Hope For The Warriors Workshop Series – Part 1 Recap: Breaking Into the Civilian Workforce with Robert Half’s Richard Deosingh

As part of our ongoing mission to support career transitions for veterans, military spouses, and caregivers, Hope For The Warriors launched the first installment of our new Workshop Series with an incredible partner: Robert Half.

This session, titled “Breaking Into the Civilian Workforce,” featured insights from Richard Deosingh, District President at Robert Half, who answered real-time questions from our warrior community. From addressing employment gaps to standing out in a competitive job market, Richard offered clear, practical advice that empowered attendees to take actionable next steps.

Here’s a recap of the key takeaways:

What Are Hiring Managers Really Looking For?

According to Richard, technical skills matter—but what truly sets a candidate apart is their attitude, adaptability, and aptitude. Employers want to see that you can grow with the company, embrace challenges with a positive mindset, and communicate effectively in a team environment. Emotional intelligence and collaboration are highly valued across all industries.

How Should I Handle a Resume Gap?

Honesty is key. Richard encouraged attendees to be transparent about gaps while showing initiative—such as enrolling in refresher courses, pursuing certifications, or contributing to open-source projects. These actions demonstrate your commitment to staying current in a fast-moving industry.

How Do I Get Started in Cybersecurity?

Begin by earning a recognized entry-level certification like CompTIA Security+, GIAC, or CEH, Richard advised. Combine that with a degree in computer science or IT, and seek roles in IT audit, compliance, or network security. Hands-on labs and simulations—as well as internships—can significantly boost your credibility.

How Can I Build a Network from Scratch?

Don’t underestimate the power of LinkedIn. Richard recommended creating a professional LinkedIn presence, following companies you admire, and connecting with recruiters and industry peers. Engage in conversations, join groups, and attend virtual events to grow your visibility.

Is Remote Work Still Viable?

Yes, but expectations are shifting. Richard noted that while remote jobs still exist, many companies are moving toward hybrid models. Stay open to flexible opportunities and emphasize your ability to thrive in both remote and in-person environments.

How Else Can I Prepare for a Cyber Career?

In addition to certifications, Richard recommended reading cybersecurity blogs, joining online communities like r/cybersecurity and Cybrary, and participating in Capture The Flag (CTF) competitions to develop problem-solving skills and stay on top of industry trends.

Should I Disclose Veteran or Disability Status?

“Yes,” said Richard—truthfulness is important. Many employers, especially federal contractors, actively seek to hire veterans and people with disabilities. Focus on your value, skills, and experience. Let your qualifications shine.

What If I’m Aiming for an Executive Role?

Richard shared that Robert Half supports professionals at all levels—including executives—and never charges candidates for job placement or coaching services. While firms like Spencer Stuart, Korn Ferry, and BlueSteps also support senior professionals, Robert Half offers career support across fields like technology, finance, and legal at no cost to candidates.

How Do I Translate Military Leadership to Civilian Roles?

Military experience builds skills in leadership, accountability, and decision-making under pressure. Richard encouraged attendees to reframe their service using civilian language, like “project manager” or “operations lead,” and highlight outcomes and team impact.

What’s the #1 Resume Mistake Veterans Make?

Failing to translate military jargon into civilian terms. Avoid acronyms and focus instead on responsibilities, results, and leadership experience that align with the job you’re applying for.

What If I’m Returning to Work After SSDI?

Richard emphasized the power of resilience. Be upfront about your employment gap and share how you’ve remained engaged, whether through volunteer work, skill-building, or courses. You’re not starting over, you’re moving forward.

How Can I Respond to Bias in an Interview?

If you sense bias, Richard recommends staying professional and focused. Re-center the conversation around your strengths, experiences, and value you can bring to the team. Lead with confidence and quantify your accomplishments when possible.