Confidence Classic: How to Get the YES You Want with Heather!
In this episode of Creating Confidence with Heather Monahan, Heather shares lessons from her career in sales, publishing, and public speaking about the role of persistence in achieving professional success. She recounts receiving 14 rejections before securing her book deal, applying to over 100 TEDx events before gaining acceptance, and navigating various career setbacks that ultimately led to better opportunities. Through these experiences, she illustrates how rejection often stems from factors unrelated to personal worth and explains strategies for identifying true decision-makers and reframing objections.
Heather also addresses the importance of maintaining professional boundaries and honoring commitments. She reflects on how years of excessive flexibility diminished her perceived value and shares how enforcing firm boundaries transformed her career trajectory. The episode covers practical approaches for building evidence-based cases, positioning requests as mutually beneficial, and declining demands that conflict with existing agreements without compromising professional relationships.
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1-Page Summary
Perseverance Through Rejection
Heather Monahan's career journey illustrates that persistence through rejection is essential to achieving success. Drawing from her experiences in sales, publishing, and public speaking, she demonstrates that rejections are not personal failures but necessary steps toward accomplishment.
Rejections Are Part of Business, Not Personal Failures or Reasons to Quit
Heather explains that rejection is inevitable in professional pursuits, particularly in sales where hearing "no" is routine and carries no personal judgment. A rejection might stem from timing issues, not reaching the actual decision-maker, or various other impersonal factors. She notes that early-career professionals often give up after only three attempts, but her 20 years of sales experience taught her that real breakthroughs require persistence beyond three, five, or even ten tries.
Examples Illustrate That Success Often Follows Numerous Rejections
Heather's career provides compelling evidence of this principle. After perfecting her book proposal, she received 14 rejections from her agent before finally succeeding on her fifteenth attempt—her "lucky number 15." She applied to over 100 TEDx events between late 2018 and early 2019, facing rejection each time until a chance connection helped her refine her pitch and secure acceptance. Similarly, after being turned down for a promotion despite exceptional performance, she looked elsewhere and landed a better role in Boston within two weeks. During the pandemic, she persistently advocated for her book's hardcover edition despite paper shortages and initial refusals, ultimately succeeding through calm strategizing.
Distinguishing Between Rejection and Decision-Making Determines if "No" Is Final
Heather emphasizes never accepting a "no" from someone who cannot give you a "yes," as many rejections come from gatekeepers without final authority. She learned to identify true decision-makers and pitch directly to them, ideally face-to-face. When rejected by Rachel Hollis' agent, she asked for alternative suggestions, which led her to Peter Economy, who helped develop her successful book proposal. Heather views rejections as signals that a pitch isn't yet compelling enough, revealing opportunities to refine approaches or reach more relevant decision-makers.
Strategic Approaches To Overcoming Objections
Heather's experiences demonstrate that overcoming objections requires inquiry, evidence, relationship-building, and strategic alignment with organizational values.
Strategic Questions Turn Objections Into Opportunities
When HarperCollins canceled her hardcover edition due to pandemic paper shortages, Heather responded with curiosity-driven questioning. She discovered that high-profile authors and those with audiences likely to purchase higher-priced books were still receiving hardcovers. Her targeted questions revealed both the selection criteria and an opportunity to reposition her request by demonstrating she met those criteria.
Building a Case With Evidence Can Reverse Objections
Heather conducted thorough research, noting her LinkedIn audience had grown to over 220,000 business professionals—demographics statistically more likely to purchase hardcover books. She highlighted her November release timing, aligning with holiday gift-giving when hardcovers are preferred. This evidence-based approach positioned her book as commercially viable.
Positioning As a Partner for Mutual Success Increases the Likelihood of Gatekeeper Advocacy
Rather than demanding direct access to decision-makers, Heather framed her pitch as mutually beneficial and equipped her intermediary at the publisher with compelling data. By expressing confidence in her contact's ability to present the case, she empowered her advocate, resulting in approval for the hardcover edition.
Understanding Organizational Values Enables More Effective Positioning
Heather's TEDx experience further illustrates this principle. She initially highlighted her speaking credentials, but TEDx clarified they valued speakers who support their volunteer-driven mission and align talks with specific themes. Only when she repositioned her application to showcase alignment with their priorities did she succeed.
