Navigating Legal Challenges as General Counsel

“We’ll handle it.” That phrase almost broke my team. When I was GC at a fast-scaling company, every week delivered a fresh storm of priorities. Revenue teams needed faster contracts. Finance demanded spend reductions. Product launched AI pilots without legal review. And leadership expected Legal to move at the speed of execution without ever slowing the business. I tried to say yes. I thought it showed partnership. But it created confusion and resentment. We delivered everything, and somehow, it still wasn’t enough. This pressure is accelerating in the age of AI. Expectations scale. Resources don’t. And Legal is often the last to be consulted but the first to be blamed. The problem is not capability. It’s clarity. The most effective GCs are not trying to cover every ask. They are naming the tradeoffs, translating risk into business language, and building frameworks that help executives choose with intent. One reframed AI pilots by mapping value to risk. She launched only in low-friction areas and backed it with data. Her dashboard showed where Legal accelerated deals rather than blocked them. That shift earned trust. Another made it a habit to name tradeoffs in meetings. Instead of reacting to urgency, he paused and asked which path best supported this quarter’s strategy. That question changed how the business saw Legal. Not as a bottleneck, but as a navigator. I share more on this shift in my latest newsletter: The Most Dangerous Answer a GC Can Give: Yes to Everything. Legal cannot automate its way out of impossible asks. But it can clarify the choices, make risk visible, and help the business decide what truly matters. What’s one tradeoff you’ve made that shaped better decisions? #GC #AI #CorporateCounsel -------- 🚀 Olga V. Mack 🔹 Building trust in commerce, contracts & products 🔹 Sales acceleration advocate 🔹 Keynote Speaker | AI & Business Strategist 📩 Let’s connect & collaborate 📰 Subscribe to Notes to My (Legal) Self

𝗔 𝗖𝗘𝗢 𝘁𝗼𝗹𝗱 𝗺𝗲 𝘁𝗵𝗲𝗶𝗿 𝗻𝗲𝘄 𝗚𝗖 𝘄𝗮𝘀𝗻'𝘁 𝗹𝗶𝘃𝗶𝗻𝗴 𝘂𝗽 𝘁𝗼 𝗲𝘅𝗽𝗲𝗰𝘁𝗮𝘁𝗶𝗼𝗻𝘀. 𝗜 𝗮𝘀𝗸𝗲𝗱 𝘄𝗵𝗮𝘁 𝗹𝗲𝗴𝗮𝗹 𝗶𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲 𝘁𝗵𝗲𝘆 𝗯𝘂𝗶𝗹𝘁 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲 𝗵𝗶𝗿𝗲. 𝗦𝗶𝗹𝗲𝗻𝗰𝗲. I see this pattern regularly in PE-backed and growth-stage companies. They run a search, find a strong candidate, make the hire. Then the new GC arrives on day one to find no paralegal support, no contract management system, no organized outside counsel relationships, and a budget that assumes legal will cost roughly what it cost when the CFO was managing it on the side. The GC spends the first six months doing work that should sit below their pay grade while simultaneously trying to build credibility as a strategic advisor. That tension burns through goodwill fast, and it's entirely preventable. 𝗧𝗵𝗲 𝗺𝗶𝗻𝗶𝗺𝘂𝗺 𝗶𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲 𝗮 𝗚𝗖 𝗻𝗲𝗲𝗱𝘀 𝗼𝗻 𝗱𝗮𝘆 𝗼𝗻𝗲: • One support hire. A paralegal or legal operations coordinator who can handle routine contracts, NDA flow, entity maintenance, and document management. This single hire frees the GC to focus on the work that justifies their compensation. • An outside counsel framework. Before the GC starts, identify two or three firms for the company's primary legal needs and establish rate agreements. The GC should inherit working relationships from the start. • A realistic budget. Legal spend will increase. If the company's been spending $500K annually on outside counsel with no in-house function, the first-year budget with a GC, support staff, and continued outside counsel needs should be modeled honestly. Surprising the GC with budget constraints after they start creates friction that damages the relationship early. • A clear mandate from the CEO. The GC needs to know in writing what the company expects them to prioritize in the first 90 days, whether that's integration work, compliance gaps, commercial contract standardization, or litigation oversight. This should come from the CEO directly, not delegated to HR or outgoing outside counsel. Without that clarity, the GC is guessing, and the leadership team is evaluating them against expectations that were never communicated. Companies that invest in this infrastructure before the GC starts tend to see faster impact and higher retention. The ones that skip it often find themselves back in a search within a couple of years. #GeneralCounsel #ExecutiveSearch #PrivateEquity

