Sidley Austin LLP - The Inside View

This Midwestern mega-star has been making money moves by mastering associate mentorship and its signature mix of litigation, transactional, and regulatory practices.

‘And when we’re back in Chicago, we feel it! An international powerhouse named Sidley!’ (Sorry, we can’t get the song out of our heads either.) Whether it’s Frank Sinatra or Michael Jackson’s eponymous songs about the city, Syd and Carmy from The Bear or deep-dish pizza, the Windy City’s got a little something for everyone. So, it shouldn’t come as much of a surprise that Sidley Austin is no different. As one associate put it: “Sidley has a large presence – it’s top of the market in pretty much everything and has a wide array of practices.” Don’t just take this insider’s word for it either: Chambers USA ranks Sidley Austin amongst the best in the country for its work in areas like appellate law, capital markets RMBS securitization, energy transition, financial services regulation, hedge funds, international trade (customs), trade remedies & trade policy, life sciences regulation and rail transportation. That’s not to mention top tier banking & finance, corporate/M&A & private equity, pharmaceutical products, insurance, IP and litigation rankings in the firm’s home state of Illinois.

“...If you want a good rep for the work and the people, you can’t do any better than Sidley.”

“Within Chicago, if you want a good rep for the work and the people, you can’t do any better than Sidley,” one associate told us. Aside from the firm’s “stellar reputation,” it was the focus on associate development and the family-friendly vibe that sealed the deal for associates: “Based on the stuff that you hear while you’re at law school, Sidley had a great reputation for being more family-oriented,” an interviewee shared, while another added that: “First and foremost, I wanted a firm that felt like it had a great mentorship program and culture of support. During my interview, mentorship was a central topic – there is no shortage of people who want to help you.”

But Sidley's reach expands far beyond Chicago, with offices split between 11 domestic offices spanning coast to coast, setting up camp in cities like New York – its largest office – DC, Los Angeles, Century City, Houston, Miami, and Dallas to name a few. Most of the associates on our list were based in New York, with Chicago and DC following closely behind.

Strategy & Future

“We’re 158 years old – we’ve been around for a while!” partner and chair of the firm’s management committee, Yvette Ostolaza, tells us:“We’ve got an interesting past too. We represented Mary Todd Lincoln, and Michelle and Barack Obama famously met at our firm.” She’s right too – Sidley’s storied past is a fascinating deep dive, and it’s been at the forefront of numerous historical events. When asked what sets Sidley apart from the other firms, Michael Schmidtberger, chair of the executive committee, adds: “We’re distinguished by the depth and breadth of our regulatory practice across industries, but building that kind of depth and breadth takes history, and Sidley has been building that for some time.”

“…when there’s an issue that comes up, we don’t just have people who’ve seen it before. We have people who have written the rules on it.”

Across the firm’s key practices, “when there’s an issue that comes up, we don’t just have people who’ve seen it before. We have people who have written the rules on it,” Schmidtberger explains. Part of this broad base of expertise comes from Sidley’s international reach and “balanced portfolio,” Ostolaza chips in: “The way that our firm is managed between litigation, transactional, and regulatory work has been really beneficial.” And growth is clearly on the mind. Sidley recently opened a Miami office with a particular focus on highly regulated industries such as healthcare, energy, transportation, and infrastructure. Schmidtberger confidently assures us that they are investing in these centers and many more because even though “shorter-term trends favor the US market, we play the long game at Sidley.”

The Work

While litigation and M&A & private equity were by far the most popular destinations for junior associates, a good number will find themselves in groups like investment funds, global finance and financial institutions. The rest were split between areas like capital markets, healthcare, and energy. If you love the hustle and bustle of a global farmer’s market (as well as a little bit of haggling), you’ll love the staffing system at Sidley: “It’s totally free market,” one source laid out. “It’s also completely cross office too, which I like,” another added, “you have to be comfortable knocking down doors and introducing yourself to people.” While many juniors candidly shared that “it’s a little uncomfortable” at the beginning because “it takes a little time to ramp up to build those relationships, once you get your legs underneath you, you are able to work with the partners you like again and again.” The exception to the rule is the corporate group, where for the first two years juniors are part of a staffing system where everything is centrally assigned based on your responses to a weekly availability report. But, once you’re a third year, “you’re out of that system. We’re a big group, so the way they have it set up is helpful. By the end of it, you know who you like and what work you want to do.”

