The people who made this one.
What happened at OneDigital on September 16 was live and unscripted. We did not record it, on purpose. The evening ran on a game board. People drew sealed envelopes at the door and read the questions aloud when called, and five people answered in front of the room that had asked. If you were there, you know. If you were not, there is no recording you missed. You missed the room, and this page cannot bring it back. So it takes another route to the same subject, and it hands the people who were there something they did not already receive.
TehShan Lee built the evening and ran it: Event Program Manager before the doors opened, Moderator once they did. She wrote the question bank below and designed the shape of the evening it ran in: four rounds, with questions sorted into three tiers from easy to personal. She held prep meetings, so every question asked was one the panelist had selected. None of the questions were a surprise to panelists, which is how the room could go deep.
Recalculating, the way a GPS says it when you have left the route on purpose.
Part 1 sorted pivots into six types, smallest change to largest: change how you work, move within your field, same field but a new industry, change countries, change careers entirely, and re-enter after a stop. The coach refers to them by number below.
The Informational Interview.
Every guide to changing careers tells you to go have informational interviews. Find someone who made the move you want to make and ask them thirty minutes of questions. That assumes you will get the whole thirty minutes. Whether a stranger gives you their time comes down to their calendar, who referred you, their role, their company, and where they are in their own career. Almost none of that is about you. Worth knowing, before you take a run of polite silences personally. What follows is the workaround and a backup plan. Stop asking for the thirty minutes and start offering a list of questions they can pick three from. And have a separate five-minute plan. Everything is below, in detail.
The Question Bank.
If you were in the room on September 16, this is the bonus. The questions you watched being asked are here for you to ask, with the rules that made them safe to ask in public and a way to use them one person at a time. If you were not in the room, this will still work. It is a way to have the conversation the panel had, one on one, with someone who has made your move. A panel cannot tell you how you look to them. One person can. TehShan wrote this bank for the Detour Stories panel, and it is published here in full.
Ground rules, before anything else.
You are not asking for a job, a referral, or a lead. Not now, not later. If one shows up, it shows up on their own, and it shows up because you never asked.
You are asking for their read. How the move looked from inside it. What it cost. And if you earn it, what you look like from where they sit.
The only request in the whole conversation is the second conversation, and even that is offered as a menu they can decline without awkwardness.
The test, for both sides. Everyone has been in a store when the clerk walks up with "how may I help you," and everyone has said "just looking." Neither person said anything real. The clerk made an offer that forced a response, you put up a defense, and both of you backed off a sale that was never happening. An informational interview with a job request hiding in it is the same transaction with the roles reversed, and the receiver can feel it coming. If either of you can feel it turning into a sale, it already did. Stop selling. Do not make anyone say "just looking" to you.
So here is what you do say. Something like: "I'm trying to understand what a move like yours actually looks like. Could I send you a short list of questions and have you pick three you'd be willing to answer?" That is the whole request. The next section gives you the list.
Two conversations, two goals.
They said yes, so consent is banked and you can go deep, the way the panel could because the panelists had picked their questions. You want to leave knowing how they did it, what it cost them, what it is like inside, and what they make of you. The bank below is built for this, in segments you can take in whatever order the conversation gives you.
Nobody at a networking event agreed to be interviewed. They agreed to hold a drink and talk to whoever is in front of them. You are not there for information. You are there so they want to talk to you again. Two questions and a request, answerable standing up. Pay attention to whether the other person is looking for a way out of the conversation. The card below fits on a phone.
Pick an approach.
This is about comfort, not skill. The questions underneath are the same. The posture on top is yours to pick, and you can pick a new one tomorrow. Sending an email counts. Never following up does not.
You are good at networking and fine asking questions of strangers. You know your questions, you keep the conversation moving, and you remember to make the request at the end; the list is in your head. Your risk is not shyness. You fill the silence. You skip asking what you look like from their side, because that one feels exposed. You leave with a great conversation and no second one. So watch the close.
You can talk to anyone once it starts, but the word networking puts you off. Ask one great question and follow its thread in conversation to a natural end. Only turn to your list if and when that first thread ends and there is still time to chat.
You can do it if you have something to hold, so the list is the prop. "I am working through a set of questions that people who pivoted have been kind enough to answer; mind if I read from it?" Say you are reading from a page and it stops being awkward. Now they have a page to react to instead of a person to size up. Hand them the printable version and let them point.
