When is it Okay to Ask?

Getting to yes
You give me way too much credit if you think your potential customers read my blog. You misunderstand and misapply influence and you're giving away your inexperience with new media. Let's be clear, I still like you, I just find it easy to skip over your pitch.

Go build your own audience.

I wrote here almost five years ago. Plenty of time to build an audience. Check your “ask” — should you be pitching me? Most of the time the answer is no. You know it because your pitch is easy to ignore. So if your pitches go that way, rethink your approach.

Steven Pressfield describes the issue along the same lines I would. He says it better:

My problem is I like to think of myself as a nice guy. This is not good. I’m working on getting over that. There are people out there who are what I would call social sociopaths.

They’re not actual murderers or criminals; they won’t hurt you. But, for whatever reasons of character or upbringing, they are utterly without empathy. They have no sense of the value of another person’s time or hard-won skill or hard-earned reputation. If you’ve got it and they can use it, they want it. They want it now. They want it free. And they want it again and again.

The irony is if you struggle with asking you are likely on the right path to doing it right — and will likely go the extra mile to learn how to make it work.

I continue to address this topic from various angles because it is an important one at a basic human level. We are not all knowing and all seeing and it is good to look to each other for support, counsel, and to enrich our lives.

It's never too late to learn good manners, and public examples may be too one-dimensional to provide enough high-quantity and high-quality exposure with feedback to help with learning through perceptual knowledge, as Kathy Sierra teaches in her latest book. She wrote it to help us with this question when we design experiences and build products, so go get your copy of her new book Badass: Making Users Awesome if your “ask” is about that.

Influence is connected with interestingness and if you are looking for ideas on how to relate to the people you are trying to reach, I did a fairly deep dive on techniques and approaches in my talk on influence.

Is it enough to connect with people in social networks, or should we try to meet people face to face? This is a very good question we discussed yesterday during our conversation on separating myth from reality in personal branding — the two-hour program will be available on demand here with a special bonus (in Italian.)

I use LinkedIn mostly for professional purposes, so I connect only with people I have met. I am not alone in this. The worst thing you can do on LinkedIn is send one of the allotted “in” emails — reaching out to someone without being connected, usually with an “ask” — and then never answer when they respond. Individuals who position themselves as executive recruiters might want to rethink this one. LinkedIn's algorithmic prompts are near impossible to miss, so if you have done that, you know it.

Social media creates opportunity in so many ways — by making it easier to find like-minded individuals through posts, events, interactions, and more, including collecting our own digital impressions. By looking at what we share, write, and post, we can access a treasure trove of information about how we show up. What is that picture?

Email is just like many other forms of public outreach and it will serve you well seeing it that way:

  • it's a tweet when corresponding with busy people — get to the point, politely
  • a Facebook post when writing to a friend — share of yourself
  • a pin when paying a compliment to someone
  • an Instagram to inspire and delight

Social media, email, technology in general gives you the tools to accomplish more things. But it still comes down to what you do with them. So before you go ahead and ask around, ask yourself — have I done my part?

When and how to ask make a big difference in getting to yes. Helping others achieve their goals is a great way to start.


For a bit of fun, here are Top Ten Signs You're Drinking your Own Kool-Aid When Pitching Bloggers.