What a weekly email to your network actually looks like

The counteroffer is decided in the first conversation

Most hiring executives treat a counteroffer as a late surprise. In my experience, it's almost never a surprise. It's the predictable result of a question nobody asked early enough.

When a senior candidate takes a first call, they're rarely running from something. They're curious. Curiosity is enough to get someone through a shortlist interview, but it isn't enough to get them through a resignation conversation with a CEO who has known them for nine years.

So the real work happens before the candidate ever meets your hiring committee. In the first or second conversation, a good search partner should be able to answer three things clearly:

• What would have to be true for them to leave, in their own words, not ours.
• Who in their life gets a vote on this move, and whether that person has been part of the conversation.
• What their current company would likely offer to keep them, and why that wouldn't be enough.

If those answers are vague, the candidate may still be excellent. They're just not ready yet, and pushing them to a final round only moves the problem to a more expensive moment.

The other half of this sits with the hiring company. Candidates read a slow, uncertain process as a signal about the culture they'd be joining. A long gap between final interview and offer gives their current employer time to act, and it gives the candidate time to wonder whether you really want them.

The searches I've seen close cleanly share one habit. The hiring committee agrees on the decision process, the approvers, and the compensation range before the first finalist interview, not after.

If you have a leadership search open, or one coming in the new year, ask your search partner one question for each finalist: what will their current employer say when they resign, and how do we know it won't change their mind? If the answer is a shrug, you don't have a finalist yet. You have an interested candidate, and it's far better to learn that now than after the offer letter goes out.

Your add-backs are a claim, not a fact

Most founder-owned companies run personal and one-time expenses through the business. That's normal, and it's why we talk about adjusted EBITDA instead of the figure on your tax return. The adjustments, or add-backs, are where real value lives.

Here's the part owners don't hear early enough. A buyer doesn't accept an add-back because it's reasonable. They accept it because it's documented, consistent, and clearly won't recur after closing. Anything that misses one of those tests becomes a negotiation, and negotiations after the LOI almost never move in the seller's favor.

The founder I mentioned had a strong business and a clean customer list. But one of his larger add-backs was a family member's salary he described as a role that would go away. The buyer's diligence team asked a simple question: who does that work after closing? Nobody had a good answer, so the adjustment came out, and the valuation conversation reopened.

The add-backs that tend to get challenged are familiar: vague one-time costs that seem to happen every year, owner compensation adjustments with no market comparison, and expenses nobody can tie back to a receipt.

None of this is about hiding anything. It's about doing the buyer's homework before they do it for you. When you've already answered the hard questions, your diligence feels calm, your timeline holds, and the number in the LOI is much more likely to be the number at closing.

The two week test

When owners ask me what their business is worth, they usually expect me to talk about revenue. What I actually start with is a simpler question. If you left for two weeks and didn't answer your phone, what would happen?

On a Main Street deal, the buyer is almost always an individual. Often it's someone leaving a corporate job, putting their savings on the line, and borrowing the rest through an SBA loan. They aren't buying your equipment or your logo. They're buying the confidence that the cash flow will still be there after you hand over the keys.

That's what owner dependence really means. It's not a judgment on how hard you work. It's a measure of how much of the seller's discretionary earnings walks out the door with you.

Buyers and lenders both look for it, and they spot it fast. Here's where it usually hides:

• Customer relationships that run through your cell phone instead of the company's
• Pricing and estimating that lives in your head
• Supplier terms based on a handshake with you personally
• A key employee who stays because of you, not because of the job
• Licenses or certifications held only in your name

None of these is a deal breaker on its own. Plenty of good businesses sell with an owner who's deeply involved. But each one makes a buyer more nervous, and nervous buyers ask for longer transitions, bigger seller notes, or a lower price to cover the risk.

The encouraging part is that this is one of the few things that affect value that you can actually work on yourself, without a consultant or a big investment. It just takes time, which is why I bring it up years before anyone is ready to list.

Your P&L and your bank account are telling two different stories

A founder I worked with last spring had the best quarter in the company's history. Signed contracts were up, margins were healthy, and the P&L showed a solid profit. Six weeks later, she was calling her banker about the line of credit.

Nothing was wrong with the business. The problem was timing. She'd hired ahead of the new work, her two largest customers paid on long terms, and a big annual software renewal landed in the same month as payroll for three new people. The profit was real. The cash just hadn't arrived yet.

This is the most common surprise I see in founder-led companies, and it usually shows up right when things are going well. Growth eats cash before it produces it.

The fix isn't a more detailed budget. Budgets answer whether you'll be profitable this year. The 13-week view answers a simpler and more urgent question: will we have enough cash every single week between now and next quarter? It doesn't need to be fancy. It needs to be honest and updated every week.

The magic isn't in the spreadsheet. It's in the weekly habit of comparing what you expected with what actually happened. After a month or two, you start seeing the gap between contracts and cash long before it becomes a phone call to the bank.

So before you finalize next year's hiring plan, find your lowest cash week. Open a blank sheet, list the next 13 weeks across the top, and fill in only the big items: collections from your top customers, payroll, and anything sizable that hits once or twice a year. It'll take about an hour. If the lowest week makes you uncomfortable, you've found that out while you still have time to adjust start dates, renegotiate payment terms, or talk to your bank from a position of calm rather than urgency.

Your calendar shows your time. It doesn't show your energy.

Most of us plan our weeks around hours. A meeting is an hour, school pickup is twenty minutes, and dinner with friends is an evening. On paper, two weeks can look identical. In real life, they can feel completely different.

That's because the same hour can give you something or take something from you. A walk with a friend who really gets you is an hour. So is a phone call that leaves you replaying every word for two days. Your calendar counts them the same. You don't.

The practice I teach is an energy audit, and it works backward instead of forward. Rather than planning a better week, you look honestly at the week you just had. Here's how it works:

• Open last week's calendar, or write out what you remember doing each day.
• Next to each block, mark a plus if it left you with more than you brought to it, a minus if it took more than it gave, and an equal sign if it felt neutral.
• Don't judge the marks or try to fix anything yet. You're only gathering information.
• Circle the two minuses that surprised you most.

The circled ones are where the real insight usually lives. The obvious drains rarely surprise anyone. It's the quiet ones that matter, like the standing coffee you've outgrown, the volunteer role you said yes to three years ago, or the evening scrolling you'd call rest even though you never feel rested afterward.

Set aside ten minutes on Sunday evening and run it on the week behind you. Use a notebook rather than your phone, because writing by hand slows you down enough to be honest with yourself. Then pick just one minus and ask a gentle question: what would make this a little lighter? Not gone, just lighter. Small adjustments you actually keep will serve you far better than a big overhaul you abandon by Wednesday.

A client ran this audit for the first time last spring and found that her hardest days weren't her busiest ones. They were the days with no breathing room between commitments. The work itself was fine, but the constant switching wore her down. She didn't remove anything from her life. She added fifteen minutes of open space between two meetings each day, and this is how she described it to me a month later.