Jennifer Speciale
Designing the Career You Actually Want
In this brand new episode of Brave UX, Jennifer Speciale helps leaders rewrite the rules of career growth 🚀, redefine executive presence 🧠, and build unapologetic clarity in an uncertain market 🌍—sharing why designing your career is the ultimate act of leadership 🎯.
Highlights include:
- Why You Are the Prize
- Helping Leaders Find Hidden Career Options
- What Recruiters Really Look for on LinkedIn
- Why Job Descriptions Are Designed to Be Vague
- Flipping Interviews into Conversations
Who is Jennifer Speciale?
Jennifer Speciale is the Founder and Executive Leadership Coach at Speciale Executive Leadership, where she helps ambitious leaders navigate critical career transitions and unlock new executive opportunities 🚀.
She spent over 15 years in leadership roles at Amazon, McKinsey, Indeed, and Google, shaping global teams in experience design, executive leadership, and digital transformation. At Amazon, she led executive recruiting for design, helping build the teams behind flagship products, while at McKinsey, she built a global Experience Design team and expanded the firm’s digital talent strategy 📈.
Jennifer’s impact goes far beyond recruiting—she has coached over 100 leaders into executive roles across top companies, delivering more than half a million dollars in collective salary growth in 2024 alone. Through her proven frameworks, she’s redefining what executive presence means and helping leaders discover hidden, game-changing opportunities ✨.
Transcript
- Jennifer Speciale:
- My dream is that all candidates believe that they are the prize. The important nuance there is as a candidate to present yourself in a way that makes obvious that you are the right fit. However, if you are not the right fit, it is to everyone's advantage that you not get the job. And so clients that don't get an offer or don't get that job, I tell them that's a gift, that's a save. They know something that you don't and you have to trust that.
- Brendan Jarvis:
- Hello, and welcome to another episode of Brave UX. I'm Brendan Jarvis, managing founder of The Space InBetween, the behavior-based UX research partner for enterprise leaders who want an independent perspective to align hearts and minds. You can find out more about me and what we do at the spaceinbetween.co.nz. Here on Brave UX though, it's my job to help you to keep on top of the latest thinking and important issues affecting our field of design. I do that by unpacking the stories, learning and expert advice of a diverse range of world-class leaders.
- My guest today is Jennifer Speciale. Jennifer is the founder and executive leadership coach at Special Executive Leadership where she helps ambitious leaders take the next step in their careers, whether it's transitioning from consulting to industry, stepping into their first VP role, or unlocking new executive opportunities. Her coaching blends executive branding, strategic career transitions, and leadership agility to ensure her clients don't just land the role they excel in it.
- Before founding special executive leadership, Jennifer spent over 15 years in leadership roles at some of the world's most influential companies, including Amazon, McKinsey, indeed, and Google. She has been on the inside of high stakes hiring decisions, shaping recruitment strategies, and building global teams in experienced design, executive leadership and digital transformation.
- At Amazon, she led executive recruiting for design, helping shape the teams behind the company's flagship products. At McKinsey, she built a global experience design team expanding the firm's digital talent strategy and spearheading leadership initiatives.
- Jennifer's impact goes far beyond recruitment. She has coached over 100 leaders into executive roles at companies like Amazon, Google, McKinsey, and beyond. In 2024 alone, she helped to deliver over half a million dollars worth of salary growth for her clients through her proven framework for career acceleration. She's changing the way design leaders navigate their careers making executive presence more than just a buzzword in helping leaders uncover unlisted game-changing opportunities. And now she's here with me for this episode of Brave UX. Jennifer, a very warm welcome to the show.
- Jennifer Speciale:
- Thank you. Thank you so much. I'm super happy to be here.
- Brendan Jarvis:
- Oh, it's great to have you here. It really is great to have you here. And I understand that you're joining me from Italy and that you may have also been recently training for a marathon. What's the story there?
- Jennifer Speciale:
- Yes, my husband is from Florence, and my son, somewhere in his early high school career decided he really wants to attend university here in Italy. And over dinner one night, we all sort of hypothesised fantasised about, well, what if you attended high school in Italy and kind of got the lay of the land and worked on your Italian language skills and got a hang of the culture? And so almost on a whim we applied to some different schools and one of the schools he did the interview and they said, we very much accept you and so much so we'd like to offer you early acceptance. So that was about a year ago, and instead of only attending his senior year, we're here for his junior year, we sort of dropped everything and we're still building that plan as we're living it. So now I'm here with both my kids and they're in school and we're living in Florence, and I'm training for the Florence Marathon in November.