“…they don’t bring us in to solve small problems. Most of the things we’ve done have been in the headlines.”

Litigation juniors belong to practice area teams, but “we’re welcomed and encouraged to work with clients across industries,” including but not limited to securities and shareholder litigation, product liability, ERISA, white collar defense and investigations, antitrust and competition, global arbitration, IP, and Supreme Court and appellate matters. Clearly, there’s a little bit of something for everyone, and even better, “it’s all high stakes litigation,” one source proudly divulged, “the stuff I’ve worked on is really interesting, meaty work because they don’t bring us in to solve small problems. Most of the things we’ve done have been in the headlines.” Of course, the nature of the beast is such that – on the regulatory side in particular – there’s plenty of research tasks. But that’s not all. Those we spoke to talked about “a lot of responsibility for everything except the live performance aspects of the work,” an interviewee detailed, “clients hire the partners to stand up in court, and that’s just the deal!” That said, the tasks that associates do get to take ownership of include written advocacy, fact development, drafting briefs, and assisting with depositions. The general consensus was that there’s plenty of leeway to get stuck in: “I’m surprised at how much ground-up drafting I’ve been able to do,” one noted. “It’s not just ‘send me the best seven cases you can find and let me write it up.’ Instead, they let me take entire halves of the brief – it’s been a pleasant surprise.”

Litigation clients: Morgan Stanley, Citigroup, Huawei. Represented Johnson & Johnson in securities fraud litigation concerning allegations that the company’s Baby Powder contains asbestos and causes cancer.

When asked about their work, one M&A and private equity associate laughed, “I don’t think there’s one answer! If you ask the 100+ people in our group, you’d get a different answer from everyone.” And that we did – no two answers from our interviewees were the same. The laundry list included the technology and knowledge property aspects of large M&A deals, capital markets offerings, drafting licensing technology for companies like Meta and Disney, poison pill adoptions, working with big pharmaceutical and biosciences companies to help them create a drug, and corporate governance work. Jeez! Luckily, this extensive scope didn’t faze our associates – in fact, they were grateful: “I’ve really enjoyed the opportunity to build my skillset,” one insider chirped, “It’s a good way to compare what different types of clients look for in terms of legal service.” While the typical first year tasks are “probably the same as anywhere” – drafting certificates and disclosure schedules, doingchecklists and deal coordination – we heard that “people will give you work you’re ready for when you’re ready – and ask – for it.” So, “what people are doing by their second year looks different depending on how much they’ve taken ownership.” Often, “it’s just me and a partner,” or “I’m meeting a client by myself.”

Corporate/M&A clients: Nordstrom, The New York Times Company, Volkswagen. Represented Allkem Limited in merger of equals with Livent Corporation to create the world’s third-largest lithium chemicals producer in a deal valued $10.6 billion.

Over in global finance, the practice is split between leveraged and structured finance, “two pretty separate groups with a little overlap.” In leveraged finance, associates work on commercial lending with banks or non-bank lenders in loans to other companies, while structured finance has more of a focus on consumer assets, looking at the range of financing solutions for non-bank finance companies which involves “lots of loans and purchasing portfolios.” In terms of responsibility, we were told that some of the documents in structured finance “do feel like grunt work, but also there’s a lot of substantive work that I’ve ended up doing. Credit agreements, indentures – you work on both pretty substantively as second year.” And due to there being “holes in that mid to senior level of associates in our group, juniors end up with more responsibility relative to our seniority – which is a good thing overall!”

Global finance clients: Bank of America, Wells Fargo Bank, JP Morgan Chase. Represented Athene Holding and its subsidiaries in refinancing and amendments of existing debt contracts in a matter valued at $3.86 billion.

