Top 10 Questions I Hear All the Time

Q: What’s the biggest mistake job seekers make?

A: Would it surprise you to know it’s not something with your resume or cover or profile? Nope. The biggest mistake is not networking before you need it! Start building your network today–connect to colleagues, friends, family, and community members on LinkedIn and offline. Don’t think of this as transactional work, or you’ll get transactional results. Here’s how to network with impact:

1. Share content or useful links regularly, both on LinkedIn or in person or mail–be generous. Give away a book that helped you or clip a magazine article, even. 

2. Forward people jobs or information that will help them.

3. Remember names/special occasions or events–know people’s family and pets, and kudos them on a new job or offer to lend an ear if they have a layoff. Be the thoughtful one–you’d be surprised how much this sets you apart.

4. Be in it to help first, receive second–generous people have generous careers. 

5. Spend just 15 mins a week either connecting to someone new (phone, in person, etc) or reconnecting with a former colleague. That’s 52 meetings in a year and 52 people you have a fresh reference point with down the road. 

It’s easy not to network and build relationships, but the fact is all of our careers depend on the quality of our relationships. As my good friend and economist Jason Schenker says: Do you have people you could call to give you a job tomorrow? If your answer is no, not at all, it’s time to start building more relationships. And remember: you’re in it to add value and help, not to sell. Not to quickly ask for reciprocity.

Q: How do I make a career pivot?

A: In a job seeker’s economy, like we saw during the Great Resignation, it’s easy to tell your 60-second pitch to a recruiter if you’ve got good experience and potential. In tighter economies with more people on the hunt, it’s key to get incredibly dialed about how what got you here will make them money there. 

Do:

• Spend time talking about your transferable skills.

• Assure and prove that you’re a quick learner who knows the latest (ChatGPT, etc) and can add value fast. Talk at the speed of the company and hiring manager, not your old job.

• Have a tight 45-second story on how your non-traditional background makes you more valuable and why. (Imagine it going against a traditional background 45-second story, and figure out how to make yours better. Practice with a colleague.)

Don’t:

• Expect to go from one job you’ve got experience in and then on to a dream job–you may need to take a step back or sideways to move to a new industry or role. 

• Ask the people with your previous role experience to advise on next steps–you need to informational interview (please don’t call it that) with people who have the roles you want and get their advice. Ask for 10 mins in whatever format they prefer (phone is generally easiest because it can happen when they’re on the subway, for ex.)

• Try one approach and stick with it–keep adjusting and learning. You’re on a growth curve, so embrace and demonstrate that growth mindset.

Q: What do you look for when you hire people?

A: I’ve hired dozens of talented folks in nearly 20 years and across companies, and it all comes down to a few things:

1. They’re learners–they know they’re never done building skills, and they demonstrate they’re active learners and open to feedback. 

2. They’re prepared but curious–they have good questions, and they know my business. They’re not confused in interviews. 

3. They talk about hustling to add value right away while also realizing there’s nuance to this role. This can look like sharing a brief “I did a quick sample to show you” or talking through an idea you have and exploring it in the interview. They’re not in the passenger seat–they want to drive and can drive, but they’re also not running at 100 MPH in the wrong direction when you discuss the role. 

4. They can think on their feet and adapt to different interviewers and styles–if I’m fast-paced and have a lot of questions, they can match me with quick, tight answers. If I’m probing for more detail after every answer, they realize they’re being too vague and start leaning into specifics. In short, someone it would be easy to be stuck in an airport with–and no, that doesn’t mean we’re friends or they’re like me or went to my school–it means it’s not work to communicate. They make it easy.

5. Bonus:They’ve got recommendations on their LinkedIn profile or similar vouches from people–being someone people took time to write about in glowing detail sets them apart from people where we don’t know if they play well with others.

Q: What are the biggest red flags for companies?

A: There are a few I look for.

• It’s never better than in the beginning, so know what you see at the offer stage is the best it will be–if they’re patient, empathetic, and interested in win-win, great. If they rush you, make you feel like a pain, or act like you’re one of many they could get, red flag!

• Rescheduled or missed interviews, whether they apologize or not. Shows a lack of concern for your time.

• Projects to prove your value during interviews. This shit is free work for the company. And no, I don’t care whether it’s paid or not paid work. It’s unfettered access to your IP. Say you’re under NDA that prevents this type of work if you’re employed now or share a link to your portfolio or other work you’ve done if not. Emphasize how your resume and answers let them know who they’re getting.

• Pacing mismatch with your desired style. If you’re a hustler and the interview process drags on, you’ve probably got a slow moving culture. You may get bored or feel stifled. If they’re rushing you and you can’t keep up, consider whether you want to work at that speed.

• Lack of commitment to the things you care about–social justice, DEI, sustainability, work from home–whatever it is, look to see if they care too.

Q: What matters most in negotiating a job offer?

A: Deciding what you need before the offer comes. Know the salary, benefits, and extras you must have to move forward. Don’t wait to see what they say–it makes your decision making harder to respond from a place of being unprepared. And at the end of the day, be willing to walk away–that’s the best secret to all the negotiating you’ll ever do. What’s meant for you can’t miss you.

Q: What skills matter most right now and in the future as we fly toward a GenAI-powered world?

