
People in Transition · 2026-08-03 · 29 min
Key moments - from our scoring
Substance score
45 / 100
Five dimensions, 20 points each
Nicolette Hemingway shares actionable career coaching guidance for job seekers at all levels. The conversation covers foundational job search strategy - starting with self-reflection on values and organizational fit before applying, then tailoring resumes and cover letters with keywords from job descriptions to beat Applicant Tracking Systems (ATS). Hemingway emphasizes that employers screen resumes in 10 seconds or less, making formatting (standard fonts like Calibri or Verdana, clean black-and-white layouts) critical. For career transitioners, particularly those moving from government or military to private sector, the biggest adjustment is cultural - moving from formal hierarchies and acronyms to first-name informality. She recommends Transition Assistance Program (TAP) classes for military separatees and advises scanning resumes through free ATS-matching tools to achieve 80%+ keyword alignment. Interview preparation focuses on professional appearance, research-backed questions, and post-interview thank-you emails (only 15% of candidates send them, yet they're often decisive). Hemingway also addresses older workers, ageism mitigation through continuous skill-building, AI's expanding role in hiring, personal branding consistency across LinkedIn and other platforms, and networking as genuine relationship-building rather than self-promotion. Her book, Five Secrets to Nail that Job, emphasizes looking the part, talking the part (preparation), and understanding that effective job search takes 2.5 months on average.
Use keywords and phrases directly from the job description and aim for at least 80% keyword match. You can test this using free or paid ATS-scanning tools before submitting. Make sure your resume uses a standard font like Calibri or Verdana, maintains uniform formatting with no shading or multiple colors, and keeps everything in black and white for maximum clarity.
Bringing the culture, language, and acronyms from your previous organization into a new one. Each organization has its own culture, terminology, and norms. Research the new organization's culture through their website, imagery, and by asking during interviews what kind of culture they have.
Only about 15% of candidates send thank-you emails, yet hiring panels often consider only those candidates. Sending one signals genuine interest and respect for the interviewer's time, and it's frequently the deciding factor when multiple qualified candidates are competing for the role.
Attend Transition Assistance Program (TAP) classes provided by every military branch, which teach how to translate military language and terminology into private sector language. The biggest adjustment is moving from formal chain-of-command communication (using titles and 'yes, sir/ma'am') to first-name, less formal interactions.
Reflect on what makes you happy to come to work each day (values, industry, mission), look at organizations that mirror those values, and take free online assessments to identify your strengths, weaknesses, and what you truly enjoy doing.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains established career coaching advice that is broadly applicable but rarely novel or surprising to B2B operators. While specific tactics like resume keyword matching (80% ATS threshold) and the thank-you email conversion story (3 of 20 candidates) provide some concrete data, most recommendations are standard platitudes: target your resume, research company culture, develop soft skills, network authentically. The pacing includes substantial filler (lengthy networking analogy about underwater basket weaving, Zootopia movie reference) that dilutes insight density.
Out of those 20 people, only three people sent a, uh, thank you email. Guess what? They only considered those three people
you want to at least hit for 80% or higher in terms of your resume matching the job description
The episode recycles widely-known career frameworks with minimal fresh perspective. Concepts like personal branding, soft skills, culture research, and dressing appropriately for interviews are standard fare in career coaching. The guest offers no contrarian takes, first-principles thinking, or counterintuitive arguments. The military-to-private-sector transition advice is somewhat relevant but still relies on conventional wisdom (culture shock, acronyms) without deeper analysis of why or how to truly navigate the shift.
