New Book from Brad Blickstein WWPED: What Would Private Equity Do?

Legalweek Recap: The State of RFPs–or Trying to Compare Apples to Ham

RFPs of the Past

The session began with some history, or an exploration of RFP 1.0 and RFP 2.0. As panelists recalled, in the beginning, RFPs were informal and relationship-driven. Or in other words, many law firm partners reacted to being asked to complete one with an attitude of “How dare you.” As Brosnahan said, “This has come a long way in a short period of time, from something that was offensive and presumptuous to a structured process that happens automatically.” And as Blickstein noted, “Clients were also offended at having to do business this way.”

The next iteration, RFP 2.0, made strides through standardized procurement-driven processes with structured proposals. In reality, law firms were often expected to produce voluminous documentation to answer a host of irrelevant questions. In many cases, that translated to, “I’m publishing an encyclopedia, and you’re going to write it for me.”

According to Winmill, 2.0 represented an expansion. “More companies were doing RFPs, they were doing it for more types of legal services, and they were also involving more people internally,” he said. “I have great empathy for the law firms that filled these things out. They would get RFPs and would often say the questions were inconsistent, they didn’t make sense, they were multipart, and some were just dumb.”

Part of the issue came from RFP questionnaires being written by committee–everyone wanted to weigh in, and every change required consensus. That led to a process that was clumsy and clunky. As Blickstein noted, “Folks don’t often think about the result of that collection of data when asking those questions.”

Looking Ahead to RFP 3.0

Now that the legal industry is past the RFP 2.0 phase, the panel took a look at the future. And right now, the process doesn’t yet match the pace.

When creating RFPs, the situation currently is “one size fits none,” as Brosnahan described it. “You’re asking for input from people that have different offerings, different skills, and different pricing models,” she said. “You want them to level set that in a way that lets you choose from apples and apples. But they may be offering ham. It’s impossible to normalize those things.”

According to Winmill, some companies are better than others when it comes to the RFP process. But many of them still struggle to write relevant, concise RFPs. “I see a lot of kicking of the can down the road in in-house departments,” he said. “It takes a lot of work up front for an in-house legal department to say ‘We’re buying green apples, we’re going to design the RFP for those apples, and we’re going to invite green apples to our RFP. So we’re going to write good questions about green apples.’” He said that approach requires more time than most people have. “So instead they take the template they’ve used before, and they send it to their friends.”

The panelists also noted that a key tautological theme of today’s RFPs requires using AI to draft responses and then drafting responses about the use of AI. But more seriously, the panelists pointed to the ability of AI and centralized data to dramatically increase the speed of drafting responses. However, AI slop is still a major concern.

Being able to easily find information from past RFPs represents a key value driver from AI.  “You have a universe of information from past RFPs and experience data,” said Maziarek. “To me, that’s the asset that allows firms to articulate the unique value they can bring to clients in their RFP responses, provided it is curated and leveraged accurately. But the slop part is huge, because we are in the stage where we have a lot of content.”

Grabowski pointed to the expense and time involved in completing RFPs and where AI can help address that challenge. “It’s important to not take everything that comes over the fence. The attorneys that we work with think that since we have these tools, it’s going to be easy now,” he said. “And there is no easy button.” However, better data and AI allow firms to conduct a profitability analysis on the front end and evaluate which RFPs are worth responding to, or which parts of certain RFPs make more strategic sense. 

On the client side, the panel pointed to AI as an excellent tool for reviewing both answers to RFPs as well as consolidating questions or eliminating those that aren’t truly necessary. 

The panel concluded with a list of dilemmas that remain with RFPs:

On Display at Legalweek: Unintended Homogenization, Or the Claudification ofMarketing

If you’re overwhelmed by Legalweek hot takes, you’re not alone. But I’d like to offer one
I’ve been thinking about a lot since leaving New York. I won’t belabor the change of
venue (better, modern facilities) or the change in the commute between
hotel/show/events (long and generally unpleasant). Instead, I want to focus on the
exhibit hall—specifically the booths—and, even more specifically, the booth messaging.
In my 20 years(!!) of attending this show, the exhibits have never been so lovely. They
were all sleek, well-designed, and welcoming. But the booths, and the messages they
featured, were all…the same.


