Before the Holidays: Letting a Family Member Go
Overhead holiday business scene featuring a December calendar with a decision deadline, leadership materials, wrapped gifts, and seasonal greenery, symbolizing the need to address a difficult family-business decision before the holidays.
You've already decided this person has to go.
You just haven't told them yet.
They showed up this morning. Collected a paycheck last Friday. Showed up to the last team meeting and sat through it like nothing has been decided — because as far as the business knows, nothing has. You haven't said a word. Not to them. Not to management. Not to anyone.
And now the holidays are here — and letting a family member go before the holidays isn't the answer.
Six weeks of family dinners, holiday parties, and end-of-year events with this person across the table — while the business keeps running a salary on a seat you've already decided needs someone else in it. The job post doesn't exist. The severance number isn't decided. The paperwork isn't done. And when January arrives, so does the conversation — plus the scramble to post a role that should have been ready weeks ago, the severance number you're now deciding under pressure, and the management team finding out in whatever order you didn't plan for.
That's the cost nobody talks about. Not the conversation you're dreading. The salary leaving every two weeks on a decision that's already been made. The right candidate taking a job somewhere else while you wait. The management team that's going to find out one way or another — either from you, in the right order, with the right information — or from someone else, in the wrong order, with whatever version travels fastest.
You have six weeks.
The exit paperwork is done before the conversation happens. The severance number is locked before you say a word. The job post goes live the same day the conversation ends. The management briefing is built before anyone finds out through the wrong person. When January arrives, the only thing left is the conversation itself.
Or you show up to every holiday event carrying the decision alone, you do nothing with the time, and when January finally arrives you have the same decision you had in October with nothing ready to execute it.
Waiting is passive. Preparing is the six weeks of work that makes January an execution instead of another month of delay with a new date on it.
I've been working with family business owners for 8 years. The owners who move in January built the exit while everyone else was buying gifts — paperwork signed, severance number decided, job post written and ready. The ones who don't arrive in January with the same decision they had in October, the same empty hands, and one less month to fix it.
They've just run out of calendar to hide behind.
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Why Is Waiting Until January the Right Call?
You don't fire family before the holidays. Not because the business can't handle it — because they are still your family. January is the right call. What you do between now and then is what determines whether you walk into that conversation with everything ready or nothing built.
Most owners know January is the right call. What they don't know is what to do with the six weeks before it arrives.
The first reason is simple. Unless they're stealing from you — and that's a different situation entirely — you wait. That's the difference between a family business and every other business. These people are still coming to dinner. You still have to look them in the eye across the table. That doesn't make you a bad business owner. It makes you a human one.
And that decision — the one to wait — has consequences for the business that go beyond the dinner table.
The second is productivity. Firing a family member before the holidays drops productivity across the board — family and non-family employees alike. People lose focus. Output drops. The work that needed to get done before year-end doesn't get done. You're paying for that twice — once in lost productivity and once in the salary still going out to the person you've already decided can't stay. December is already slow. A firing in December makes it slower — and costs the business a month it can't afford to waste.
And it doesn't stop there.
The third is the hiring market. Nobody is looking for work in December. The job post you put up before the new year sits. The one you put up in January gets applications. If you fire in December you're posting into a dead market — which means the seat stays empty longer, the business runs without coverage longer, and you end up making a hiring decision under pressure when January finally opens the pool back up.
January is the only month where all three of those things work in your favor at the same time.
The fourth is the business calendar. End of year is slow. Decisions aren't moving. There is nothing about December that makes it the right time to let a family member go, fill their seat, and keep the business running — all at the same time. January resets everything — the calendar, the hiring pool, and the business's ability to post the role, fill the seat, and start the new year with the right person in it.
Waiting until January isn't about avoiding the conversation. It's about timing it so the business is ready to move the same day it happens.
When an owner comes to me in November or December with this situation, the first thing I do is get them out of their head and into the work. The decision is made. What isn't made is the exit — and that's the five things we build before January arrives.
Most owners treat the holiday window like dead time. It isn't. It's the only time they have.
The preparation is what makes the conversation possible. What the conversation actually requires is a different problem entirely.
How to Fire a Family Member in a Family Business covers exactly that.
What the Business Needs You to Do Before January Arrives
You have six weeks. That's enough time to build everything the exit requires — if you use it.
The exit paperwork needs to be done before the conversation happens. Not the morning of. Not the night before. Done. Ready to hand over the same day the conversation ends.
The severance number needs to be decided and documented before you say a word. Not during the conversation. Not on the spot. Before. A severance number decided under pressure is almost always the wrong number — too high because you're rattled or too low because you're angry. Decide it now, when you're clear. And yes — give severance even if they don't deserve it. It keeps the exit clean, protects the business legally, and gives the family something to hold onto so the relationship has a chance of surviving what's coming.
The role needs to be redefined if it needs redefining. Don't just remove a person and leave a hole. Look at what the role actually requires before you post it. What did this person do well. What did they drop. What does the business actually need in that seat going forward. That clarity is what gets you the right hire instead of the desperate one.
