I am 30 days into a new Division President role. The CEO I report to lives three states away. That one fact has shaped almost every decision I have made since day one.
TL;DR: When you join as a Division President reporting to a parent-company CEO in another state, the first 90 days are not about hitting numbers. They are about installing a clean communication rhythm, surfacing decisions early, and giving the CEO enough signal to bet on you without micromanaging. Get that wrong and every quarter after is harder.
The job is not what you think it is
The job description says run the division. What it actually says, between the lines, is teach the CEO how to trust you.
A CEO who hired you took a bet. They sized you up in interviews, talked to your references, and then handed you a P&L they cannot watch in person. Every week you do not give them a clean signal, they fill the gap with assumptions. Some of those assumptions will be wrong. A few will be expensive.
Most new division leaders show up ready to perform. They have built their career around hitting numbers and they want to keep doing that. The instinct is right. It is not the first instinct that matters, though. The first instinct that matters is making the CEO comfortable enough to leave you alone.
The first 90 days are not about proving you can run the business. They are about removing the CEO’s reasons to worry. That sounds soft. It is not. It is the most concrete thing you can do for the company in your first quarter.
Install the rhythm before you need it
The biggest mistake new division leaders make is waiting for the CEO to tell them how often to talk. By the time the CEO asks, you have already missed the window.
Here is the cadence I set up in week one:
- Weekly 30-minute call. Same day, same time, no agenda required.
- Monthly written update. Two pages max, sent the Friday before our first call of the month.
- Quarterly in-person visit. I fly to them or they come to me.
- Same-day text or short call for anything that crosses a defined threshold.
The cadence matters less than the consistency. If the CEO knows Tuesday at 10 is the call, they save their questions for Tuesday at 10. If they do not know when the next call is, they call you on a Thursday afternoon when you are mid-shift on a job site.
A predictable rhythm is also how you protect your own time. Without it, you are always interruptible. With it, you can spend the rest of the week running the division instead of bracing for the next call.
Surface decisions early, even small ones
In your first quarter, over-communicate decisions before you make them. Not because you need permission. Because the CEO needs to learn how you think.
When I am weighing a hire, a vendor change, or a project I want to bid on, I send a short note before I act. Something like: “I am leaning toward X for these three reasons. Going to act on it Friday unless you flag anything.” That gives the CEO a clean opt-out without forcing a meeting.
Two things happen when you do this. First, the CEO gets calibrated on your reasoning, so by month three they trust your output and stop asking for the reasoning. Second, if your logic is missing something obvious, you find out before you spend money on it.
This is not the same as asking permission. A CEO who hired you does not want to micromanage your hires. A CEO who hired you does want to know how you think about a hire before you make ten more of them. The pre-decision note gives them that, cheaply, in writing they can read at 6 a.m. with their first cup of coffee.
The trick is the time-bound default. “I am acting Friday unless I hear otherwise” is very different from “What do you think?” The first one moves the work forward. The second one parks the decision on the CEO’s desk. A CEO three states away does not need more decisions on their desk. They need fewer.
How to disagree without burning the relationship
You will disagree with the CEO inside the first 90 days. Probably about something that matters. How you handle that one moment shapes the next two years of the relationship.
A few rules that have held up for me across three decades of running businesses:
Disagree in private, never in front of the team. If a CEO directive lands in a group meeting and you push back live, you have just told everyone in the room that the CEO can be overruled in public. That damages them more than it helps you, and it damages you too, because the CEO will not forget it.
Bring the alternative, not just the objection. “I do not think we should do X” is a complaint. “I do not think we should do X, here is what I would do instead, here is what I think it costs us if we are wrong” is a strategy conversation. CEOs do not have time for complaints. They have time for options.
Separate the two questions. The first question is “are we doing the right thing.” The second is “who decides.” Sometimes you lose the first one and that is fine. You should never lose the second one quietly. If a decision is yours to make and the CEO is reaching past you, name it. “I hear you, and I am going to make a different call on this one. Here is why.”
