Ask for help! 4 rules for getting great advice


Knowing how to ask is so insanely valuable. There’s a whole world of people out there that are absolutely fantastic at what they do and 95% of them are totally willing to help the right people.

The rules of getting help:

1. Ask

99% of the world doesn’t get here. Afraid of rejection, don’t want to look stupid, don’t think of it. There’s all kinds of reasons not to get here. If you need help with something, identify the people that are great at it and ask them for help. Yes, 90% of the people will probably ignore you (nothing lost here) but 10% might actually reply. Think about how powerful that can be.


2. Be specific in your ask

Make it easy for the person you’re asking to actually help you. I get asked for help a fair amount and the majority of the time it’s, “I’m interested in the startup sales space, do you have time for a coffee?” That’s a really hard thing to say yes to. My time is pretty valuable to me, and it’s nowhere near as valuable as many of the people that I reach out to for help. I’ve spent too many hours on “15 min coffees” that become a conversation that could have been gleaned by just reading my linkedin profile.

“I’m starting a sales team and evaluating how to setup early for scale and success, I had some specific questions on choosing the right CRM and key metrics to look at, do you have any advice?”

A question like this is easy to answer, in fact I could reply via email. That’s very easy for me to do, and I typically will. I want to help. If there’s some smart conversation back and forth, it might make sense to go for a drink or coffee and discuss more. 

Then if I’m going to spend my “valuable” time for the meeting. I’ll know (or at least have a better idea) that it will be useful.

Tim Ferris has some great suggestions here on his post 5 Tips For Emailing Busy People


3. Add Value

If you are taking your precious time to help me out with something I need. I’m always trying to figure out how I can return the favor. Generally, I’m seeking help from someone “above” me on the ladder, so it’s hard to figure out how to do this. I’m asking a successful sales leader for advice, how can I possibly add value to him? Well… sometimes it’s my network, I can introduce him to someone that could be a valuable junior hire. Sometimes I’ve come across a sales tool that he might not know about. Maybe I have a lead on tickets to the sold out game this week. Maybe we were chatting about how much he loves BBQ and I know of a great restaurant that just opened up downtown. I don’t know.

The best “thank you” emails I get end with something like, “I thought you mind find X helpful based on our conversation. Thanks again and please let me know how I can return the favor.”


4. Follow-up!

The most important tip I’ve picked up in the last 5 years: Follow up with the person that’s helped you. Let them know how your advice went and how you’re progressing!

This week one of my sales reps asked for help from our CRO re: the XYZ account. Steven, our CRO, took his time to sit down, talk through the situation and offer his best advice. The sales guy, Josh, was incredibly thankful. He took the advice, applied it, and it worked pretty well. Now, he has a semi result.

Right at this moment marks the most important point in asking for help and building the future relationship. Follow up and tell that person how it, went and thanks again.

If people are taking their time to help you, it means they generally want to help. That also means they’d appreciate knowing how it turned out and how you’re doing. There’s no such thing as a selfless deed, it feels good to help people.

Steven, happened to come up to me, wondering if the advice he gave Josh was helpful.
Dave: “Yeah, it was great thank you so much, Josh didn’t follow-up with you?” Steven: “Nope”.
Dave: “He should have.”
Steven: Yes, he should have.”

What Josh should have written is something along the lines of:

Hey Steven,

Wanted to follow up about the issue you helped me out with regarding XYZ and their agency. In a nutshell, I asked directly for dates and an IO, and she said she would try – I then gave a little of the human element like you suggested, so she understood where I was coming from.
Sure enough, she came back saying she not only pushed and got it approved, but moved up to May and back into Q2. Should be signed soon.
Thanks for the advice, worked out even better than I expected.



Some of my best connections are those that I originally asked for help on one thing or another whom I thought would never respond, and now have I great relationships with. Brian Wong of Kiip recently wrote a great piece about how asking for advice can even be the best way to land funding!

Those that are able to close the loop are appreciated and valued, and receive a lot more help in the future ; )

Like with anything else new, it’s hard to remember to do these things. I try my hardest to put some kind of positive triggers in place to remind myself to follow up, just like I would with any client.