Make That Ask A Tell

When I am in discussions with a potential new client and we get to the part about how she is going to win support for her coaching from her male boss, almost always she starts with, “I’ll ask….”

I stop her right there.

Women and men use language at work differently explains Georgetown University linguistics professor and researcher Deborah Tannen, in her seminal best seller, “Talking from 9 to 5: Women and Men at work.”

Men talk to establish position and gain status. They are more interested in the bottom line. They speak directly and to the point, projecting power and assertiveness (even when they don’t feel that way).  “We should do it this way.” “I’m in charge.” “I deserve a raise.”

Watch men do this, which isn’t hard because men do it all the time. Men are far more likely to tell than to ask. They declare their position and then fight for their ideas. They don’t ask for raises; they tell the boss why they should get one. “I should get a raise. Here’s why…” or, “I’m ready for a promotion because….”

A woman talks to establish rapport and build relationship. It is a process for her and she uses various softening techniques to help with that. Turning a statement into a question is common. Lois Frankel (Nice Girls Don’t Get the Corner Office).

 includes this as one of the 101 Unconscious Mistakes Women Make That Sabotage Their Careers: “Don’t you think we should…?” Or hedging: “I sort of….” “This could be…..” Sometimes women discount their message before they even say it: “I could be wrong but….” Male colleagues are likely to hear these softening words as indications of insecurity or worse, incompetence.

Rarely does a woman understand that to a man, asking suggests a lack of confidence and competence. He concludes she does not know the answer and he must make the decision or give permission. This sets her up for getting a “No.” Telling implies that she knows what she’s talking about and therefore he should pay attention.

Here’s how I coach a client to get support from her boss for anything e.g. a project launch, new head count, an executive coach, etc.

First, we prepare a justification in advance. Any recommendation benefits from a compelling business case and don’t expect to figure it out once you get in front of the boss. State the problem clearly. What situation or circumstance needs to be addressed? What do you expect the outcome of your proposed solution to be? How will the team or organization benefit? Explain what you need and be prepared to back it up with a justification.

Next we begin to formulate and write a script. Writing it down forces clarity and allows for hammering out the rationale. We adjust the script until she agrees it is a case she can make to her boss.

Then, we role play the conversation. This gives her the opportunity to hear her argument out loud and also starts the process of memorizing so once she goes live, she can focus on the reaction she gets rather than how to say it.

It doesn’t always work. At least not right away. One client had to make her case for an executive coach  three separate times before her manager agreed to fund it. Each time she improved her rationale, which built more resolve and fed her confidence until her determination literally made her unstoppable.  In a debrief with me, she observed that the company had paid for his MBA and he had worked on school assignments during work hours. That expense was many times greater than her request. When she added that to her argument, she won approval. She continues to draw on that win when she needs encouragement to go after what she wants from work.

Sometimes the Tell works a lot better than anyone expects. In two other cases, both clients said little more than “I want to work with an executive coach.” Here’s what happened next:

“My boss said, ‘Thank God! I’ve wanted to help you but I haven’t known what would be helpful.’” He wrote the check.

“Todd’s response was, ‘That’s a great idea and what took you so long?’” He also wrote the check.

We still get some good laughs out of that.


1.    Prepare your business case. Proper Prior Preparation Prevents Poor Performance

2.    Write a script using declarative statements. Don’t ask. Tell.

3.    Practice out loud. Role play with a trusted ally.

4.    A “No” means “Not now.” Avoid framing it as a personal attack. Refine your justification and try again.

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