Kicking off a job search can feel overwhelming. It takes motivation to put yourself out there, and it’s emotionally draining when you don’t know where to go next. The good news is there are simple techniques to surface new opportunities and set yourself apart from all the other applicants. Who Got Me Here is a podcast about connections, career building, and relationships. In this episode, Annie and Jamie will share advice on tapping your network, making great asks, and acing the interview. If you know someone who has been laid off or is coming to you for career advice, share this link. The recommendation might prove immensely helpful in thinking about their next career move.
Kicking off a job search can feel overwhelming. It takes motivation to put yourself out there, and it’s emotionally draining when you don’t know where to go next. The good news is there are simple techniques to surface new opportunities and set yourself apart from all the other applicants. Who Got Me Here is a podcast about connections, career building, and relationships. In this episode, Annie and Jamie will share advice on tapping your network, making great asks, and acing the interview. If you know someone who has been laid off or is coming to you for career advice, share this link. The recommendation might prove immensely helpful in thinking about their next career move.
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“Don't think about the job search as a one-time campaign. This is really about developing your career. So success in a job hunt and success in your career is about the number of good relationships that you can foster. These are the people that are going to be your advocates and sources of your next career opportunity. Reid Hoffman said this, “if you're looking for an opportunity, you're really looking for a person.” So you want to think about developing good relationships throughout your career and keeping track of those people. The second thing is really about the number of quality touches. It's about how many people you reach out to, how many conversations you're able to set up, and quality means that you're taking the time to craft good asks of different people. And then, finally, acing the interview. You want to make sure that, if it's a company that you love, you are the best candidate and you're going to land that job.” - Jamie Grenney
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Episode Timestamps:
*(02:11) - Introducing Jamie Grenney, CMO and Head of Product at Connect The Dots
*(02:47) - A story about Annie Riley, Host of Who Got Me Here
*(05:12) - Advice for first steps and getting tactical with job searching
*(14:54) - Building relationships and making good asks
*(19:02) - Relationship refreshes as a means of reconnecting the dots
*(27:56) - Keeping conversations going by following up on initial connections
*(31:02) - A multi-time CMO’s advice for acing the interview process
*(37:48) - How to decide which company to accept an offer from
*(40:14) - Final piece of advice - don’t think about the job hunt as a one-time campaign; think about relationship building as the key to career success
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Sponsor:
Who Got Me Here is brought to you by Connect The Dots, mapping professional relationships so you can find the strongest connections to the people and companies you want to reach. Visit ctd.ai to learn more.
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Links:
Narrator: We all have that person in our lives who seems to be connected to everyone. You can be intentional about your network while still being human. In order to build strong connections with others, you really have to be strongly connected with yourself. I believe that meaningful networking has been the single greatest contributor to my good luck. You can't connect the dots looking. You can only connect them looking backwards.
[00:00:31] Annie Riley: Welcome to Who Got Me Here, a podcast about making connections matter. I'm your host, Annie Riley, and today we wanted to do a special episode of Who Got Me Here focused on job searches. So typically we have a guest on, we talk about their career story, their advice for relationship building, how they think about networking and their own.
And this time we are going to dial in specifically on job searches. We hope that this episode can become a resource for anyone who is currently on a job hunt. In this moment in time, we're recording this in Winter 2023, feels like there's been a record number of layoffs. I personally feel like everyone I know is thinking about some kind of transition, whether they've been laid off or.
And many, many people are embarking on job hunts right now, so we wanted to be responsive to that. We're a podcast all about connections and career building and relationships. We want to talk about how you can use tools from our show to really build your next step in your career. So to join me today, I have a special guest for this special episode.
We have Jamie Grenney on the show, who is CMO and Head of Product at Connect The Dots, which is the sponsor of this show. And before Connect The Dots, Jamie spent 11 years at Salesforce and has worked for four unicorn companies across his career. Jamie has been an awesome partner in developing this show and has some great work experience of his own to share with us, including specific tactics about how he has tackled job searches over the course of his career. So welcome, Jamie. We're so excited to have you on the show.
[00:02:16] Jamie Grenney: Oh, Annie, thank you. You've been a spectacular host for this podcast. Both in your interviews, people Dunno. This is Annie's first time doing a podcast and she is just a. Annie is also kind of, she's dug deep into her network and many of the guests that you hear are ones that she works to form a personal connection with. So Annie, thank you for all your help with who got me here.
[00:02:39] Annie Riley: It has been so much fun. I've loved this project and I'm excited for what we're gonna do today and beyond this episode.
[00:02:46] Jamie Grenney: Yeah, before we kick things off, I, you know, Annie has been a friend of my sister and a family friend for many years. And the Annie that I know, years ago, she reached out to me and this was after she had a great run at Hotel Tonight.
