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Dana Whitfield · Getting to a decision
Coaching
Agreeing a change to what you're doing
Dana is not going to say no to your face today, and that is the risk rather than the reassurance. The most likely version of this meeting is one that feels fine while you are in it and then quietly stalls afterwards.
Expect Dana to slow the pace down and ask careful, specific questions about how the change affects what is already running. That is a shift from how she would normally take something like this. Ordinarily she would look for reassurance that the relationship is fine, then go along with it.
Do not mistake quiet agreement for settled agreement. If Dana goes along with the change quickly, without asking much, that is more likely to be discomfort with pushing back than genuine comfort with the plan.
Watch for when Dana stops asking questions and starts talking about how the change will land with her own team. That is a good sign.
Ask Pyper…
Pyper can be wrong. Use your own judgement.
Dana WhitfieldProject ManagerAgreeing a change to what you're doingIn person
Three free preps. Private to you. Works in your browser.
ACAlex
Back to Dana Whitfield
Dana Whitfield · Getting to a decision
Coaching
Agreeing a change to what you're doing
Dana is not going to say no to your face today, and that is the risk rather than the reassurance. The most likely version of this meeting is one that feels fine while you are in it and then quietly stalls afterwards.
Expect Dana to slow the pace down and ask careful, specific questions about how the change affects what is already running. That is a shift from how she would normally take something like this. Ordinarily she would look for reassurance that the relationship is fine, then go along with it.
Do not mistake quiet agreement for settled agreement. If Dana goes along with the change quickly, without asking much, that is more likely to be discomfort with pushing back than genuine comfort with the plan.
Watch for when Dana stops asking questions and starts talking about how the change will land with her own team. That is a good sign.
Ask Pyper…
Pyper can be wrong. Use your own judgement.
Dana WhitfieldProject ManagerAgreeing a change to what you're doingIn person
ASK PYPER
Give me the short version
How to open
Questions to ask
New meeting prep
What do you know about them?
Person
Job title
Situation
Scenario
How you'll meet
Stance · Focus
Notes
Get my coaching
A few facts in. A clear read out.
Mark Evans · General Manager
Megan Torres · Marketing Manager
Dana Whitfield · Project Manager
Min Lee · Finance Director
People in this role often have a natural style that is Dominant: decisive, brisk, and keen to get to the point.
People in this role often have a natural style that is Influential: expressive, ideas-led, and drawn to the big picture.
People in this role often have a natural style that is Steady: methodical, plan-led, and focused on what happens next.
People in this role often have a natural style that is Conscientious: careful with detail, wants the reasoning before the answer.
Tap a style to see someone else.Choose a style to see someone else.
What's Mark usually like?
I haven't met Mark yet
Grumpy. Listens if challenged.Slow to trust, fiercely loyal after.
What's Megan usually like?
I haven't met Megan yet
Warm one day, snappy the next.Defends their team. Hates blame.
What's Dana usually like?
I haven't met Dana yet
Guarded at first, then funny.Says yes, then backtracks.
What's Min usually like?
I haven't met Min yet
Stiff in groups, candid one-on-one.Quick temper, quick to forgive.
More examples
That's Mark's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Mark is likely to show up, and what to do about it.
That's Megan's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Megan is likely to show up, and what to do about it.
That's Dana's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Dana is likely to show up, and what to do about it.
That's Min's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Min is likely to show up, and what to do about it.
Works with what little you knowA name, a job title and the meeting are enough to start, even if you've never met.
Builds on what you knowTell Pyper what they're usually like, in your own words. It adds that to their natural style.
Then reads the meetingNo one is the same in every meeting. Pyper works out how this one changes them, and coaches you.
For meeting people.
A few facts in. A clear read out.
Works with what little you knowA name, a job title and the meeting are enough to start, even if you've never met.
Builds on what you knowTell Pyper what they're usually like, in your own words. It adds that to their natural style.
Then reads the meetingNo one is the same in every meeting. Pyper works out how this one changes them, and coaches you.