Most legal teams aren’t trained for war.   But they’re in one.   → Sanctions.  → Trade controls.  → Supply chain instability.  → Sudden exits from foreign markets.   And the pressure lands directly on legal.   I was on a call with a legal director last week.   She looked exhausted.   Not because of the volume of work.  But because the rules kept changing — overnight.   > “Scott, I’m supposed to protect the company.   > But how do you protect anything when the ground keeps shifting?”   One day it’s a policy change in Europe.   Next day, it’s a new regulatory risk in APAC.    And the day after, a supplier pulls out because of conflict escalation.   Here’s the uncomfortable truth:   Legal counsel are being forced to navigate geopolitical complexity with operational expectations that haven’t evolved.   You’re still expected to:    → Review contracts  → Close deals  → Limit risk   But now?    You also need to anticipate:   - Political volatility - Financial sanctions - Cross-border liability.   No extra time. No extra support.   That’s not just unsustainable.    That’s dangerous.   If you're a legal leader trying to keep up, here’s what I tell my clients:   1. Start scenario planning— even for “low probability” risks   2. Speak up in strategy meetings — you have insight no one else does    3. Push for operational backup — geopolitics is not a one-person job   4. Reframe your value — you’re not just legal, you’re risk intelligence     Legal shouldn’t be catching falling bricks.    You should be helping decide where the walls go.   If you're navigating legal in a world on fire — you don’t have to do it alone.   Let’s talk. ------------------ Hi, I’m Scott Harrison and I help executive and leaders master negotiation & communication in high-pressure, high-stakes situations. - ICF Coach and EQ-i Practitioner - 24 yrs | 19 countries | 150+ clients  - Negotiation | Conflict resolution | Closing deals 📩 DM me or book a discovery call (link in the Featured section)

In-house counsel see outside counsel as too expensive, too academic, and not business-savvy. Outside counsel see in-house teams as risk-averse, last-minute, and indecisive. As a former public company General Counsel and as a current law firm partner, here’s what’s really going on: Different incentives. In-house counsel are judged on efficiency, budget control, and business partnership. Their job is to get to “yes” quickly—but carefully. Outside counsel are trained to issue-spot, document risk, and protect against liability. They’re rewarded for depth, caution, and thoroughness. Different perspectives. In-house teams see the whole business ecosystem: revenue, politics, deadlines, culture. Outside counsel, by design, focus only on the legal issue in front of them—and bill accordingly. Different expectations. In-house wants practical answers. “Can we do this?” Outside counsel responds with memos and case law. “It depends.” So yes, there’s frustration and misalignment. But it doesn’t have to be this way. Here are 5 actionable ways to bridge this divide: 1. Align on Outcomes, Not Just Assignments. Don’t start with “write this memo” or “file this motion.” Start with: “What’s the business goal here?” “What does success look like in 6 months?” The best outside counsel don’t just execute. They co-create strategy. If you’re not aligned on the destination, don’t be surprised when the roadmap is expensive, winding, and filled with detours no one wanted. 2. Embed Firms in Your Business. Invite your law firm partners to product launches, earnings calls, or business unit meetings. The more they understand your world, the more useful—and less academic—their advice becomes. 3. Treat In-House Like a Client AND a Colleague. Outside counsel, don’t just take orders—ask questions. Offer options. Push back respectfully. In-house counsel often have internal battles to fight—politics, budget, turf wars. Help them win those battles. Make them look good. Be their secret weapon. 4. Relationships Matter. Really. Want to be the outside counsel that in-house calls first? - Learn the business model. - Know their board cycle. - Follow their 10-Ks. - Ask them what keeps them up at night—and solve that problem. Being a trusted advisor isn’t just about technical brilliance. It’s about emotional intelligence, business savvy, and a little bit of humility. 5. Skip the Treatise. Give Me a Bullet Point. In-house lawyers don’t have time for ten pages of “on the one hand…” They need: - The issue - The risk - Your recommended path forward You’re not writing for a judge. You’re writing for a C-suite executive who wants to know, “Can we do this, and if not, how close can we get?” Bottom Line: The tension isn’t personal—it’s structural. But the solution is cultural: shared understanding, mutual accountability, and trust. That’s how legal “vendors” become strategic partners.