And she said, I think I'm gonna do a sabbatical. I'm gonna take a couple months off between jobs. Well, I said, what are you gonna do? And she said, well, I've got a couple months and I think I'm gonna spend a month working on a presidential campaign. I think I'm gonna spend a month going to visit national parks and I want to go to a foreign country and learn a language.
And I was so impressed that one Annie reached out to kind of, I was honored that, that I had the opportunity to talk with her on the front end of that, uh, sabbaticals. But it just, it, it's, you know, the, the podcast that we're gonna deliver today is about job hunts, but it is really important to think about, you know, kind of your, your lifelong career.
In that case, Annie was, was essentially setting up stories that she'll be able to tell for the rest of her life. So that's a little bit about your host, Annie Riley.
[00:03:46] Annie Riley: I remember that conversation. Well, I think we were at Four Barrel in San Francisco with all the coffee snobs, just like digging into the plans for that.
And I think I hit two outta three. I didn't work on the campaign, but I did hit a lot of national parks and became high beginner in Espanol. So, you know, really making moves over here and I appreciate that, Jamie, cuz I had a friend listen to the show and she said to me, you never introduced. You're really failing at your own tips on the networking show, so I appreciate the kind words and appreciate that context.
For sure. Maybe as we dive in to talk about job searches specifically, could you share with our listeners why this episode is important and meaningful to you, and kind of why we're doing this at this moment in
[00:04:36] Jamie Grenney: time? Yeah, I mean, you set it up in the beginning. Right now in our economy, it feels like you're hearing about layoffs all the time.
You know, particularly in. And no one is immune. You know, you have startups, but you also have big companies like Google and Amazon and Microsoft and Twilio kind of all laying people off. And so we have friends who are impacted. You know, I have old colleagues and cousins and this and that who have reached out saying, ah, I got hit by the layoff, and what should I do?
So I'm excited to take a little bit about what I've learned in my career, but also what we've learned from our guests on who got me here and see if we can pay it forward and create a great resource for, for anybody's.
[00:05:13] Annie Riley: Amazing. So let's get tactical with this. You know, if you find yourself embarking on a job search for whatever reason, maybe you were part of a round of layoffs, maybe you're just thinking about making a move.
What is the first step? What do you advise people to do at the beginning of that
[00:05:30] Jamie Grenney: journey? You know, for me, whenever I start a job search, I'll typically start by creating a list and I'll create a new Google sheet, and my list is all of the people that could be helpful in my job. And so there's friends and families, they're old colleagues, they're C-level executives.
I've got a list of my recruiters and, and investors, and so that list becomes foundational because over the course of that job hunt, I'm going to do my best to sort of speed date and go through and and tap into those individuals who can be helpful. Now, if I were to start a job search today, I might use Connect the Dots product that sponsors this show just because it makes that process a whole lot.
With my spreadsheet approach, it's kind of a pain to keep all the information up to date. I need name, title, company, you know, their current role. And that information, you know, is constantly changing. So with Connected, that's what you can do is in about 15 minutes you can connect your, your email, your LinkedIn, and create a graph of everyone you've ever met and every company that you've ever engaged with.
And using that as a starting point isn't. Better way because everything is scored by relationship strength. So you can see those people who, who are gonna be your, your best advocates.
[00:06:45] Annie Riley: Okay? So you make the list and I love that you named. People from all different parts of life, and this is something that we heard from the guests who have joined the show as well.
They've gotten intros to jobs and they've gotten advice from not just the senior people on their teams, but fellow interns or people that they've hired their own direct reports who are even earlier in their career than our guests were at the time. So you make this sort of full list of anyone who can be helpful, including.
All different profiles of people, not just the ones you necessarily are looking up to or have been your manager in the past. And then what do you do with this?
[00:07:22] Jamie Grenney: What happens next? Yeah, so what happens next is I start with my list of people and then my next step is oftentimes create a list of companies and the companies that I wanna work for.
And many of those are, are top of mind. You know, they're really easy to come up with the, the usual suspects, but you might wanna do a little bit of a, a spike to broaden. You might want to look for lists of companies like what venture investments have been made, what are the fastest growing companies? You might go on review sites like G2 Crowd to see what products are being scored very high by the community.
The broader your list at the outset, the easier it is to kind of find those things that might be loose connections that might not be on your radar right away. The other step that I like to take is, is I like to look at where former coworkers have. So I had a long run at Salesforce and inside Connected Dots, I think I have about, uh, 2,500 strong and familiar relationships, and many of these are are coworkers.
So look at a company like Salesforce or like Okta or like own backup, and I'll click on the former tab and I will see where all of those employees are today. Once again, this is about, you know, finding companies that might not have been on your radar originally, but if you have a coworker, a former coworker who is now working.