A: This is my personal point of view and something I speak about to clients quite often. 

We’ll always need strong communicators. I know that’s vague. People who are concise, organize their thoughts rather than giving us a rambling adventure with no point, and think fast on their feet with a quip, a stat, a hot take, or a fun aside. People who deliver what they say in a way that you know they’re on top of their shit. Get cozy making a presentation (deck) with a quick turnaround and delivering it smoothly.

We also need agile, resilient people who know how to pivot and hustle. The world is changing fast–and as we say at LinkedIn, if you’ve not changed jobs, your job is changing on you. So get good at change. Be a ringer who shows what resilience looks like when there’s a miss. If your manager has to get you through shutting down and getting upset all the time, don’t expect a lot of career growth.

And on that note, be easy for your boss and your peers. This doesn’t mean you have to smile and be nice or a pushover–it means people trust you and look forward to collaborating with you because work gets done easily and without conflict. It means you’re sought out for advice and quick to get on board for key things but know how to be diplomatic on controversial decisions or directions. 

Know enough data and GenAI to not get left behind–bring your skills up to baseline so you’re in the loop. 

Finally, be open. I can’t tell you how many people I see wanting promotions or juicy assignments but when they get feedback, it’s “don’t talk to me that way.” Ask for feedback proactively, and when you get it, say thanks. That doesn’t mean you do it all or believe it all–it does mean you get a reputation for openness–which means you’ll get more opportunities to grow, which means you will get what you want in the long run. 

And PLEASE, PLEASE don’t tell your boss or colleagues their feedback is subjective–everyone’s feedback is. It’s what we’re paid to give each other at work and expected from boss to employee. I’m not saying put up with feedback that crosses an HR line in some way, by the way. But I am saying get used to the world not being fair (sorry, folks), find the nugget in it that can help you get ahead, and don’t get a reputation for whining in disagreement. We all get reviews or feedback we vehemently disagree with–you’re not unique. It’s what we do next that people look at. I’ve been there, done that. It only stunted my growth by about a year. No prize, no great enlightenment, and my boss certainly didn’t suddenly agree with me because I was noisy.

Q: How do I get over a really stressful or toxic job I left and move forward?

A: Yikes, I’m very sorry this happened to you. I wish we all had the best bosses of our careers at honest, amazing companies all the time–truly. More often than not, companies with cultures like this have little support or training for their people or HR. Folks are doing the best they can or can get away with, all with what they have. 

My advice is to vent/get out the grief and anger with your friends or a counselor or therapist or coach (or me!). It’s important for your sanity to find a way to process what was awful and use it as fuel to find better next time–without complaining in your next interview about why you left the last role. And bestie, don’t trust feelings of inadequacy or incompetence it left you with. Start talking to yourself like you’d talk to your best friend. And go read Mel Robbins’ High-Five Habit for a daily dose of “you got this.” You do!

Q: Do I hold out for work that makes me happy?

A: I used to expect work to make me happy–I now expect it to pay my bills. That’s not me being a cynic jaded by Corporate America. I work for a great company and have great work life balance. It’s about realizing I’m not my title. If your job makes you happy, I love this for you. If it doesn’t, I don’t automatically think you have a problem or need to bounce. You can get happy outside work. 

Here’s what I mean. Over the years, I’ve found it’s important to cultivate multiple identities in your life so that you’ve got your eggs in many baskets. That means your identity doesn’t go away if you lose your job or if you have to stop running to have back surgery (like me). You may be a bookkeeper, a husband, a budding chef, a woodworker, and a devoted son–know those identities. Work on all of them. Don’t let happiness or not at bookkeeper define your life. I’ve found that looking for neutral leaning toward happy across your portfolio of identities is a richer way to live and keeps your whole life in much more of a healthy balance.

Fact or cap: Hot takes on trends in career world right now. (True or false….)

A:

• I need a cover letter - fact–do them, personalize them, and give yourself a leg up. But do I wish they’d go away? Yes!

• I should do job interview projects to prove I know what I’m doing - cap! Do not, unless you really want the job. It’s never better than in the beginning–and if the people hiring you don’t trust your expertise without free or paid work to show them, move along. 

• The Open to Work badge on LinkedIn makes me look desperate - cap! Using this green banner immediately distinguishes you for recruiters. Unless you’re Sr. Director +, I advise using it. You can also turn on Open to Work in the background and not display the badge. Make sure you let people know you’re looking at any level. 

• It’s bad to move jobs every 1-2 years - cap! There is no normal anymore. People move around, people stay for 15 years. Tell your story right to back it up as a strength either way. 

• I shouldn’t negotiate salary in a down economy - cap! It never hurts to ask, and I’ve never once seen an offer rescinded for negotiation. (They can be rescinded if you don’t respond in time if it’s an exploding offer with a timestamp.) Anchor on the key 2-3 things that matter in negotiating–don’t ask for 10 things.  And know your alternatives for each one if you get a flat out no. Such as: if 10k more on salary is a no go, can they add two weeks of vacation or could they swing a $10k signing bonus up front? 

• It matters when you apply for a job - fact! Jobs right now are often getting 500+ applicants in the first 24 hours. Have alerts set, and be ready. You’d rather be application #8 than #487.