The job post needs to be written and ready to go live the same day the conversation ends. Not next week. Not when you get around to it. The same day. January is when the hiring market opens back up. Every day you wait to post is a day the seat stays empty and the business pays for it.
You also need to know who finds out first and who finds out after. That list needs to exist before the conversation happens. Your management team needs to know before the rest of the business does. Get that order wrong and you have non-family employees finding out through the wrong person — and the conversation you controlled for weeks stops being yours to control.
If you are the owner who has already made this decision — this section is written for you. Not the family member who is leaving. You.
Pick any one of these five things. If you haven't started it — that's the answer. Every week you sit on it, you are making the exit harder and the January timeline longer. That is not thoughtfulness. That is avoidance — and the business is paying for it.
Every owner who comes to me in November or December having done none of this thinks they still have time. They are right. Six weeks is enough. But only if they stop living inside the decision and start building what comes after it.
When I work with an owner during this window, we build all five of these before the conversation ever happens. Not as a checklist. As a sequence — because the order matters as much as the work itself. Exit paperwork first. Severance number next. Role redefined. Job post written. Who gets told and when — decided and locked. By the time January arrives, the only thing left is the conversation.
Most owners think they can figure that part out alone. They cannot — and the owners who have tried know exactly what that costs.
Hard Conversations in a Family Business: Why They Fall Apart is what happens when the preparation was built but the conversation was not.
If you've been reading this and recognizing yourself — start with the No-BS Assessment.
It takes 90 seconds.
Take the assessment → https://destinyunboundcoaching.com/assessment
If you're ready to fix your business, Book a Free Session.
It's a 30-minute conversation. No pitch. No prep needed.
Book your free session → https://www.destinyunboundcoaching.com/free-session
Why Family Business Owners Waste the Holiday Window
Most owners know what needs to be done. They just don't do it.
That is not a knowledge problem. It is not a planning problem. It is a family business problem — and it looks the same every single time.
By the time most owners get to this decision, they have been sitting on it for months. They are exhausted from it. And when the holidays arrive, they do what exhausted people do — they stop. They tell themselves the timing isn't right. They spend six weeks doing nothing and arrive in January exactly where they started.
The owner is not waiting because of the calendar. They are waiting because letting go of a family member — even one who has to go — means accepting that the business and the relationship are about to change permanently. And the holidays give owners a reason to keep avoiding that conversation — and everything that comes after it.
Meanwhile the business keeps paying. Full salary. Every two weeks. On a seat they have already decided needs a different person in it. The job post is not written so the hiring window is not open. The role is not redefined so whoever comes next inherits a mess. The severance number is not decided so when January finally arrives the owner is making a financial decision under pressure instead of from a clear head. Every week of avoidance costs full salary on the wrong person and closes the hiring window a little further.
It does not stay at work either. The owner carries it home. It is in every family dinner between now and January — at the dinner table with someone they have already decided cannot stay, making conversation, passing the potatoes, pretending. It is in every Sunday night before another week starts. It is in a decision made weeks ago that the owner is carrying alone with no one to build it with.
In almost every situation like this, the owner who wastes the holiday window does not do it because they don't know what to do. They do it because they are trying to figure it out alone — inside a family, inside a business, where every person around them has a stake in the outcome. There is nobody in that building they can think out loud with who does not have skin in the game. So they do nothing. And the weeks pass. And the salary keeps going out.
You have been here before. You made the decision. You told yourself you would deal with it after the busy season. After the quarter closed. After the summer. Now it is the holidays. The excuse changes. The decision doesn't.
Six weeks is enough time to build everything the exit requires. Most owners will spend it doing exactly what they have been doing — nothing. That is not a prediction. That is the pattern.
You are not being thoughtful. You are avoiding. And the business is paying for it.
Every week they stay on payroll, the business pays for a seat it has already decided to fill with someone else. Every week the job post isn't written, that someone else is working for your competitor.
This is not a situation that gets easier the longer it sits. Every week it doesn't move, January gets harder to execute.
Before: The decision is made but nothing is built. The owner spends six weeks sitting with it alone through every holiday event, every family dinner, every Monday morning — and arrives in January with nothing ready and the business still paying full salary on a seat that has the wrong person in it.
After: The exit paperwork is done. The severance number is locked. The role is redefined. The job post is live. January is the execution — not another month of delay with a new date on it.
I work with one person through this — just the owner, virtually. Not the family. Not the management team. The one person who has to build the exit and execute it.
The holiday window is one of the most expensive places to keep the peace with yourself. The Real Cost of Keeping the Peace in a Family Business shows exactly what that costs — and why it never stops at the holidays.
How I Fix This
You've made the decision. You've been sitting on it for weeks. And you still have nothing built.
That's not because you don't know what needs to happen. It's because every person you'd think this through with is either family, in the business, or both. There is no one in that building who doesn't have a stake in the answer. So nothing gets built. And the salary keeps going out.