One, they've vetted that company, they've been through the interview process and, and they think that they've found something pretty good. And two, you've got an advocate inside that company who can at very least tell you about it and, and see if there are opportunities there. So those are some tips for sort of expanding your list of potential companies that you can go after.
[00:08:58] Annie Riley: Yeah, I really like that. So you actually are surfacing the companies that you have worked at in the past and figuring out who from those places. Um, where have those people gone? Where have they gone on to? And then do any of those companies. Strike my interest. How do I feel when I look up their product?
When I think about that company, we heard some great advice from one of our guests, April Underwood, on this topic. She, uh, built her career at companies like. Google, Twitter, slack and started her own investing group, hashtag Angels. And I remember she was saying that when you're looking at a potential company, you really wanna love the product and you ideally want to pick a company that keys in on a cultural trend.
That is happening at that moment in time, and I thought that that was really great advice, especially as people are building that list, like you're describing sort of to, as you build the list, look at the companies and compare, oh, do I like this product? Am I genuinely interested in it? And what, what cultural trend is this keying in on?
And do I think that's going to be growing, moving
[00:10:03] Jamie Grenney: forward? You wanna be energized by the opportunity and energized by the person that you're ultimately working for and the, the team that you surround yourself. That's totally true. If you're just a mercenary, it's gonna be no fun. That said, at the outset of your search, you do wanna keep a little bit of an open mind.
You know, there have been companies that I've gone to work for where at first glance I was like, wow, this doesn't seem like something I'm very interested in. I mean, own backup was about, you know, backing up data in the cloud. I was like, is that something that I could get excited about? And through the interview process and the people that I spoke with, I got more and more excited over time.
So don't cross companies off too. Yes. When you get to the finish line, you should feel confident that you have really vetted this and are excited to go to work there. The other piece of advice, you know, Todd Sasser was another guest that you had on Todd. He started a company called BrightRoll, which he sold to Yahoo, and he's also been a successful venture investor.
But his career advice is find anything that feels like a bull market and embed yourself in it. You know, any place that you're gonna get outsized returns on ambition and work. So that is definitely a really good screen, is to look for growth, look for customer success. And one way I do that is I go onto LinkedIn and it might be a, a premium feature, but LinkedIn will tell you how fast the company is growing from a hiring perspective.
And so you can see like, is it on a downward trend or is it on an upward trend? If you can get in with a company that is growing fast, that's doubling every year, that's gonna open up new career opportunities and it's gonna build
[00:11:36] Annie Riley: your brand. Yep. I thought that was great advice as well. And that one I think can be tough right now when we're in this economic climate.
You know, there you hear about so many layoffs from so many well-known, well-respected companies, and I think it can. Easy to feel a little down on, you know, the opportunities that might exist. And you know, there are though industries and companies out there that are growing, especially some early stage startups that might start with a really lean team.
And that was one that Todd said, you know, those are places where if you're willing to do the work, you're willing to put in the time. You don't necessarily have to have the knowledge, the expertise, the background in that space, but if you're willing to sort of stand out. Will an ambition perspective, then you can really build your career in those types of companies.
And I thought that that was great advice for this moment in time in particular.
[00:12:28] Jamie Grenney: Yeah, with those earlier stage opportunities too, it's about betting on the person, betting on the c e o of the company and does that person have the track record or the ambition to run it all the way and is it in the right market that it is a big addressable market and this company has a, a shot at being disruptive.
Sometimes job hunts feel a bit like being a venture investor. You're trying to size up the, the growth prospects for a company, and it's not an exact science, but the more people you can talk to, the more people you can bring into the search, the better chance that you have of getting it right.
[00:13:03] Annie Riley: Mm-hmm. Yep.
And checking in with your energy after you meet the people. That came up in our conversation with April Underwood as well. And I think that that's so important because you know, maybe the product doesn't stand out. Like you were talking about own backup and you're like, well, is this something I'm interested in?
I'm not really sure. But you can meet the people, you can get into a role that you enjoy, the work involved. And as long as you are sort of learning and connecting with those people, it can be a great opportunity. And I think our guests have reminded us time and time again that each company you go to, Those individuals become your network moving forward.
And so, you know, just spiking on the people and how you feel around them, what you think you can learn from them. That is so, so important as everyone embarks on finding an opportunity that isn't just gonna be a job, but ideally it will be a place that they can thrive and grow and bring that network forward to things they do from that point on.
[00:13:57] Jamie Grenney: Yeah, we heard that from so many guests. April Underwood, I think was the one who said, But Molly Graham said the same thing when she leaves the company. She creates a list of all of the people she was really impressed by, and she makes a point at staying in touch. And over the course of a a 10, 20 year career, you work with so many people who know your work product well, who know you know your origin story really well.
