30-day difficult conversations practice plan

Hard talks, handled

“I can raise the thing I’ve been avoiding, stay calm, and come out with an agreement instead of a fight.”

Who it’s for: Anyone at work who needs to give feedback, push back, own a mistake or ask for what they need.

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

Open the conversation you’ve been avoiding: one issue, the goal you share, and what you hope to leave with.

01Your starting lineToday is a measurement. Raise the missed handoffs with a peer the way you normally would, then do a one-minute rep on confident language, because hard talks are where most of us soften our words until they disappear.
02Say why you’re hereHard conversations go sideways when the other person is guessing what’s coming.
03One issue at a timeWhen we finally raise something, it’s tempting to bring everything that’s been building up.
04Pick the momentWhere and when you say it changes how it lands. Hard news in a corridor, in front of others or five minutes before a meeting tends to put people on the back foot.
05A calm first sentenceNerves tend to show up as speed: the opener comes out in one breath and sounds like an accusation or an apology.
06Start from what you sharePeople hear a hard opener as an attack unless they can see what’s in it for both of you.
07Week one replayCheckpointReplay the day 1 conversation at the same difficulty and compare.

WEEK 2 · DAYS 8–14

Describe one behaviour and its impact as facts, then ask, so feedback becomes a problem you solve together.

08Behaviour, impact, questionDescribe one specific thing that happened, what it cost, and then ask what’s getting in the way.
09Facts, not verdicts“You’re dismissive” is a verdict, and people fight verdicts.
10What’s behind the first answerThe first reason people give is rarely the whole reason.
11Make vague feedback specificVague feedback is hard to act on and easy to resent.
12The cost of staying the sameImpact isn’t only what already happened; it’s where things are heading.
13Keep your voice levelWhen we describe something that bothered us, our pitch and volume tend to rise, and a fact starts to sound like an accusation.
14Two weeks inCheckpointReplay the day 1 conversation and compare it with days 1 and 7.

WEEK 3 · DAYS 15–21

Name the feeling in the room and own your part, so the other person can hear the rest, even when it gets heated.

15Name the feelingWhen someone is annoyed or defensive, naming it plainly, “you sound frustrated, and that’s fair”, usually cools the room faster than explaining yourself.
16Own your partMost hard conversations have some fault on both sides.
17A clean apologyWhen the mistake is yours, a clean apology has three parts: what you did, what it cost them, and what you’re doing about it.
18Give their words backWhen someone says something loaded, repeating their last few words as a question, “only being rigorous?”, and then waiting, gives them room to say more.
19When they get defensiveDefensiveness is usually fear of looking bad, not a sign that you’ve got it wrong.
20Clear is kindIt’s hardest to be clear with people we like, so we blur the message until it’s kind but useless.
21Three weeks in, tougherCheckpointReplay the day 1 conversation at tough: Jordan deflects harder and gets prickly.

WEEK 4 · DAYS 22–30

Hold your position without heat, trade instead of caving, and leave with who does what by when.

22Hold without heatWhen you’re pushed, the steadiest response is to restate your position once, calmly, without new justifications.
23Set the boundary as a normBoundaries land better as a proposal than a complaint.
24Bring the caseAsking for something goes better with one or two concrete facts than with how you feel you deserve it.
25Trade, don’t caveWhen you ask for something, offer a structure that lowers the other person’s risk: a trial, a review date, a measure you’ll both watch.
26Ask them to chooseRaising workload goes better as a priorities question than a coping question.
27When the first answer is no“Budgets are tight” is rarely the end of the conversation; it’s usually the start of the real one.
28Who does what by whenA hard talk that ends with “great, let’s keep an eye on it” usually ends up back where it started.
29The whole conversationTomorrow is the capstone, so today run the whole arc in one conversation: say why you’re here, describe what happened, name the pressure, own your part, hold what you need and close with a date.
30The same talk, tougherCheckpointReplay the day 1 conversation at tough and compare it with your first attempt: how you opened, whether you described facts or verdicts, whether you found Jordan’s real pressure, and whether you left with a checkable agreement.

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.