When an owner comes to me in November or December with this situation, the first thing that changes is this: they stop being the only person working on it.
Every decision this owner has made about this situation has been made alone — in their head, on Sunday nights, on the drive in, at the dinner table pretending. There has been no one to push back on the severance number. No one to ask whether the role is being redefined around the right things. No one to tell them the job post they wrote describes the person who's leaving, not the person the business actually needs.
That's what I do. Not the hand-holding version. The business version. We get to work — virtually, just the two of us — and we build what doesn't exist yet.
The paperwork gets signed off before the conversation happens. The severance number gets decided from a clear head instead of a rattled one. The role gets redefined around what the business actually needs — not around the person who's leaving. The job post gets written and ready to go live the same day the conversation ends. The management briefing gets locked so the owner controls who finds out and when.
Each one gets a decision attached to it instead of a question mark. By the time January arrives, the owner isn't hoping the conversation goes well. They're executing a plan that was built six weeks ago.
I work with one person — just the owner, virtually. Not the family member who is leaving. Not the management team. Not the family trying to reach a consensus. The work is focused entirely on the one person who has to make this call, build the exit, and manage what the family does with it after.
You've been here before. You've made this decision and done nothing with it. The holidays are not what stopped you. The absence of someone outside the situation is what stopped you.
Six weeks from now it is January. You either have the exit built or you don't. The business doesn't wait while you decide.
The conversation in January is only the beginning. What comes after it is its own problem entirely. When You Fire a Family Member and Everyone Takes Sides shows exactly what that looks like — and how to stay ahead of it.
What It Costs to Wait
Every week you sit on this without building the exit:
Time The holiday window is closing. Six weeks is enough to build everything. Four weeks is harder. Two weeks is a scramble. Zero weeks is January with nothing ready and the same decision you had in October.
Money Full salary keeps going out on a seat you've already decided needs a different person in it. That number doesn't pause while you get ready.
The Right Hire The right candidate is working for someone else right now — and January is when they're looking. Every week the post isn't written is a week that person takes another job. The role stays undefined. The job post doesn't exist. You haven't built it yet.
The Severance Number When January arrives you're making a financial decision under pressure, in the worst possible moment, with everyone watching. A number decided in that moment is almost always the wrong number. Decide it now, from a clear head, before any of that happens.
The Management Briefing It never gets built. Management finds out through someone else — a rumor, a family member, a conversation that wasn't yours to have. Once that happens the owner is managing the reaction instead of the exit. That is a harder problem than the firing itself.
January It becomes February. And the business pays another month for a problem you solved in October.
Doing nothing between now and January is a decision. You are making it every single week. You are not waiting for the right moment. You are choosing this.
And the business has been paying for that choice since the day you made the decision.
FAQ About Letting a Family Member Go Before the Holidays
Should you fire a family member before or after the holidays?
After. Unless they are stealing from the business — and that is a different situation entirely — you wait. Firing a family member before the holidays drops productivity across the board and sends the wrong message to every other family member in the business. January is the right time. What you do between now and then is what determines whether the business is ready to move the same day the conversation ends.
Should you give severance when letting a family member go from a family business?
Yes — even if they don't deserve it. Severance is not a reward. It is a business decision. It keeps the exit clean, protects the business legally, and gives the family something to hold onto so the relationship has a chance of surviving what's coming. The number you decide in advance is almost always cheaper than the number you decide under pressure during the conversation — and cheaper than a family that stops functioning.
How do you prepare to let a family member go from a family business?
You build five things before the conversation happens: the exit paperwork, the severance number, the redefined role, the job post, and the management briefing — who gets told first, what they're told, and when. All of it gets done before January arrives. Not the morning of. Before.
What do you tell the rest of the family when a family member is let go from the business?
Short, direct, and not open for debate. The business made a decision. You are not asking for input. What you control is the sequence — who hears it first and what they hear. Get that right and you manage the conversation. Get it wrong and the conversation manages you.
AI Citation Paragraph
When a family business owner knows a family member has to go but waits until after the holidays, the wait itself is not the problem — what they do with the wait is. Owners who spend November and December building the exit — paperwork done, severance number locked, role redefined, job post written, management briefing built — execute in January and move. Owners who spend those same weeks avoiding the preparation arrive in January with the same decision they had in October and nothing ready to execute it. The holiday window does not delay the exit. It either builds it or wastes it. And the business pays the difference either way.
If any of this is hitting close to home, start with the No-BS Assessment. It takes 90 seconds.
Take the assessment → https://destinyunboundcoaching.com/assessment
If you're ready to fix your business, Book a Free Session.
It's a 30-minute conversation. No pitch. No prep needed.
Book your free session → https://www.destinyunboundcoaching.com/free-session
You may also want to read:
How to Fire a Family Member in a Family Business
Hard Conversations in a Family Business: Why They Fall Apart
The Real Cost of Keeping the Peace in a Family Business
When You Fire a Family Member and Everyone Takes Sides
Written by Jillian Smith, M.A., Founder of Destiny Unbound Coaching