And so that becomes the foundation of your network. So choosing companies is not just important for the job and the paycheck, but it's also going to set you up for career success in the long.
[00:14:30] Annie Riley: Yep. Absolutely. Okay, so back to the steps of the job hunt and the recommendations we would give to folks who are embarking on that journey themselves.
You recommend people make these lists. You got this list of people, people who you know, you are friends, our direct reports, our former managers, all types of people. And then you've got this list of companies that you're like, oh, I'm curious about that. You know, you, you're maybe interested in the product or you see that it's a growing space.
What happens now? Cause I think this is actually where a lot of people get. You know, you've got the list and you're like, oh, I, I wanna reach out, but what do I say? And maybe it's awkward, right? Maybe I haven't been in touch with that person in some time. What's your advice for getting over that hurdle?
[00:15:12] Jamie Grenney: We should make asks more often, and we're intimidated to do it, but we should make asks more often.
It does require that you are long-term greedy, not short-term. Because if you're just transactional, coming back to people and asking for, Hey, do you know any jobs? Do you have any opportunities? They're not gonna be willing to help you out. So this episode is about the time that you are searching for a job, but it's important that you're a dot maker throughout your life.
And we've heard a time and again, like you wanna be a good teammate, a good friend, you want to invest in other people. You wanna find ways to be. You wanna go above and beyond. So when it comes time to make an ask, you've built up some goodwill. The other thing that I think is really important in the investment stage, in the creating your dots stage is to look for genuine connection.
You know, there are good people all around us that we encounter every day. And if you can make a connection and I'll, I'll explain how, if you can make a connection, you can pick that up five years down the road, 10 years down the road, and. So one of the best books I read last year was, was a book called Friends by Robin Dunbar.
And he's got terrific advice, but one of his pieces of advice is they're a handful of dimensions to, to any friendship, and they're, they're pretty universal. It's a common place of origin, it's common interests, it's a common worldview. It's a similar educational background. It's a love for music and a sense for humor.
And if you can go into a conversation and as, as Molly would say, She asks, asks you a question, she listens very hard and she asks the next question, if you can go in and really dig deep to kind of find out where we have this common bond. If you can hit on one or two of those dimensions, chances are you've got a level of trust and friendship for life with that person, and you can come back to them.
So a lot of it is about setting up these conversations throughout your life so that you can come back and tap back.
[00:17:12] Annie Riley: Yeah, I think that that shared history, shared interest is so important and we heard many of our guests talk about pointing that out, reminding people of that when you're doing that outreach.
So the outreach isn't just, Hey, how are you? Can we catch up? Which is vague. And you know, people's most precious resource they have is their time and attention. Uh, and they're like, what is this about? What am I getting into? Right? But hearkening back doing a callback to something that you shared together or sort of making those connections over time.
Hey, thinking of you, I remember Michael Jaconi, who came on the show, who is a successful entrepreneur. He talked about how he loves fishing. And he identifies other people in his network. I think in this case it was an investor, a business partner who also loved to fish, and when he catches a really big striped bass, he sends them a text with a picture of it.
And these texts of, of pictures of phish just go back and forth and back and forth. So I think sometimes we think it needs to be such a high bar around what we reach out about. Like, I won this prize, or, you know, I have this exciting update, but sometimes it can be as simple as calling back to a shared connection or something that.
Know this person likes, makes you think about them.
[00:18:25] Jamie Grenney: Well, Annie, the other thing that I've seen across all of these interviews that we've done on the show is that the biggest difference between the average person and the top 1% is their ability to start conversations and keep them going. There are a couple ways they do this.
One is by hosting events. Some people have that as a superpower and they love to bring people. And it could just be bringing three people together for lunch, or it could be getting them together for a sporting event or, you know, Todd talked about bringing CEOs together to, to talk about common problems.
But people who are able to host Vince and facilitate that, that is a great way to create bonds between folks. I think the second category of things that we've seen is people that are really good at relationship refresh. Sometimes it's just that simple text like Michael had where is like, hey, thinking of you, you know, was out today fishing and that's it.
And sometimes you're intimidated to send that text, but if you've ever been a recipient of that, you always know. It feels good. It feels good to know that other people are thinking of you. Yeah. People like to be thought of. Yeah, they do. They. And if you wanna push the relationship refresh thing a little bit further, my New Year's resolution last year was to do a hundred relationship refreshes in a hundred days.
And it sounds like a crazy ambitious, you know, thing to do. But what I did is I came up with a list of a hundred people and I tried to pick them from all walks of life. You know, people, I went to grade school with, high school, with college, you know, people I worked with, people I knew. And I reached out to all hundred and said, Hey, here's, uh, something I post on LinkedIn to explain like what I'm doing.