Employers value skills such as leadership, excellent communication, whether that's verbal or in writing, collaboration, flexibility, adaptability, ethics, critical thinking, interpersonal skills
You are your best brand ambassador. Whether you're in leadership or you're in an entry level position
Nik Hemingway brings 20+ years of interview panel experience and operates as a practitioner (career coach, resume writer), which is genuinely relevant. However, the episode lacks depth on the guest's own business metrics, client outcomes at scale, or high-profile transitions she has managed. Her background in government and public health is mentioned but not leveraged meaningfully in the conversation. She is a solid mid-tier practitioner but not a standout operator with proven high-stakes results to share.
she brings more than 20 years of experience serving on interview panels, along with a strong background in public health, government services, and leadership
Nike helps people move forward with confidence through career coaching, interview preparation, relationship resume writing, executive coaching, and women's empowerment coaching
The episode provides a few concrete data points (3 of 20 thank-you emails, 80% ATS match threshold, 2.5 months average job search duration, Google dress code example) but is otherwise light on specifics. Most advice lacks named examples, real case studies with measurable outcomes, dollar figures, or timeline specificity. The military transition advice references TAP programs by name but does not cite specific client transformations or quantifiable results. Many recommendations remain abstract ("develop skills," "research culture").
Out of those 20 people, only three people sent a, uh, thank you email
you want to at least hit for 80% or higher in terms of your resume matching the job description
The host asks reasonable follow-up questions ("When you said pictures, what do you mean by that?" and questions about AI's keyword matching) but rarely pushes back or probe deeper. Most questions are softball opening statements that invite predictable answers. The host does not challenge claims, ask for exceptions or failures, or explore tension in the guest's advice. The conversation flows pleasantly but lacks the edge and genuine intellectual friction that would indicate strong interviewing craft.
When you said pictures, what do you mean by that?
Can you talk to us in terms of how AI is used in that screening process? What have you seen?
Computed from the transcript - who did the talking, and the words that came up most.
Whether you're looking for your first job, changing careers, transitioning from the military or government to the private sector, or simply trying to stand out in today's competitive job market, this episode is packed with practical advice you can use immediately. Our guest, Nicholette "Nik" Hemingway , is a career coach, interview preparation expert, résumé writer, executive coach, and the owner of Nike H Speaks LLC. A retired military officer with more than 25 years of leadership experience and extensive experience interviewing candidates at the city, county, state, and federal levels, Nik knows exactly what employers are looking for - and the mistakes that keep qualified candidates from getting hired. She is also the author of 5 Secrets to Nail That Job! and has helped countless professionals gain the confidence and skills to land their next opportunity.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Welcome to People in Transition, the podcast where real stories meet real growth. I'm your host, Bob Gurris, and today I'm excited to welcome Nicolette Hemingway, also known as Nike, the owner of Nike H Speaks, llc. Nike helps people move forward with confidence through career coaching, interview preparation, relationship resume writing, executive coaching, and women's empowerment coaching. She brings more than 20 years of experience serving on interview panels, along with a strong background in public health, government services, and leadership. She's also the author of Five Secrets to Nail that Job. Naik is the kind of guest it brings both practical advice and real encouragement, especially for anyone navigating a career change, trying to break into new opportunities, or simply needing a fresh start. So settle in because this conversation is going to leave you informed, encouraged, and ready to take your next step. Naik, great to talk with you today.
Speaker B: Yes, Bob, thank you for the invitation. I am looking forward to this.
Speaker A: Nick, let's jump right in. For someone who is actively looking for work right now, what's the very first thing they should do to get organized and focused on their job search?
Speaker B: That is a great question, Bob. The first thing I would say is looking for a job is a process. It's a job in itself. So be patient and give yourself grace. And by that I mean you're going to get rejection emails, you're going to get no responses from your applications. But you have to keep on at it. Organize. Look at what organizations you want to focus on. Is it a large organization? Is it a small one? Look at what you value. Is it teamwork? Is it volunteering? So look at those things first and then prepare your job search. Then you can focus on the organizations that have the same values that you have and what you're interested in. You don't just want to throw resumes out there with no goal in mind.
Speaker A: Yeah, probably too many people, when they start their search immediately think that, okay, I need to start sending applications in, start responding to ads and so forth, as opposed to doing some of that reflective work about their interests, their values, and what they're looking for.
Speaker B: Correct. And that's what makes a lot of people anxious because they're just putting resumes out there and they're not really focusing on what type of job that they're really looking for and what they really want.
