Welcome to BlueSteps Career Advisor Spotlight, a series where we feature top BlueSteps executive-level career coaches and advisors from around the world. In this series, we will conduct interviews with highly experienced and qualified professionals who specialize in guiding senior executives through the complexities of the job market. Our guests will share their insights, perspectives, and strategies on a range of topics, including executive job search, career advancement, personal branding, and leadership development.

We're delighted to feature Don Orlando as our latest in the BlueSteps Career Advisor Spotlight series. Don is a highly experienced executive coach and career advisor with a passion for helping senior-level professionals achieve their career goals. With over 20 years of experience in executive search and career development, he brings a wealth of insights and expertise to his work with clients.

My experience and qualifications as a career coach:

I was a full-service career coach before the industry had a name for what I do.

I am my clients’ confidant. I am the only person they can turn to in complete confidence. Those with whom they interact don’t have my experience, certifications, and professional development. Just one of the credentials I hold is shared by only ten other people on earth.

I’ve been a board member for two career development professional organizations and a monthly contributor to the trade magazine for more than a decade. My résumés and cover letters appear in more than 50 books. I’ve attended more than 25 professional conferences and spoke at many of them.

For 30 years, I’ve supported private, not-for-profit, and public sector executives. One of my clients rose from a very senior government post to be a full member of a president’s cabinet. The Air Force asked me to design, deliver, and instruct their first Executive Transition Assistance Program, which continues to this day.

What is your approach to helping clients transition into new executive roles?

I help clients rise above the sea of pernicious and ubiquitous “folklore” about career advancement. I leverage their proven excellence to find the career which is right for them—as they define “right.” We rise far above “keywords,” responsibilities, and “tips & tricks.”

When I help them build networks of the best practitioners, my clients learn precisely which questions to ask, of whom to ask them, and how to interpret the answers. Experts have told them what it really takes to succeed.

We also explore how many opportunities there are, sometimes right down to the ZIP code. Clients understand more than pay, perks, benefits, bonuses, and severance. They know what it takes to succeed in any culture they might encounter. That wisdom guides every action they take, every document I write for them, and every version of their brand.

Since top jobs may never be advertised, we use advanced techniques to respond to announcements and help recruiters. Because my clients know how, when, where, and to whom they make their brand visible, the best jobs seek them out.

What strategies do you use to help clients improve their résumés and cover letters?

My clients know the roles and missions of every document I write. Each word, each phrase, each sentence, and each paragraph matches their excellence against corporate needs. My documents are entirely focused on ROI. They prove my clients will make organizations much more money than it takes to hire and retain them.

We also know no collection of nice sounding adjectives, traits, or “keywords,” means anything standing by themselves. I use “living, breathing” examples of problems my clients solved, how they solved them, what the results were, and the context of each.

My cover letters never rehash the résumé or task the reader with calling them. Hiring officials know how my clients got the commanding results shown in their résumés.

I also specialize in the professional bio. These are never backward-looking summaries. They lay out the profit-building actions my clients will deliver through innovation and business development.

The power doesn’t stop with résumés, cover letters, and bios. The “job cinching” letters I designed have never failed to get second interviews.

How do you stay up to date on the latest trends and best practices in executive coaching?

I must leverage the latest trends, best practices, potential legislation, cultural differences, and data sources. My clients don’t have enough hours to tackle those challenges.

Because I taught critical thinking to senior executives, I can zero in on the best sources and translate data into information my clients can use almost intuitively.

I also rely upon my own professional mentors: well-respected career development colleagues. All are smarter and better informed than I am.

I don’t limit myself to mining career resources. I must understand international political and economic trends by subscribing to respected media channels globally.

How do you handle difficult or sensitive situations that may arise during coaching sessions with executives?

I never forget: all my clients are under stress. Everything I do affects their lives and the lives of their families, for years to come. And so I listen—really listen—to my clients and suspend all judgment.

Because a career coach should never tell clients what to do, I help them envision their optimum end states. That helps them apply their excellence to reaching those goals. We focus on the future, not the past.

I help clients forgive people and organizations who treated them badly. That has nothing to do with tolerating bad behavior. I help clients learn from each stressful time. They don’t allow difficult people or situations to dictate any part of their lives.

How do you help clients prepare for and negotiate job offers?

My clients see job offers as opportunities for coalitions, not contests. We don’t focus just on the job offer. I make sure my clients can judge the future that lies beyond every offer.

I make certain my clients have access to data that define their worth. More importantly, my clients know precisely what it takes to really succeed in any job and which visible indicators their boss will use to judge their success. They know which resources, including access to people and wisdom, they must have.

How do you tailor your coaching sessions to meet the unique needs of each of your executive clients?

I prepare even before my first conversation with every potential client. Earlier versions of their résumés and cover letters, their LinkedIn profiles, their social media posts, provide clues about what matters most to them.

Before every meeting, we both know what the client will be able to do at the end of the session that they couldn’t do before. I often provide detailed note-taking devices. These never substitute for conversations. Rather, they relieve clients of the need to take notes and serve as outlines they can tailor to themselves. I equip them with lifetime skills and discernment. Finally, every client knows they can contact me any hour of any day or night—holidays and weekends included.

How do you approach coaching for executive-level interviews?

I counter stress-inducing “folklore” about interviews such as supposed top 10 (or is it 25?) questions and answers. My clients treat every interview as a conversation between interested people to solve problems.

They strive to find which problems keep any interviewer up at night. That keeps the interview on track since every executive must be a problem solver.

They rely upon “Orlando’s First Law of Employment:” everything they see, everything they hear, everything they read, have been condoned or encouraged by the leadership—without exception.

We find the best companies by comparing what they think their brand is with what their customers think. Customers of the very best companies see the brand just as the company does. We don’t target those who don’t pass this basic test.


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