The Importance of Boundaries and Honoring Commitments
Heather stresses that respecting boundaries and commitments safeguards professional reputation and value. Her experiences show how over-commitment and excessive flexibility can diminish respect from clients and colleagues.
Boundaries and Commitments Safeguard Professional Reputation and Value
For years, Heather accommodated every request, rearranging plans and canceling commitments when clients or her company demanded changes. She reflects that this signaled her word was negotiable and her time less valuable. Despite years of flexibility, her company fired her after 14 years, reinforcing that removing boundaries prevents others from valuing her contributions appropriately. She now emphasizes that honoring commitments as agreed demonstrates reliability and deters unnecessary pressure.
Declining Requests That Violate Agreements Protects Commitments and Prevents Problems
Heather recounts a keynote speech in Italy where the organizer sought to extend the trip beyond her original Monday-to-Wednesday agreement, conflicting with her Thursday speaking engagement and family obligations. In the past, she would have rearranged everything, but she now views this as unsustainable. She communicated clearly about her unavailability, maintaining integrity while offering to help brainstorm alternatives, such as identifying other speakers.
External Changes Don't Require Full Cost and Logistical Absorption
Heather notes that last-minute issues, like the organizer's agent failing to book flights according to the original timeline, are not her responsibility to resolve by changing her schedule. She suggested fractional private jet options or booking another speaker, demonstrating helpfulness while maintaining her boundaries without absorbing costs of others' mismanagement.
Respecting Commitments and Boundaries Enhances Professional Value and Prevents Devaluation From Excessive Flexibility
Heather underscores that repeatedly renegotiating terms erodes respect and limits opportunities. Professionals who uphold firm boundaries project scarcity and reliability, making their services more highly valued. Her reputation grew significantly after enforcing boundaries—her recognition as a Top 50 keynote speaker in 2022, invitations from Google and Harvard, and fees thirty times higher than before all followed her refusal to accommodate last-minute changes. She affirms that knowing your worth and refusing to make every request your problem are vital for maintaining professional value and self-respect.
1-Page Summary
Additional Materials
Counterarguments
- Persistence through rejection is important, but it can also lead to wasted time and resources if the goal is unattainable or the approach is fundamentally flawed; knowing when to pivot or stop is also a valuable skill.
- Not all rejections are impersonal; sometimes feedback or rejection is based on personal fit, skill gaps, or genuine shortcomings that should be addressed.
- While many breakthroughs require persistence, some opportunities are highly competitive or limited, and repeated attempts may not always yield success regardless of effort.
- Focusing solely on persistence may overlook the importance of adaptability, learning from feedback, and strategic change rather than simply trying more times.
- Pitching directly to decision-makers is not always feasible or appropriate in all organizational cultures or industries, and bypassing established processes can sometimes backfire.
- Building a case with evidence does not guarantee reversal of objections, as decisions may be influenced by factors outside the professional’s control, such as budget constraints or shifting organizational priorities.
- Strictly maintaining boundaries and refusing flexibility may sometimes be perceived as uncooperative or rigid, potentially harming relationships or missing out on collaborative opportunities.
- Declining requests that violate prior agreements is generally positive, but in some cases, reasonable flexibility can build goodwill and long-term trust with clients or colleagues.
- Enforcing boundaries and refusing last-minute requests may not always lead to greater recognition or higher fees; outcomes can vary depending on industry norms and individual circumstances.
- Knowing one’s worth is important, but overestimating it or refusing to compromise can sometimes result in lost opportunities or alienation from potential partners.
Actionables
- You can create a personal rejection tracker to log every professional rejection, note the reason (if given), and brainstorm one new way to refine your approach or identify a better contact for each entry; review the tracker monthly to spot patterns and plan your next steps.
- A practical way to strengthen boundaries and self-respect is to draft a “commitment contract” listing your top three non-negotiable priorities for the next quarter, then use it as a reference before accepting new requests or projects to ensure you don’t overextend or compromise your values.
- You can practice pitching your ideas to a friend or peer who role-plays as a skeptical decision-maker, then ask them to invent objections or redirect you to someone else; use their feedback to develop strategic questions and evidence that address real-world pushback and gatekeeping.
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Perseverance Through Rejection
Heather Monahan’s journey demonstrates that persistence in the face of rejection is fundamental to achieving success. Through her experiences in sales, publishing, and public speaking, she illustrates that rejections are not failures, but necessary steps on the path to accomplishment.