And I included a accounting link and said, if you've got 20 minutes, it'd be awesome to connect. And out of that, you know, things started popping up on my calendar and I had times at nights and weekends and in the mornings and things like that, and it was only a 20 minute, you know, request. It was like, grab 20 minutes on my cal.
And there was no set agenda, but it flowed so naturally. There are people I hadn't talked to in 20 years, and you just picked things right back up. It's one of those things, those a hundred relationships are people that I can go back to this year or next year with a greater level of familiarity. So a really fun exercise if you're looking to build richer and deeper relat.
I love
[00:20:40] Annie Riley: that one. I remember when you did that, and what I loved about it in particular was that it was only 20 minutes, and that feels totally doable. You know, in a, in a moment in time when people are so protective of their calendars, people are booked back to back. So frequently just having 20 minutes to check in and having that be the expectation that gets set up front.
Cause I think sometimes people say, Hey, you wanna catch up? And you're like, oh my gosh, is it gonna. An hour long conversation. I don't have time for this. And sometimes you want to, but the bar just feels too high. And so just scaling it down to 20 minutes I think is so, so helpful. And I like the idea even of a, of a job hunt as a relationship refresh moment.
You know, so people who are going on these job hunts might be thinking, oh, I gotta ask all these people for time. You know, it's, it feels maybe burdensome or people feel reluctant about it. But if you just think about this reframe of your job hunt is a relationship refresh moment, a chance to reset on some of your networking tools.
And then, you know, once this job hunt is done, you can do. In an ongoing way, and hopefully it's that much easier because you've had all these touchpoints with these people, um, in this calendar year while you are, you know, embarking on this search. I even just like that as a reframe for what people who are job hunters are doing right now.
They're refreshing relationships.
[00:22:05] Jamie Grenney: Yeah, absolutely. And, and the time commitment, again, if you take 20 minutes times a hundred and there's some sort of administrative cost of pulling that list together, you're talking about a 50 hour. And every day on your calendar, you'll have one or two relationship refreshes.
And it is so energizing to be able to talk to say, Hey, here's where I am in life. And is a really, really good thing to do.
[00:22:28] Annie Riley: Absolutely. And I also love that you posted it on LinkedIn because there might have been people who, you know, there's probably the list of people who you thought of, oh, it'd be great to catch up with this person or that person.
We were probably connected to many, many more people than. On your LinkedIn, and so by posting it, you put it out there, you put this intention out there and probably had a much bigger reach. Did you actually find that people were then reaching out to you? How did that LinkedIn component play into the relationship refreshes?
[00:23:00] Jamie Grenney: Yeah. I mean, some of the people commented and said, Hey, put me on the list. I'd love to catch up. And so that's one of the benefits. And also other people were just like, well, why is Jamie hitting me up for 20 minutes? And I could have a link to this to explain like what I was trying to accomplish in this a hundred day goal.
And it's sort of two different purposes. I'd say the other thing on, on a job hunt and just in life is thinking about how do you do things at scale? And so it could be a annual email that you send out to a bunch of people to say, this is what's new in my life, both personally and profess. Or it could be posting things on, on LinkedIn to, to kind of get your name out there and kind of get back on people's radars and just as important as posting is going in and commenting on other people's work and just showing that you're interested in care and have a point of view is another way to spend some of that time of your job
[00:23:52] Annie Riley: hunt.
Yep, absolutely. I think we had several guests comment on having a steady drum. Out there in the world reminding people that I'm still here, I'm still alive, I'm still, you know, doing things and interested in things. I think we heard that from Todd and Michael and several others, and it's about finding the version of it that works for you.
I remember when Page Ma Zad came on the podcast. He's the founder of PIR VC and was the first money into companies like DoorDash and Dropbox and some other really iconic technology companies, and he talked about how he loved hosting events. Which is one of the things that you mention here. And you know, he's super social, loves meeting people, and so for him, events are a great way to put his name out there, gather people together.
In fact, it was the way that he inserted himself into the conversation and made the huge career in life transition from selling Persian rugs in Palo Alto as an I. To becoming a venture capitalist and having the opportunity to put those checks into those companies at that very, very early stage. He did that by hosting events where he could bring people together who he knew might not have met each other otherwise.
And so for him, for Todd Events, parties, things like that work. But I remember Page Mon saying, you know, he had a partner who didn't like events, and that person would write content. And, you know, put content out there onto blog posts and LinkedIn and that was sort of his way of putting out to the world, Hey, I'm here.
This is what I'm interested in. Um, and so both of these fall into the category of doing things that scale to your point, but finding the version of it that works for you and your personality and become something that you can sustain. Cuz if you like doing it, then you're probably gonna do more of it over.