Of course, most centered on or mentioned GenAI. Not a surprise. What was a surprise
were the nearly identical value props everywhere, many with eerily familiar wording as
you walked the hall. Even the booth designs themselves were sometimes hard to tell
apart. There are a lot of very talented marketing people in legaltech, and they work with
lawyers, all of whom traffic in creative, unique, and eloquent words. So, why did the lack
of differentiation hit me before I reached the second aisle?


“Well, everyone is talking about GenAI” was my first thought. It is, after all, one of the
most seismic inflection points that the legal profession has ever experienced, and the
resulting change has been compressed into an unbelievably short timeframe. So, of
course, it would be the focus of most of the exhibits. Mystery solved. Moving on.
Until, as I was walking down 39th Street, avoiding the horse mess and construction, a
colleague sent me a report that she’d run through AI to see what it might do with a
design we were working on for a client. And it struck me that it bore an undeniable
resemblance to another design that someone else had sent me weeks before (and by
resemblance, I mean almost identical.) These were completely unrelated subjects and
formats, and from entirely different marketing teams. And yet, the similarities were eerie.
So, it occurred to me that maybe GenAI itself really is causing this lack of differentiation,
but not for the reason I originally assumed. How many of the smart, experienced
marketing professionals in our space felt the need (or the pressure) to “run this through
AI” before finalizing their booth graphics?


I spend many hours discussing AI with clients, and I know that it really shines in
situations where you can standardize processes and apply it to large datasets. When
these situations exist (as with eDiscovery), the technology saves incredible amounts of
time and energy by sifting through data to inform strategy in a way that humans simply
cannot.


I’ve also read a lot of legaltech marketing from a wide range of vendors selling a wide
range of products and services, and have felt for a while that things are getting a tad
repetitive.

But it wasn’t until I saw it in action in one room that it became clear: legaltech marketing
is experiencing an unintentional homogenization. Is this the result of a mature market
that is favoring efficiency over creativity? Or is it Claudification?


Josie Johnson is Chief Client Experience Officer at Blickstein Group, where she designs
and executes marketing programs that produce brand equity and generate revenue for
legal tech companies, alternative legal service providers, and innovative law firms.

Tips for a Successful Awards Strategy

They can also take an enormous amount of time, turn into pay-to-play opportunities with little value, or just be a frustrating experience. The key is to be strategic about which awards to pursue. Rather than ignore them completely or chase them indiscriminately, it’s important to have a plan. Want to get the most from your awards? Here are XX tips.

  1. Understand Your “Why” and “How”

Think about your reasons for pursuing awards. There are many professional and personal reasons to do so. They can help promote your business, demonstrate your expertise, highlight successful matters with clients, get you in a room with people you’d like to know better, and be a reward for work well done. Different awards can help accomplish different goals, so it’s important to think about why you want to submit nominations. 

It’s also important to understand how much of a priority awards are for you right now. That means being realistic about how much time, energy, and money you have to invest. Awards aren’t free; there may not be an application fee, but they always take time.

One approach is to target one or two meaningful awards a year. Other people—particularly those building a newer practice or expanding into new markets—may choose to be a little more active. There is no right or wrong approach, but your answer helps narrow the field quickly. If you’re only going after one award this year, it needs to be a strong, high-impact one. If you’re pursuing multiple ones, you may be able to balance a mix of aspirational and more attainable ones.