- Brendan Jarvis:
- And how's that training been going?
- Jennifer Speciale:
- Well, we're off to a slow start and my AI tool that I've asked to give me a plan has suggested that my goals are ambitious, that I'm going to have to really push hard. I thought that training for a marathon at the end of November, starting in February was a good time, but apparently it's ambitious. So I guess I'm going to have to step up my game, but I think it'll be really interesting. I can't imagine a more beautiful experience
- Brendan Jarvis:
- From what I gather about you, Jennifer. You're someone who perseveres. So I have no doubt that you'll be able to achieve that ambitious plan. And I think if you have at least six months, you should be okay. I think when it comes to Florence though, from what I know, I've never been there, so tell me if I'm wrong, that one of the major risks to your training will be running and looking at all the beautiful things and not looking where you're going and perhaps tripping up and ending in some trouble there.
- Jennifer Speciale:
- Indeed. And actually that is a problem almost on a daily basis anyway, not even running, just generally walking because the sidewalks are made of stones that have been there forever and they're super uneven. And heels are not part of my wardrobe at all anymore because there's always some opportunity to stumble, even just wearing the most casual shoes. So I can't imagine it'll have to be something I really practise for going over all the cobblestones, trying to watch the time as well.
- Brendan Jarvis:
- Yeah, most definitely. I can imagine it would be very difficult to keep on time in such a beautiful place with so much history. And speaking of history, I understand you mentioned there that your husband was from Florence, but I also learned that your father, his heritage is from Sicily and you grew up in America, but I get the sense that Sicily is still a place that has a special place in your heart. What does that Sicilian heritage mean to you?
- Jennifer Speciale:
- Yeah, it's so interesting. Actually. My husband's kind of amazing at tracing lineage and heritage and helped correct some of the story that my dad and I thought we knew about our family, and we discovered that our family is not only from Palermo, but really from the AI Oan islands. And so last October, my husband and I travelled to Selena de Marina, which is where part of our lineage, the re family, RE, which is actually a really popular name in New York is from. And they were very entrepreneurial. It's kind of neat now having started my own company, which is something I never really thought I would have the guts to do, or the know-how to kind of muddle through all of the trials and tribulations that go with starting your own company and going to the Aian Islands and sort of looking into the faces of people and wondering, do I look like them?
- Do they think I look like them? And just feeling the history and knowing. We went to the mayor's office, it's called Synco and Italian, and reading through the journal entries of all of these people and finding the gravestones of my relatives and knowing that they were ship captains and shippers, and they first expanded down to Argentina and later went to Palermo and then from Palermo to New York just knowing what bravery must have been required. And I think that's true of any immigrant, but perhaps particularly so many years ago. So it's very inspiring in America, we, I'll speak for myself, don't have a deep true sense of our history. My husband, there's a street in Florence named after them, or it is their family name or whatever. Italians have a strong sense of their family history. British have the long sense of their lineage. So Americans were always, were much more like quilts and patching it together. And it's interesting to learn about the different makeup, different composition, all my ingredients I guess you could say.
- Brendan Jarvis:
- Yeah, it almost sounds like it's been somewhat of a grounding experience to find those roots. And it's interesting you mentioned the journey that you've embarked upon recently in terms of your leadership and coaching practise. You also mentioned there that some of your forebears had been ship captains, and I hadn't heard much about the Olian Islands until I was researching for our conversation today, but just drawing a thread between what you've been describing there in terms of that entrepreneurial journey and what's required to make that work as an immigrant or as someone that's embarked on the sea. I'm not sure if you knew, but the old Olian Islands are named after aioli, which is the ruler of the winds that was encountered by Odysseus, a famous adventurer that was in Homers Odyssey. So they have a really important place in the western mythical tradition to them as well. Yes. And I was curious, just to give some colour for the people that are listening to this, when you first went to the Olian Islands, did you get a sense of that, that sort of mythical presence? Was there anything like that that resonated for you when you were there?