[00:25:44] Jamie Grenney: You are so right. You can build up new muscle, but if you, if you can fall into something and that is your flow state, that is your superpower even better. So lots of ways to accomplish the same goal. I
[00:25:54] Annie Riley: remember Todd talking about if folks are reluctant to talk publicly about their projects or they might be saying, who am I to send a quarterly update to people?
I don't feel that excited about what I'm doing. I'm, I'm trying to break into a new space. He recommended doing things like putting together a list of things I'm reading. Interesting articles that I've encountered, cool podcasts I've listened to, aggregating different resources and putting those out.
There can also be a way of creating a steady drumbeat and inserting yourself into a conversation potentially for an industry that you wanna break into, or a type of company that you wanna join. And so, you know, a lot of people feel nervous sometimes to put themselves out there, and there are ways to dip a toe in by aggregating resources and content if that's something that
[00:26:41] Jamie Grenney: feels more comfort.
People want to bet on winners. They wanna bet on people who are, are passionate. And so if you can show a little of that passion and ambition, then it goes a long, long way when it comes time to asking
[00:26:54] Annie Riley: for help. I think that also relates to the follow up. You know, this is something that you've talked a little bit about, you know, following up with people.
Sometimes I will have a conversation with someone. It's delightful. They tell me all about their interests and ambitions and then, you know, I don't hear from them again, and I wonder, Hmm, did they follow up on that? What are they up to? What advice do you have for folks, especially job seekers, once they have the conversation, once they have the touchpoint, how do they do that?
Follow up? What are your recommendations?
[00:27:24] Jamie Grenney: Let's say it's even before the meeting. I think that doing your research is very, very important and with a lot of people, if you're trying to get to a CEO or somebody at the executive level, oftentimes they've done something on on YouTube or a podcast, and you can listen and learn a lot about their perspective.
And if you craft a message to them saying that, I've done my research and here's why I'm interested in speaking with you, specif. It goes a long, long way. And so that sets up a good meeting on the front end because you can make good use of their time. They know your passion. But then on the back end, the follow up is important.
And the best practice I like the most is it comes from this guy Jason Davis. He's the C e O of Simon Data. And every time Jason has a meeting or a lot of times, he'll send a really simple text message after the meeting just saying, Hey, it was great to catch up today. Thanks for swinging by the. And that allows him, it creates the space to have a one-to-one conversation with that person in the future.
And so a month later, he might go back to his text messages and kind of scan through them and say, well, who did I send text messages to about a month ago or two months ago? And just pop back into that chain with the quick update. So I do think that you've gotta find ways, not just to make that initial connection, but to keep the fire alive.
[00:28:41] Annie Riley: Having that paper trail to say, oh yeah, we talked about this. I wonder how that's going. And then you know it's there. You can follow up that much more easily. The other thing that came up with many of our guests was giving people a graceful out or a graceful plan B, when you're making the ask, and I just wanna mention that briefly because so often when we do reach out, we are asking for time, and sometimes people have that available for us, even if it's, if it's just 20 minutes, you can make the most of that.
But sometimes people. Can't do that. Maybe they're just too slammed or they have something going on in their life that precludes them from taking that call. And so I thought that that was great advice to sort of, when you make the ask, you reach out and you just say specifically what you're looking for.
Hey, I'm, I'm looking for a referral to this company, or, I would love your advice on which companies are growing that I could embed myself in next. And just be open to the fact that they might be replying via. Or they might send you to the recruiter on the team and then that person you get to have a call with.
So I just would love, um, to touch on that briefly and just get any thoughts that you have on sort of this graceful plan B and being open to any direction that the response might take you.
[00:29:51] Jamie Grenney: Yeah, you're dead on. You wanna make it easy for them to say yes and easy to say yes can mean a couple things. It could be you're asking them for insight or an.
And so if they're not comfortable giving you the introduction, you know, you say like, could you provide me a little bit of insight? And that could be very quick to provide a quick response like, who is the hiring manager that's quick. Something that they can do very easily and get you a step closer to your goal.
There are other times where. If you, if you provide a ask that is very, very open-ended, sometimes it's just, it's hard. You're putting all the work on the recipient and the recipient has to think of companies or think of open job opportunities. Whereas if you spun that around and you said, Hey, here are three companies that, that have really peaked my interests.
Let me know if you've got strong connections there or any. At that point, they can react very quickly to the three companies that you've proposed. They know roughly what you're looking for and they can respond fast. The hardest requests are are, Hey, will you give me 30 minutes on your calendar? You're not telling 'em what you're looking to accomplish in that 30 minutes.
And then they get on the call and they're like, where's this conversation going? A common
[00:31:03] Annie Riley: phrase that people rely on when doing this outreach is Pick your. I get so many messages and I, early in my career, I sent messages saying, Hey, can I pick your brain? And it's like, about what? For what purpose? You know?
