It Doesn’t Hurt To Ask… Does It?

A newspaper with headline "No Way Jose!!!"

On LinkedIn, a stranger sent me a message complimenting me on an interview I conducted on my Great Minds Drink Alike podcast. I could tell from his message, that he watched the session, paid attention, and gave me a genuine compliment, so I accepted his connection request. However

The very next message, he asked if I would make a personal introduction to the guy I interviewed to assist him in selling his product to them. He specifically asked if he could “pick my brain” about how to sell them and what his approach would be. For the record, “pick your brain” to a consultant who gets paid for our advice is the equivalent of “pick your pocket” because they don’t want to pay for the meeting or the advice. When I declined to help him, he said, “Well, it never hurts to ask.”

We’ve been taught the mantra “It never hurts to ask,” but that’s pretty damned far from the truth, particularly if you want to have a relationship with the person you’re asking.

If you’re looking for a quick hookup or a one-night stand, it’s probably okay to walk up to anyone and just “ask.” You’re most likely to get ignored or turned down – in the worst case, slapped. But there’s no harm because you weren’t trying to develop a meaningful relationship with this person anyway and you’re not likely to see them again. That’s the JERK’s approach to “prospecting.”

However, if you want to form a meaningful relationship with someone, you DO have to be careful about what you ask for. It CAN hurt to ask because you haven’t earned the right to get your request granted. It hurts to ask because now I’ve put you in the category of a selfish idiot who doesn’t respect me, my time or the value I bring – you were looking at me as a one-night stand who could satisfy you in the moment, but nothing more. What could you get? Now I won’t take any future questions, interactions or requests from you, and I’m certainly not going to do anything to help you succeed. If I’m someone who can help you, it DID hurt to ask.

When you ask someone to make an introduction to someone or to use their relationship capital to get you in the door, you’re asking for a LOT, especially if the person doesn’t know you, hasn’t done business with you, and cannot vouch for you personally. That’s why it’s easier to get a sale than to get a referral. A referral requires me to put MY name on the line for YOU.

Dumb salespeople use this approach all the time: “Robin, I want to buy you coffee/lunch so I can attempt to sell you something.” Where’s the value in that for me? Do you honestly think I put so little value on my time that I’m willing to give it away for a $5 cup of coffee? Or a “free” lunch? It’s not only stupid, it’s insulting.

Mike Rowe, who we’ve had at our Boot Camp event in the past, gets hundreds of requests to come speak, endorse a product, make an appearance, do an interview or write about a particular topic. He turns most of them down because the people asking are NOT willing to pay for him to do the work. I know because his manager told me. It’s rude – and once they ask for something and assume they have the right to request he work for free, his manager blocks them and stops responding altogether.



Robin Robins and Robert Herjavec

That’s why even though I have a great relationship with Kevin O’Leary, Marcus Lemonis and Robert Herjavec, I would never ask them to do an interview or presentation for free. That’s PART of the reason why they take my e-mails and calls. I DO know it would “hurt to ask” for something that is selfish, so I don’t.

When you’re prospecting and attempting to get meetings with key prospects or people you want to partner with, be very careful about your initial ask because it WILL label you for the rest of your interactions, and first impressions last.

This year at the Roadshow, my focus is on helping MSPs hit the RESET button on your business model, target market and marketing strategy. To go UPSTREAM NOW for better, higher-paying clients and differentiate yourself not only from the ankle biters in your market area but also from the larger, more well-funded MSPs and the more aggressive “Super MSPs” that are gunning for your BEST clients…as well as going upstream to sell co-managed, raising your rates and being able to compete for and WIN big contracts by delivering advanced cyber security protections and compliance-as-a-service. There’s much work to do. If this is important to you, then join us at the 2022 IT Marketing Roadshow.



FREE Marketing Plan With Your Roadshow Attendance

There’s no doubt about it: Robin Robins has helped more MSPs and IT services companies to grow and prosper, liberating them from stagnation, frustration, drudgery and low incomes. For over 20 years, Robin has been showing MSPs and IT services firms how to implement marketing plans that attract higher-quality clients, lock in recurring revenue streams and secure high-profit contracts. Her methods have been used by over 10,000 IT services firms around the world, from start-ups to multimillion-dollar MSPs. For more information and a FREE copy of The MSP’s Ultimate Guide To IT Services Marketing And Lead Generation, go to


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