- Jennifer Speciale:
- Absolutely. The islands themselves are so beautiful, just kind of walking around and thinking about how old they are. And not all of the Olian islands are fully inhabited. Some of them are posh and jet set. We visited those briefly, but then we went to another one where the primary inhabitants are donkeys. So it's a little bit like New Zealand where there are more donkeys than humans, and New Zealand has more sheep than humans, or it used to
- Brendan Jarvis:
- Many more sheep than humans, many, many, many more.
- Jennifer Speciale:
- So we went to different islands that were like that. And I'll never forget, we had lunch at this restaurant and the woman that was serving us had captured all of the fish that we ate that morning herself. She was very proud of herself. I don't know if she was down for her cook or her restaurant was new or if she was just really proud of that always, and that's always what she did. But it does feel very mythical because you can see the islands, you can see there are many of them, and you can see some of them depending on which island you're on. Some of them are closer than others, and you can only imagine what it must've been like trying to travel in between those and the first that were on those and how they worked it out and thinking about somebody getting a ship, even a big ship and finding Argentina, navigating there. So yeah, there's so much natural beauty and the shape of the mountains and the hills. It's very beautiful. It's very inspiring. I had my first client from a terrace on the AAN islands.
- Brendan Jarvis:
- Congratulations. I'm sure that's quite a special one actually, to be able to bring your work in the things that you've learned in America to someone that inhabits one of those islands.
- Jennifer Speciale:
- That's right, yeah. Wasn't a good hair day. Lots of humidity, but that's okay.
- Brendan Jarvis:
- Yes, you get that hair where I've now moved to, which is Wellington, it's known as windy Wellington, so I can say goodbye to good hair days, that's for sure. Hey, just before we move off, Italy and Sicily and that part of the world, that part of your history, you've previously remarked that the storied and sometimes troubled history of what we now call Italy has provided inspiration to you in terms of the stories that come from that land. What's one of those stories that stands out for you that's perhaps it's been particularly relevant to you now as you have become an entrepreneur, or perhaps it's something that has been with you for some time, but I'm curious, is there something that stands out from the history of Italy in terms of its stories that is special for you?
- Jennifer Speciale:
- So I'm studying Italian. It's a language I think that you could study without end, just the prepositions alone are a challenge. But just recently we studied some cultural figures and there's a woman that is known historically as a politician, which I really like. I think that America has a lot of things going for it. Of course, women's rights and advancement are something that I care deeply about. I talk to my clients about it all the time, men and women. And so I think it's really interesting that this woman from the 15 hundreds, she is suspected that she's the illegitimate daughter of a pope and another woman. And actually I want to find out who her mother was because her father was a pope and she became a very strong, powerful person. She wasn't very great. She's also known for using poisons as part of her tactics if people didn't acquiesce. But she was fierce and she was a strategic negotiator. And I think it's notable that it's not uncommon for there to be a lot of strong female figures in Italian history. And it's not something that they have to force themselves to do to show a balanced array of historical figures. They just exist and they are admitted to and they're kind of part of the mix. And I find that very inspiring.
- Brendan Jarvis:
- I believe even the current prime is it Prime minister in Italy is a woman.
- Jennifer Speciale:
- Her politics are questionable, maybe a little conservative for some of my taste, but just on the merit of her acquired skills and position, it's still very respectable. She's definitely endured a lot of her own controversy, and I think she is navigating it well, even if I don't agree with a lot of her, the things that she agrees with,
- Brendan Jarvis:
- Hopefully she doesn't resort to the use of poison. She won't add that to her list of black marks.
- Jennifer Speciale:
- That's true.
- Brendan Jarvis:
- Thinking now about what you are doing, so you were in executive leadership roles inside those wonderful companies that I mentioned in your introduction companies like McKinsey and Google and also at Amazon, and you've started a leadership coaching practise recently. I'm curious, what types of executives are you coaching and what are the problems that you're helping them to solve?
- Jennifer Speciale:
- So I have a deep expertise in design. I've been in UX design slash experience design slash service design for almost two decades. I sort of found my way into it through a friend. I was in the startup world of Manhattan and Fjord Design pre Accenture was looking for a recruiter to build out their executive leadership team. And they were not in a very good state at that time. The founders were very self-aware that they were creatives and not great at billing clients. They would forget to build clients and didn't really care about that, but then people couldn't be paid and of course created all kinds, not a sustainable business plan. So I started there. I met a woman named he Y that is very much a luminary in her own right, and we were just got on a house on fire from the first meeting and built the executive leadership team there.