And we heard from each and every one of our guests this constant theme around, don't send messages like that. Don't say, can I get your advice? Can I pick your brain? Be specific about what you're hoping to learn, or what you're hoping to ask this person for. Okay. So we've talked a lot about making these.
Doing your research, crafting a good ask, let's say, you know, for those job hunters out there that lands you an interview, you know, the research, everything you've done so far, that should position you, you know, for as much success as you as possible in the interview. But Shami, what's your advice around that interview stage?
[00:31:52] Jamie Grenney: Uh, the interview stage is, is so important. It's important because every time you meet with someone, you're trying to earn the right for the next convers. To meet with another member of the team or, or get a, a step closer. So you wanna make a great first impression and every single interview you wanna ace.
And at the end, you know, if you've invested a bunch of time, you wanna push yourself just over the edge, over the other candidates that they're considering. So it's really, really important when you've found a good company, when you've gotten that interview to do your. Years ago I interviewed at Okta and it was a company that, you know, I really wanted this job.
It was amazing. It was running the product marketing and enablement team. It was a, a company that was growing fast. I love the culture and so for me, doing the research meant getting to know all of the people I knew at Okta. And Okta has a bunch of Salesforce folks, but they were in different departments.
And so I would talk to somebody in sales and I would talk to a sales engineer and talk to somebody who ran the services organiz. Even though they weren't involved in the hiring process, they could put a good word in for me and they could give me more context into the company. And I also did my research by reaching out to CIOs who I thought might use Okta.
And I asked them kind of, what's your experience with the product? And by doing that, I felt more prepared for the interviews. But I also had them looking at me saying, wow, this guy is really working his network to kind of learn about our customers and the pains and, and all of that. That's great initiative.
And then the last thing I did is, is, I mean, this, this interview process went on for 23 interviews, so it was, it was a long one, but I took the time to watch the entire user conference, all the breakout sessions on YouTube, and I did it in 1.5. But I walked into the interviews and I could tell customer stories as well as as anyone because I had really gotten up to speed on the product.
So, you know, it's an example of the types of things that you can do to really prep for interviews, but the warmer you can make them feel, you know, dropping names of people you have in common and dropping names of customers you've talked to. That's huge. And then afterwards following up, following up with samples of your work or links of things that you talked about or, you know, a personal note goes a long, long way.
So that's a little bit on acing the interview process.
[00:34:12] Annie Riley: That's such great advice around talking to customers and hearing their stories. Because a great byproduct of that is you probably felt way more confident in the product when it came time to make the decision. You aced the interviews, you have the offer in hand, and you're like, should I take this leap?
Is this the right company for me? And because you had done all that research, you were both more prepared for the I. And you had a lot more data to know if this was gonna be a good career move for you. So I think that is super smart advice. And then the other thing I heard in what you just shared, just to call it out explicitly, is a little bit of patience.
23 interviews. I've never heard of a process that long. And you know, I could see myself getting impatient or frustrated like, oh my gosh, is it ever gonna end? And sometimes these things take time. It just made me think of Paige Man, za again, founder of Repair vc, talking about recruiting his partner, Mar.
And he said it took several years to convince her to start this firm with him, and now they have this incredible fund with this lasting legacy and all this success. 23 interviews, four years to recruit a business partner. Sometimes if you wanna move in a specific direction, these things can take time.
And that was just the other thing I heard in that anecdote that I wanted to call out explicitly
[00:35:35] Jamie Grenney: such an important lesson. You know, in a hot job market, you might have two interviews and they ship you an offer letter, but with that type of a dating process, you could miss things. You could miss really important flags that mean that the opportunity isn't what you thought it.
And that can take, you know, years off your life, years off your career kind of if, if you make those wrong steps. So the upside of, of a job market, which is a little bit tougher, is the process is gonna take longer cuz they're gonna wanna vet more candidates. But you have more of an opportunity to make sure that it's a right fit.
And so, you know, there's, there's upside downside in
[00:36:10] Annie Riley: that. Yep. Let's talk about that piece of this process a little bit more, determining what is the right fit, making the decision. You know where to take your career next. This is a big one for people because again, the company you joined, the projects you work on, these people that you do those things with, they become your network.
The experiences you have become, the stories that you can tell about what you've accomplished and what you've learned. These are the skills that you're gonna build. So I think it can sometimes feel like a pressure cooker for people, you know, how do I make the right choice and wanting the right choice to just magically appear.
What advice do you have for how people can ultimately decide which company to join, which job to take, which projects to pursue?
[00:36:58] Jamie Grenney: Part of it is a numbers game and a numbers game meeting. The more conversations that you kick off, the more well informed you'll be and the more opportunities that you should have when you get to the finish line.
