Let's be honest about December: Nobody's conducting a comprehensive legal audit between now and January 2nd.

You're finishing projects. Planning holiday time. Thinking about 2026 goals. Maybe checking out mentally by the 20th.

And that's completely fine.

But here's what separates businesses that hit their 2026 goals from businesses that spend the year in crisis mode: What they do in January.

While most business owners wait until March—when issues become urgent, when opportunities get missed, when small problems become expensive crises—strategic business leaders use the first 60 days to get ahead.

After 15+ years as a business attorney and litigator in Milwaukee, I can tell you: The problems that blow up in Q2 are almost always visible in Q1. You just have to look.

This guide will show you exactly what to look for—and more importantly, when and how to address it before it derails your growth plans.

Why January Matters (And December Doesn't)

I have a lot of conversations in December that sound like this:

"We should probably update our employment handbook."
"I know we need to review that vendor contract."
"Our partnership agreement has some gaps we should address."

And my response is always: "Great. Let's schedule that conversation for January."

Not because it's not important. Because strategic planning requires bandwidth—and nobody has bandwidth in December.

But January? January is different.

Your competitors are still in holiday mode through mid-January. Your team is back but not yet overwhelmed. You have a window—usually about 4-6 weeks—where you can make strategic decisions before the Q1 chaos fully hits.

The businesses I work with who win in Q1 all do the same thing: They use January to identify what could derail their plans, and they handle it before it becomes urgent.

Let me show you how.

The Three-Phase Framework: December, January, February

This isn't about doing everything at once. It's about being intentional across three distinct phases:

• December (Week of Dec 16): The 15-Minute Identification
• January (Weeks of Jan 6-31): The Strategic Conversations
• February (Weeks of Feb 3-28): The Implementation Sprint

Each phase builds on the previous one. Each phase is realistic given what's actually happening in your business.

Let's break it down.

Phase 1: December - The 15-Minute Identification

Timeline: This week (before everyone mentally checks out)

Goal: Not to fix everything. Just to identify what needs attention in January.

Grab a notebook. Set a timer for 15 minutes. Answer these questions:

The Three Critical Questions:

1. What business goal do I have for 2026 that requires legal infrastructure first?

Are you planning to:

• Expand to new locations?
• Make an acquisition?
• Hire significantly?
• Enter new markets?
• Change your business structure?
• Take on major new clients or contracts?

Each of these requires different legal groundwork. And most take 60-90 days to implement properly.

2. What legal issue have I been avoiding because it's not urgent yet?

You know what it is. The thing you keep pushing to "next month."

Maybe it's:

• Vendor agreements you've never actually read
• Partnership or shareholder arrangements that need updating (review Wisconsin business entity requirements)
• Employment policies that don't reflect current law
• Contracts that worked at $5M but won't protect you at $15M
• Compliance gaps you're aware of but haven't addressed

3. What would happen to my business if [worst case scenario] happened tomorrow?

• Key partner wants out
• Major vendor fails to deliver
• Employee lawsuit
• Data breach (see Wisconsin's data breach notification requirements)
• Regulatory investigation
• Customer disputes payment

Could you handle it? Do you know what your contracts actually say? Do you have documentation in place?

That's it. 15 minutes. You're done for December.

Write down your top 3 issues. Put them somewhere you'll see them January 6th.

Now go enjoy the holidays.

Phase 2: January - The Strategic Conversations

Timeline: Weeks of January 6-31

Goal: Have the conversations that help you understand what needs attention—and what doesn't.

This is where strategic business leaders separate from reactive ones.

Reactive businesses wait until March when something's broken. Strategic businesses use January to understand their exposure before it becomes a crisis.

The Three Conversations Framework

Most business owners don't need comprehensive legal audits. They need three targeted conversations based on their business goals for 2026:

Conversation 1: Risk Assessment (First half of January)

• What could derail our 2026 plans if we don't address it?
• Where are we exposed that we don't realize?
• What gaps exist between "we think we're fine" and actually being protected?

Conversation 2: Strategic Contracts Review (Mid-January)

• Which agreements support our growth and which limit it?
• What needs to be renegotiated before renewal?
• Where do we have leverage now that we might not have later?