Mark Evans · General Manager
Megan Torres · Marketing Manager
Dana Whitfield · Project Manager
Min Lee · Finance Director
People in this role often have a natural style that is Dominant: decisive, brisk, and keen to get to the point.
People in this role often have a natural style that is Influential: expressive, ideas-led, and drawn to the big picture.
People in this role often have a natural style that is Steady: methodical, plan-led, and focused on what happens next.
People in this role often have a natural style that is Conscientious: careful with detail, wants the reasoning before the answer.
Tap a style to see someone else.Choose a style to see someone else.
What's Mark usually like?
I haven't met Mark yet
Grumpy. Listens if challenged.Slow to trust, fiercely loyal after.
What's Megan usually like?
I haven't met Megan yet
Warm one day, snappy the next.Defends their team. Hates blame.
What's Dana usually like?
I haven't met Dana yet
Guarded at first, then funny.Says yes, then backtracks.
What's Min usually like?
I haven't met Min yet
Stiff in groups, candid one-on-one.Quick temper, quick to forgive.
More examples
That's Mark's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Mark is likely to show up, and what to do about it.
That's Megan's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Megan is likely to show up, and what to do about it.
That's Dana's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Dana is likely to show up, and what to do about it.
That's Min's starting point.Their natural style, plus anything you know about them. But no one is the same in every meeting. Next, tell Pyper about the meeting and it will coach you on how Min is likely to show up, and what to do about it.
For meeting people.
Same person. Different meeting.
It's natural to prepare for the person you know. But the same person can show up very differently, depending on the meeting. Pyper gets you ready for the person who actually turns up.
DW
Dana WhitfieldProject Manager at your client · usually steady and easy to deal with
Dana in two different meetings. Tap to switch.
Getting to a decisionIn person
Agreeing a change to what you're doing
Just the two of you, in person. She may not like the change.
USUALLY
Easy to get on with, agreeable in the meeting itself, and inclined to avoid friction.
TODAY
“Dana is not going to say no to your face today. The most likely version of this meeting is one that feels fine while you are in it and then quietly stalls afterwards.”
WHAT TO DOAsk Dana directly what concerns her about the change before you ask for a decision. That is what gets you the real answer rather than the easy one.
Same person. Different meeting.
It's natural to prepare for the person you know. But the same person can show up very differently, depending on the meeting. Pyper gets you ready for the person who actually turns up.
DW
Dana WhitfieldProject Manager at your client · usually steady and easy to deal with
Getting to a decisionIn person
Agreeing a change to what you're doing
Just the two of you, in person. She may not like the change.
USUALLY
Easy to get on with, agreeable in the meeting itself, and inclined to avoid friction.
TODAY
“Dana is not going to say no to your face today. The most likely version of this meeting is one that feels fine while you are in it and then quietly stalls afterwards.”
WHAT TO DOAsk Dana directly what concerns her about the change before you ask for a decision. That is what gets you the real answer rather than the easy one.
Difficult momentsOnline
Something your team did has caused a problem
With Greg Holloway, her boss. She had to explain your missed deadline to him.
USUALLY
Easy to deal with and quick to keep things comfortable between you.
TODAY
“Expect Dana to be careful rather than warm… to want the facts pinned down precisely before she commits to anything.”
WHAT TO DOGive her the detail unprompted: what went wrong, what you are doing about it, and what it means for the rest of the delivery. Do not make her ask for it.
MT
Megan TorresMarketing Manager at a company you'd like to work with · usually warm and quick to react
Initial discussionsOnline
Her boss asked her to look at options. Not her idea.
Your first call. Just the two of you.
USUALLY
Easy to talk to, quick to warm up, and happy to let the conversation range.
TODAY
“Underneath the warmth, she is likely to be more careful than usual about what she commits to.”
WHAT TO DOAsk directly why her boss asked her to look at this, and what they'll want to know when she reports back.
Putting something forwardIn person
Testing your thinking before you propose
With Daniel Kim, her boss, who hasn't met you yet.