So if you start with a big list at the start of the process and, and you work that list really hard in the beginning of the process. And hopefully you're going to see a bunch of opportunities when you get to the, the finish line. You wanna have, ideally have two offers on the table so that you can compare and contrast them, or maybe even more than two offers on the table.
But the more looks you get, the better you're going to be at, at judging whether something is good or not. What you wanna avoid is taking something outta desperation. And I've been in, at this spot in my career, there was a, a job that I took and I had a pit in my stomach when I signed the offer. And my tension was that, ugh, this job hunt has taken so long.
I don't know what the next opportunity is even gonna be. And so it could be a month away, two months wait. And so I had this pit in my stomach and I took it. And I will say like it's something that I've learned from because that definitely took momentum out of my career because I chose the wrong opportunity.
And so it's really important to trust your gut, to give yourself as much runway as possible and to have as many data points or conversations going into your decision as you can. Absolutely.
[00:38:18] Annie Riley: I remember talking to Kate Taylor, who's built her career at companies like Salesforce and Dropbox and now as the global recruiting lead at Notion, and she said that when she has accepted job offers and made these types of career decisions, she goes out to her network and asks a ton of people what they think.
Which job offer do you think I should take if I wanted to move my career in this direction, which would be the best offer for me to. And then at the end of the day, she takes all that information and she just sits with herself. She goes, And tries to figure out, okay, I have all this data. How does it feel?
To me, kind of looking for that pit in the stomach, that gut reaction that you're describing, and you know, it sounds so simple, but it's actually really hard to do, to cut out all that noise and to search within yourself to say, which is going to be the direction I wanna move in. Of course, we don't have a crystal ball, but we can rely on those instincts.
I. To know what's gonna be the next move. Knowing that you can always make a change after that. You want it to be a place you can stay a long time, but people make a lot of career moves over the course of their lives and a lot of these things are not permanent
[00:39:26] Jamie Grenney: decisions. Yeah. Trust your gut. The other thing I would recommend, there's a great book by Chip and Dan Heath called Decisive.
It provides a number of frameworks to, to look at a. An important decision like your job hunt, and if you can run through the questions in a book like that, then it really helps you narrow down and feel confident in this decision you ultimately make. Absolutely.
[00:39:48] Annie Riley: So we have covered. The full gamut of the job search experience from making your lists, you know, doing your outreach, how to approach those conversations around making connections, really listening, lots of different ways to do follow up, create that steady drumbeat.
I'm here, I'm alive, these are the things I'm interested in. These are the projects I'm working on. And ultimately deciding on a career move. Once you've had the interview, you've sort of aced that process. Is there anything else that you wanted to talk about or any other advice that you have for folks who find themselves in a job hunt
[00:40:21] Jamie Grenney: these days, don't think about it as a one time campaign.
This is really your career in developing your career. So success in a job hunt and success in your career is about the number of good relationships that you can foster. These are the people that are going to be your advocates and sources of your next career opportunity. Reid Hoffman said this, if you're looking for an opportunity, you're really looking for a.
You wanna think about developing good relationships throughout your career and keeping track of those people. The second thing is, is really about the number of quality touches. It's about how many people you reach out to, how many conversations you're able to set up, and the quality means that, that you're taking the time to craft good asks of different people.
And then finally, acing the interview. This is just about, you know, you wanna make sure that if it's a company that you love, that you are the best candidate and you're gonna land
[00:41:13] Annie Riley: that. Absolutely great advice for anyone at any stage in their career, and I hope that this episode has been helpful toolkit and resource to folks who find themselves in a job hunt at this moment in time.
And I just love this idea of making this a refresh moment, a reset moment, an opportunity to build these new habits that you're describing that will help you yes, in this specific job hunt at this moment in time and in an ongoing way throughout your career, if you can keep them up. And the more you do it, you know, I took a meditation class and the teacher said, this stuff is dose.
And I think that goes for the tactics that you're describing as well. They are dose dependent. The more you do it, the more you're going to get out of them. Anything else that you wanted to share, Jamie, before we close out?
[00:42:01] Jamie Grenney: No. Annie, thank you again for being the host of Who Got Me here. Every single episode is filled with golden nuggets.
It is so fun to hear how people reverse engineer their career, look back at their career, and inevitably it's a relationship that helped them make that break and get to the next. And all of the guests that you've had on the show have this attitude that they wanna pay it forward. And I think that that's true.
If you've been successful in life, you wanna find ways to help other people. So, um, really good perspective and I encourage people to tune in.
[00:42:33] Annie Riley: Awesome. Thanks so much, Jamie, for joining us today and for all this helpful advice for people who are job seeking, people who want to build their network over time. I hope that this episode, and every episode that we record, can be helpful to folks. So thanks so much for joining us. I think that's the show.
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