(Dontae Rayford is a New Business Development Manager @ Google, Stanford undergrad, NYU Stern MBA grad, and cool dude)


Age and a few gray hairs automatically signal an uptick in the number of requests for coffee chats that one receives. Having lived through and seemingly survived a countless number of reorgs, a revolving door of leaders, and a spectrum of roles and responsibilities most certainly puts one in a position to share their thoughts. Nevertheless, a large sample size of life and professional experiences does not necessarily equip one to give good advice.

As I’ve begun to take inventory of those instances in which I’ve sought advice and of those in which I’ve been sought out to share my views, there have been at least three types of advice-giving styles that I’ve focused my energies on avoiding.

“Listen to me, I’m projecting!”

Without question, being asked to share advice with a friend or colleague is flattering. You feel important. And by virtue of feeling important, you feel as if you should have important stuff to say. However, some advice givers find authority and comfort in such conversations by casting themselves as the antagonist in the situation.

“If I had this opportunity at your age, I would do X, Y and Z.”

If the recipient fancies themselves to be a disciple of the advice giver, the “projecting” approach may be appropriate! However, given the likelihood that advice is being sought from multiple individuals, the risk of advisor/mentor whiplash increases significantly.

“I don’t know much about this, but I do know…”

If you don’t have anything nice to say, don’t say anything at all. If you don’t have anything relevant to say, you’ll probably try to create some analogous tale that draws from your own personal experiences.

Don’t get me wrong, sometimes this can be a very effective methodology! Yet, many run the risk of conflating issues and alluding to similarities that don’t actually exist. The process by which an advice seeker chooses their next job likely has very little to do with how you decided what the eat for breakfast!

Sure, that “analogy” method isn’t always that bad. But unless one is well-versed in telling the same tale and having their mentee respond positively every single time, this approach poses a significant risk of crashing and burning. So proceed with caution!

“Well let’s dig into this a bit more to explore what you really want!”

What exactly does the advice seeker want to take away from their session with you? I’d reckon that the majority of advice seekers already know what they want to and will do before showing up at your doorstep. Many seek advice for the purpose of reinforcing decisions that they’ve already made in their heads.

If this “mind is already made up” assessment is true, advice givers are will be most useful if they challenge assumptions and better understand the inputs that are governing the recipient’s decision-making process.

Are you optimizing for money? Are you optimizing for experience? Are you optimizing for title? Or, maybe you’re optimizing for commute?

This isn’t necessarily a time to play devil’s advocate exclusively. However, the infusion of some questioning that counters the recipient’s worldview can help to distill their true motivations and can assist the advice giver in understanding what type of feedback will be most useful. It always helps to meet the recipient on their terms and lead the conversation in directions that they either consciously or subconsciously want the discussion to go.

Sure, with this method you still run the risk of confusing the shit out of them. But if executed appropriately, you’ll ensure that you’re providing input that is relevant.

So what’s the best approach?

I’m obviously biased toward approach #3. But that’s only because it suits my advice-giving style and mimics the type of advice that I like to receive. These sessions should interactive and help provide a framework by which decisions can be made.

Obviously, no one approach is perfect and you may find yourself utilizing multiple approaches for any given conversation. Regardless of how things unfold, know your style, embrace it and work on getting better at it! Not unlike other skills, advice giving requires practice and attention to detail.

And no matter what your takeaway from this piece is, never forget that advice giving is not about making decisions for someone else. It’s about listening and doing your best to share constructive input.

The onus is on the recipient to determine what the hell they want to do with any advice that you share!

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Dontae is a tech professional living in Oakland. He's originally from LA, is sad about Kobe's retirement and gets emotional when listening to music.

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