  1. Decide Which Awards to Pursue

Once you know why you want to pursue awards and how much you have to invest, the next step is identifying which awards are actually worth your time. One of the easiest and most revealing things to do is look at past winners. Ask yourself: Is this the type of firm or organization I want to be associated with? Awards and honors function as a form of positioning. Being listed alongside peers you respect can reinforce your credibility. Being grouped with those that don’t align with your practice—or feel out of step with your market—may not add much value or even cheapen your brand.

And then there’s always the question about pay-to-play. Many awards require an entry fee or sponsorship. That shouldn’t automatically be a disqualifier if it’s within your budget. Some pay-to-play awards have credibility and real networking value. They may put you in the company of people you want to build relationships with. On the other hand, some are just money grabs. If you can’t figure out what the criteria are, who the judges are, or what the organization hosting the award actually does, that can be a real red flag.

And some awards appear free on the surface, but require you to purchase a table or attend an event if you win. That’s not bad, of course, but it is something you need to budget for. The key is evaluating what you’re getting in return for any award: visibility, validation, connections, or business development opportunities.

  1. How to Stay on Top of Deadlines

One of the biggest stressors around awards is scrambling at the last minute. The way to avoid that is straightforward, but it does require some planning and discipline: track information on an ongoing basis.

This can be a spreadsheet or some kind of centralized tracking document that includes award names, categories, deadlines, and entry requirements. This needs to be a living document. Deadlines often shift. Categories change. New awards emerge. Current ones disappear. If you’re targeting multiple awards, checking in once a month or so is usually enough. 

Beyond that, one of the most valuable things to add is something like “Potential Highlights.” This is where you track wins, outcomes, or moments that might be useful later—successful outcomes you are particularly proud of, repeat appointments, or notable feedback.

This is especially helpful because it can be easy to forget details when you’re deep in your work and day-to-day practice.

  1. Know the Keys to a Winning Entry

A decent submission lists facts. A winning submission tells a story. Judges often review dozens—sometimes hundreds—of submissions. Experienced judges may get a sense within the first few sentences whether they feel your award is a contender. That means your strongest points need to appear early. Don’t save the good stuff for the end. Or worse, the middle, so judges have to dig to figure out why you should win. Instead of starting with your name, title, organization, and years of experience, focus on your winning argument. Open with a compelling introduction that clearly answers the question: Why should this person win this award, rather than another nominee? 

Storytelling doesn’t mean exaggeration. It means context. Instead of listing cases, explain why they mattered. Rather than stating outcomes, explain challenges. What made the situation complex? What was at stake? What did you bring that made a difference?

It also means that you have to be willing to promote yourself and do a little honest bragging–don’t sell yourself short! And these stories can often be leveraged and tailored across multiple award submissions. There’s no need to start from scratch every time. That might mean adjusting emphasis, reframing language, or highlighting different aspects of the same experience.

With that in mind, success stories do age. For lifetime achievement or career-spanning awards, evergreen content is valuable. But many category-specific awards have defined timelines, often looking at work from the past 12 to 18 months. Using outdated examples can weaken an otherwise strong submission. And whenever possible, try to be specific. Details and data can tell a strong story. 

  1. If at First You Don’t Succeed…

One of the hardest things about awards is that you never fully know what the judges are thinking. Criteria are usually subjective. Panels may change. People often overestimate how personal the outcome can feel, especially when you know others who won when you didn’t. Failing to win doesn’t necessarily mean you didn’t have a strong submission. It may just mean there was an unusually competitive field, or that another submission aligned more closely with that year’s focus.

The most important thing to remember is this: Awards are not verdicts on your worth. They are opportunities. If you don’t win one year, you can—and should—try again. 

  1. And When You Do Succeed

Once you’ve won, it’s time to get the word out! There’s value in promotion and derivative content you get from being named a finalist or to a short list. And if you are named a winner after being short-listed, that’s worth another follow-up. You can highlight these successes in LinkedIn posts, and even press releases or blogs. 

Awards can amplify your credibility, reinforce your brand, and support business development, but only when you pursue them intentionally. By prioritizing the right opportunities, tracking the right information, preparing realistically, and telling compelling stories, you can approach awards not as a guessing game, but as a strategic extension of your practice.

