DBT DEAR MAN Skill

A senior manager regularly signals what he wants in meetings through leading questions and indirect comments, then expresses frustration when others don't respond as he hoped. He describes himself as direct but his team and peers experience him as unclear.

Frame the worksheet as a delivery problem, not a communication style overhaul. 'You know what you want — the worksheet helps you state it in a form other people can actually respond to. The Assert step is the one worth spending time on: write exactly what you are asking for, one sentence, before you're in the room.' Clients who resist direct communication often have an implicit belief that the other person should figure it out — worth naming: 'Is there a concern about what it means to ask directly? About how it looks?'

If the Assert section contains a question instead of a statement — 'Could we possibly...?' or 'I was wondering if...' — the client has not completed the step. The Assert step requires a declarative sentence with a specific request. Ask him to read it aloud and notice whether it is something the other person could say yes or no to, unambiguously.

Start with the Assert section. Ask him to read it aloud. Then ask: 'Is that what you actually want, or is that a softened version of what you want?' That question often surfaces a more specific underlying ask that the written version papers over. Then move to R — Reinforce: 'What did you name as the benefit to them? Is that genuinely true, or was it invented to smooth the ask?'

A VP knows how to advocate but tips into aggression when she feels dismissed. She wins short-term compliance while creating lasting wariness in peers. She wants to maintain her directness without the collateral damage.

Position DEAR MAN as a structure that lets her stay in the conversation longer without tipping into the register that triggers defensiveness. 'You don't need to become less direct — you need the sequence to hold when the pressure goes up. The M step is the one that matters most for you: staying on your objective when the other person reacts in a way that pulls you off it.' Clients in this pattern often resist any tool that sounds like softening. Name it: 'This isn't about lowering your intensity — it's about channeling it so it doesn't undercut your own outcome.'

Watch whether the M (Mindful) section identifies specific pulls — particular words, particular behaviors from the other person — or stays vague ('if things go sideways'). The more specifically she can name what historically pulls her off-track, the more the preparation is doing real work. If M is empty or generic, she has not thought through the moment where the conversation gets hard.

After the conversation, start with the debrief question from M: 'Did anything pull you off your objective? What was it?' Then compare what she wrote in Assert with what she actually said in the room. The gap between the prepared statement and the in-room statement tells you whether the structure held under pressure.

A recently promoted director has been given an additional project that conflicts directly with a strategic priority she owns. She has never declined an assignment from her manager and is uncertain whether she is allowed to push back at her level.

Frame the worksheet around clarity, not confrontation. 'This isn't about refusing — it's about having the conversation in a way that lands as problem-solving rather than resistance. The Describe step matters most here: if you start with the facts of your current load before you say anything about the new project, the ask makes sense in context rather than looking like avoidance.' Clients who have never declined an assignment often fear what it signals — worth checking whether she has a story about what no means.

Watch the A (Assert) step for hedging language: 'I'm not sure I can...', 'I might need some help with...', 'Would it be possible to...'. The worksheet requires a direct statement of what she is asking for — a delay, a resource, a re-prioritization decision. If the Assert section does not contain a clear ask, the conversation will not produce a clear outcome.

Start with the D (Describe) section and ask: 'Did you state the facts without interpretation — or did the description already contain your concern about the request?' Then move to N (Negotiate): what was she actually willing to offer as a path forward, and did the conversation stay there long enough to explore it?

A chief of staff negotiates agreements — on scope, pace, decision rights — and then watches them erode within weeks. She is clear in the room and unclear in the follow-through. Each new conversation about the same issue starts from scratch.

Position this tool around the N (Negotiate) step specifically. 'The conversation you're having isn't the problem — it's that the outcome isn't holding. This worksheet helps you build the Negotiate section with more specificity: not just what you will accept but what you will not, and what the path back looks like if the agreement gets ignored.' Some clients in this pattern need to see that negotiation includes naming the consequence of non-compliance, not just the preferred outcome.

If the Negotiate section lists only what she is willing to accept — and nothing about what happens if the agreement is broken — the structure has a gap. The negotiation needs to include what she will do when the boundary is tested again. If that section is empty, ask: 'What's the plan when this comes up again in three weeks?'

After she has used the tool and had the conversation, return to the Negotiate section and ask: 'What specifically did you agree to, and what did they agree to? Is that written down somewhere other than this worksheet?' The durability of the agreement often depends on whether it was made explicit in both directions.