Speaker A: Nike, is there anything that is really important that job seekers should be doing today to help improve their chances of getting hired?
Speaker B: Yes. One of the things I think of is you must target your resume for each particular job. I remember I was teaching a workshop on resume writing. And a gentleman in the course was saying, oh, he sent out like 200 resumes and he didn't get a response. I said, well, can you bring me a resume? Can I look at it? And so he bought it in the next day. And I told him, no wonder you're not getting any responses. This is generic. It has to be tailored to that specific job. So each resume, each cover letter is for that job. And you have to use the keywords and phrases in that job description to put in your resume and your cover letter.
Speaker A: Mike, when people are trying to transition into a new career, what have you seen as the biggest mistake that they make as they're setting up their plans?
Speaker B: That is a really good question, Bob. One of the things I've seen is that they're trying to bring the culture of their previous organization into the new one. Uh, each organization has its own culture. You can't come in with an established culture into a new culture. And using language from your old culture. For example, having worked in government, they use acronyms for everything going into a new organization, there are going to be new acronyms. So what you may have said in your previous organization may not be understandable in your new organization.
Speaker A: Any suggestion in terms of how to find what that culture is in your new organization?
Speaker B: Yes. A lot of times organizations put their culture on their website. So that's part of your research. When you're looking for another job, look what the culture says. And also pictures will give you an idea. And even when you're interviewing, you can ask, what type of culture does this organization have if it hasn't been stated on the website?
Speaker A: When you said pictures, what do you mean by that?
Speaker B: When you're on the website, a lot of times companies will have pictures, uh, of employees working or just various pictures of, um, what that organization does. And that can give you a feel, to an extent, of the culture. For example, everyone is in suits that you see on the website. So that may give you an idea that that's more of a formal culture. Whereas if you see people say in work gear, then that may be a little more relaxed culture.
Speaker A: Like if someone is feeling stuck in their current career and just doesn't know where to begin, what's the two or three first steps that you would recommend that they take?
Speaker B: One step I would recommend would be to reflect what makes you happy to get up each morning and go to work. Is it values? Is it the industry that you're in what gets you going? A second recommendation would be be to look at organizations that mirror your value, whether it's volunteering, whether it's just doing your project, whether it's more of a family atmosphere, look at those values. And the third thing I would recommend is there are, ah, plenty of free online assessments. Do some of those assessments because that could help you as well identify your strengths in terms of skills, identify weaknesses, and identify what you truly enjoy to do.
Speaker A: M. This is all fine and good, but I need a job. Do you coach people that if they're just taking something just to have the job, they're settling for it? Is that a direction to pursue?
Speaker B: Yes. A career coach is great. And that's something that I work with clients on in terms of assessments to see what they're interested in or if they're ready to pursue a particular field, especially if they're transitioning from one industry to another.
Speaker A: That, I think leads us to talking a bit about, um, transferable skills. What are the transferable skills you think that employers value most, no matter what industry someone is coming from?
Speaker B: Uh. Oh, that's a good question, Bob. Employers value skills such as leadership, excellent communication, whether that's verbal or in writing, collaboration, flexibility, adaptability, ethics, critical thinking, interpersonal skills. A lot of people don't do well with others, and those are things employers are looking for. Decision making, you know, team oriented, uh, the soft skills, those are transferable no matter where you go. And those are some of the skills I mentioned that employers are really looking for.
Speaker A: We touched on resumes earlier, and I think that they can kind of make or break, certainly in that first impression. You know, statistics are that hiring managers, search firm people spend 10 seconds or less looking at that resume. So that first impression is really important in your experience. What makes a resume clear and strong and effective in today's marketplace?