Top Takeaways From the Chicago Law Department Operations Survey Roundtable


Generative AI is a moving target

In the survey, 58% of legal operations professionals cited pressure from executive leadership as one of the primary drivers for pursuing generative AI. With the growing momentum behind AI-based efficiency and innovation mandates, in-house teams are being pushed to move fast.

During the roundtable, many participants said they would answer certain questions differently today than they did six months ago when the survey was administered. For example, several people shared that their chief legal officers have recently indicated that using generative AI in legal is not only a mandate from executive leadership. It’s become a business obligation to find effective ways to use the technology. This sentiment rang true for a variety of professionals, from organizations across the spectrum from tech-resistant to highly innovative.

In terms of how legal teams are using generative AI, there was significant discussion about how different teams are responding to mandates from leadership to incorporate the technology into their daily work. Some were highly focused on measuring and making progress toward efficiency gains they were trying to achieve with existing internal resources. These individuals said they were focused on a specific problem they had identified and then attempted to solve that problem with AI. For example, one professional explained a successful effort to conduct a first-level review on unreviewed bills, helping their attorneys reduce the time required to review invoices. Participants also acknowledged the importance of quality, well-organized data to their success. This was instrumental for the legal department that had succeeded in streamlining its billing review processes.

Others were trying to incorporate AI for specific tasks but continued to struggle with integrating it into their standard workflows or identifying what to use it for in legal use cases. One roundtable participant said she implemented a brief internal survey to gauge the adoption of AI as a means to continuously evaluate the value being derived from such solutions.

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Pressure on outside counsel

Participants also discussed the ways they are articulating to outside counsel that they should use generative AI, how they should apply it and what the cost savings are expected to be. There was a general consensus that expectations for outside counsel have risen, especially around cost control, as some legal departments expressed that they view generative AI as a way to reduce reliance on outside counsel and cost-effectively maintain internal headcount.

Still, legal operations professionals have varying degrees of comfort with outside counsel using this technology. Those who had formed strong partnerships with their outside counsel were seeing the best outcomes: by asking their law firms to use AI and reduce their rates, they were pairing their requests to use AI to reduce rates with clear discussions of what that would entail.  

Even with clear parameters, however, AI has created some tension between in-house and outside legal. As legal teams dictate that their law firms must use AI in all matters and show how it’s saving money, they often in parallel prohibit counsel from using their data to train the firm’s models. This is reasonable, but if the scale of work for that client isn’t past a certain threshold, it becomes difficult for law firms to justify establishing and maintaining an isolated large language model instance.

Generally, the roundtable discussion underscored the ongoing issue of inside counsel not always knowing how to leverage legal operations in leading negotiations with providers. Many technology and rate discussions continue to be counsel to counsel, versus legal operations to firm professionals, which undermines the impact legal operations teams can have on effectively managing outside spend and technology return on investment.  

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Resource management driven by technology

The roundtable also included a brief discussion on alternative legal service providers and expectations that they bring technology to the table. It was clear that legal departments are more comfortable having conversations about technology with ALSPs than they are with outside counsel.

Additionally, participants said they believe AI will begin driving some internal headcount savings, though they remained unsure of exactly how that would manifest. Many indicated they’re looking for more understanding and guidance about how to navigate the tradeoffs and allocations of work between AI and internal resources. Anecdotally, as legal teams invest in AI, they are trying to stay budget neutral in 2026 and show cost savings in 2027, so many said they are waiting to add more people to their team until after they have some evidence as to the savings that AI might provide over the coming one to two years.

Looking ahead, legal operations leaders understand their role in becoming more vocal about how their department approaches AI and responds to technology mandates. They are looking to demonstrate value, improve the balance across internal, external and technology resources, and set the tone for strategic innovation.

Learn more about the Law Department Operations Survey