Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Make a First 90 Day Plan That Actually Works
Transcript
- Lucas: There is a single document that separates senior leaders who own their first quarter from those who get owned by it. It is a 90-day plan — but not the vague calendar of meet and greets most people write on day one. Luna: Right, the classic 'I will have 75 coffee chats and then figure it out' approach. I've seen that fail spectacularly. Lucas: Exactly. So today I want to walk through a specific framework I've seen work at the VP and C-suite level. It comes from a former division head at a Fortune 50 industrial company — I'll call her Sarah — who took over a business unit that had missed revenue targets for six straight quarters. Luna: That is a high-stakes starting line. You do not have the luxury of a slow ramp. Lucas: No. And the thing Sarah did that most leaders skip is she divided her 90 days into three distinct phases. Not two-week sprints, not monthly themes — three precise blocks with different objectives. Phase one was a five-week listening tour. Phase two was a three-week synthesis and alignment memo. Phase three was a six-week quick-win execution push. Luna: Wait — five weeks just listening? That feels long when the business is bleeding. I imagine the board was getting twitchy. Lucas: They were. But Sarah had a pre-negotiated agreement with the CEO that she would not be judged on any operational metric until day 91. That is part of the framework — you have to lock in that protection before you accept the offer. Otherwise you end up firefighting in week two and you never build the strategic foundation. Luna: So the listening tour has to be structured. It cannot just be 'let me meet everyone and see what happens.' What did she actually do? Lucas: She had a standard set of 12 questions. Every conversation — direct reports, skip-levels, customers, suppliers — same questions. She was not looking for opinions. She was looking for patterns. Questions like: 'If you could change one thing about how this business operates without asking permission, what would it be?' And: 'What is the one number in our monthly reports you think is misleading?' Luna: That second question is very smart. It surfaces the quiet data problems that often mask the real trouble. Lucas: Exactly. Over five weeks she logged about 60 of those conversations. She color-coded the themes — red for systemic risk, yellow for operational friction, green for quick wins people already knew about. By week five, she had a heat map of the business. Not an opinion. A pattern. Luna: And then phase two — the synthesis memo. Three weeks. What goes into that document? Lucas: A synthesis memo is not a strategy deck. It is a pre-decision document. It says: here is what I have learned, here are the three biggest risks I see that the current leadership team may not be acknowledging, and here are the two quick-win opportunities I believe we can execute in the next six weeks without major investment. It ends with a specific request — 'I need your approval to proceed with these two initiatives by end of week nine.' Luna: That forces the CEO and the board to pick a side early. Are they with you or not? Lucas: Right. And if they hesitate on something you consider critical, you find out in week eight, not month eight. Sarah's memo had one contentious recommendation — she wanted to halt a legacy product line that was still contributing 15 percent of revenue but burning 40 percent of engineering hours. The board pushed back. She used the memo to facilitate a structured debate, and they compromised on a six-month phase-out instead of an immediate stop. Luna: That is a concrete win from the process. She avoided a battle but got the direction shift. Lucas: Exactly. Then phase three — the six-week execution sprint. The goal is not to fix everything. The goal is to demonstrate you can move a needle. Sarah picked two initiatives: first, reducing the order to cash cycle from 45 days to 30 days by changing one approval workflow. Second, consolidating three regional sales teams into two groups to eliminate overlap. She did not touch the product roadmap, did not reorganize R&D, did not cut headcount broadly. She chose operational quick wins that were visible and measurable. Luna: And those wins build credibility for the harder decisions later. The board sees you can execute before you ask for the big bet. Lucas: Precisely. By day 90, she had reduced the cash cycle by ten days — about $8 million freed up — and the sales consolidation was on track to save $2 million annually. The board's attitude shifted from skeptical to cautiously supportive. She earned the right to present a full turnaround plan in quarter two. Luna: I want to push back a little though. This sounds ideal for a turnaround or a new role from outside. But what if you are an internal promotion? You already know the organization. Does the framework still apply? Lucas: Yes, but with one crucial difference. An internal leader should compress the listening tour to three weeks maximum, because you already know the surface-level patterns. The danger for internal hires is confirmation bias — you think you already know who the problem people are. So Sarah's advice for internal leaders is to spend the listening tour exclusively with customers and frontline employees, not with peers and executives you already know. Luna: Interesting. So the listening tour is designed to surface blind spots, not validate what you already believe. Lucas: Exactly. And the synthesis memo becomes even more important for internal leaders, because you have existing relationships that may make it harder to deliver hard truths. The memo creates a formal distance that lets the message land without the personal baggage. Luna: One thing I have seen trip people up in the first 90 days is hiring. A new VP comes in, feels pressure to fill a key role quickly, and makes a bad hire in month two that takes a year to undo. Lucas: That is such a common trap. Sarah had a rule — do not make any external hire in the first 60 days unless the role is a genuine emergency. Instead, use interim internal resources or contractors. The reason is simple: you do not yet know the actual performance standards of the role. You might hire for the old job description, not the job that needs to exist. Luna: So you are protecting your ability to redefine roles before you fill them. That is strategic patience. Lucas: Exactly. The one exception she made was hiring an executive assistant. That hire is too important to delay because they manage your calendar, your stakeholder mapping, your information flow. She interviewed three candidates in the first two weeks and made an offer by week three. That is the only hire she accelerated. Luna: That makes sense. The gatekeeper is foundational for everything else. Lucas: There is one more element I want to mention because it is often overlooked: managing your own energy. Sarah scheduled a three-day offsite alone — no team, no calls — at the end of week seven. She used it to read the synthesis memo again, reflect on the board's feedback, and decide which battles to pick. Most senior leaders fill every hour of the first 90 days and then wonder why they are exhausted and reactive. Luna: A scheduled thinking retreat. That is a luxury most people do not give themselves. Lucas: And yet it is probably the highest roi time block in the entire first quarter. Because the decisions you make in week eight set the trajectory for the next two years. Luna: Quick honest thing — a handful of listeners chip in monthly through buy me a coffee dot com slash fexingo, and that is literally what funds making this many of these episodes. If we have helped you think through a career move or decision, that is where the show lives. Lucas: Yeah, no ads, no sponsors — just listener support keeps it going. We appreciate everyone who contributes, whether it is a one-time coffee or a monthly thing. Luna: Exactly. And it keeps the content exactly as it is — no influence from anyone else. So back to the first 90 days: what about the exit? When do you know the plan is not working and you need to course-correct? Lucas: That is a great question. Sarah had a personal rule: if by day 45 she had not identified at least three people on the leadership team who were genuinely excited about her direction, she would consider it a red flag. Not that she would quit — but she would escalate the conversation with the CEO about cultural resistance. The 90-day plan is also a diagnostic. If you are hitting resistance on all fronts, that is data, not failure. Luna: So the plan is both a roadmap and a sensor. You use it to navigate, but also to measure whether the organization is ready for the change you represent. Lucas: Exactly. And that is the difference between a senior leader who succeeds in a new role and one who just survives. The ones who survive react. The ones who succeed have a structured plan that surfaces problems early, builds credibility through quick wins, and protects their authority to make the bigger moves when the time is right. Luna: If someone is starting a new role in July, what is the one thing they should do this week to prepare? Lucas: Draft your listening tour questions now. Not the full plan — just the 12 questions. Share them with a trusted mentor and get feedback. By the time you start, you will have a tool that saves you from the overwhelming temptation to just start doing things. The best first 90 days are the ones where you talk less and listen more, until you know where to push. Luna: I think that is the single best piece of advice for any senior leader stepping into a new role. Listen first, move second. Lucas: And move with precision. That is the whole game.