Three months into my first GC role, I casually mentioned "this feels risky" in a hallway conversation. Days later, a roadmap was on hold. That's when I learned: As an exec, there's no such thing as "just thinking out loud." Here’s what I had to unlearn—and relearn—on the job to become a function leader: 𝗬𝗼𝘂𝗿 𝘄𝗼𝗿𝗱𝘀 𝗰𝗮𝗿𝗿𝘆 𝘄𝗲𝗶𝗴𝗵𝘁. I once torpedoed a deal with a single email. Just the facts and legally sound, but by the time I grabbed a coffee, the deal was sinking. In this seat, a well-placed period can read like a full stop. 𝗬𝗼𝘂'𝗿𝗲 𝗮𝗹𝘄𝗮𝘆𝘀 𝗼𝗻 𝘀𝘁𝗮𝗴𝗲. An offhand remark about a project's poor odds caused panic. There are no throwaway lines when people hear from you once a month. 𝗬𝗼𝘂 𝗱𝗼𝗻'𝘁 𝗻𝗲𝗲𝗱 𝘁𝗼 𝗸𝗻𝗼𝘄 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴. Some of my best moments came from saying, “I don’t know...let’s ask my team.” Credibility doesn't come from knowing all the answers but from knowing when to cede the floor. 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘁𝗿𝘂𝘀𝘁 𝗮𝘂𝗴𝗺𝗲𝗻𝘁𝘀 𝗹𝗲𝗴𝗮𝗹 𝘀𝗸𝗶𝗹𝗹. As a Deputy GC, I nailed a regulatory briefing. The exec smiled, thanked me… then turned to Sales for the call. That day I learned something: legal skills 𝘢𝘭𝘰𝘯𝘦 don't give you a vote in the Room Where It Happens. Trust and skill do. 𝗚𝗲𝘁 𝗼𝘂𝘁 𝗼𝗳 𝗹𝗲𝗴𝗮𝗹'𝘀 𝗹𝗮𝗻𝗲. “What’s our exposure?” isn’t always the right question. Sometimes it’s “what’s our margin?” or “what will customers want?” A GC’s job is to be a useful executive who happens to know the law. 𝗧𝗵𝗲 𝗹𝗮𝘄 𝗶𝘀 𝗮 𝗺𝗲𝗮𝗻𝘀, 𝗻𝗼𝘁 𝗮𝗻 𝗲𝗻𝗱. Don't stop with what the law says. Translate it: “Here’s what that means for our goals, timeline, and risk profile.” 𝗬𝗼𝘂'𝗿𝗲 𝗮 𝘃𝗼𝗶𝗰𝗲 𝗼𝗳 𝗶𝗻𝘁𝗲𝗴𝗿𝗶𝘁𝘆. Integrity's not always a speech. Sometimes it’s a quiet “Not this way” in a room moving too fast. Sometimes it’s saying nothing until you know what turns the tide. 𝗦𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴'𝘀 𝗮𝗹𝘄𝗮𝘆𝘀 𝗯𝗿𝗼𝗸𝗲𝗻. Running a company's like walking over red hot coals with a leaky fire hose. So you must ask: Where am I now? Where do I need to be? How can I get there? And focus on blazes that matter most. 