Speaker B: One thing is to make sure your resume is in a standard font and to stand out. You don't have to do Times New Roman. Everybody in their grandmother uses that font. Try Calibri, try Verdana. Those will stand out. But you want everything to be uniform. You don't want shading, you don't want different colors throughout your resume. You want it to be all in line. I've seen some resumes that look busy in terms of they'll have something on a small column here to the left, and then they'll have something that's too busy. It said 10 seconds or less. So you want to stand out. And those are some simple ways the font making sure everything is uniform and just making sure everything is black and white.
Speaker A: Nike, uh, networking is Oftentimes a dirty word for people. It makes them really uncomfortable. How do you build meaningful professional relationships without feeling like you're selling yourself?
Speaker B: One thing I suggest is to be a part of an association. If you're in a career where you can join professional associations, do those because that gives you the entrance into networking with professionals in your industry. And you're not necessarily selling yourself. If they have a networking function, that's where you're going to network and meet people. But anyone can be in your network. From your neighbor to high school college classmates, anyone can be in the network. So you're not selling yourself. If you're. Hi, Bob, I understand you're in underwater basket weaving. So am I. I'm so glad we're able to make that connection. I am currently looking for a job. Can you suggest an underwater basket weaving organization for me to look into? It's really simple. You're not selling yourself. It's having a conversation.
Speaker A: Someone told me about networking that it is more giving than receiving. What does that mean to you?
Speaker B: I think it's giving of, uh, your time in terms of making sure you connect with your network. For instance, I would feel a little funny reaching out to you if I haven't talked to you in like two or three years. It's okay to send someone a quick text, you know, three or four times a year. Hey, Bob, I hope things are going well. Just check in to see how you're doing, that kind of thing. So giving is really giving your time and giving the implication or the feeling that you actually are genuinely caring about that person.
Speaker A: Yeah. Plus you might be able to assist that person that you're networking with in something that they're struggling with. Maybe a new contact, maybe a reading. It could be any number of things that you might be able to give to that person that you're trying to network with. And that makes you feel good because you helped them before they helped you. Yes, Nike. Many professionals talk about personal branding or leadership branding. What is those things really mean to you and why does it matter even if someone is not in a management role at this time?
Speaker B: Oh, uh, that's a really good one, Bob. My grandson and I like the movie Zootopia. And then there's an animal on there. He wants to be like an elephant. And so he's like, that's what I tell people. Toot your own horn. You are your best brand ambassador. Whether you're in leadership or you're in an entry level position. You want to, uh, establish yourself as a leader and under One particular thing. So, for example, um, maybe your brand is integrity. You do everything with integrity. People will know you for that. Hey, Bob is known for being an integral person. But as your roles change, your brand should change as well. So if you're middle management, say integrity is your brand. When you go into the upper management, maybe mentoring is your brand. So you want to mentor the younger executives to give them tips and tools of how to advance into upper leadership. So your brand changes as your roles change. But everyone has a brand. I would tell my leadership, I don't have a problem doing whatever you ask me, as long as it's not illegal, immoral, or unethical. So they knew those were three things I definitely stood by. That was part of my leadership brand.
Speaker A: And the thing you want to make certain is that every outward facing communication about you is in line with that brand. You can't be saying one thing on LinkedIn in and another thing on your cover letter and another thing as you're networking with people, that would cause that brand to be incongruent and kind of, um, confusing to the marketplace. Am m I hearing that correctly?
Speaker B: Right? You're exactly correct. Because if you can write your sentence out and say, what do people know Bob Gerst for? So if what comes to mind is integrity, then okay, you know, that was your brand that you were trying to present and you're on the right path. Or they'll say, oh, it's mentoring, but you're saying integrity. So then you're going to have to reevaluate and change your brand to integrity. So you're right. What you do here, there, everywhere should stay in line with the leadership brand that you are saying you're doing.
Speaker A: Nick, you've got a lot of experience with people moving from the government sector or military sometimes into the private sector. What are some of the biggest adjustments that people making that shift should prepare for?
