Talking to your boss about outcomes
They set the goal you were given. Changing its shape looks, from where they sit, like loosening a promise they already made to somebody else.
Start here: what they’re under
Your boss is accountable for a commitment that was almost certainly made in output form — a date, a launch, a line in a plan. Asking them to swap it for an outcome sounds like asking them to be vaguer with their own boss. So don't ask for vaguer. Offer them something safer to promise: a number they can stand behind, and an early signal that tells them months in advance whether it's coming.
An opener that doesn’t start a fight
“Can I show you how I'd measure success on this? I want to check we'd both recognise it when it happens.”
The conversation
In order, and none of it requires a slide. Each move teaches by doing something to a real goal rather than explaining a principle.
Bring one real goal, not a philosophy
Pick the goal they care most about this quarter — theirs, not a tidy example. Rewriting one live goal in front of them teaches more than any explanation of outcomes over outputs, and it can't be filed for later.
Show both versions side by side
The output as it's written today, and the outcome underneath it. Then ask which one they'd rather report on. Let the pair of sentences make the argument so you don't have to.
Keep their deliverable in the frame
Outcomes over outputs has never meant “no deliverables”. Say it plainly: same work, same date, different definition of done. Most resistance is the fear that the work is being renegotiated.
Ask for exactly one thing: the baseline
“Can we agree what the number is today, before we agree the target?” That single question does more teaching than a deck, because it's the question nobody can answer with a milestone.
What you’ll hear back
Every one of these is reasonable from where they sit. Answer the fear underneath, not the sentence.
“I need something concrete I can commit to.”
- What’s underneath it
- They're afraid an outcome can't be evidenced, and they'll be the one standing there without an answer.
- Something you could say
- “An outcome with a baseline, a target and a date is more concrete than a delivery date — it says what we'll have, not just when we'll be finished.”
“The board wants dates.”
- What’s underneath it
- Dates are the currency they're paid in. You won't win by devaluing them.
- Something you could say
- “Then let's give them both: the date the change should show up, and the early signal we'll see weeks before that.”
“We already know what to build.”
- What’s underneath it
- They may well be right. What they're hearing is that their judgement is being questioned.
- Something you could say
- “Then let's write down what we expect it to change. If we're right, that's the win we get to claim. If we're wrong, we find out in weeks instead of at go-live.”
“This lets the team off the hook.”
- What’s underneath it
- Outcomes sound softer than deadlines to anyone who hasn't tried to hit one.
- Something you could say
- “It's the opposite. An output you can finish is easier to hit than a number you have to move.”
What to leave behind
Send one paragraph, not a deck: the outcome in the “from x to y by when” shape, the one leading indicator, and the deliverable still sitting inside it. Ask them to correct it. A boss who edits your outcome owns it.
How you’ll know it landed
- They quote your measure back to you in a meeting you weren't in.
- They ask “what's the baseline?” about something that has nothing to do with you.
- A goal you didn't write turns up in outcome shape.
Note that “they agreed” isn’t on the list. Agreement in the room is cheap; the test is what happens to the next goal written without you.
Rehearse it first
Paste this into Claude or any assistant — ideally alongside one of our coaching skills. It coaches you on the angle, then role-plays my boss so you can practise before it counts. Bring a draft through the coach first and it will be included here.
I want to help someone else write better outcomes. I'm not asking you to fix my own goal right now — this is about the conversation. Who I'm talking to: my manager, who set this goal and is accountable for it upwards. They are under pressure to commit to dates and deliverables. What I want from the conversation: to agree an outcome — a baseline, target, timeframe and one leading indicator — without them feeling I am renegotiating the commitment or questioning their judgement. Coach me, then rehearse with me: 1. Ask me what this person is actually measured on, and what they'd lose if my version won. 2. Help me find the version of the outcome that makes their job easier, not harder. 3. Then role-play them — sceptical but reasonable, not a cartoon — and let me practise. Push back the way they really would. 4. Afterwards, tell me which of my sentences would have landed and which would have started a fight. Use the bettergoals.ai outcome principles as the standard: start with customer and problem; outcomes over outputs; treat the outcome as a hypothesis; measure movement and impact with a baseline, target and timeframe; connect it to strategy and value; and write it so anyone can understand it. Ask one question at a time. Don't invent facts, baselines or quotes about my organisation — if you need something, ask. No names or personal details: refer to everyone by their role. I want to leave with sentences I would actually say out loud, not a script that sounds like a consultant.
When a chat isn’t enough: one hour, one goal
The same agenda works for a team, a leadership group or a PMO. It is deliberately not a course — there is no theory section, and everything that gets rewritten is real work. Running it? The goal-jam-facilitator skill will help you plan it, and the Outcome Canvas is the one handout you need.
0–10 · Why we're here
One goal from your own area that you know is output-shaped, and the honest story of what it cost. You go first, and you use your own work as the cautionary tale.
10–20 · The one question
“Could we finish all of this and nothing be better for anyone?” Run it over two or three real goals from the room. Don't define anything yet.
20–40 · Rewrite one goal, together
Pick the goal with the most energy behind it. Fill in who it's for, what changes for them, the baseline, the target and the date. Leave the gaps visible rather than guessing numbers.
40–50 · Check it, out loud
Run the draft through the Outcome Coach and read the gaps together. Argue with the score — that argument is the session.
50–60 · One commitment each
Everyone names one goal they'll rewrite this week and who they'll show it to. No template rollout, no follow-up deck.
Five ways this goes wrong
- Sending the principles as pre-reading. Nobody reads homework about goals; bring a goal instead.
- Correcting somebody's goal in public. The point is to make outcomes feel safe, and a corrected goal in a group chat teaches the opposite lesson.
- Leading with the vocabulary. “Outputs versus outcomes” is our shorthand, not theirs — describe the change you want and let them name it.
- Bringing a scorecard to a colleague. The check exists so you don't have to be the marker.
- Trying to convert everyone. One boss and one peer who write real outcomes will out-teach any campaign.