𝗗𝗼𝗻'𝘁 𝗱𝗿𝗶𝗻𝗸 𝘆𝗼𝘂𝗿 𝗼𝘄𝗻 𝗞𝗼𝗼𝗹-𝗔𝗶𝗱. The minute I’ve thought, “I’ve got this nailed,” I’ve usually been standing on a trapdoor, foot on the release. 𝗡𝗼 𝗽𝗿𝗼𝗯𝗹𝗲𝗺 𝗴𝗲𝘁𝘀 𝗲𝗮𝘀𝗶𝗲𝗿 𝗯𝘆 𝘄𝗮𝗶𝘁𝗶𝗻𝗴. Problems are like avocados; they don’t ripen, they just rot. It's best to do hard things early, while you can still change outcomes. The hardest part of being GC is shifting from individual effort to collective effectiveness. The best part is realizing you’re not the whole engine anymore: You’re an oar in a bigger boat, moving faster and farther than you ever could alone. 𝗚𝗖𝘀: What do you wish you knew sooner? 𝗔𝘀𝗽𝗶𝗿𝗶𝗻𝗴 𝗹𝗲𝗮𝗱𝗲𝗿𝘀: What's the hardest lesson you're learning right now? #𝐆𝐞𝐧𝐞𝐫𝐚𝐥𝐂𝐨𝐮𝐧𝐬𝐞𝐥 #𝐋𝐞𝐠𝐚𝐥𝐋𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩 #𝐈𝐧𝐇𝐨𝐮𝐬𝐞𝐂𝐨𝐮𝐧𝐬𝐞𝐥 #𝐥𝐚𝐰𝐩𝐫𝐚𝐜𝐭𝐢𝐜𝐞

The toughest part of being a first-time GC? It’s not the legal work… it’s navigating all the moments with no playbook. I learned this as the first lawyer at a venture fund. The technical legal skills that made me successful at a law firm suddenly felt incomplete. No processes to lean on, no precedent to guide me. Every decision required judgment calls with imperfect information: - Is this risk worth taking? - Build the process now or later? - Speed vs. protection? And when everyone looks to you for answers, where do you turn? This is what pushed me to start building networks with other GCs. Not just for legal expertise, but for those "am I crazy?" moments that every solo GC faces. Having trusted peers to gut-check my thinking made all the difference. They didn't tell me what to do - they helped me pressure-test my own reasoning. Looking back, I see how those solo GC experiences helped shape my approach to leadership: 1. Getting comfortable with uncertainty - perfect information is rare in startups 2. Building relationships before you need them 3. Trusting your judgment, but creating systems to verify it 4. Focusing on teaching others to spot issues, not just solving them yourself The most valuable skill isn't having all the answers - it's knowing how to find them when you need them. You may be the only lawyer in the room, but you don't have to go it alone. Find your trusted circle.