Rejections Are Part of Business, Not Personal Failures or Reasons to Quit
Rejection is inevitable in any business or professional pursuit. Heather points out that, especially for those with a sales background, hearing "no" is normal and expected; it carries no personal judgment and rarely means poor performance. A "no" might stem from not dealing with the actual decision-maker, not yet fully clarifying benefits to the other party, bad timing, or several other impersonal factors. It is simply a part of the process and should not be treated as a definitive setback.
Heather notes that early-career professionals and salespeople often give up after only three attempts. Drawing from her 20 years of sales experience, she stresses that this is not enough effort; real results and breakthroughs require persistence beyond three, five, or even ten tries. Multiple rejections should never signal the end; they are often just the beginning of the journey.
Examples Illustrate That Success Often Follows Numerous Rejections
Heather Monahan’s career is filled with stories of overcoming relentless rejection before achieving breakthroughs. After spending months perfecting her book proposal, she received 14 firm rejections from her agent. Despite being told "nope, this is not gonna work" each time, Heather refused to quit. On her fifteenth attempt, her proposal was finally accepted—what she calls her "lucky number 15."
Similarly, Heather pursued a TEDx talk by applying to over 100 events between late 2018 and early 2019, writing painstaking applications each time. She was rejected over 100 times, but persisted. A chance connection at a Miami event led her to someone from TEDx who reviewed and explained why her pitch was falling short. By refining her approach, she finally received the acceptance she had worked so hard for.
Persistence also helped Heather in her corporate career. After transforming a lagging business unit and significantly increasing its performance, she pitched herself for a bigger role directly to the company president—and was turned down, despite exceptional results. Not deterred, she looked outside the company, pitching herself elsewhere and landing a better role in Boston within two weeks. Likewise, while working with HarperCollins during the pandemic, she faced setbacks regarding the release of her book’s hardcover edition due to a paper shortage. By staying calm, strategizing, and persistently building her case, she eventually succeeded in getting the hardcover edition approved.
Her journey reveals that every significant achievement was preceded by numerous rejections, and it was only by persisting far beyond the point where most people would have quit that she found success.
Distinguishing Between Rejection and Decision-Making Determines if "No" Is Final
A critical lesson Heather shares is the importance of identifying who holds the true authority to say "yes" or "no." Many rejections come from initial gatekeepers who lack final decision-making power. She emphasizes never to accept a "no" from someone who cannot give you a ...
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Perseverance Through Rejection
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Clarifications
- A literary agent represents authors and their work to publishers. They evaluate book proposals to decide if the project fits market demand and their client list. Agents negotiate contracts and help secure better deals and rights for the author. Their approval is often crucial for a publisher to consider a book seriously.
- A book proposal is a detailed document authors create to pitch their book idea to publishers or agents. It typically includes a summary, target audience, market analysis, author credentials, and sample chapters. Multiple submissions are common because publishers receive many proposals and may reject ideas that need refinement or don't fit their current needs. Authors revise and resubmit proposals to improve clarity, appeal, and alignment with publisher interests.
- TEDx events are independently organized conferences licensed by TED, where speakers apply to present talks on various topics. Each event has its own selection committee that reviews applications based on relevance, originality, and speaker readiness. Because many applicants compete and criteria vary, repeated applications help refine the pitch and increase chances of acceptance. Persistence allows applicants to learn from feedback and better align their talks with event themes.
- Gatekeepers are individuals who control access to decision-makers but do not have the authority to make final decisions themselves. They often screen requests, manage schedules, or filter communications to protect decision-makers from unnecessary interruptions. Understanding who the true decision-maker is helps focus efforts on the person who can approve or reject proposals. Bypassing or gaining the support of gatekeepers can be a strategic step toward reaching decision-makers effectively.
- Pitching directly to decision-makers is more effective because they have the authority to approve or reject proposals immediately. Intermediaries may filter or alter the message, reducing its impact or delaying decisions. Direct communication allows for immediate feedback and the chance to address concerns on the spot. It also builds personal rapport, making it harder for decision-makers to dismiss the pitch casually.
