The First 90 Days

Your first day is not about impressing anyone with your knowledge. It's about earning the right to have opinions later. What to do: • Meet as many people as possible • Ask everyone: "What do you do? How does it work? Why do you do it that way?" • Listen 80%, talk 20% • Don't critique anything — even if you see obvious problems • Take notes on everything What NOT to do: • Don't suggest changes • Don't reference how you did it at your last company • Don't start restructuring the chart of accounts • Don't schedule a "town hall" to share your vision Your only job on day 1 is to be curious and present. People are watching you — and they're deciding whether to trust you or resist you. This decision happens fast and it's hard to reverse.

Before you fully understand the business, build the 13-week cash forecast. Yes, it will be imperfect. That's the point. Building it forces you to: • Ask the right questions: "Where does this cash come from? When does it arrive?" • Find gaps in your understanding fast • Identify the first cash crisis before it hits • Earn instant credibility: "I've been here 3 days and here's our cash picture" Then monitor it DAILY. Not weekly. Open the bank accounts every morning. Watch what comes in, goes out, and what's pending. Within 2-3 weeks of daily monitoring, you'll have an intuitive feel for the cash rhythm of the business that no report can give you. Measure your success in predicting. Each week, compare your forecast to actuals. The variance tells you what you don't understand yet — and that's where you dig.

Interview every key leader one-on-one in the first week. Not formal interviews — conversations. The critical meeting: Cash Flow Mapping Bring key leaders into a room and walk through: 1. How do we sell? 2. How do we process that sale? 3. When is it recorded? 4. In what software, email, notebooks, spreadsheets? Document every random spreadsheet you hear about. These shadow systems are the real operating system of the company. The modern approach (2026): • Record every meeting with AI transcription • Feed transcripts into Claude: "Map the complete business flow from this conversation" • Generate Mermaid diagrams instantly — visual process maps • Review with the team: "Is this right? What's missing?" • Store everything in Obsidian or your note system In 2 weeks you can have a complete picture of how cash flows through the business that would have taken 2 months the old way. Go to lunch with different departments. Not just the C-suite. The warehouse manager, the sales rep, the project coordinator. They know things the leaders don't.

Most new finance leaders skip the admin staff. Huge mistake. The admins ARE the operating system of the company. Sit down next to every admin position. Watch everything they do. Ask "why do you do it that way?" They know: • Where the workarounds live • What actually happens vs. what the process document says • Which systems talk to each other and which don't • Where things break every month The review cascade: 1. Watch them work — observe, don't judge 2. Review process with them — document what they do, identify inconsistencies 3. Review with the team — share what you learned 4. Review with key leaders — coach them to understand the big picture While you're learning, you're also coaching and building relationships. Find bridges between departments that don't talk to each other. You're the only person who sees across all functions — use that perspective.

Forget SWOT. It's academic and passive. Run a Headwinds Analysis instead. Headwinds = everything blocking the team from performing at their best: • Technology constraints • People issues (wrong seats, skill gaps, turnover) • Process bottlenecks • Location/logistics problems • Cash/capital constraints • Customer concentration risks • Regulatory burdens How to run it: 1. Ask each leader independently: "What are the top 3 things blocking your team?" 2. Compile the list — you'll see patterns 3. Bring everyone together: "Here are the headwinds I'm hearing" 4. Rank by impact × solvability 5. Pick the top 3. Attack those first. Everything else waits. Why "headwinds" not "weaknesses": • Headwinds imply something you can navigate (not a permanent flaw) • Headwinds are felt by the whole team • Headwinds create urgency • Headwinds are the foundation for every technology and process decision

You will face pushback. Guaranteed. How you communicate determines whether it's productive pushback or destructive resistance. "Explain your vision slowly and not from an accountant or detailed point of view. Relate the vision to the audience you're speaking with." The same insight needs different language: • To the operations manager: "This will help your crews get paid faster and reduce the paperwork that slows down job starts." • To the sales leader: "This will give you real-time pipeline visibility so you can forecast commission accurately." • To the CEO: "This reduces working capital by $X and gives you a 13-week cash picture every Monday morning." Use AI to translate: feed your analysis into Claude and ask it to rewrite for each audience. Same insight, different framing, every time. The quiet ones are your biggest risk. The loud resistors tell you what they think. The quiet ones nod in meetings and back-talk you later. Build feedback loops. Find front-line advocates. Give them a role and recognize their leadership.

At Bobbitt Design Build, Josh faced a massive Procore rollout with heavy resistance. His approach: "I took the biggest obstinate jerk and made him the biggest advocate by personally solving his problems with the software." The playbook: 1. Identify the loudest resistor 2. Don't fight them. Don't go around them. Go TO them. 3. Ask: "What's not working for you?" 4. PERSONALLY solve their problems. Not delegate. Personally. 5. Give them ownership — they drive all complaints, meet with you weekly 6. Celebrate their wins through their manager 7. Once they flip, everyone follows "You serve those who are on the front lines. Treat them that way." Also build your advocate network: • Find 3-5 naturally positive front-line people • Give them a formal role as the voice of their team • They gather feedback, surface concerns, report back to you • Reward them — this is leadership development in real time Change follows a curve: Announcement → Implementation struggles → The Valley (max frustration) → The Pinnacle (more buy-in than pushback) → New Normal. Most companies give up in the Valley. Push through with grace.

By now you should have: ✓ A 13-week cash flow you monitor daily and report weekly ✓ A complete cash flow map of the business ✓ Admin processes documented with inconsistencies flagged ✓ A ranked headwinds list with the top 3 identified ✓ Advocates on the front lines ✓ Relationships across every department ✓ The trust to make recommendations Now — and only now — start making changes. Start with quick wins: • Fix one obvious process that wastes everyone's time (like CHE's manual expense reporting → CenterCard) • Pick the #1 headwind and attack it • Present your first unsolicited recommendation to the CEO • Build one thing nobody asked for that makes someone's life easier And the big move: working capital. "I took CHE working capital from $4 million to $750,000 by managing the drivers." That's $3.25M in freed cash. No new revenue. No cost cuts. Just managing: • AR: collect faster • AP: optimize payment timing • WIP/Inventory: don't let cash sit • Deposits: get cash before you spend it This is often the single highest-ROI thing a new finance leader can do.