- And later she was recruited McKinsey and she brought me with her. So we did all these things. And so I have this deep expertise in design and I've been in design for a long time, but I've also worked with a considerable number of consultants who are trying to leave consulting, whether they're management consultants or technology consultants. Being in the consulting world is a very different animal than being an industry role, being at a regular company, a normal non-con consulting organisation, and it can be really challenging to translate your skills because so much of your work seems ephemeral or seems temporary. So I care deeply about helping people translate their skills that are fungible those skills that what may seem esoteric and a consulting organisation actually are very applicable in other organisations. So I won't say I'm industry agnostic. I definitely have a focus on coaching people that are in design and technology and consulting spaces, but I have had some lawyers as clients and A-C-T-O-A-C-I-O. So I feel very grateful and very happy that my framework can be industry agnostic even if my expertise is not.
- Brendan Jarvis:
- I understand. Well, let's focus in on design leaders in terms of the application of your framework and the expertise that you've developed throughout your career. So when you are having that initial consultation with the design leader who's considering their next big thing, whether that's inside the organisation or perhaps they're looking at something entirely different, a new organisation, what's the first question that you typically ask them or what's your starting point? What is it that you want to know about them and what they're trying to achieve?
- Jennifer Speciale:
- Right now? I feel like design is at a pivotal moment. So a lot of my first clients were people who had been impacted by layoffs. Now a mix of people who have been impacted by layoffs and who are looking for a brand new role, but I also have a mix of people who are looking to get promoted. And so I typically start with trying to understand do they have a concrete outline or a concrete idea of where they want to go? What does success look like for 'em? And very often my clients that have been impacted by layoffs, they say I'm really open-minded and I tried to steer them away from that. I actually don't want my clients to be very open-minded and through conversation and through learning about them, which sometimes can happen in an hour, you can really accomplish a lot in 60 minutes.
- I try to really uncover at least some general themes to see some sort of spikes, some natural proclivity to certain industries or certain kind of work or certain kind of company size so that I can help them have their goal take shape even if they have a very specific promotion in mind. Maybe it doesn't have to be that promotion, maybe it's actually not that promotion, but it's something near it or something similar. I try to coach my clients to become very unapologetic about their goals and their passion, and as they pursue those things that give them butterflies, they start to realise I don't want to be open-minded, don't be open to anything. I want to be very specific because my clients are typically around age 50 plus or minus around 10 years. And people always, my clients I will say typically feel like, oh God, I'm 50 now, or I had just turned 47.
- And they usually say it with a bit of panic. And so I'm here to say that actually this is going to be one of the best years, one of the best, potentially the most important phase of your career. It doesn't necessarily have to mean you have the biggest role at the flashiest company, like now you're finally going to lead a gigantic UX team at Apple. Your definition of success, your definition of your crescendo at this fulcrum at age 47, age 50, age 55, whatever it is, might be a smaller or a mid-size company, A startup that's a hot mess and you're hiring the whole design team and actually that's what you love. You want to mentor, you want to be closer to craft, but you also want to lead. Or maybe you want that big fat role at Amazon leading a team of 500, but whatever it is, I think it's so important to understand if the person I'm talking to has any idea which direction we're going in, and very often they don't and that's why they're relying on me, and that's a good thing because I have the ability to listen to somebody and pick up on patterns and ask certain questions that illuminate certain facets of them, help them to really understand where they want to go and be unapologetic about it.
- It's actually such an exciting process and each time I go through it with a client, I just can't believe the role that they have found in the end. And I talk a lot on my side and in my work about how my clients design their new role, and that's because they really do. My clients aren't finding new roles that are posted. They're not finding them through LinkedIn. They're not finding them from having applied on a website and people that are getting promoted. Sometimes it's not the role that they were going for. It's not if p then Q, they're starting at P and they're going for like R or maybe maybe there's a new team that they can evolve and that's actually the promotion. So true to design thinking, it's all about start where you are and it's one of the things I love most about design thinking is start where you are. I always tell them, don't feel like you have to schedule your first session once your portfolio is to your liking. You may never have your portfolio to your liking. I don't know one recruiter that really likes their LinkedIn profile or really likes their resume, we always hate it. It's always a work in progress. And the same is true with the portfolio.