Speaker B: You're right, Bob. Uh, a lot of my clients have been transitioning from the military and from government. The biggest transition that they have to make is culture. Because in the military especially, it's a chain of command and they use a lot of acronyms. And so when they're going to the private sector, a big adjustment for them is the culture, the verbiage, and how to address people. So, for instance, being in the military, you're usually being addressed by yes, sir, yes, ma', am, or yes, captain, yes, major, it's by titles. In the private sector, it's a lot less formal. Normally, people are addressed by their first name, so that's a big adjustment. A lot of my military people have to get used to in the acronyms. So definitely study the culture. Look at rephrasing military terms into real world terms, because that is one of the main adjustments that they have.
Speaker A: Anything that they can do to prepare for that or get better at making that transition from government or military to the private sector?
Speaker B: Yes. Pretty much every branch of the military has a transition assistance program, and they actually give tips and tools of how to translate military language into private sector language to help them ease in there. So every transitioning military member is given that option, and I definitely encourage them go to those TAP classes because it's going to give you a wealth of information to help your transition, uh, be a lot easier.
Speaker A: The job market has changed really a great deal even in the last few years. What do you think job seekers should focus in on now if they want to stay competitive?
Speaker B: Definitely focus on skill building, because that can come up in an interview. What skills have you developed over the last two or three years? So that's whether you take more advanced Microsoft Office suite classes, a, uh, public speaking class, maybe a writing class. You want to always be learning something new because employers look for lifelong learners.
Speaker A: We should probably talk about the elephant in the room, that being artificial intelligence. What are you seeing the impact of that on job seekers now and in the future?
Speaker B: AI is definitely playing a big part in the job market. First thing you're dealing with AI is the ATS Applicant Tracking System. Every organization has that because that's taking the place of human eyes going through hundreds of resumes. So there's AI in that. And then in terms of you building a resume or even preparing, AI can help you with that. But you have to make sure that you put your personality into it, you put the personal element in it, because AI is definitely here and it's not going anywhere. It can help you or it can hurt you. So use discretion in terms of how you use AI with your job hunting.
Speaker A: Can you talk to us in terms of how AI is used in that screening process? What have you seen? I mean, is it they look for key words, or they look for key experiences, or they look for key companies. What is that AI looking for to help job seekers know what they're kind of dealing with?
Speaker B: AI is looking for keywords and phrases in that resume in that cover letter. And depending on how they have it set, it's a certain percentage you, you want to at least hit for 80% or higher in terms of your resume matching the job description. And there are Some tools out there that you can scan your resume in, some of them are free for like a couple of uses, and then some of them turn into a paid subscription. My advice is you want to have your resume as close to good before you put it into that system. It will point out some things for you, but it's still up to you to redo your resume to conform to what it's suggesting.
Speaker A: Naik, what if I'm an older job seeker? Can you describe kind of what some of the barriers are for that older worker and what are some of the things that they can do to help overcome those barriers?
Speaker B: That is a great question, Bob. I'm actually working with a client who is an older job seeker. And that client has some trepidation about going into the job market again. And one thing older workers bring, you bring dependability. You know, you like to stay on a job for many years. You are timely. Also, you bring knowledge. Those transferable skills, they go with you everywhere. Especially if you're in an industry that you've been in for a while. You bring industrial knowledge. You also are willing to get in and do the work. So there are a lot of skills that older workers bring to the workforce. You're steady, you're reliable. So employers like that as well. Don't look at it as, oh, wow, I'm too old. Of course, ageism, um, happens, but you can mitigate that by staying current in skills in your industry. Even if you're transitioning to a totally new industry. Then make sure you're getting certifications, you're taking classes. That brings your knowledge base up to speed.
Speaker A: You know, you spent years on interview panels and coaching, um, candidates and recruiting yourself. What have you seen candidates who stand out have as skills, characteristics, style. And then let's do the flip side of that question. What have you seen candidates who struggle in the interviewing process that people who are listening to this should make certain that they avoid.