You would rather begin by email, text, or a LinkedIn message, and that is allowed. Your approach is written: you get the name at the event or from someone who was there, and the next day you send the list, two lines about yourself, and the menu sentence, pick any three, answer in writing or on a call, whichever you prefer. It spends the least of their time and gets a surprising yes rate, because a written request is easy to say yes to on a Tuesday night. What you give up is their read on you. That does not come across on paper. If the alternative is never asking at all, it is a fair trade. Your five minutes at an event is getting a name and leaving, and that is a legitimate outcome.
You would rather not walk up alone, so you go with someone from the community and work as two: one asks, one listens and holds the list, and you trade. The listener can ask for a read on you on your behalf, "from what you have heard, what would you tell her to do first," which is far easier to ask about a friend than about yourself and far easier to answer. Two people also split a room, which halves the cold walk-ups. This is two people learning, not two people running a pitch. Whoever you walk up to will know which one it is almost immediately.
The thirty, in segments.
One way a half hour could go if everything lined up. It will not line up. So treat these as segments and not a schedule. Start where the conversation starts. Stay where something is landing. Skip the rest. The pauses are where you notice what is landing, so let them sit. Questions marked added are not in the original bank; they are the ones a one-on-one can ask that a panel cannot.
- Sixty seconds of you first: what you were, and what you are aiming at. added
- What triggered the pivot, and how did you know it was time?
- Was there something about your old career you were running away from, not just running toward something new?
- What would have had to be different for you to stay? added
- How did you get your first role in the new field with no direct experience?
- What did your resume or pitch look like during the transition?
- What skills transferred that surprised you?
- What did you have to build from scratch?
- Was there a gatekeeper you had to win over, and how?
- How long did it actually take versus how long you expected?
- If you’re comfortable sharing, how did you fund the transition?
- What got worse after the pivot that you did not expect?
- Did the new field live up to what you imagined, or did you just trade one set of problems for another?
- What did you have to let go of (identity, salary, status)?
- When did you stop feeling like an imposter in the new field?
- What story did you tell yourself to keep going when nothing was working?
- Did your relationships change, and how did you handle people who doubted you?
- Was there a moment you almost quit the pivot?
- Knowing what you know now, what do I look like from where you sit? added
- What would you do in my position in the next ninety days? added
- What would make you take a chance on someone like me? added
- Who specifically helped you, and how did you find them?
- Who else should I talk to, and may I use your name? added
- What is one thing you wish someone had told you before you started?
- What would you do differently?
- What role did luck play, and how did you position yourself to catch it?
- If you had tried this two years earlier or later, would it have worked?
- Do you think of yourself as someone who pivoted, or did you reframe your whole story?
- Would you do it again, knowing everything you know now?
The five, for the parking lot.
- Open with the room. What brought you tonight? What did you make of the panel?
- Find the pivot without asking for one. What were you doing before this? The ones who moved will tell you in the first sentence.
- One high-yield question, if they did. What surprised you most about the move? Or: what do people outside the field get wrong about it?
- The room referral. Who else here should I be talking to? It is free for them to answer, and in a crowded room it is the best thing they can hand you.
- The close. Would you be open to thirty minutes sometime? I would send a short list, with two lines about me, and you pick the three you feel like answering.
If you attended Part 1, some of these will look familiar. The one-thing-you-wish question and "would you do it again" are two of the five Tammy Rainey put in Tool 11. "Who specifically helped you" is her "how did you get here," with the mechanics exposed. Same questions, asked with more room to answer. The printable version, with the thirty and the five on one page, is here.
The question bank is by TehShan Lee and Tammy Rainey, written for the Detour Stories panel and published here with their permission. The segment ordering, the read-on-you questions, and the five for the parking lot were added by the JobNet 2.0 team to adapt it for one-on-one use.
This event was an informational interview with an audience. Five people agreed to be interviewed in public, and that is the only reason it worked. Ginny Conboy, Michelle Miller, Teresa Abrahamsohn, Triparna Chakraborty, and Teresa Solis: JobNet 2.0 and baHRC thank you for your insights and your time. Your stories are yours, and the people in the room heard them.
- Ginny ConboyPanelist
- Michelle MillerPanelist
- Teresa AbrahamsohnPanelist
- Triparna ChakrabortyPanelist
- Teresa SolisPanelist
To the audience: thank you for the engagement and the focus. A panel only works if the room shows up for it. This one was lively, and that was you.