Conversation 3: Growth Infrastructure Planning (Late January)

• What legal foundation needs to be in place before we execute our plans?
• If we're expanding/acquiring/hiring, what do we need ready?
• What should we be thinking about now that we can't fix quickly later?

What These Conversations Actually Uncover

For businesses planning expansion:

• Are your vendor contracts scalable or will they break at higher volume?
• Do your employment agreements allow you to hire in new states?
• Is your corporate structure set up for multi-location operations?
• Do you have the right insurance and liability protections?

For businesses considering acquisitions:

• Would your legal documentation pass due diligence?
• Are your contracts and records organized?
• Do you have known compliance gaps that would kill a deal?
• Is your ownership structure clear and documented?

For businesses with partners:

• Is your partnership or shareholder agreement up to date?
• Are valuation and buyout provisions clear?
• What happens if someone wants out, gets divorced, or dies?
• Are decision-making processes documented?

For businesses with key vendor relationships:

• Do you understand what you actually agreed to?
• Are liability provisions balanced or one-sided?
• Do you have termination rights if performance fails?
• Are you protected if they get breached or go under?

For all businesses:

• Is your employment handbook current with Wisconsin and federal employment law?
• Are your contracts protecting you or just the other party?
• Do you have the right insurance coverage for your current operations?
• Are you compliant with industry-specific regulations?

How to Schedule These Conversations

Option 1: One comprehensive planning session (2-3 hours in mid-January)

• Cover all three conversations in one meeting
• Best for businesses with multiple complex issues
• Allows for integrated strategy discussion

Option 2: Three focused sessions (45-60 minutes each over 3-4 weeks)

• Spreads decision-making across January
• Easier to schedule with busy calendars
• Allows time to gather information between meetings

Option 3: Quick assessment + follow-up (30 minutes + as needed)

• Initial call to identify priorities
• Focused follow-up only on issues that need attention
• Most efficient for businesses with clear priorities

The key: Schedule something for January. Don't wait until March when it's urgent.

Phase 3: February - The Implementation Sprint

Timeline: Weeks of February 3-28

Goal: Execute the fixes before Q2 chaos hits.

Once you know what needs attention, February is execution mode.

What Implementation Actually Looks Like:

Weeks 1-2: Priority Items

• Vendor contract renegotiations or replacements
• Partnership/ownership agreement updates
• Critical compliance gap remediation
• Employment policy updates

Weeks 3-4: Foundation Building

• Contract template improvements
• Documentation organization
• Staff training on updated procedures
• System implementations

The Outcome: Clean legal infrastructure before your growth plans kick into high gear.

Common Mistakes (And How to Avoid Them)

After working with hundreds of Wisconsin businesses, I see the same patterns:

Mistake #1: Waiting Until Something's Urgent

What it looks like: "We'll deal with that partnership agreement when we actually need to make a decision about expansion."

Why it's expensive: When you need to make a decision IS when you have the least leverage. Fixing legal infrastructure under pressure costs 3-5x more than doing it proactively.

The fix: Handle it in January when there's no urgency, no deadline, no leverage imbalance.

Mistake #2: Treating Legal as Separate from Business Strategy

What it looks like: "Let me finalize our growth plans, then I'll bring in the attorneys."

Why it's expensive: Your growth plans might require legal infrastructure that takes 60-90 days to implement. Finding that out after you've committed to timelines creates crisis.

The fix: Include legal planning in strategic planning from the start. What you discover in January shapes better February decisions.

Mistake #3: The DIY Trap

What it looks like: "I'll just use this template I found online."

Why it's expensive: Templates don't account for Wisconsin-specific requirements, your business model nuances, or current regulatory changes. What works for a California software company won't protect a Wisconsin manufacturer.

The fix: Templates are starting points, not solutions. Have someone who understands Wisconsin business law review what you're actually signing.

Mistake #4: Not Connecting Legal to Growth Goals

What it looks like: Treating legal review as compliance checkbox rather than growth enabler.

Why it's expensive: You miss the opportunity to position legal infrastructure as competitive advantage. The business that cleaned up their legal documentation before they needed to? When opportunity came, they could move fast while competitors took 6 months.