- During the pandemic, global supply chains were disrupted, causing shortages in raw materials like paper. Paper mills reduced production due to labor shortages and safety measures. This led to higher costs and limited availability of paper for publishers. Consequently, book printing schedules and formats, such as hardcover editions, were delayed or altered.
- Securing corporate promotions often requires demonstrating consistent high performance and aligning with company goals. Candidates usually need approval from multiple levels of management, including direct supervisors and higher executives. Internal politics, budget constraints, and organizational restructuring can complicate the process. Networking and direct communication with decision-makers increase the chances of success.
- In publishing, the hardcover edition is often the first and most prest ...
Counterarguments
- Persistence alone does not guarantee success; factors such as privilege, access to resources, timing, and luck can play significant roles in achieving breakthroughs.
- For some individuals, repeated rejection can lead to diminishing returns, wasted resources, or emotional burnout, making strategic withdrawal or pivoting a more rational choice than continued persistence.
- Not all rejections are impersonal; sometimes feedback or rejection is based on genuine shortcomings in skills, product, or approach that require substantive change rather than just persistence.
- The narrative may underemphasize the importance of learning from rejection and adapting, rather than simply persisting with the same approach.
- In some industries or contexts, repeated attempts after rejection can be perceived as unprofessional or disrespectful, potentially harming reputation or relationships.
- The focus on indiv ...
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Strategic Approaches To Overcoming Objections
Heather Monahan’s experience navigating publishing and speaking opportunity roadblocks demonstrates that overcoming objections is a dynamic blend of inquiry, evidence, relationship-building, and strategic alignment with organizational values.
Strategic Questions Turn Objections Into Opportunities
Faced with having the hardcover edition of her book canceled due to pandemic-induced paper shortages, Heather responded not with anger but with curiosity-driven questioning. When HarperCollins Leadership informed her that portions of their agreement, including hardcover publication, were now void for smaller titles, she first clarified whether any authors were receiving hardcovers. The publisher admitted that high-profile authors like Will Smith and Brene Brown, or those with audiences that spend on higher price-point books, were prioritized.
Heather’s targeted questions revealed both the criteria for hardcover selection—sales potential and audience spending habits—and an opportunity: If she could demonstrate her value according to these criteria, she might reposition her request.
Building a Case With Evidence Can Reverse Objections
Armed with this insight, Heather conducted research to build a thorough, evidence-based case. Reviewing her original proposal, she noted exponential growth on LinkedIn, her largest platform, now exceeding 220,000 business professionals—an audience statistically more likely to purchase hardcover books and with greater disposable income. She gathered data detailing LinkedIn demographics and the overlap with typical hardcover buyers, such as business professionals and people over thirty.
Strategically, Heather highlighted her book’s November release, aligning it with the holiday season. Data on consumer habits showed hardcover books are favored as holiday gifts, further strengthening her argument that a hardcover edition for her business-focused, gift-timed book was not just possible but commercially savvy.
Positioning As a Partner for Mutual Success Increases the Likelihood of Gatekeeper Advocacy
Recognizing the importance of her intermediary at the publisher, Heather framed her pitch as mutually beneficial, showing how a hardcover would serve both her interests and the publisher’s bottom line. She offered to supply data and research, asking if her contact would "fight" for the case if Heather provided compelling evidence. The intermediary agreed, feeling empowered by Heather’s thorough preparation and trust.
Heather equipped her advocate with every relevant data point and, rather than insisting on attending the decision meeting herself, ex ...
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Strategic Approaches To Overcoming Objections
Additional Materials
Counterarguments
- While Heather Monahan’s approach is effective in her specific context, not all individuals have access to the same resources, data, or professional networks to build similarly compelling cases.
- The strategy of aligning with organizational values and building relationships may not always overcome systemic biases or entrenched gatekeeping practices, especially for those from marginalized backgrounds.
- Relying on data-driven arguments and strategic positioning may not be feasible in industries or situations where subjective preferences or personal relationships outweigh objective evidence.
- The emphasis on mutual benefit and empowerment of intermediaries assumes a level of goodwill and openness from gatekeepers that may not exist in all organizations.
- The approach described may require significant time and effort, which could be prohibitive for individuals managin ...
Actionables
- You can create a simple checklist before any important request or pitch that prompts you to identify the other party’s top priorities, recent public statements, and organizational values, so you tailor your approach to what matters most to them rather than what matters most to you.
