Feeling stuck? Here's how to know when it's time to leave your job | Ada Chen Rekhi

My hot take is that for the vast majority of people, they probably do not need a coach. And what I often push people on is if you're thinking about getting a coach, which is usually an indication that they have a feeling of being stuck or they have a problem that they're trying to solve, I ask them, 'What are your goals when it comes to coaching?'

"Curiosity loop" refers to Ada's term for seeking advice from multiple different experts rather than relying on one coach's perspective.

If you're looking for a mentor, a coach is actually a terrible mentor in some ways because it's this one person's opinion. It's actually way better to run a curiosity loop, for example, and get the benefit a couple different minds on a specific topic and hit their wheelhouse of things that they know about.

Half of people that founder their coach literally went with the first coach that they talked to. It's that your buddy said, 'I work with this great coach.' And then you go and you hire your buddy's coach. I think that's a totally fine way to go find a coach, but I would actually really just urge people to talk to a couple because what works for your friend may not work for you.

If you take a frog, and you throw in a pot of boiling water, it'll jump out. But if you take a frog and you put in a pot and you increase the temperature degree by degree by degree, the frog doesn't notice and before it knows, it's boiled alive. And how I apply this to your question to come back and circle back to it is that, it's really easy to be a victim of inertia.

I really look at it from the lens of learning. What can I learn here, and how am I growing and developing? So there might be an argument for you to stay at a job for two decades. If it turns out that every single day you're being really challenged, you're learning new things, you're deriving a lot of meaningful enjoyment out of your work.

My role at LinkedIn was really explicit. I even told my manager this when I first came in, 'I'm here to learn to be a better founder.' So there were a lot of things when I started connected, which I didn't know how to do very well, I didn't understand growth. I was fair to middling at pricing. I really didn't understand how to build a subscriptions business and how to price it.

I wouldn't have gotten those opportunities if I just let them promote me or I followed a strategy where I was just focused on trying to get the biggest title. Instead, I was focused on those learnings and those experiences.

I really look at it from the lens of learning. What can I learn here, and how am I growing and developing? So there might be an argument for you to stay at a job for two decades. If it turns out that every single day you're being really challenged, you're learning new things, you're deriving a lot of meaningful enjoyment out of your work.

Ada defines "curiosity loops" as systematically asking multiple people structured questions to gather diverse perspectives and advice.

One of the big reasons why I think curiosity loops are really useful is that it really fights the fact that there's a lot of bad advice out there. And it's not bad because it's not well-intentioned, but it's bad because it's not contextual.

It's a terrible outcome to wake up one day and be late career and feel trapped because you have a certain lifestyle or a certain expectations of the people around you that you have to go work this job, but then you look at yourself in the mirror and you're not happy going in there. I think that's a terrible trap that we should all try to avoid as we navigate our career paths and find the thing that's most optimal for us. Which is usually a mix of career success, but also meaningfulness and alignment in the work that we're doing with our values.

A good example... Well, let me start with a bad example of a question. A bad example of a question is, what should I do with my career next? It's just such a poorly formed question because it's really vague, it's not specific. It puts a lot of cognitive load on other people, and the output that you're going to get from it is probably going to be similarly bad. Garbage in, garbage out.

Ada Chen Rekhi is an executive coach and entrepreneur being interviewed on Lenny's Podcast, a popular product management show.

A curiosity loop is essentially going to a whole bunch of people. In this case, I sent out an email very quickly to about 10 or 11 people and asking them, 'Hey, here are nine topics for Lenny's Podcast. What are two or three of the topics that resonate with you and why?' And I got back such an incredible amount of information for about 20 minutes of work.

A "curiosity loop" is Ada's term for systematically asking multiple people structured questions to gather diverse perspectives on a decision.

One of the big reasons why I think curiosity loops are really useful is that it really fights the fact that there's a lot of bad advice out there. And it's not bad because it's not well-intentioned, but it's bad because it's not contextual.

Eating your vegetables is really this idea around how little kids don't really develop an appreciation for vegetables until they're 10 or 12 exposures in. So the researchers say, 'Expose kids to vegetables 10 or 12 times, even if they don't like it, because that's what it takes to get someone to like something.'

You have to do things a number of times before you really develop an affinity for it. Because the first time you do it, you're just not going to be good. So my mini example of that was early on in my career, I was really awkward and not very good at networking.

I gave myself this rule where I had to go out once a week for a couple of months, go to an external event, and I would count out 10 business cards. And the rule was, I had to hand out all 10 of those business cards by introducing myself to people that were new, and touch the back wall of the venue of that event and then I could leave.

Ada Chen Rekhi interviewed over 80 founders and executives about their coaching experiences to research what makes coach selection successful.

These founders and executives when they thought about it, they actually said so much more about, it was actually this amorphous sense of vibe with the person, how safe you felt with them, how deeply you would explore with them, and how well they got you, and remembered the pieces of the conversation and help you put it together. Way more than potentially some experiences that they'd had.

Over the course of seven years, I went from my first job, which was basically this entry level sales job at Microsoft, working on Microsoft adCenter to SVP of marketing at SurveyMonkey, leading a global team. And when I reflect back on what works across my early career, it really comes down in a nutshell to this career concept of explore and exploit.

Figure out, maybe the night before, the one thing that you want to get done in your day, and then at the earliest opportunity, just try to give yourself five minutes on it. Just five minutes. And the reason why I say five minutes is that there is this challenge that I experience and maybe other people experience as well, which is really just productive procrastination.