The fix: Ask: "What legal infrastructure would make my 2026 goals easier to achieve?" Then build that.

The Cost of Waiting Until March

Let me tell you what March looks like for reactive businesses:

The Partnership Dispute: Two partners, been working together for 12 years. Partnership agreement from 2013 had a "we'll figure out valuation later" clause for buyouts.

One partner wanted to retire in March. The other assumed they'd just work it out.

They couldn't agree on valuation. No mechanism to resolve it. Business operations suffered for 6 months during the dispute.

By the time they called me, they needed:

• Business valuation (expensive, time-consuming)
• Mediation
• Updated partnership agreement under pressure
• Interim operating agreement while dispute resolved

What a January conversation would have done: Updated the partnership agreement with clear valuation methodology and buyout terms. Would have taken 3-4 weeks to negotiate while everyone was still friendly.

These aren't hypothetical. These are real Wisconsin businesses (details changed to protect confidentiality) I've worked with.

The pattern is always the same: The problem was visible in January. It became expensive in March.

Your January Action Plan

Here's exactly what to do:

This Week (Dec 16-20):

1. Do the 15-minute identification exercise above
2. Write down your top 3 issues
3. Put them on your calendar for January 6th

Holiday Break (Dec 21-Jan 5):

• Let it go
• Don't think about it
• Enjoy your family
• Come back rested

Week of January 6:

1. Review your December notes
2. Schedule the January conversations
3. Block February calendar for implementation
4. Get clear on priorities

Weeks of January 13-31:

• Have the strategic planning conversations
• Get proposals or roadmaps for fixes needed
• Make decisions while there's no pressure

February:

• Execute the implementations
• Handle the fixes
• Get ahead before Q2 chaos

The January Planning Conversation

Every January, I have the same conversation with strategic business leaders:

"What could derail your 2026 plans if you don't handle it now?"

It's not a sales pitch. It's a planning conversation.

Sometimes it's 20 minutes: "You're actually in good shape, here are two things to watch."

Sometimes it uncovers issues that need addressing: "Here's what we should prioritize and why."

Always, it's worth having.

Because here's what I've learned after 15+ years as a business attorney and litigator in Milwaukee:

The difference between businesses that hit their 2026 goals and businesses that spend 2026 in crisis mode is usually one January conversation.

The businesses I work with who succeed don't have fewer legal issues. They just address them before they become urgent.

They review vendor contracts before renewal, not after breach.

They update partnership agreements while everyone's friendly, not during a dispute.

They build legal infrastructure before expansion, not during crisis.

They treat legal planning as strategic advantage, not compliance burden.

What Makes This Different from "Just Call a Lawyer"

I'm not just a business attorney. I'm a litigator.

That means I've seen what happens when:

• Contracts fail
• Partnerships fracture
• Compliance gaps get discovered
• Vendor agreements blow up
• Employment issues escalate

I've sat in depositions, reviewed discovery, negotiated settlements, tried cases.

And here's what that litigation experience teaches:

The expensive problems are almost never complicated. They're simple things that weren't addressed proactively:

• The vendor agreement nobody reviewed (page 23 had the liability cap)
• The partnership buyout clause that said "we'll figure it out" (you won't)
• The contract renewal nobody negotiated (auto-renewal trapped you for 3 years)
• The employment handbook from 2015 (Wisconsin employment law has changed significantly)

My job isn't just to review your contracts. It's to see what I've seen blow up in litigation—and make sure it doesn't happen to you.

That's the value of working with a business attorney who's also spent thousands of hours in complex commercial litigation.

I know what to look for because I've seen what happens when it gets missed.

Schedule Your January Planning Call

If you're reading this and thinking, "I should probably have that conversation"—you're right.

Here's what that looks like:

Quick Assessment (30-45 minutes):

• What are your 2026 business goals?
• What's your current legal infrastructure?
• What gaps exist that could derail those goals?
• What should we prioritize in January-February?

No pressure. No obligation. Just clarity.

Sometimes the answer is: "You're in good shape, here's what to monitor."

Sometimes we identify issues worth addressing proactively.

Always, you leave with better understanding of your risk and options.

For Milwaukee & Wisconsin Business Leaders