Wayne Rainey handled hospitality and production, Tammy Rainey ran the floor and kept time, and Jenny Vonderwerth opened the room at OneDigital in Cupertino. And to the registrants who sent questions ahead: one reached the stage, and the rest are taken up below.
Seven questions you sent in. A coach takes them, and calls in the readers when it helps.
Registration asked what you would ask the panel. Seven of you answered. One question reached the stage, and the panel's answer stayed in the room. Six did not, and the honest truth is that the panel could not have answered most of them well anyway. They are questions about how a pivot looks from the other side of the table, and every person on that stage sat on your side of it.
So a career coach takes them here, one at a time, and calls in the three people who will actually read you when a question needs them. Sometimes all three. Sometimes one. Sometimes nobody, because the answer is yours to make and no reader changes it. Watching who gets called is part of the point: it is how you learn which reader your own question is really for.
A word on who is answering. The coach has spent a long career on the recruiter's side of the desk and has made a move of their own; that is their standing, and it is all of their story you will get here. The three readers price you in different currencies. The machine cannot infer, so evidence has to be written. The recruiter is asked, by every applicant, to endorse a stranger at the risk of their own credibility, and a pivoter is not a bad candidate but an unpredictable one; the newer the recruiter, the less they can afford you, which is arithmetic, not judgment, and also tells you who to approach. The hiring manager hires because they must, interviews the way they were once interviewed, and reads a pivoter as time: the time to bring you up to speed and the time to work out whether they can.
Each answer ends with two pointers: where this sits in Part 1, and what to ask a pivoter about it if you use the bank above.
The panel took this one live, and I am not going to repeat what they said; it was theirs and it belongs to the room. Here is the part they could not tell you, because they were sitting on your side of the table. In all the years I have read resumes, a gap by itself has never ended a candidacy. The silence around it has. Every reader you pass through fills silence with their own worst guess, and the three of them guess differently, which is why this is the one question where I have brought all three in.
What you can do is take the guessing away. Write one sentence: what it was, that it is over, and what you did with the time. Say it out loud until it sounds like you and not like a lawyer. Then put the dated version of that sentence into the gap itself, on the resume and on the profile, so the machine sees an entry instead of a hole and the humans see someone who is not hiding anything. That is the whole move.
Guardrail: one sentence. The longer version is for the interview, and by the time you get there it will be a conversation, not an explanation.
I never see a gap as a question. I see one entry end and the next begin later, and I weight what is recent, so a recent gap followed by a thin entry leaves you lighter than the person next to you. Anything dated in the space changes that. I do not judge what it is.
A gap is the first thing the manager will ask me, so I need to answer it in one sentence before I submit you. Hand me the sentence and the gap is a fact. Make me construct it and I will usually spend my credibility on someone simpler.
I read a gap as ramp. A gap plus a pivot is two ramps, and I am already short on time. Show me the gap pointed the way you are heading now and one of the ramps disappears.
Let me reframe this one a little, because I think the question is asking for something the panel could not honestly give. Everyone on that stage could name their moment. Every one of those moments was named in hindsight. In real time it is rarely a moment; it is a drift you notice you are already in. Tammy's gut-check from Part 1 is the honest version of the question: could one conversation fix it, are the skills realistic, are you running toward something or only away from something. Sit with those three before you do anything else.
Then here is the practical part, and it is the part nobody says out loud. The moment you knew does not matter to anyone who will evaluate you. What matters is the first dated thing you did about it. A decision is free; nobody can see it and nobody can price it. A course you finished, a project you shipped, a conversation you can reference, a bridge role you took: those cost you something, and cost is what reads as serious.
So stop trying to be sure, and do one dated thing this month in the direction you are leaning. If you do it and feel nothing, that is data too. Note what drained you and what did not, and weigh the pattern before your next dated thing. Part 1's Energize Test is the longer version of that reading. Guardrail: one finished thing beats three announced ones. The trail you are building is made of completed things.
I do not know that you decided anything. I see the vocabulary on your history change at some date, or I do not. The moment you knew is, to me, the moment you started writing it down.
Two questions in one, and the second one, about picking up a new skill, is really a question about learning anything new, not about AI in particular. That is a different conversation than the one this page is having, so I am leaving it with Tool 6 in Part 1, where the how-much-training question lives. The first question is the one I can help with.
