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There are aspects of Don Draper, the Mad Men advertising executive, I wish to channel. Not the Rico Suave part or the 5 o’clock shadow. It’s the fist-slamming, declarative part of him when he’s around his clients that gets this ad agency principal stirred up.

In one episode, he told the chief executive of an account he wanted that his current agency did awful work — not his exact term — and he confidently boasted that Sterling Cooper would have its account. My head instantly hummed as if I were at a church service celebrating the rebirth of business.

I know I occasionally have trouble separating TV life from real life. And I know that asking what Don Draper would do isn’t necessarily going to translate into a plan of action for my agency, Door Number 3. Right after that Mad Men episode, several of us met with a prospective client that sells a high quality commodity product from 15 or so retail stores. The company has been in business for 30-plus years but it has been experiencing a decline. Its usual advertising isn’t getting them the usual results.

After much pre-pitch research, our team identified several factors that may be affecting the company’s business: the rise of competition and the rise of more affluent, discerning buyers. We prepared a list of recommendations focusing on media buying, messaging and public relations. One was that the company’s name had become a hindrance; it didn’t reflect the quality of the company’s products and customer service or speak to the customers it was hoping to attract. Easily confused with competitor names, the name did little to help the company stand out. So I scripted into the presentation, near its conclusion, a rather daring suggestion to change the name – something I honestly felt the company needed to hear.

When I rehearsed the presentation with our team, my colleagues pushed back. After some debate, we collectively modified the script to this: “Is your name working as hard for you as it could be?” The feeling was that, after all the time and research we put into getting to this point with the client’s executives, we shouldn’t risk alienating them with such a bold position. While the business owner in me saw the wisdom of this approach, the Don Draper in me bridled at our lack of nerve. It’s the careful blend of those two qualities, wisdom and nerve, that makes sense for a business owner – especially at the outset of a relationship.

While I believed the name change would be beneficial, I also knew that some people on the client side of the presentation would be likely to have an attachment, even an emotional investment, in the name. They or their predecessors may have created it; the people who created it might still be part of the decision-making team. It might make more sense to tread lightly and avoid the risk of being shut down. The other, very real challenge is that advertising is highly subjective. Almost everyone likes to think he or she is an expert — which makes for lots of experts with differing opinions.

When we introduced the question of their name working as hard as it could for them, there were a few eyebrows raised and glances exchanged, but no one ran from the building screaming. In the end, the presentation went well, and we are moving to the proposal stage.

I used to do stand-up comedy. That experience has helped me tremendously in the business world. I know when we’ve got the room and when the crickets are winning. At a presentation, if we step in it, I can tell right away. Eyes on the other side of the table grow distant, body language shifts and people start checking their phones. The question is, what do you do next? Do you change your routine, presentation, subject matter, approach? Or do you stick with what you believe in, what you prepared, and what you are probably most comfortable with? Basically, the question is, when the potential new business opportunity is heading south, do you abandon the script and go rogue?

I’ve wondered if being bold attracts bold customers. These type of clients are immensely desired by an ad agency. Sameness is lameness in the marketing world. But the reality is that many companies and institutions, with their own pressures, financial considerations and politics that we know little about going in, don’t feel they have the luxury to be bold. And we always acknowledge that clients and potential clients know their businesses best; our role is to overlay that knowledge with solid marketing advice and the ability to help focus messaging to the target audience. The Don Draper in me wants to put our strategic thinking out there without hesitation. The business owner side of me wants to earn their trust first before risking entering tender territory too early in a relationship.

Still, we keep a novena candle flickering for being bold and putting a stake in the ground for what we believe in. How bold will we go when we get to the proposal stage? I will let you know.

MP Mueller is the founder of Door Number 3, a boutique advertising agency in Austin, Tex.