Speaker B: Oh, that's good. One thing I've seen time after time over the years with candidates who stand out are they're professionally dressed, they're polished from head to toe, they're prepared, they've done their research on the organization and on the job, they ask thoughtful and meaningful questions during the interview. And number one thing that makes them stand out, they send that thank you email after the interview to highlight how they're the best candidate for the position. So if you flip that, if you do the opposite, if you don't come in looking professionally polished, if you don't come in prepared, we know it definitely, if you don't ask questions, we know that you're just looking for a job. If you don't send that thank you email, that will let us know that, uh, you're not the candidate for the job. I have an HR friend, probably about four years ago now. They interviewed 20 candidates for a position. Out of those 20 people, only three people sent a, uh, thank you email. Guess what? They only considered those three people because those three people took time out of their schedule to thank the interview panel for their time and they were the only ones considered. Even though some of those 17 people were more qualified than the three they did not get considered.
Speaker A: Nike. I love the title of your book, five Secrets to Nail that Job. It really sounded like a very practical guide. Uh, what's the two or three key themes or secrets from the book that our listeners can use right away to be more successful as they go through their job search?
Speaker B: Sure. My book, Five Secrets to Nail that Job talks about interviewing. And one secret I'll talk about is look the part. You want to be professional looking. You want to be polished from head to toe. Your grooming is great. You want to make sure that you're not coming in there where your cologne or perfume comes in before you don't wear any. So you want to look like, hey, I belong here. I'm the best candidate. The second one I would say is talk the part. And by that I mean be prepared. Do your research on that organization, knowing that job description, asking those intelligent questions. At the end, when they're done with their questions and they always ask, do you have any questions for us? You better. I tell my clients, you better have at least two questions to ask. Because if you don't ask questions, the panel's going to think, oh, that person's not interested. So that's two of the secrets I'll talk about.
Speaker A: And you can really get a sense of that, how you should dress by looking at those pictures again that are on the website, right?
Speaker B: Yes. For example, if you're interviewing with Google, you know, normally Google is jeans, T shirt and some, um, Converse. You may want to step it up a notch and put on some khakis, a polo shirt, and some casual shoes. You always want to dress a level above what you see on the website. Of course, if everybody's in a suit on the website, you better go in there with to see. That'll give you an idea of how, uh, to dress.
Speaker A: Nick, what do you think the recruiting process looks like in the future? If you had your crystal ball, what do you think are going to be the key things that job seekers, the future need to keep in mind? Because statistically, even if they find a job today, they're probably going to be looking for another job sometime in the future. And how do you think that that process is going to change?
Speaker B: I think it may come to more of you getting an introduction to get that job. I think it'll be really heavy on networking because jobs may become scarce. And I would rather bring Bob on because I know Bob. I know his work ethic, I know how he does things. So I'd rather recommend Bob than John Doe from the street, who I don't know anything about. I don't know the work ethic. I don't know how they would thrive in this type of environment. So I think it'll be more of personal, uh, recommendations.
Speaker A: Thank you. Our listeners, after this session today, they're going to be overwhelmed. They're going to say, oh, my goodness, she gave so much information, so many great insights. What's the one or two things that you want to make certain that they take away to help them be more successful in their job search?
Speaker B: One thing to remember is, you know, you, you know your background, you know what skills, you know, experiences you bring to the table. Make sure you highlight those in your resume. Highlight those when you're doing your interview. You're your best brand ambassador. The second thing I would say is, again, be patient. Finding a job is a process. On average, it takes two and a half months to get a new job. So that means constantly applying. You want to be patient with that process.
Speaker A: I really hope today's conversation has fired you up and gave you the push to take bold steps in your own career journey. You don't have to face change alone. Together we can turn uncertainty into momentum and momentum into results. This is your time to lean in, get clear on what you want and go after it with confidence. If you ready to make the next move, your best one yet. I know that Nike and I would be honored to help coach you through those changes. I'll have in the show notes how you can get a hold of, um, her. Let's start building that future you've been dreaming about. Your next chapter is waiting, so let's make it happen today. Nike, thank you so much for joining us today and for all that you shared.
Speaker B: Thank you, Bob, for having me. I enjoyed this conversation.
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