.

You can start by asking them a direct question on social media. This rolls right back to Step One, making yourself known to them.

Once you’ve worked your social media magic on them, move forward by sending a more detailed request via email.

For example, you could shoot them a quick message reading something like:

Hey first name,

My name is Sabrina and I have been following your work for a long time. I think your latest [ insert blog, book, podcast, TEDtalk, whatever] was great and I learned a lot about [ insert what you learned].

I’m reaching out to you today because I was hoping to get advice on [insert your very specific subject – with a very specific question]. I think I could learn a lot from you because you have been so successful with this in your business.

Look forward to hearing back from you,


If you follow this approach, then chances are they will respond positively. Just remember, when the opportunity comes to talk with them, be polite, appreciative, and then get to the point.

From there out, do your best to remain a part of their network.

  • Comment on their website or social media
  • Share their latest work
  • Feature them on your website – if applicable
  • Send out a “touching base” email
  • If you know you’ll be at the same conference or workshop, make sure to say hello and thank them again

If you maintain a relationship, and continue to add value for them, you might land a phone or Skype call. Maybe even a quick cup of coffee and chat. You can learn a lot in 30 minutes if you know exactly what you want to ask.

Networking and maintaining relationships are essential when you’re in business, so even though it may have started out with you wanting to pick their brain, you should see this as an opportunity to grow the relationship.

You never know what doors could open down the road, for either of you.

About the Author Sabrina Taylor

Sabrina Taylor is a sassy writer and online manager with an inappropriate love for Buzzfeed, pizza and CrossFit. She has over 5 years experience working with businesses helping them build effective communications and marketing strategies. She is currently living in the hot and humid mountains of Northern Thailand, dreaming of hoodies, snow and Canadian bacon (first world problems, amiright?!).

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