- Brendan Jarvis:
- You mentioned starting where you are and you also mentioned how some of your clients still are people that have been impacted from the layoffs that have been going on. Now that seems to me that there are quite a few people still out in what I would describe as a career wilderness. They're looking, they may have been looking for quite some time, perhaps they're actually not looking. Perhaps they're in a job that is just not really fulfilling. Maybe they took it out of fear or a bit of desperation after a previous layoff. But people generally, there's more people than perhaps before pre COVID that are in that uncomfortable position or one of those two uncomfortable positions. Now, relevant to this, you've previously said, and I'm going to quote you now, don't feel stuck. Don't believe that you're stuck. There are always, always options. I think the worst thing ever is to think that you have no options. You always have options. So thinking back on those clients that you've coached that have perhaps come from that position of feeling quite stuck where they are in their career, how do you help them to find options when they're having difficulty seeing those themselves?
- Jennifer Speciale:
- We start by reformatting their LinkedIn profile, which sounds very simplistic and superficial. I had one client ask me, isn't this just putting lipstick on a pig? Well, no, actually you're not a pig. It's not cosmetic, it is not superficial at all. The result is superficial because it is your marketing tool. But the process of redefining your LinkedIn profile actually goes quite deep because you are recreating your LinkedIn profile again, unapologetically going after what you want, and that's where the hope starts to come. That's when you start to see options. That's when possibilities present themselves. When you put all of your efforts, your portfolio, we always create case studies. So I tell them, you can have your great big blob, your great mass of work, which is your portfolio, but we will extract, we do a double click and have ideally three very coherent case studies that are extremely simplistic, organised and developed for any audience so that A CFO could read it and make sense of it.
- A design leader with a short attention span could look at it and make sense of it. A recruiter that hasn't been trained in design and has every candidate at their fingertips can look at it, make sense of it and understand your metrics, your value proposition, your impact that you've created. So this process of not necessarily redefining who you are via the tool of LinkedIn, but re-articulating what you want, not just having these things be a confessional of everything you've ever done. I always say like, I'm not necessarily super religious, I use this figuratively, but your CV or your LinkedIn profile is not your priest. It's not your confessional, it's your marketing tool. That doesn't mean flub your metrics or unduly exaggerate, particularly with women, they're always shy to say, well, I don't know that it was 40%. It may have been 37. I'm like, that's classic how women are trained.
- We downplay everything, say 40. Just the scrutiny of that gives the validity of your metrics. It makes me believe you more and that will come through to your readers. So the process of recreating the LinkedIn profile and orienting it exactly to where you want to go rather than everything that you have done creates that hope. And it sounds perhaps contrived or even maybe a little bit hokey, but it's just so accurate and I've just seen it with all of my clients. It creates the hope, it creates the focus, and with the hope and the focus comes the distraction from the frustration, the sense of rejection, the sense of maybe I'm outdated, maybe I'm irrelevant, maybe I'm too old, maybe I'm 55. Maybe I should just start thinking about retirement. No, those are ridiculous concepts. The market is not telling you to give up on yourself.
- The world is not telling you to give up on yourself. Don't give up on yourself if you don't want to give up on yourself, don't make that decision and in fact reconfigure all of your outward facing things, your marketing tools to project what you want, which will then attract what you want. And everything just starts to fall into alignment. It's unbelievable. I tell people, you are finding your tribe, your new tribe, and it's that old expression of everything that you've done before is not what will get you to everything where you're going now. You've got to be more strategic. You have to retool, you have to re-strategize. It's actually the smartest time to start working with a coach. If it's not me, make it somebody. So many people feel like, God, I'm so seasoned. I should know how to do this on my own. I should be good at this.
