Asking for advice

As I’ve gotten more senior in my career, I get pinged a lot for advice.? The ask comes in many forms:

• “I’d love to pick your brain”
• “Can we catch up for coffee”
• “I’d love to hear what pain points you have”
• “Do you know of any interesting roles”

When I am asked for advice, I have four immediate thoughts:

1. I’m honored people ask
2. I want to help because I frequently asked for advice early in my career (and still do) and want to give back
3. I struggle to help because the asks aren’t effective
4. I’m slightly frustrated when the ask is from someone I don’t know yet.? Asks from my network I always try to give back but cold asks for my time that aren’t focused are challenging

I’ve reflected on this recently, helped by some great podcasts (see below), and have written this article to share tips on how to ask for advice effectively.? And, at the end, I share the processes I have built to scale how I help people.

I hope this article comes across as positive and helpful to you.? Many people will just ignore ineffective asks but, by sharing what is challenging about them, I hope it provides insights that can spark more people helping each other..

1. Nobody else can tell you what the market wants??

I get asked several times a week about my pain points but even though I’ve lived in GTM systems and strategy my entire career, I can’t give general wisdom that will help you at this stage.? This excerpt from a great podcast highlights why this approach won’t get you there.

“The typical story of finding product market fit is you create some product and go ask the market what it wants and then based on feedback you A/B test and refine your product."?

"You both have to know your technology and …. make the market pliable.? In new markets the customer doesn’t know the value they want.? There is a ton of work you have to do to hammer the market and make it accept it.? Work on your product and then work on the market.? By work on the market I don’t mean do interviews. ? Customers feel like they need to answer something.? So they’ll just make something up. ? ….. The most successful companies have a true north vs looking to the market for it” ? Martin Casado on Invest with the Best Podcast (see direct link to key section)

Instead of asking for my pain points, bring your unique insight on the market (what have you discovered, believe that nobody else does) and ask for specific feedback.? I love this because it helps me learn and provide valuable input.

2. Have specific questions to show that you are serious

If you are asking for general advice I will struggle to help and frankly that advice is not worth much from anyone.??

“The only real sincere (ask for) advice is a very tactical and specific question.? Most advice questions are fundamentally unserious.”?

“A 12 year old comes up to Mozart and asks him how do I write symphonies.? And Mozart says ‘go to music college and study the greats’ ? The 12 year old goes ‘you were writing symphonies when you were 12’ ? And Mozart says ‘Well i didn’t go around asking people how to write symphonies.’ ? And I think that is so profoundly true that if you catch yourself asking “how do i start a company or something similar’ you know you are not serious.”? ? Jeremy Giffon on Invest with the Best Podcast (see specific link at 1:16:04)

Take the time to read everything I’ve written / watch a few of my podcasts and come with a very specific question you know I can help you with.

3. Make yourself memorable if you want to be remembered

I want to help everyone I meet but it is hard to.? I try to do it in-the-moment (see above) but it is even more challenging to remember someone later who had a vague ask.? I often hear “if you see any interesting job opportunities send them my way”.? I really want to help these people, but as this article shares, the lack of specificity won’t yield results.

“It is really good to be specific because then people remember.? If you say to somebody ‘oh I’m just excited to work at a hot company’ that isn’t really helpful because… who isn’t?!”? Nick Mehta on Who Got Me Here podcast

The best way you can have me think about you and send you ideas is to be specific and niche down.? Whether this is in your job search as the article highlights or as a founder don’t be vague.

4. Don’t ask for advice if you are selling something

I get many early stage founders asking for advice on their product.? But many often pivot to trying to sell me on their product.? This doesn’t work (at least with me).

I give candid, open advice but the second it becomes clear that it is a sales pitch I shut down.? I’m not going to share our challenges / inner thinking if that information is used to pitch your solution to address my pain points.??

If you are asking for advice on your product, you probably are early stage and not ready to sell to enterprises yet - any enterprise will struggle to adopt an early stage company given data security and maturity.??

How I help with asks for advice

I truly love helping people.? But, given my experiences refined by these insights above, I’m very careful where I invest my time. ? I’ve built the following approach to scale how I help people:

• I share this article and hope that it will guide them with a more specific question ??Feel free to share this as well with others.
• I write.? I love writing my thoughts down and have found it so powerful.? Most people asking for advice haven’t take the time to read my writings so I redirect there as non-specific questions on GTM strategies, RevOps, Data and leadership are generally answered in my writing
• I share books that have influenced me.? Below are just a few of my favorites (I love learning about ones others share out too)

The Cold Start Problem - deep insights on marketplace businesses

Traction - the best quick read on the basic tactics of scaling a business

• I give of my time asynchronously. ?I’m insanely responsive on LinkedIn (assuming the ask is specific and I can help -- I generally reply within 24 hours to existing connections - please don’t cold invite me…)? Given my day-job and personal passions, finding "time to chat" is difficult.? But if people send me a pitch deck or loom (showing they’ve done hard work in advance) I am happy to send back a loom or LinkedIn voicenote (I love the personality both of these convey).? I can often find time on an evening / weekend to respond with personal thoughts
• I chat on my commute ??I truly do like helping people.? I take 6-8 calls a week from founders and people I respect on my drive/walk.? This allows me to focus on the discussion while getting outside (away from zoom). ? I prioritize people who make specific asks and those I want to build relationships with.? I have a calendly link I will send to people I’m open to chatting with.

Other Thoughts

Wondering how to build a relationship before asking for advice? Here are my tips on networking.