Trust The Process: How to maximize your job search

During your working years, you will spend 40–60% of your waking life at your job. Yet most of us spend just a few hours prepping a resume, talking to a few contacts, and lobbing in applications for whatever thing we plan to spend years of our lives doing. We are selling ourselves short.

I’ve helped a couple hundred people get jobs thanks in part to my past work at Venture for America, I’ve hired a few dozen folks directly, and I still periodically encounter friends who are thinking about a job transition, so this is my attempt to help.

If you’re impatient, just skip to The Process. If you like stories or you’re a skeptic, we can walk through some of the mindsets and approaches that limit our options.

In our heads, we all believe in The Serendipity Method of job hunting.

Think back through your last few career transitions. How did they happen? Did you lob in a cold application? Know a friend who liked their company? Get called by a recruiter for a specific role? Wow, you’ll say. It was serendipity!

That’s right! There’s another way to describe serendipity: passivity. It’s how most of us approach most things. We let the universe put things in front of us, on its timetable, within its parameters. This is adaptive given that we’re communal creatures and there are butterfly effects and maybe we don’t quite have free will, but passivity isn’t going to maximize your chances of the most rewarding career you can find. Many of us are passengers on our own career journey, even as we are extremely active within our jobs.

The career-serendipity approach can work out just fine, and that’s dandy. If you get called by a recruiter for a perfect job, or an old colleague lets you in on something amazing they’re doing, say yes! Don’t muck around hitting the brakes, stalling out, and killing chemistry. Go for it. You don’t need me.

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Most people, though, need a structured process. If you don’t get lucky, you’re going to face choices, time constraints, and encounter setbacks. You‘ll do better if you manage your psychology and the process itself with the rigor you would your actual job.

There are a few archetypes of job seekers:

If you’re an Intentional Searcher, you’ve been looking for The Right Job. You’ve likely put together some thoughts about the industry, role, company size, location, and work culture that suits you best, or that is the proper next step. You might have a target list of companies that you’re trying to get connected into. You’ve done the soul-searching, and you know you want to work in clean energy. Or, for Nike. Or, as a Chief People Officer.

This approach is very common among type-A folks, but it means you’ve closed out 90% of the possible things that you could do. You’re guessing at what the best you can do is. You’ve faceted your search down to a handful of potential options. Often, you’re trying to guess at who you want to be when you grow up, which is a cardinal sin of job searching in my opinion. We can’t quite know how we’ll change over the next decade, and often we forget that we will change at all. A decade ago, you couldn’t predict exactly where you’d be now — why should the next ten years be any different? If you’re an intentional searcher, I ask you to open your mind.

Or! You’re the Spray and Pray Searcher. Why are we wasting time reading about finding a job? You could have applied to six jobs in the time it takes some other putz to read this post. Unfortunately, you’re not taking the time to tell the right story, dig for intros, and ensure you’re following up enough to get noticed. Eight thoughtful applications beats 80 shitty ones, and the hiring manager who picks a rando Indeed applicant is definitely not the boss you want — it’s called adverse selection.

We also all know the Ladder Climber. They’re locked in on a specific type of company and role that aligns with a vision of how the next ten years will unfold. Many people at professional services firms (consulting, finance, law) operate this way. The vision is usually to make partner. Externalities — money, reputation — usually are a key piece of the puzzle here. Nothing wrong with that. This mentality works well for linear progress.

Last, there’s the Shy Searcher, who puts one toe in the water at a time. This is most of us, in my experience. Even very confident people are hesitant to go all-in on finding a new job. The possibility of rejection scares us. We tap one connection for an intro. Apply to a couple roles, and then sit back on our haunches and wait, expanding the search only if we don’t find a winner, or if our manager gets even more unbearable. We try not to tell a lot of people; we don’t want word getting back to our colleagues, or people knowing that we’re stuck. Being gung-ho is scary. I get it. But you have to get shots up to make shots.

If you only have one option, you have no leverage. You will have to settle for whatever you land first, or make the unlikely decision to turn down something pretty good in the hopes of something great.

You deserve a different approach to job transitions — one that can change not only what you do, but how you think about yourself, and who you know, and what you’re capable of. We all get impostor syndrome. We all underrate our own resources and capabilities. Careers are less linear than they have ever been, you’re capable of more than you know, and getting a job is as much driven by who you know as ever. That’s why there’s a Process.

