You Build the Future. We Protect It.
Your company is scaling fast. Your insurance should keep up.
WithCoverage replaces your traditional broker with an AI-native team of insurance experts and attorneys who understand startups.
40+ carriers compete for your business instead of 2 or 3.
We operate on a Flat Fee instead of broker commissions.
Policies, claims, and COIs in one place as you scale.
1,000+ fast-scaling businesses (Gopuff, Physical Intelligence, Polymarket) replaced their traditional broker with us.
Let us review all your policies for free to show you how we can save you money and better protect your ambitious business.
Your broker will not be notified. This is simply our way to earn your trust.
Covering today
The year-end review that should have been a conversation in March
Why good managers sit on bad news, and who pays for it
The Four Delays: the stories we tell ourselves to put it off one more week
The two-minute surprise test
For members: The No-Surprises Kit, with a 15-minute prep sheet, the first 60 seconds word for word, a five-move conversation, scripts for when it goes sideways, the follow-up email, a pre-review check for your whole team and a 30-day plan. Join here
Since March
Tom's review was on a Thursday in December.
Hannah had been dreading it for weeks. She'd typed "below expectations" into the draft, deleted it, then typed it again.
None of it was new. Since March, Tom's reports had come in late and thin. Twice, a client had spotted errors before Hannah did. She'd started rewriting his work on Sunday evenings so nobody else would see it. When his deadlines slipped, she quietly passed pieces to Leah, who never complained.
In April, she told herself it was a blip. In June, that he had a lot going on at home. In September, that it would be fairer to raise it properly, in the review.
So she raised it in the review.
Tom went very quiet. Then he asked the question every manager in that chair dreads.
"Why is this the first time I'm hearing about it?"
She didn't have a good answer. There isn't one.
He said one more thing on his way out. "If you'd told me in March, I'd have had nine months to fix it."
In January, Leah asked to move teams.
Composite, drawn from conversations with leaders. Details changed.
The kindest-feeling mistake in management

Last week was about the truth your team doesn't tell you. This week is the other direction: the truth you're not telling them.
If you've got one of these conversations waiting, you're in good company. In a 2016 Harris Poll for communications firm Interact, 69% of managers said something about their role made them uncomfortable communicating with their team. 37% said they were uncomfortable giving direct feedback on performance if they thought the person might react badly.
Waiting costs more than it feels like it does. Joseph Grenny and David Maxfield, two of the authors of Crucial Conversations, surveyed 1,025 people and found that each avoided conversation cost an average of $7,500 in lost time and resources. Half of the people they surveyed spent a week or more avoiding the conversation instead of having it.
In the UK, Acas puts the cost of workplace conflict at £28.5 billion a year, just over £1,000 for every employee. Its conclusion was simple: deal with problems early, and you save time and money.
Then there's the review itself. Gallup found that only 14% of employees strongly agree their performance reviews inspire them to improve. Nearly half get feedback from their manager a few times a year or less.
And it doesn't stay with one person. In Will Felps's famous "bad apple" experiment, an actor was placed in work groups to play a slacker, a jerk or a downer. Those groups performed 30 to 40% worse, and the others started copying the behaviour.
Tom wasn't a bad apple. But Leah was watching the whole time. Your best people aren't watching the problem. They're watching what you do about it.
OpusClip started with clips. Now it edits entire videos.
With OpusClip 4.0, drop in raw footage, toggle on the edits you want, and get back a finished video. You never have to touch a timeline! Speech cleanup, captions, AI B-roll, Viral Hook, Motion Graphics: it's all there. Try it for 40% off your first month of Pro Plan.
The Four Delays

Nobody decides to avoid a conversation for nine months. You decide to put it off one more week, about 36 times in a row.
Every delay comes with a story that sounds reasonable. Here are the four I hear most in coaching, and what each one really costs.
The Wait: "It'll sort itself out." Sometimes it does. Usually it doesn't, because the person doesn't know there's anything to sort. To them, silence sounds like approval.
The Kindness: "They've got a lot on." Kim Scott calls this ruinous empathy: sparing someone's feelings today at the expense of their future. If something really is going on, that's a reason to talk sooner and adjust together, not to say nothing.
The Cover: "It's quicker if I just do it." Every rewrite and quiet reassignment hides the evidence from the one person who needs to see it. And someone, usually your most reliable person, is paying for it.
The Save: "I'll raise it properly in the review." A review is where you sum up conversations you've already had. It's the worst place to start one: formal, rated, and too late to change the outcome.
All four feel like kindness. None of them is kind to the person who finds out in December.
Quick poll
Which delay is yours?
The two-minute surprise test
Imagine you had to write everyone's year-end review tonight. Then answer these honestly, with a name and a month, not a feeling.
Is there one review you're already dreading writing?
When did you first notice the problem? Write down the month.
Have you said it to them in plain words, the way you'd write it in the review? Not hinted. Said.
What have you done instead? Rewritten, covered, reassigned, vented to a peer?
Who else on the team is carrying it?
If the month you wrote down is before September, they've lost most of a year they could have spent fixing it.
If your honest answer to the third question was "I've hinted", it hasn't been said. Most people don't hear hints. They hear "all fine".
And if a name came to mind for the last question, you've got two conversations to have, not one.
One thing before Monday
Book 20 minutes with that person before next Friday. Not a review slot. Not with HR. Just a 1:1 and a closed door. Start here:
I want to talk about something I should have raised a while ago. That's on me, not you. I'd rather we deal with it now, while there's still plenty of time to fix it.
That's the hardest sentence. Everything after it gets easier.
What's waiting below the line
Booking the meeting is the easy part. Knowing what to say in minute two, when they go quiet, get defensive or ask why you didn't say something sooner, is the work.
Below is The No-Surprises Kit: a 15-minute prep sheet, the first 60 seconds word for word, a five-move structure for the conversation, scripts for when it goes sideways, the follow-up email that makes it stick, a check to run across your whole team before you write a single review, and a 30-day plan that gets you to review season with nothing left unsaid.
Join today and The No-Surprises Kit unlocks right now: the prep sheet, the scripts, the follow-up email and the 30-day plan.
Every week, members get the full playbook behind each Thursday essay, plus monthly group coaching calls, a templates library and a community of managers who get it.
Member offer: 20% off the annual plan, for as long as you stay a member.
Try it for a month. If it doesn't earn its place, I'll refund you.
Most managers figure this out the hard way. You don't have to.
You're making the calls, having the hard conversations, carrying the weight of the team, on your own, in your head, at 11pm before the next 1:1. It doesn't have to be that way.
Upgrade to a paid membership and get:- Sitting on a performance conversation for weeks because you don't know how to start it → monthly 1:1 leadership coaching
- Making big calls with no one to sense-check them against → community access with events
- Facing the same leadership problems on repeat with nobody showing you a better way → monthly training and guest speakers
- Wanting the frameworks you've missed, not just this week's → full newsletter access + 200+ article archive
- Leading alone, with no one who actually gets the job → a support network of people doing the same work