Career Development

“I have always felt like Sidley has been invested in our long-term development,” one associate was happy to share. “This is not a place designed to use you for a couple years, burn you out, and then replace you with someone fresh out of law school,” as evidenced by the multitude of training and mentoring opportunities available from the get-go. When you start at Sidley, juniors are assigned an associate and partner mentor to have “check-ins with early on,” but “over time, you build relationships with other partners and associates informally.” While we heard that the mentorship program is “pretty well-designed,” insiders were particularly pleased with the training on offer: “There’s more training than I expected – in a good way!”  Associates were especially excited at the prospect of attending the Built to Lead program: “We’ve paired with the business schools at Northwestern, Columbia, and Kellogg to go away for a few days and do mini-MBA classes. It’s great because it teaches you about the practical implications of what you’re doing.”

Hours & Compensation

Billable hours: 2,000 target

The juniors we spoke to – regardless of practice - considered their 2,000-hour target achievable: “It would be harder if pro bono, 50 hours of knowledge management, and 25 observational training hours didn’t count,” one associate caveated. Up to 50 hours of DEI activities also counts towards the target, but any creditable non-client hours are all capped at 200 hours. So, 1,800 hours should be purely client billables. Due to the nature of the market, this is sometimes difficult to hit. A corporate associate even joked that “we probably billed 1,000 hours in our first year, and we’re all still here!” It’s a “clear metric,” though, so the target is really just a target; “there’s no incentive to go above it,” especially since the bonus structure is lockstep.

Sidley’s associates are hard-working but “we have a life outside of work too.” We heard that juniors are working from around 8:30 to 6:30 on a regular day. When matters start to heat up, late nights and early morning aren’t uncommon, “but the firm does a good job of supporting us when we’re under stress – part of that is the flexibility of the hybrid working policy.” With no formal policy, three days a week in-office is encouraged, and practices don’t generally have an anchor day so the “goal is to be in the office more days than not.”

Pro Bono

Sidley has fully bought into pro bono, and its associates are sold on it as well: “It’s one of my favorite things I do here,” one source admitted, and “you can do however much you want!” Up to 200 hours can count as billable – “you can, of course, go over that” soit’s “really encouraged, especially for juniors when it’s harder to get work.” So much so, in fact, that the firm recognizes all lawyers who have done more than 60 hours of pro bono in an internal calendar year, which is a “source of pride” for many.Most opportunities are sent around via email, with the exception of the Emerging Enterprises program. “It’s really cool!” one interviewee enthused. “You’re developing companies in different countries all over the world, so you offer pro bono legal services to help them set up their LLC,” although “you need a partner to work with you on that.” Not to worry, though – there are plenty of solo missions “across the spectrum” that juniors can embark on including immigration, housing and veterans rights, criminal appeals, domestic violence. What’s more, “you can stand up in a trial for a pro bono matter as early as you want to!”

Pro bono hours

  • For all US offices: 155,334
  • Average per US attorney: 82.61


The consensus across the board was that “the people have been incredible.” Because cross-office collaboration is so common at the firm, associates had enough firm-wide perspective to share that “Sidley prides itself on a friendly culture that’s well-followed.” The DC branch was described as “a little more academic,” perhaps due to the nature of their regulatory and litigious practices, while in the Miami office, “they’re all like best friends – it doesn’t feel like you’re in BigLaw.” The Californians are “incredibly nice! They’re super patient and forgiving,” and Chicago was described the same way, as it’s more “family oriented.” And even though we were told that Sidley’s New York office has a bit more of a “cutthroat, high-strung” feel, interviewees reassured us that this is largely a consequence of the intense vibe of New York BigLaw as a whole.

The firm hosts a fair number of events where lawyers can wind down, especially during the summer when “the best of Sidley comes forward.” Insiders recalled being taken to Chicago Cubs games, going to “cool clubs and restaurants,” and a Chicago architecture boat cruise. Affinity groups also host events specific to them, for example, Black@Sidley rented out a box to see the likes of Drake, Kevin Hart, and the Chicago Bulls, which was “awesome!” Because there are so many associates with families, the social life is understandably a little quiet outside of the summer, but that’s generally appreciated – “everyone is really nice, but people aren’t trying to force camaraderie so there’s no pressure to go to social events when they do happen.”