This is a same-field, new-industry move, pivot type three in Part 1, and it is more doable than it feels from inside it, because you are keeping the craft and changing the dictionary. Recruiting is recruiting: volume, speed, quality of hire, the systems you ran, the managers you kept honest. What changes is the words and the pressures. A mortgage sales organization hires quota carriers, worries about ramp to production and churn, and lives inside licensing and comp plans. Nobody there will do the translation for you, and you have to know the pressures well enough to speak to them. So the work is translation, not reinvention. Pull three postings from the lane you want, list the words they use for what you already do, and rewrite your three best results in those words. Then find one person recruiting in that world and offer them the menu from the bank above.
Guardrail: translate, do not inflate. If a word in their dictionary describes something you have not done, it does not go on your page. One true translated sentence carries more than five hopeful ones.
The crossover is a co-sign I can make if I can point to one thing that translates: a volume you handled, a system you ran, a pipeline you built from nothing. Give me that and I can describe you in a sentence the sales-side manager recognizes.
I am hiring for my industry's problems. Name one of them in my words and show me you have handled something like it, and I am pricing a short ramp instead of a full one.
I want to take the second half of this first, because it is the harder half and the one that gets the least honest advice. A pivot across fields and across borders is two unknowns stacked on top of each other, and every reader you will meet prices the unknown they can check. So the most practical thing I can tell you is to build the checkable thing first, before the resume, before the networking, before anything. I call it a local anchor. It is one of three things: a credential this market recognizes, a short engagement in this market even if it is contract or volunteer, or a person here who has seen your work and will say so. People in your position tend to build the anchor last, after months of applying into silence. Build it first.
Then do two pieces of translation. Relabel what you brought: the local equivalent named next to the original degree, the title restated in terms this market uses, so it weighs what it should. And write yourself a transfer table with three columns: what carries over directly, what you have already re-learned for this market, what is still open. Use it in every conversation. It does the reader's analysis for them, and it is the most reassuring thing a hiring manager can hear from someone whose background they cannot fully read.
Guardrail: you do not owe anyone your whole journey. The readers here price the anchor and the honest gap list. The story is for the people who earn it.
I do not know you are an immigrant unless a credential, a location, or a date tells me. What I see is whether your history reads in this market's vocabulary. A degree I do not recognize weighs less than it should until you relabel it.
Two unknowns stacked is a hard co-sign. What I need first is something local I can check: a credential I recognize, a person here who knows your work, a role in this market even if it was short.
This is the question the whole page is built to answer, so let me be plain. The standard advice says to network your way into the new industry, and it leaves out the part that makes people give up: the people in that room mostly cannot afford strangers, for reasons that have nothing to do with you. Their time, their credibility, their calendar. You watched the workaround at Detour Stories. An engaged group got ninety minutes with five pivoters, and nobody had to ask anybody for a favor, because the community paid the cost of the room. You cannot manufacture that alone, whether or not you were there. You can borrow its method.
Stop asking for favors and start offering choices. Take the question bank above, hand it to one person who has made a move like yours, and ask them to pick any three. That is the whole ask. Aim a level or two below the people you eventually want to reach; they have more time, they know what the hiring managers actually want, and they are the ones who mention names when a seat opens. Before you send anything, make your headline and summary say what you will say in the conversation, because they will look you up first. Then do it once. One person, one conversation, three questions. Write down what you learned. Do it again at whatever pace your life allows.
Guardrail: no job request, not in the first conversation and not in the follow-up. Warm-up questions first. The second conversation is theirs to offer, and the ones who offer it are the ones who will vouch for you later.
I get asked for coffee more than I can say yes to. I say yes when the request is small, specific, and costs me nothing to answer; three questions I can choose from beats "can I pick your brain." And ask the people one level below me. They have the time, and they know what I am actually looking for.
You asked for one thing, and I will give you one, though it is not the inspirational kind. In every pivot I have watched work, the decisive factor was a person who could describe what you did, specifically, to someone who had not seen it. Not a cheerleader. A witness. Everything else on this page, the translation, the weight, the sentence, is about making your history legible. A witness is the one thing that makes it credible, because it is the only evidence a reader did not have to take your word for.
So find three. A translation ally who will read your materials and tell you what still sounds like the old field. A reference in the new field who can describe one thing you did there, even something small. A former manager who will take the call and say what you were like in a room. Ask each of them for one specific thing, not a general favor, and make one of the three visible: a recommendation, a post you wrote together, a public thank-you. You mentioned you coach others through this. Then you already know the most useful thing you can do for someone else: be their witness.