- I should just know how to do this by myself on my own. No, actually some of the best, most seasoned executives have completely lost the art of storytelling. You just have so many brilliant things to talk about. You get in an interview and you don't know where to start, and so you overshare, you forget metrics. You're cramming in 13 stories in one answer, and it comes out disorganised. So it's really the perfect time to work with a coach. It's the perfect time to retool and really prepare yourself for your most exciting part of your life, which doesn't mean the biggest, it's how you define it
- Brendan Jarvis:
- And it sounds like you help people to do that definition to get that clarity. You talked in terms of focus there and from that focus and clarity, almost like sculpting something out of what they've done previously, it gives them that injection of clarity and enthusiasm that they need to get them into the right position to be hired so that they can project themselves the best way they possibly can. And that's certainly a very valuable thing. I do want to ask you though about the more hard nosed other side of it. So that's your contribution I suppose, as a coach is helping them to do that. But you've also been on the other side as an executive recruiter, and I'm keen to understand if we zero in on LinkedIn in particular, just what is it that you are looking for in people's profiles for those big roles when you come across them? Or perhaps I'm very naive, right? Perhaps you're not even looking at them, perhaps it's all automated. What insight can you share with people as to what's really critical for them to get right from the other side of the fences perspective, which is those people that are the hiring managers or recruiters that are looking at those profiles?
- Jennifer Speciale:
- I am very hard on my clients because I love them, and sometimes you just have to give the really hard feedback, which is I have absolutely no idea what you want to do. Your profile tells me nothing. It can be filled with bullet points and things that they've done and this litany of everything that they ever did with the design process and granular detail that just bores anybody to tears and doesn't actually impart any understanding whatsoever of the person. So when I'm looking at a person's LinkedIn profile, I want to understand what is your expertise one and what do you want to be doing? I can certainly have enough experience to where if I see an undergraduate in English history or something that's not designed, but then maybe a master's in something HCI or something related, or maybe they have no education, but then they've got a nice steady trajectory and design, I can usually make up in my mind what their trajectory was.
- I can create that common thread and even lots of seemingly incongruent career jumps or industry changes, I can make that story in my mind and then confirm it with the candidate. And I'm almost always right, but a lot of people don't have that desire to understand the common thread, understand the story, take the time to look for the common thread. So you have to make it very easy, very spoonfed for your reader. People are less and less patient and reading. They're looking for very quick things, very specific things on a LinkedIn profile. They want to see a clear leadership trajectory. Sometimes that means don't put your literal title, but put your title of what you actually did. Maybe you were actually partner level, but you were called something like expert, which doesn't mean anything to the outside world. Maybe you were engagement manager. That doesn't mean anything to the outside world. Put your title that actually has meaning to an average bear, somebody who has a short attention span, short on time and lots of candidates and make yourself easily understood very quickly and interesting.
- Brendan Jarvis:
- It's a must when there's literally thousands of people in some cases going for one role, and that won't always be the case, but it certainly means it's more important currently than it ever has been before. We've been talking around about the importance of clarity in the LinkedIn profile, both from the perspective of the person orientating their career or reorientating their career, and also the recruitment side of things where people are looking for potential candidates to fill positions. And I want to talk now about an area of recruitment that you've described as intentionally vague, and that is the job description for some of these roles at big companies like the Amazons and the Googles of this world. You've cautioned your clients previously about relying too heavily on those jds. Why is that and what is it that you advise them to do instead when they're looking at these job descriptions?
- Jennifer Speciale:
- By and large job descriptions are for mid to large organisations created based on codes. It's a formula you have to sufficiently satisfy certain employment laws. At Amazon, it was a number of different categories, so you had to fill in literally certain boxes as you composed in this sort of template coded job descriptions. And there's some narrative, but it's all relatively vague. And ideally, most organisations have job descriptions that are sufficiently vague because now we should all be aware that research shows us that men will apply to jobs if they believe they have somewhere between 40 and 60% of the skills required. And women will apply to jobs when they believe they have somewhere between, I've read some studies that say 80 to a hundred percent of the skills women by and large are very easily deterred from applying to a job if they don't believe they meet a free single bullet point.
- It's dreadful and it's makes me very upset. But it's something in our training that starts early. We are taught to be apologetic and agreeable, and so that filters through almost everything that we do in our lives. And it's very difficult to fight against that internally. And even you're sitting alone and you're applying to jobs online and you feel guilty, you know, should be applying to jobs online. It's a struggle. And so anyway, all of the research shows us that the job descriptions, good job descriptions are sufficiently vague so that it casts a larger net so that more women will apply to those roles. And I've talked to, I was giving a presentation in Mexico City about women in leadership and this SVP at Oracle approached me and said, I've got these two women that I want to apply to this open role and they're just not doing it.