Diversity, Equity & Inclusion

We heard that “in terms of BigLaw, the diversity is pretty good right now, a lot better than it has been in the past.” Another junior commented that, “In every definition of DEI, every team I work on is a great example of that.” With “well-publicized” affinity groups, attendance for events and meetings is high – particularly in Sidley Women. After we were told about their afternoon tea events, one associate shared of the group, “Women are pretty well-represented. The chair of the firm is a Latina woman.” Ostolaza emphasizes that “51% of committee chairs are women, and 51% of US associates are women.” She goes on to tell us about the Built to Succeed program, “which is in place to provide scholarships to first generation students and students who lead groups focused on inclusion.” Schmidtberger adds, “The best of the best rise to the top at Sidley, regardless of their background. The firm is built to succeed but people are built to succeed at the firm.”

Get Hired

The first stage: recruitment on and off campus 

OCI applicants interviewed: 2,836 

Sidley interviews at law schools and job fairs across the US and also accepts direct applications to the firm’s website portal. Each office decides at which schools they will interview. A mix of partners and associates conduct the interviews. “We try to engage alumni of the law school when we are doing interviews,” says Jennifer Connelly, Sidley’s national legal recruiting director, “as we feel that fosters a natural connection with the students.” Interviewers use behavioral based questions, which, according to Connelly “allows us to best understand past decisions and how those decisions can help gauge future performances.” Interviewers also want to see candidates demonstrate their analytical and leadership skills. 

Top tips for this stage: 

“Come prepared to talk about anything listed on your resume and be thoughtful regarding questions about the firms in which you are interviewing.” – Jennifer Connelly, recruiting director 


Applicants invited to second stage interview: 1,177 

Callbacks also vary office to office, but candidates typically spend at least two hours in one-on-one interviews with partners and associates. In some instances, there may also be a lunch or dinner with some junior associates. Behavioral questions are still on the table at this point, but interviewers will likely want more detail on candidates’ practice area interests. Connelly says that at this stage “we’re looking for candidates who stand out – those who are able to best articulate their interest in the firm, while also demonstrating that they bring exceptional experiences and skills to their practice areas of interest.” 

Top tips for this stage: 

“Reach out to the lawyers you met during the recruiting process or to Legal Recruiting with any follow up questions you have about your interview.” – Jennifer Connelly, recruiting director

Summer program 

Offers: 741

Acceptances: 330 

Sidley summers are encouraged to get experience in different practice groups – again, the program varies from office to office. Connelly advises associates to “use every opportunity during the summer to meet as many lawyers and learn as much about the firm and the practice as possible.” There’s a centralized assignment system but summers can also take work directly from lawyers. At the end of the program, associates’ assignment to a particular practice group will vary – you guessed it – by office. 

Top tips for this stage: 

“It’s always a lot of fun, but it’s good to make sure all the summers know that they don't have to attend every single event.”  a second-year junior associate 

“Work on projects that interest you the most, but also take a chance to do something in a practice area that is unfamiliar to you.”  Jennifer Connelly, recruiting director 


Sidley Austin LLP

One South Dearborn,
IL 60603

787 Seventh Avenue,
New York,
NY 10019

Main areas of work

Services: Corporate governance, global finance; employee benefits and executive compensation; global arbitration, trade and advocacy; IP litigation; technology; commercial litigation and disputes; white collar defense and investigations; regulatory litigation; government strategies; restructuring; tax 

Agribusiness and food; energy; banking and financial services; hospitality; insurance; investment funds; global life sciences; entertainment, sports and media; real estate; REITs; technology 

Firm profile

 Sidley is an elite global law firm with US$3.1 billion in revenue powered by lawyers who practice at the highest level of the profession. Backed by 158 years of experience, we deliver superior service to a high-caliber group of market-leading clients worldwide, while placing a premium on collaboration and diversity.

Our firm boasts a roster of 2,300 lawyers who wield deep experience in litigation, transactional, and regulatory matters spanning over 50 legal disciplines and industries.

With 21 offices, including our new Miami office, situated in major commercial and financial capitals around the world, our lawyers possess the cultural awareness and legal acumen needed to advise clients in today’s global economy. Follow Sidley on Twitter @SidleyLaw.