Guardrail: ask for what they have actually seen. A reference who has to imagine your work is not a reference, and every reader on this page can tell the difference.
The most important person in a pivot, from my side of the desk, is whoever lets me say "I checked" instead of "I believe." Have those people ready before I need them, so the check takes me a day and not a week.
Three words, and they carry a whole story. This is pivot type one in Part 1, changing how you work, with a stop in the middle that also makes it type six, coming back after a break. The panel did not seat that story, and I am not going to pretend the rest of this series covers it. What I can tell you is how the two readers who matter here actually behave, and it is different from what a long career prepares you for.
The buyer of consulting is not hiring a person. They are removing a problem. Walk in with a career and they are quietly pricing how long you will stay and whether you will mind reporting to someone half your age. Walk in with their problem named, in their words, and the cost of leaving it alone, and every year you have becomes the asset instead of the question. So the first move is not a website or a business card. It is one scoped engagement: a problem you have solved many times, offered to one person who has it, at a defined scope, even at a modest rate. The day it starts, write it down on the resume and the profile with a title and a date, because until you do, the machine still has you retired. Lead every conversation after that with the problem, not the career. The late-career page on Part 1 has the fractional and interim framings if you want the shape of the offer.
Guardrail: narrow beats impressive. A three-month scoped project you finished outweighs a decade of titles for this reader, because it answers the only question they are asking.
I buy a consultant to remove a problem, not to add a person. Show up with the problem named and the cost of ignoring it, and your years are the asset.
Retirement, to me, is a long entry that ended and nothing since. The first engagement, however small, written with a title and a date, is a new entry in a new category. Until then you are still retired as far as I can tell.
One story this series does not cover: coming back after a break. Two of the seven entries, the resume gap and retired-to-consultant, are the same story from different directions: coming back after a stop. That is pivot type six, re-entry, in the Part 1 taxonomy, and none of the five panelists' stories is that story. This series does not cover it. Saying so plainly beats pretending the toolkit already does.
A first two weeks, if you want one.
Nothing here needs permission, a referral, or a job opening. What it needs is one list, one person, and the discipline to let them pick.
Pick your approach and read the rules.
Decide which of the five postures you are on a given day, and read the ground rules until the store metaphor is yours. Sending an email counts. Never following up does not.
Guardrail: pick the posture you will actually use. Admiring one is not the same as using it.
Find one person.
Someone who has made a move like yours, ideally a level or two below the people you eventually want to reach. From the room, from the community, from someone who knows someone. If an event is on the calendar, take the five and go; if not, take the correspondent’s route and write.
Guardrail: one person per email or text. Do not batch it.
Offer the menu, have the thirty.
Send the bank, let them pick three, ask those, and ask for their read on you only if they open the door to it. Afterwards, write down what you learned and what they said you look like from where they sit, because that is the read you cannot get anywhere else.
Guardrail: no job request, not in the conversation and not in the thank-you.
Then repeat at whatever pace your life allows. It gets easier in that order. Rules, then one person, then the next person.
Part 1 was the map. Part 2 was five people who have driven the roads on it.
Both parts run on the same list: the six types of pivot from Part 1, smallest change to largest.
TehShan Lee
TehShan Lee is a JobNet 2.0 Co-Architect and a fractional HR consultant who builds people operations for rapid-growth organizations, most often in biotech and life sciences as they move from research into commercialization. She has led HR at Slingshot Biosciences and Nephrosant and ran HR operations for Alibaba Group North America. For JobNet 2.0 she carries much of the program design and delivery. For Detour Stories she built the format. The question bank, the phases and tiers, and the method that let the panel go deep in public: every panelist chose in advance which questions they would be asked.
Connect with TehShan on LinkedIn.
Published by baHRC
baHRC (Bay Area Human Resources Connections) is the host organization for the Recalculating Series and the publisher of this companion. baHRC lives at its events calendar, bahrc-events-2026.netlify.app. Every session companion ends up there.
JobNet 2.0 is the program within baHRC focused on career navigation. This is a JobNet 2.0 session companion under the baHRC publishing imprint. The coach and the three readers are a recurring feature of this series, written by Wayne Rainey of The Career Cantina. They appear in Part 1 as well. Question bank by TehShan Lee and Tammy Rainey. Written and produced by the JobNet 2.0 team.
