30-day leadership communication practice plan

Lead the conversation

“I can say the hard thing clearly, keep the relationship, and leave every conversation, up, down or in a full room, with a real agreement.”

Who it’s for: New and experienced managers who lead people, and anyone who has to influence up or across without the authority to insist.

All 30 days

Each day is one idea, taught in plain words, put to work in a drill and a live conversation, then carried into a real one.

Checkpoint days replay day 1, so you can hear what changed.

WEEK 1 · DAYS 1–7

Say what each conversation is for, lead with the point, and hear the pressure underneath what people say.

01Your starting lineToday is a measurement, not a test. Say no to an executive the way you normally would, then do a one-minute rep on confident language.
02Say what it’s forPeople listen differently once they know what a conversation is for.
03Bottom line firstSenior listeners are waiting for the point and the ask.
04Ask before you tellWhen someone is struggling, the answer you give them matters less than the answer they reach themselves.
05Name the pressureResistance usually has a feeling underneath it: worry about status, workload or being judged.
06Let them keep talkingRepeating someone’s last few key words as a question, then waiting, invites them to say more without steering them.
07First checkpointCheckpointReplay the day 1 conversation at the same difficulty and compare.

WEEK 2 · DAYS 8–14

Bring bad news early, find the real concern, and make a case your boss can carry into rooms you’re not in.

08Concede what’s trueBad news gets more expensive every week it waits.
09Find the real concernVague answers such as “it’s the process” or “I’m not sure it’s the right time” often cover a specific worry.
10One number, not a listA case for resources lands better with one specific, checkable figure than with a long list of reasons.
11Disagree upwardDisagreeing with someone senior works best as a short sequence: the risk you see, the alternative you’d suggest, and a clear request for their decision.
12No, with a tradeA flat no ends the conversation; a no with a trade keeps it going.
13Make it checkableAgreements fail quietly when they’re vague. Before you end, play back what changes, by when, and how you’ll both know it happened, then ask if that’s right.
14Second checkpointCheckpointTwo weeks in, replay the day 1 conversation at the same difficulty.

WEEK 3 · DAYS 15–21

Hold the standard with people you lead, including the ones who used to be your peers, when they push back hard.

15From peer to managerWhen a peer becomes your report, the relationship has already changed; pretending it hasn’t makes both of you guess.
16The standard and the personThe hardest performance talks go wrong in one of two ways: you protect the relationship and blur the standard, or you hold the standard and lose the person.
17Own your share firstWhen a team misses, people listen for whether the leader owns any of it before they’ll own theirs.
18Enforce what you didn’t chooseEnforcing a policy you didn’t make tempts you to either sell it as your own or disown it with an eye-roll.
19Grow your successorSomeone who wants your job is usually the best person on your team, and blocking them quietly is the fastest way to lose them.
20Keep your best personToday combines the week: label what you hear, mirror to go deeper, and clarify before you offer anything.
21Third checkpoint, tougherCheckpointReplay the day 1 conversation, this time at tough, and compare it with your first attempt.

WEEK 4 · DAYS 22–30

Take the whole toolkit into full rooms: hard news, skeptical executives, quiet experts and hostile questions.

22Hard news to a teamWhen you announce a change, people listen for three things: what’s changing, what isn’t, and what you don’t know yet.
23Recommend, don’t reportA leadership team rarely wants your full analysis; it wants your recommendation, the one risk that worries you, and the decision you need today.
24Bring the quiet voice inThe person who knows most is often the one saying least, especially when seniors are talking.
25Take the hostile questionA hostile question in front of a crowd is really a question about whether you’ll be straight with them.
26Causes, not culpritsAfter a failure, the room takes its cue from the most senior person.
27Disagree, then commitPushing back upward only builds trust if you also know how to stop.
28No hedge, no hurryBy now the moves are yours; what gives people away under pressure is the voice.
29Close with a dateEvery leadership conversation should end with an owner and a date, including the ones about you.
30Capstone: the same no, tougherCheckpointThirty days ago you said no to an executive the way you always had.

Included in Leadership Voice, with every other track.

$39a month, or $299 a year

All nine tracks, with live rehearsals and voice benchmarks. Cancel in one click.

Measured or refunded. Six sessions in your first 30 days and no measured improvement? Every cent back. Or ask within seven days, for any reason.

One question out loud, 60 seconds: your pace, your ums and how fast you started, measured on your device. Day 1 of every track begins there.