The Process

1. The List of Names. Write down the names of everyone you know whom you admire as a professional. Former colleagues. Classmates. Friends. Their siblings you kinda know. Someone who writes smart things on Twitter. A person you talked to on the phone three years ago who went to the same school as you but you’ve never physically met. You’ll want at least 10 names on here; maybe up to 20. You’ll actually do better with people who are acquaintances/friends-of-friends/second-degree connections than your besties, so one way to get this started is to ask your friends for people who they think might be able to help. The MOST helpful people tend to be somewhat ahead of where you are in their careers, but not so far ahead that they can no longer relate. The sweet spot is 2–10 years, probably, although folks outside this range can still be helpful. Each of my jobs came from finding my way to a second-degree connection who took an interest; some of them hired me directly (thank you Fran, Adam, Mark, and Scott, as well as dozens more people who kindly took time with me. It meant a lot).
2. The Opportunities. This comes second for a reason — again, who you know is more important than what you know. Pick the companies, industries, and types of organizations you are curious about/interested in. Go broad; explore your fancies. This can be as simple as “small companies” or “something in biotech,” or all over the map like “consumer goods or healthcare or sports.” Writing these things down will help make sure your list of names is covering your interests — and will help you figure out what to talk to each person on your list of names about. For every specific company you are interested in, dig deep and find someone you know who worked or works there. Get to that person. Tell them you are applying, and ask if they have a few minutes to chat about their experience. If you don’t know anyone obvious, use LinkedIn to search second degree connections and people who went to your school. If you already don’t know these people, what’s the harm in reaching out?
3. The Coffee Chats. Reach out to everyone on this list to do a zoom meeting or a coffee. Ideally you’re face to face IRL or virtually so you can be your personable, quirky self. In these conversations you are asking them for advice about next steps in your career. You are receptive, positive. You have interesting things to say, you’ve researched them well, you want to know all about their career and choices and why they made those moves. You have a list of questions, half of which you won’t get to (do not stop at three questions). People love to talk about themselves and can be quite interesting when reflecting. The eventual purpose of this is to learn what they might do in your situation, what they think about your interests and abilities, and to get them to open doors and generate leads for you. As they say when you’re fundraising: ask for money, get advice. Ask for advice, get money. You need to have a good conversation with someone and get their brain working to generate the intros you want. Say yes to every idea that everyone on your list has. This is going to obligate you to some truly random shit. I do not care. Ideally, it will lead to many more contacts than your original list contained — say yes to coffee with each of them, and of course add them to your spreadsheet. Oh, and send a thank-you to everyone in this process. They invested time in you; they want to know how it ends! You can also use the thank-you to bump them for a follow-up/intro. I cannot tell you how many people have not told me how their process wound up — once I’ve invested time I am bought in and want to know. I once learned three years later that a person I did a forty five minute reference call for got the job and was still working there. That was not ideal.
4. The Synchronized Process. OK, here’s where a lot of people mess up: you did those first three things, but you spread the coffees out over a month or two, and you just found this really cool lead and you know someone there but you’re getting a decent offer from a kinda boring software company this Friday with a one-week clock on it and the comp is fine but not spectacular… You need to keep your timelines tight. Do ALL the initial coffees within 2 weeks. There is no valid excuse for not being able to do one meeting a day and two on weekends. Zoom has made this immeasurably easier. Get every one of your applications in within 48 hours of talking with someone about a company or role, and let them know once you did so, thanking them for their time. Have your resume 90% done before you start. There will still be asynchronous stuff happening, but you did your best. Wasting time optimizing your resume and letting that interdict your process is hiding because you’re afraid and we have no time for fear. The discomfort is part of the growth you’re experiencing.
5. The Interviews. Before you know it, you’ll be having interviews. Some of your coffees might randomly turn into interviews. You need to be ready. On another tab in your spreadsheet, spend time recollecting and writing down all of your favorite stories — the things you’re proudest of, the tough moments you went through, the accomplishments you drove. Make sure you know what you personally did, and how it drove value for the organization you were at. Ideally you have some stories to talk about during your coffees, and maybe you even repeat and refine them — ones that illustrate who you are and what you’re good at. I really don’t need to say this but please prepare more than three questions; ask about stuff for as long as they will let you. Here’s a very good list.

Managing Your Psychology

1. Commit Fully. The #1 priority in running a Process is to fully commit. If you slow down, get flaky, or narrow in too quickly, you’ll botch it. You can run The Process about once every 3 or so years — any more, and you’ll probably have tapped out your contacts or look flighty. So when you do it, you’re in. Everyone will, at some point in the process, get tentative. You’ll drop a lead. Decide you want to focus in on one industry or type of role, or that there’s one perfect company and you’re pausing everything else. Not feel comfortable pinging someone on LinkedIn whom you don’t really know that well. Push through. Try it. Re-open your parameters. Keep the momentum going. You’ll never know what you were missing and a few more hours costs you nothing relative to the potential upside. This is the MOST IMPORTANT WORK YOU WILL DO THIS YEAR and will meaningfully change your life; please treat it as such.
2. Ask Confidently. Yes, you’re using all your contacts — but they want to be used. They are your friends, mentors, friends of friends, mentors of friends. They care about you, at least a little bit. Here’s the thing: people LOVE being helpful. It feels good to help our fellow human beings, to be asked for advice and expertise. Plus, somewhere in the back of their minds, they know you’re willing to do them a solid down the line.
3. Run Down Every Lead. You chase down all the leads because it adds to your options. Remind people about things, and follow up with recruiters and companies. A friend of mine interviewed for an account management job that she thought of as a “practice interview” because the comp was low and the role was a step back. She stuck with it for a couple rounds, eventually interviewed with the COO, who thought she was great and created a new, custom-fitting role for her. It was a meaningful gig. Two years later, that COO left and recruited her to a dream job at another company in the same industry. This story sounds apocryphal but I am married to the protagonist so I assure you it is not.
4. Maintain Confidence and Leverage. Random leads give you confidence — you’re valued, you can get many opportunities, this feels good and is self-reinforcing. They also give you the leverage to ask for what you want in the job you DO most want. Your confidence is crucial. Plus, ideally, at the end of the process, you’ll have more than one offer, which allows you — even if you don’t want to — to be in the only position with any leverage: the position of someone willing to walk.
5. Have Fun and Learn Things. You’re going to get to talk to 20+ interesting people about what makes them tick. You’ve going to get to envision yourself in many different worlds, and different roles. You might learn something about yourself, or consider a path, that you’d never investigated before. That’s a mini personal growth opportunity, so enjoy it!

Done properly, this will all take 2-3 months. Sometimes it goes way faster, but in most roles, a month is a reasonable timeline from first interview to hire, and occasionally things will be slower. If they are bogging down, keep adding people to the coffee list, taking conversations, and you’ll land a terrific gig — one you can be confident was an informed, committed choice. Trust the process.