- A practical way to uncover hidden decision criteria is to ask open-ended questions like “What would make this a win for you?” or “What concerns should I address to make this easier for you to support?” during conversations where you’re seeking approval or buy-in.
- You can empower someone advocating on your behalf by sending them ...
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The Importance of Boundaries and Honoring Commitments
Heather Monahan stresses the necessity of respecting boundaries and commitments, arguing that doing so safeguards one’s professional reputation and value. Her experiences illustrate how over-commitment and excessive flexibility can ultimately lead to diminished respect and appreciation from clients and colleagues.
Boundaries and Commitments Safeguard Professional Reputation and Value
Monahan shares that, for many years, she would drop everything to accommodate others, rearranging plans, canceling other commitments, and even leaving her son for extended periods when clients or her company demanded changes. She reflects that frequently renegotiating her commitments—especially when new demands emerged after initial agreements—signaled that her word was negotiable and her time was less valuable. Instead of gaining extra value or appreciation, she found that clients and employers devalued her reliability and viewed her availability as unlimited.
Despite her flexibility and efforts to always say “yes,” Monahan recalls being fired by her company after 14 years. The very organization that had pressured her to constantly change plans and travel unexpectedly let her go, despite years of accommodation. This experience reinforced her realization that respecting her own limits is crucial and that removing boundaries ultimately prevents others from taking her seriously or valuing her contributions at their true worth. She emphasizes that honoring commitments as agreed, and not allowing others to easily renegotiate terms, deters clients from applying unnecessary pressure and demonstrates her reliability.
Declining Requests That Violate Agreements Protects Commitments and Prevents Problems
Monahan recounts a specific situation involving a keynote speech in Italy. Her original agreement stipulated that she would travel Monday and return by Wednesday night, aligning with her speaking engagement in the United States on Thursday and her son’s school and care schedule. When the event organizer sought to extend the trip to Sunday through Thursday, Monahan recognized the request conflicted with existing obligations.
In the past, she would have tried to rearrange or cancel on other clients to accommodate this new demand, but she now views this as ineffective and unsustainable. She explains that canceling existing clients or rescheduling for the sake of “responsiveness” actually creates more problems, damages relationships, and teaches others that her boundaries can be ignored. Instead, Monahan communicated clearly with the organizer, explaining her unavailability beyond the original dates and that her calendar could not accommodate the proposed change. By reasoning with the client and politely refusing to break prior commitments, she maintained her integrity while offering to help brainstorm other solutions, such as identifying alternative speakers for the event.
External Changes Don't Require Full Cost and Logistical Absorption
Monahan notes that last-minute issues, such as unavailable flights or travel disruptions, are the responsibility of the event organizer—not hers to resolve by changing her schedule. In the Italy scenario, the organizer’s agent failed to book flights in accordance with their original timeline, and commercial options became unavailable. Monahan was clear that the lack of flights was due to the organizer’s own planning and decision-making, not a justification for her to sacrifice other professional or personal commitments.
She advised the organizer to look into fractional private jet options or to consider booking another available speaker, offering her agent as a resource for additional help. Mo ...
Here’s what you’ll find in our full summary
The Importance of Boundaries and Honoring Commitments
Additional Materials
Counterarguments
- In some industries or cultures, flexibility and willingness to accommodate last-minute changes are highly valued and can lead to stronger client relationships and more opportunities.
- Strictly enforcing boundaries may be perceived as inflexibility or lack of teamwork, potentially harming collaboration or client satisfaction in certain contexts.
- There are situations where renegotiating commitments is necessary due to unforeseen circumstances, and a rigid approach could be seen as uncooperative or unsympathetic.
- For early-career professionals or those building a client base, demonstrating extra availability and adaptability can be essential for establishing trust and gaining experience.
- Some clients or employers may interpret firm boundaries as a lack of dedication or passion for the work ...
Actionables
- You can create a personal commitment tracker by listing your current professional promises and marking each with a color code for status (on track, at risk, completed), then review it weekly to spot patterns where you tend to overcommit or renegotiate, helping you proactively adjust your boundaries before issues arise.
- A practical way to reinforce your boundaries is to draft a short, polite template message for declining new requests that conflict with existing commitments, so you can respond quickly and confidently without feeling pressured in the moment.
- Yo ...
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