USUALLY
Runs with an idea, reacts quickly, and tells you what she likes before you have finished explaining it.
TODAY
“Expect her to hold some of that back and check how things are landing with Daniel before she responds fully.”
WHAT TO DOBring Daniel in yourself rather than waiting for him to ask something. Ask him directly what he'd need to see for this to make sense from where he sits.
ME
Mark EvansGeneral Manager, a stakeholder you need something from · usually decides fast
Putting something forwardIn person
Asking Mark to free up people from their team
With Jess Chen, who reports to Mark and supports the work.
USUALLY
Decides fast and moves on.
TODAY
“Expect more questions before he gets there, particularly about how the work will actually run once his people are involved.”
WHAT TO DOIf Mark raises a concern about how something would actually run, let Jess answer it where possible.
Being challengedOnline
Mark found out from someone other than you
With Dana Whitfield, who told him about the new start date first.
USUALLY
Pushes for a quick resolution and moves on.
TODAY
“Expect him to slow down and ask exactly how the change happened, who knew, and when.”
WHAT TO DOSay plainly that he should have heard it from you first, and say why that did not happen. Do not minimise it or rush to the substance of the date change.
Pyper helps you before, during and after every meeting.
1
Before the meeting
Know what to expect
What the meeting is really about, and how they're likely to behave.
Mark Evans · Being challenged · Online
Mark found out about the start date change from Dana before you told him, and that is what this meeting is really about, not the change itself. Lead with that. If you open by explaining why the date moved, you will be defending a decision Mark might have accepted, while the actual problem — that he was the last to know about something in his own area — sits there unaddressed.
2
During the meeting
Go in knowing what to look for
The signs to watch for and what they mean, so they see you on top of it, not checking a screen.
In person · Megan, with her boss Daniel
Watch for whether Megan starts speaking to Daniel instead of to you — pointing things out to him, checking his reaction, translating your thinking into terms she thinks will land with him. That is a good sign. It means she is already trying to bring him along.
3
After the meeting
Debrief within two minutes
Tap through a few questions when you have time. Pyper tells you what it means for next time.
The heart of it
And what caught you off guard?
How firm they were
How deep they wanted to go
How little they gave away
How fast they moved
Nothing much
Your feedback
Asking about mechanics is a way of testing something without having to say directly that it worries you. Dana staying guarded while doing it suggests the questions were the visible part of some unease that did not surface in words.
Asking what worried Dana got you the real answer: a yes in principle, conditional on checking with the team, rather than a yes that just ends the conversation. That is closer to what you wanted than a quick, easy agreement would have been.
4
Next time
It remembers how they were
Your next prep with Dana starts from what happened last time.
My threads · Client
Change to deliveryDana Whitfield · 2 meetings
Continue
Next meeting
Agreeing a change to what you're doing
How to open
Open with the workload detail itself, not with the case for the change. She has already accepted the rationale in principle, so going back over why the change makes sense will read as if you have not registered what she actually needs from this conversation.
Watch for
Watch for whether her questions move from what this asks of her team to when and how it happens. That shift is the signal the hesitation has cleared and she is ready to agree.
Pyper helps you before, during and after every meeting.
Know what to expect
What the meeting is really about, and how they're likely to behave.
Mark Evans · Being challenged · Online
Mark found out about the start date change from Dana before you told him, and that is what this meeting is really about, not the change itself. Lead with that. If you open by explaining why the date moved, you will be defending a decision Mark might have accepted, while the actual problem — that he was the last to know about something in his own area — sits there unaddressed.
Go in knowing what to look for
The signs to watch for and what they mean, so they see you on top of it, not checking a screen.
In person · Megan, with her boss Daniel
Watch for whether Megan starts speaking to Daniel instead of to you — pointing things out to him, checking his reaction, translating your thinking into terms she thinks will land with him. That is a good sign. It means she is already trying to bring him along.
