Laura Frederick, founder and CEO of How to Contract, hosted this webinar with Jay Harrington and Kyle Robisch, both Partners in Client Services at Latitude. Jay practiced at large firms and started one of his own, then spent years training lawyers on business development before joining Latitude in late 2025. Kyle clerked for a federal judge, spent a decade in litigation, and made partner before moving to Latitude two and a half years ago. Between them they read resumes and talk to hiring companies every day, which meant they could tell us what actually moves a candidate to the top of the pile.
Want to watch our webinar replays? Register in advance to get access to the recording for 14 days. You can sign up for our auto registration list so you are added to every webinar we host. Our paid members get permanent access to webinar recordings, plus courses, certifications, and our massive expert library. Learn more about our membership →
They covered how to decide what you want before you chase it, what the in house org chart looks like and where each path leads, how a reputation compounds inside a company and outside it, what makes a candidate memorable to the people doing the placing, why most jobs get filled before anyone posts them, and what to do when a career stalls.
Here are our top ten takeaways from the speakers' comments during the webinar:
Treat your current job as one chapter, not the whole story. Jay said he rarely sees a resume with a single employer for more than a ten year stretch, so the role you have now is a chapter in a longer career story. Every job is a rung on a ladder, and you want to be climbing the one that goes where you want to go. Drift happens when you never step back and ask that question. Give your career the same attention you give the matter on your desk today.
Choose the option that gives you more options. Jay pointed to Derek Sivers on early career decisions, where the best option is the one that opens up the most future options. Laura translated that into skills, because skills are what create options later. She spent three years in franchise work, disliked the regulatory side, and moved into tech transactions in part because the franchise bar is small and the transactional field is not.
Ask what you want from your life before you ask what you want from your career. Jay said the bigger question sits on top of the career question. Where you want to live, what kind of family life you want, how much you want to travel. After his wife had a daughter and then twins, they moved to northern Michigan, more than 250 miles from his nearest client. Work should serve your life, and the answer changes as your circumstances change.
Don't let a title pull you somewhere you don't want to go. Kyle said titles matter as a signal to the market, fairly or not, so understand what they mean. They matter less than whether you like the work and are good at it, and the happiest lawyers he knows are honest with themselves about that. Laura interviewed for a general counsel role and turned away from that path because it meant doing less of the work she loved. She was the primary lawyer on billion dollar contracts at Tesla and never held a title above senior counsel.
Get good at one thing and let the reputation compound. Jay described compounding as smart choices plus consistency plus time, the same force that works in a retirement account. Four levers compound, and those are your internal reputation, your niche, your relationships, and your ideas. The test for the first one is whether people across the organization ask for you by name when a particular issue comes up. Spreading yourself thin is what stops the compounding.
Have a thing, and be able to prove it. Kyle said the signal that jumps off the page is a specific thing you have actually done. Saying "I'm a privacy lawyer" does not get you the call. Saying you built the privacy and HIPAA compliance infrastructure from scratch at an early stage health tech company does. Pick your thing so it points where you want to go next, then put it on your resume and your LinkedIn in language a recruiter can repeat to a client.
Build the relationships BEFORE you need them. Kyle said companies increasingly hire the known and trusted commodity, so you never see the jobs until they are filled. Talking to recruiters when you are not looking shows them you are serious about where you want to go. Jay added that law school classmates and former colleagues scatter into roles all over the country and become your best source of opportunities. Reaching out after twenty years of silence rarely goes well.
Stay visible even when you're happy where you are. Jay described the familiar pattern of flipping on the open to work banner after a layoff and then furiously networking from a standing start. He recommended conferences, industry events, and posting on LinkedIn while nothing is wrong. When two candidates look similar on paper, the one who is already known has the edge. Preparation meeting opportunity is where most luck comes from.
Do something for someone else every day. Laura credited Robert Cialdini's book Influence for the habit that made the biggest difference in building her audience. Commenting on someone's post is a real gift now that comments are hard to come by, because they help that post reach more people. So is making an introduction for someone who told you what they were looking for. She hates networking and loves helping people, and the relationships came anyway.
Figure out whether you're stalled or just in a long stretch. Kyle said to answer that before you do anything else. A stall means you have capped out on compensation, responsibility, and title, and you can see where you want to go next. A long stretch is the part you push through to reach a promotion or a chance to add something to your plate. Seth Godin's advice about never quitting in the middle of the dip stuck with Jay, because in the moment you don't yet know whether a rough patch was a cost or an investment.
Subscribe to Stay in the Loop
Whether you caught this webinar live or not, our weekly newsletter keeps you current on upcoming How to Contract events and recaps like this one. Subscribe now so you never miss the practical insights.