Law schools attending for OCIs in 2024:
University of California, Berkeley, School of Law; The University of Chicago Law School; Columbia Law School; Georgetown University Law Center; Fordham Law School; University of Florida Levin College of Law; Harvard Law School; Howard University School of Law; University of Miami School of Law; University of Michigan Law School; Northwestern University School of Law; University of Notre Dame Law School; New York University School of Law; University of Pennsylvania Law School; SMU Dedman School of Law; Stanford Law School; The University of Texas School of Law; Vanderbilt; UC Davis; UCLA; UC Law San Francisco; University of Virginia School of Law; Yale Law School

Recruitment outside OCIs:
Bay Area Diversity Career Fair, Boston Lawyers Group Job Fair, Cook County Bar Association Minority Job Fair, Lavender Law, Loyola IP Job Fair

Summer associate profile:
Sidley seeks candidates who have demonstrated academic success and possess strong leadership and interpersonal qualities. The firm looks for a diverse group of individuals who are motivated by highly sophisticated legal work practiced in a collegial and supportive environment.

Summer program components:
Sidley’s summer associate program is an invaluable window into its practice and firm culture. Participants select projects that interest them and perform legal work under lawyer supervision. An essential component of Sidley’s summer program is the opportunity to learn and develop professional skills. Hands-on training includes detailed reviews of each summer associate’s work product, as well as more formal training programs such as writing seminars, a mock trial and a mock negotiation exercise. Each summer associate is assigned senior associates and partners to provide guidance and each participant receives a formal review at the midpoint of the summer program. 

Social media

Recruitment website:
Twitter: @SidleyLaw
Facebook: sidleyaustinllpofficial
Linkedin: sidley-austin