Leading a small in-house legal team comes with unique expectations. When resources are limited, the Head of Legal role shifts from simply reviewing contracts to designing how legal integrates with the business ⚖️. A question I often hear: Should the Head of Legal go around asking every team what’s on their plate and whether legal support is needed? Or should the business proactively include legal in the right meetings? In reality, it’s about balance. 𝐓𝐇𝐄 𝐑𝐄𝐀𝐋𝐈𝐓𝐘 𝐎𝐅 𝐀 𝐋𝐄𝐀𝐍 𝐋𝐄𝐆𝐀𝐋 𝐅𝐔𝐍𝐂𝐓𝐈𝐎𝐍 In a small team, legal cannot operate as a reactive inbox 📥 — nor can it sustainably “hunt” for risk across the company. Limited resources mean: - Constant prioritization 🔄 - High visibility needs 👀 - Real burnout risk 🔥 - Tough trade-offs on where time is spent ⏳ Inefficiency in a lean team quickly becomes a strategic issue. 𝐏𝐑𝐎𝐀𝐂𝐓𝐈𝐕𝐄 𝐕𝐒. 𝐄𝐌𝐁𝐄𝐃𝐃𝐄𝐃 Two common models tend to emerge: 𝐋𝐞𝐠𝐚𝐥 𝐚𝐬 𝐭𝐡𝐞 𝐂𝐡𝐚𝐬𝐞𝐫 Legal regularly checks in with teams, scanning for issues and prompting engagement. This creates visibility, but can lead to overload and a dependency culture. 𝐋𝐞𝐠𝐚𝐥 𝐚𝐬 𝐚𝐧 𝐈𝐧𝐭𝐞𝐠𝐫𝐚𝐭𝐞𝐝 𝐏𝐚𝐫𝐭𝐧𝐞𝐫 The business loops legal in by default when risk, contracts, compliance, data, IP, or people issues arise. This requires clarity and trust — but it scales far better💡. Strong organizations evolve toward the second model. 𝐓𝐇𝐄 𝐇𝐄𝐀𝐃 𝐎𝐅 𝐋𝐄𝐆𝐀𝐋’𝐒 𝐑𝐄𝐀𝐋 𝐑𝐎𝐋𝐄 In a small team, the focus should be on: - Clear engagement guidelines 📝 - Education on when legal input is required - Relationship-building with peers 🤝 - Transparent prioritization and capacity boundaries Legal is not a bottleneck — it’s a risk navigator 🧭. Regular peer conversations help create visibility into upcoming initiatives without turning legal into a roaming auditor. A lean legal function cannot scale through effort alone. It scales through structure, clarity, and shared accountability. You’re not expected to chase every issue. You’re expected to build a system where you don’t have to ✅. #InHouseLegal #HeadOfLegal #GeneralCounsel #LegalLeadership #LeanTeams #LegalOperations #RiskManagement #BusinessPartner

It takes a village, but if you don't have one... This week, I co-presented with Gregg Goldstein to Jessica Shpall Rosen's Lean Legal Collective on building legal from the ground up as solo GCs. We both discussed the challenges of building legal as a team of one and some best practices when you don't initially have a legal village of your own. Some Key Takeaways: ✅ Learn the Business - Know what you are selling, strategic goals, top-of-mind issues/pain points for the execs, etc. ✅ Listen to Learn - Join calls, schedule 1:1s, and sit in on meetings with the goal of learning. ✅ Help 5x for every 1x Ask: People are often weary of legal as the department of no. Changing that perception by being the team that says, "I am here to help," builds trust and fosters strong collaboration. ✅ Follow the $$$ - Early wins on helping generate revenue faster (fix the contracts) and reducing cost (bring outside work inside when you can). ✅ It's Lonely; Find your People. The solo GC role is lonely, so building relationships with trusted leaders is important. Having trusted peers and outside counsel to bounce ideas off of is critical. ✅ Have Exit in Mind—Most CEOs/Founders have an exit in mind. Keep your house in order (contracts, compliance, privacy, policies, etc.) so you are ready for any type of exit. ✅ Use Data for Budget Approvals - Getting money for legal tech and a legal team is always challenging when a company may not have had any legal in-house for years before you arrive. Be able to show (using data) how legal tech/people will help: increase revenue, reduce spend, mitigate risk, etc. ✅ Prioritize - There will be many priorities when building from scratch; prioritize the $$ and the big risks first. ✅ Inform Often, In the Right Tone - Communicating often is key; be sure to master how each exec likes to receive information (and tie it to concerns/goals that are top of mine). ✅ Outside Counsel—Outside counsel should be your ally, help you learn, and always make you look good to your executives. If your outside counsel isn't a strong partner, find new outside counsel. Outside counsel that goes around you or excludes you, etc., is not a good partner. ✅ Find Balance—The work will be endless, and your to-do list will continue to grow. Make sure to carve out pockets of time during your day, the quarter, and the year to do things that help you recharge. If you are solo, have a game plan for when you need a vacation (fractional GC, outside counsel, etc., can help). If you are a team of one or a small legal team, be sure to join Jessica Shpall Rosen's Lean Legal Collective. She has built an amazing community of legal professionals who offer support and guidance to one another. Any other tips you would offer that worked for you? #inhousecounsel #legalcommunity #gclife #legaltech

