How to Ask for Advice

Feat. Steve Solomon (Olympian & Enterprise Partner Senior Associate @ Uber)

The skill of knowing who to ask for advice, what advice to ask for and how to ask for it, though certainly relevant to careers, has high leverage across life and its domains more broadly.


It allows you to tap into minds with experience and knowledge far beyond your own in order to make trajectory-defining decisions.

Yet throughout school and university, we seldom have exposure to any formal training or structured thinking in this skillset.


As someone who’s always loved learning through conversation, I eventually stumbled onto 3 key factors I consider when I’m looking for advice.

1. Domain expertise: How relevant and experienced is the person you are asking to the specific area you're asking about?

2. Type of advice: What type of outcome are you seeking by asking for advice e.g. a discrete Yes/No decision, a complex problem analysis, generalised mentoring, etc. and how well can this specific person meet that type of outcome?

3. Strength of relationship: How well do you know the person you're asking, and if you don't know them too well or at all, can you leverage a strong mutual connection? This impacts the feasible size of the ask.


But in looking to stress test my own model, I decided to ask for advice on… well… asking for advice.

And one of the first names that came to mind was my friend and mentor Steve Solomon, who somehow manages the balancing act of working full-time at Uber as an Enterprise Partner Senior Associate while training for the Olympics as a 400m runner.


I was fortuitously partnered with Steve as a part of a mentoring program during my internship at Uber in 2019 (bizarrely, it turned out that his parents used to live next door to my grandparents and his dad performed surgery on my grandfather - small world!), and his newsletter about his journey to the 2021 Olympics was a big inspiration in me starting this very newsletter.


Hear his thoughts on these 3 key factors for asking advice below:

”Building a group of friends and trustees that you can turn to for advice is the single best thing you can do as a young professional.


When I ask the advice of others, the first thing that I am aware of is this:


Asking for someone's advice/opinion transfers the risk of the outcome away from you and onto the advisor. So whenever I ask for advice, I make sure that I am okay about transferring this risk. Having set this up, let me now answer your questions:


Importance of domain experience.

Very relevant for technical advice, less relevant for general advice.


For example, I exclusively talk about my athletics with current or former athletes (high domain experience). I need empathy for them to understand what I'm trying to achieve on the athletics track, so only those who have gone and done it themselves are able to truly deliver on that.


On the other hand, I seek general advice from people that I know will ask the right questions for me to solve for myself.


When I'm transferring a large amount of risk in my decision, I do so with people of high domain experience (when asking people to tell me what to do). When I'm transferring a small amount of risk in my decision, I do so with people who know me well and are capable of helping me ask the right questions (general advice).


What outcome do I seek when asking for advice?

Mostly I look for the ways people I trust to make a decision to think about the decision that I am making. But in some cases, like in a coaching relationship, I'm looking for them to make a decision so I don't have to. Take the example of a fitness class. I will pay for a personal trainer to think about my program so I don't have to. Because I trust they will make a better decision than I can (along with added benefits of motivation etc). .


Strength of relationship.

The higher the importance of the decision, the stronger the relationship needs to be. That's why I said what I said at the start: Building a group of friends and trustees that you can turn to for advice is the single best thing you can do as a young professional. Relationships compound and grow over time, and that's why creating a network of people you trust to help you today will mean you have deeper connections to help you in the future.”



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