This Firm's Rankings in
USA Guide, 2023

Ranked Departments

    • Banking & Finance (Band 4)
    • Bankruptcy/Restructuring (Band 3)
    • Capital Markets: Debt & Equity (Band 3)
    • Intellectual Property: Patent Litigation (Band 5)
    • Labor & Employment: The Elite (Band 4)
    • Life Sciences (Band 3)
    • Litigation: General Commercial: The Elite (Band 3)
    • Litigation: Securities (Band 2)
    • Litigation: White-Collar Crime & Government Investigations (Band 2)
    • Media & Entertainment: Litigation (Band 4)
    • Media & Entertainment: Transactional (Band 3)
    • Private Equity: Buyouts (Band 4)
    • Technology: Transactions (Band 2)
    • Corporate/M&A: The Elite (Band 4)
    • Corporate/M&A: The Elite (Band 4)
    • Real Estate (Band 3)
    • Tax (Band 3)
    • Antitrust (Band 5)
    • Environment (Band 1)
    • Healthcare (Band 2)
    • Healthcare: Pharmaceutical/Medical Products Regulatory (Band 1)
    • Intellectual Property: Litigation (Band 2)
    • Litigation: General Commercial: The Elite (Band 3)
    • Litigation: White-Collar Crime & Government Investigations (Band 2)
    • Telecom, Broadcast & Satellite (Band 2)
    • Antitrust (Band 3)
    • Banking & Finance (Band 1)
    • Bankruptcy/Restructuring (Band 3)
    • Corporate/M&A & Private Equity (Band 1)
    • Employee Benefits & Executive Compensation (Band 2)
    • Environment (Band 2)
    • Healthcare (Band 3)
    • Healthcare: Pharmaceutical/Medical Products Regulatory (Band 1)
    • Immigration (Band 2)
    • Insurance: Dispute Resolution: Reinsurance (Band 2)
    • Insurance: Transactional & Regulatory (Band 1)
    • Intellectual Property (Band 1)
    • Litigation: General Commercial (Band 1)
    • Litigation: Securities (Band 1)
    • Litigation: White-Collar Crime & Government Investigations (Band 2)
    • Real Estate (Band 2)
    • Tax (Band 2)
    • Technology & Outsourcing (Band 3)
    • Corporate/M&A (Band 4)
    • Banking & Finance (Band 5)
    • Bankruptcy/Restructuring: The Elite (Band 6)
    • Corporate/M&A: Highly Regarded (Band 2)
    • Corporate/M&A: Takeover Defense (Band 1)
    • Insurance: Transactional & Regulatory (Band 2)
    • Intellectual Property: Patent (Band 3)
    • Litigation: General Commercial: Highly Regarded (Band 2)
    • Litigation: Securities (Band 3)
    • Litigation: White-Collar Crime & Government Investigations: The Elite (Band 4)
    • Private Equity: Buyouts (Band 3)
    • Real Estate: Mainly Corporate & Finance (Band 3)
    • Tax (Band 3)
    • Banking & Finance (Band 3)
    • Capital Markets: Debt & Equity (Band 3)
    • Corporate/M&A: The Elite (Band 2)
    • Environment (Band 4)
    • Litigation: Securities (Band 3)
    • Private Equity: Buyouts (Band 3)
    • Litigation: General Commercial (Band 2)
    • Antitrust (Band 4)
    • Appellate Law (Band 1)
    • Banking & Finance (Band 4)
    • Bankruptcy/Restructuring: The Elite (Band 4)
    • Capital Markets: Equity: Issuer Counsel (Band 3)
    • Capital Markets: Equity: Manager Counsel (Band 3)
    • Capital Markets: High-Yield Debt (Band 4)
    • Capital Markets: Investment Grade Debt: Issuer Counsel (Band 3)
    • Capital Markets: Investment Grade Debt: Manager Counsel (Band 2)
    • Capital Markets: Securitization: ABS (Band 2)
    • Capital Markets: Securitization: CRE CLOs (Band 2)
    • Capital Markets: Securitization: RMBS (Band 1)
    • Capital Markets: Structured Products (Band 2)
    • Climate Change (Band 3)
    • Corporate Crime & Investigations: The Elite (Band 2)
    • Corporate/M&A: The Elite (Band 4)
    • Derivatives (Band 2)
    • E-Discovery & Information Governance (Band 3)
    • Employee Benefits & Executive Compensation (Band 5)
    • Energy Transition (Band 1)
    • Energy: Electricity (Regulatory & Litigation) (Band 4)
    • Energy: Electricity (Transactional) (Band 4)
    • Energy: Oil & Gas (Regulatory & Litigation) (Band 3)
    • Energy: Oil & Gas (Transactional) (Band 2)
    • Environment (Band 2)
    • ERISA Litigation (Band 3)
    • False Claims Act (Band 2)
    • FCPA (Band 4)
    • Financial Services Regulation: Broker Dealer (Compliance & Enforcement) (Band 1)
    • Financial Services Regulation: Consumer Finance (Compliance) (Band 2)
    • Healthcare: The Elite (Band 3)
    • Hedge Funds (Band 1)
    • Immigration (Band 4)
    • Insurance: Transactional & Regulatory (Band 2)
    • Intellectual Property (Band 3)
    • International Arbitration: The Elite (Band 3)
    • International Trade: Customs (Band 1)
    • International Trade: Intellectual Property (Section 337) (Band 5)
    • International Trade: Trade Remedies & Trade Policy (Band 1)
    • Leisure & Hospitality (Band 4)
    • Life Sciences (Band 2)
    • Life Sciences: Regulatory/Compliance (Band 1)
    • Offshore Energy (Band 2)
    • Privacy & Data Security: The Elite (Band 3)
    • Private Equity: Buyouts: Mid-Market (Band 2)
    • Product Liability & Mass Torts: The Elite (Band 2)
    • Projects: LNG (Band 2)
    • Projects: Power & Renewables: Transactional (Band 2)
    • Projects: Renewables & Alternative Energy (Band 5)
    • Real Estate (Band 4)
    • Registered Funds (Band 3)
    • REITs (Band 2)
    • Securities: Litigation (Band 2)
    • Securities: Regulation: Enforcement (Band 2)
    • SPACs (Band 3)
    • Sports Law (Band 4)
    • Tax: Corporate & Finance (Band 3)
    • Technology (Band 4)
    • Transportation: Rail (for Railroads) (Band 1)
    • Transportation: Road (Automotive) (Band 3)