Online · Dana, with her boss Greg
If Greg pushes hard on delivery, Dana is likely to go quiet and let him lead… do not try to win Dana back into the conversation over him — answer Greg directly and precisely, since he is the one who needs convincing, and Dana will take her cue from how that lands.
Debrief within two minutes
Tap through a few questions when you have time. Pyper tells you what it means for next time.
The heart of it
And what caught you off guard?
How firm they were
How deep they wanted to go
How little they gave away
How fast they moved
Nothing much
Your feedback
Asking about mechanics is a way of testing something without having to say directly that it worries you. Dana staying guarded while doing it suggests the questions were the visible part of some unease that did not surface in words.
Asking what worried Dana got you the real answer: a yes in principle, conditional on checking with the team, rather than a yes that just ends the conversation. That is closer to what you wanted than a quick, easy agreement would have been.
It remembers how they were
Your next prep with Dana starts from what happened last time.
My threads · Client
Change to deliveryDana Whitfield · 2 meetings
Continue
Next meeting
Agreeing a change to what you're doing
How to open
Open with the workload detail itself, not with the case for the change. She has already accepted the rationale in principle, so going back over why the change makes sense will read as if you have not registered what she actually needs from this conversation.
Watch for
Watch for whether her questions move from what this asks of her team to when and how it happens. That shift is the signal the hesitation has cleared and she is ready to agree.
Ask anything. Including what you'd never ask at work.
Ask anything about the person and the meeting. Pyper already knows who you're meeting and what's at stake. Nobody at work sees it.
DWDana Whitfield · Agreeing a change to what you're doing
What if she says her team isn't ready for it?
Pyper can be wrong. Use your own judgement.
“Take it as a practical answer rather than a deflection. This is likely to be about something concrete, like capacity, timing, or a specific piece of work competing for her team's attention.”
“The precision and directness that feel intimidating are exactly what he needs to do today, not a sign the meeting is going badly. He is not trying to catch you out further, he is trying to finish being caught out once.”
“Open it by addressing both of them, not just Megan, even though she is the one you already know. Then bring Daniel in within the first couple of minutes, before he has had time to settle into watching rather than participating.”
“Don't push for her private opinion. Get her to be specific about the brief instead.”
“Mark pushing on disruption is expected, and answering it with precise detail rather than reassurance is what reads as competent to both of them. The thing to avoid is being caught without the specifics when Mark asks, because that is what looks bad in front of your boss, not Mark's pushback itself.”
Ask Pyper
Ask anything. Including what you'd never ask at work.
Ask anything about the person and the meeting. Pyper already knows who you're meeting and what's at stake. Nobody at work sees it.
DWDana Whitfield · Agreeing a change to what you're doing
What if she says her team isn't ready for it?
Pyper can be wrong. Use your own judgement.
“Take it as a practical answer rather than a deflection. This is likely to be about something concrete, like capacity, timing, or a specific piece of work competing for her team's attention.”
“The precision and directness that feel intimidating are exactly what he needs to do today, not a sign the meeting is going badly. He is not trying to catch you out further, he is trying to finish being caught out once.”
“Open it by addressing both of them, not just Megan, even though she is the one you already know. Then bring Daniel in within the first couple of minutes, before he has had time to settle into watching rather than participating.”
“Don't push for her private opinion. Get her to be specific about the brief instead.”
“Mark pushing on disruption is expected, and answering it with precise detail rather than reassurance is what reads as competent to both of them. The thing to avoid is being caught without the specifics when Mark asks, because that is what looks bad in front of your boss, not Mark's pushback itself.”
Pyper is better. So you do better.
Only you
Built for this.
It works with what little I know.Works it out from their role and what's at stake.
It's about this person, in this meeting.Advice that fits the pressure they're under.
I can ask the awkward question.Private by design, so you can be completely honest.
It gives me a few things I'll actually use.What to look for, and how to adapt.
It's there when it's over.Debrief in private, and plan the next meeting.
It tells me straight.Tells you what's likely to happen, and why.