⚠️ If your GC is asked to “draft the contract” - you have a problem. 🛑 By the time that sentence is spoken, the strategy, pricing, promises, and timelines are usually locked after the deal has already been decided without Legal. Legal is being invited to memorialize, not to shape. The GC becomes a scribe for choices already made—forced to retrofit risk appetite to commitments that never passed through it. That looks efficient in the moment and expensive in the aftermath: mispriced risk, vague obligations, remedies that don’t match reality, renewals that leak value, and disputes that were baked in at the pitch. ✅ A GC’s value is upstream: clarifying trade-offs before numbers hit a term sheet; setting guardrails so “market standard” means our standard; insisting that promises have owners, evidence, and costed mitigations. When Legal is late, the contract only papers over misalignment—strategy says “go,” operations can’t deliver, finance eats credits, and culture learns that escalation beats governance. ⚡ If you catch this pattern in your company, try a reset: bring the GC to the planning table (pricing, structure, allocation of risk), not just the polishing table. Then let the contract reflect a decision the business owns with eyes open, not a hope Legal is asked to “make safe.” 👉 GCs: What line do you draw when you’re handed a “done deal”? 👉 CEOs/Boards: Do you want a contract drafter—or a partner who prevents bad bets? ➡️ Follow ➡️ Connect ➡️ Comment ➡️ Refer ➡️ DM to inquire further #GeneralCounsel #InHouseCounsel #LegalOps #Governance #RiskManagement #Board #Contracts #Leadership #Operations #CARMA #DealDoctor

What They Don’t Tell You in Your First GC Job Description... When you step into your first GC role, especially as the first in-house attorney, the biggest surprise isn’t the workload. It’s the culture shift. You’re joining a company that’s been doing business for years without an internal legal voice at the table. -Deals got signed on the fly. -Vendors were vetted over coffee chats. -Maybe outside counsel reviewed things now and then, but the business largely ran on trust and momentum. Now you walk in, and suddenly every contract, policy, and risk decision runs through your department, and it buries you, or you are constantly finding out about signed agreements and contracts getting signed without going through legal. Neither is ideal. It’s a massive change for everyone. At a law firm, your advice was the product. Whether they followed it or not wasn’t your problem. In-house, your success depends on whether they do. That’s where the real leadership starts. Here are a few practical ways to navigate it: 1. Listen first. Meet each functional head early, including Sales, HR, Finance, and Operations. Ask what frustrates them most about “legal.” You’ll uncover blind spots and quick wins. 2. Map the reality. Forget the org chart. Learn how things actually get done, where contracts start, who signs them, and where legal falls out of the loop. 3. Simplify and educate. If legal feels like a black hole, people will work around it. Create clear, fast processes and host short sessions to explain why it matters. 4. Model speed. Responsiveness builds trust faster than any policy ever will. Move quickly on reviews. It changes how the business sees you. 5. Get visible CEO support. Ask your CEO to make it clear that legal is part of the leadership team, not an obstacle course. Cultural change starts from the top. Being the first in-house counsel isn’t just about bringing structure. It’s about shifting how the business sees risk, trust, and partnership. You’re not just there to protect the company. You’re there to help it evolve. This won’t happen on day 1.