The CEO did not hire you to agree with them. They hired you to run a division they cannot run from another state. Agreeing on everything is not loyalty. It is abdication, and any CEO worth working for will spot it inside a quarter.
What the CEO actually wants to hear in a monthly
I have run monthly updates two different ways in my career. The first way, the way most people do it, is a recap of the last 30 days. What happened, what we hit, what we missed.
That is not what the CEO needs.
What the CEO needs is a forward-looking signal. Three things, in this order:
- What changed in the business that the CEO would not see from the dashboard. New customer wins. Key person risk. A bid we passed on and why. A safety incident. The texture under the numbers.
- What I need from them in the next 30 days. Decisions that need their sign-off. Introductions I am asking for. Capital that needs approval. Make it specific and time-bound. “By the 15th” beats “soon.”
- What I am most worried about and what I am doing about it. Not “everything is fine.” Real risk, owned, with a plan attached. If you never put a worry in your monthly, the CEO assumes you are not paying attention.
Notice what is not on the list. There is no recap. The numbers are in the dashboard. If the CEO wants commentary on the numbers, they will ask on the call. The monthly is for what the dashboard does not show.
The other reason this format works is that it forces real thinking. If you cannot fill section three with a real worry, you have not spent enough time in the field. If section two is empty, you are either not pushing hard enough or you are trying to look self-sufficient at the cost of speed. The monthly is a mirror.
A two-page monthly that does this well replaces about six unscheduled phone calls. That is your time back, and the CEO’s.
Your first 90 days checklist
If I had to give a new Division President a single page to put on their wall, it would look like this.
Week 1 to 2:
- Set the recurring CEO call. Pick a day and time and protect it.
- Send a written intent memo. What you understand the mandate to be, in your own words. Ask the CEO to correct anything you got wrong.
- Identify the three people in the parent company you need to know besides the CEO. Usually CFO, HR lead, and one functional peer. Book intro calls.
Week 3 to 6:
- Run your first monthly update in the format above.
- Surface one real disagreement, in private, with an alternative attached. Show the CEO how you push back.
- Walk every site, branch, or shop you are responsible for. Take notes the CEO will care about. Bring two of them to the next call.
Week 7 to 12:
- Make one visible call that is yours to make. A hire, a vendor switch, a process change. Tell the CEO before you do it. Do it. Report back.
- Audit your own communication. Are you calling the CEO too often? Not enough? Ask them directly. “Am I in your inbox the right amount?” is a fair question at day 60.
- Plan the in-person quarterly. Have an agenda. Do not let it drift into a social visit. Social is fine. Substance is the point.
Get those things right and by day 90, the CEO is not wondering if they made the right bet. They are wondering what else they can hand you.
That is the goal.
If your leadership team is working through new-executive transitions, parent-and-division communication, or how to build trust across geographies, I deliver a keynote on exactly this. Book Khary to speak.
About Khary Penebaker
Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.
Common questions
How often should I update a parent-company CEO in the first quarter?
Weekly 30-minute call, monthly two-page written update, quarterly in-person visit. Plus a same-day text or short call for anything that crosses a defined threshold. The exact cadence matters less than the consistency. A predictable rhythm protects both your time and the CEO's.
What kind of issues do I escalate vs handle locally?
Escalate anything legal, safety-related, or material to the parent's reputation. Escalate any decision that changes how the division shows up in the brand or commits capital above your authority. Handle locally: hires below the executive level, vendor changes, day-to-day operating calls. When in doubt, send a short pre-decision note rather than a meeting request.
How do I disagree with the CEO without burning the relationship?
Disagree in private, never in front of the team. Bring an alternative, not just an objection. Separate the question of what is right from the question of who decides, and never lose the second one quietly. The CEO did not hire you to agree. They hired you to run a division they cannot run from another state.
What does the CEO actually want to hear in a monthly update?
Three things, in this order. What changed that the dashboard does not show. What you need from them in the next 30 days, specific and time-bound. What you are most worried about and what you are doing about it. Skip the recap. The numbers are already in the dashboard.