- I don't know. He specifically wanted women in this role. And he said, I can't figure out why these two women won't do it. And I said, well, have you told them specifically that you want them to apply to the role? And he is like, well, no, I just keep hoping that's the first thing because they probably don't think they're senior enough for it. So there's this whole weird thing. He should be more forthcoming, and that's part of more men need to mentor more women. And even just that thing of telling them is a form of mentorship because those women might be thinking, I would love to have that role, but I don't have 100% of the skills. So all of this to say, I tell my clients, don't pour over these job descriptions. It is a natural proclivity. You're searching wildly to see if you're fit to uncover, unearth some secret about the culture, the organisation, how you can better articulate your experience via this job description and it will drive you crazy.
- And in fact does drive people crazy because it doesn't illuminate anything because it's by design vague. And so I tell them, open every interview, every conversation, you start with anybody from this job description. First thank them for investing time to speak with you. And the very next thing out of your mouth before anything happens is you say, of course I've researched the job description and your organisation. I just want to ask you what's really missing? What are you really looking for in this role? Because you need to get some of that detail, just get it from the human.
- Brendan Jarvis:
- I've heard you frame this kind of conversation as ideally a conversation that happens before a formal interview as well. So perhaps you're talking to the recruiter or perhaps you've had an informal with the hiring manager and you've encouraged job seekers to, and I'm going to use your own words here, ferret out whether they're truly a fit before they commit to that formal interview. And that's, as you're saying, it's a result of the vagueness of the job description. But you've said this quite specifically for a purpose, and the purpose is you've said that a bad interview, if you're not sufficiently prepared for the job or the role that you're interviewing for can permanently end up in a database and that shivers down my spine, right? That sounds like you've seen or you are suggesting that candidates who bomb out in an interview because they haven't done their research and it's not a good fit, may risk being placed on some sort of do not hire list.
- Jennifer Speciale:
- Yeah, it's dreadful. It can be a very unforgiving process. And while I happen to think it's rubbish, it's unkind, it's unfair. That's kind of just the way it is. And so I tell all of my clients, there are no informal conversations. There are no first passes that you may or may not decide to proceed. You should treat every conversation, even conversations with people, well, those warm leads or Oh, I've known him for years, we'll just have a chat. You should treat every conversation, not really with kid gloves, but treat every conversation very strategically. You should be very prepared, even if it's a 15 minute conversation and it's a company you're not sure you'll like, and it's a role you almost know you won't like maybe you know the hiring manager, maybe you don't agree with the product, it doesn't matter. You never want any opportunity for anything to be against you unfortunately, and it's so easily done these days, everything.
- My dad and I used to always joke about things going on the permanent record, and he's like, don't worry, that's really bullshit. But now it's not. Excuse my technical term there. But now there is actually the permanent record and very large organisations, some of which I've been employed by, so I know this firsthand. It is actually a requirement to first look up that and see if they've ever interviewed with the organisation before and read through the copious notes that have been taken manually because it's only recent that AI is recording everything conversation-wise. And so that's even scarier is that the subjectivity of the interviewer may be a poorly trained recruiter for design or poorly trained for recruiting or a hiring manager that is design friendly but not design trained, but doesn't get the right vibe or whatever it is you subject yourself to mountains of subjectivity. And so you really have to treat every conversation very strategically and very much in your favour and do everything possible to create a subconscious connection, a relationship, and then ask your questions very strategically, something I care deeply about.
- Brendan Jarvis:
- And one of the tactics that you've spoken about in this strategy for achieving this new role has been advising clients to spend some time reaching out to people on LinkedIn that may be working within or had previously worked at those companies that they've decided may be a good fit for them. And I'll quote you now, you've suggested that they do something and I'll quote you here. You've suggested that you in that message, ask them, and here's the quote, what is it about their background that draws you in? Tell them that because people want to hear that it's not every day people are told that something about them is interesting. So it's nice for them to hear and you automatically start to build a little relationship. Now, I've just been reading a very old compilation of letters from a chap called Lord Chesterfield, and he was a British Lord back in the 18th century, so we're going back quite a while now.
- And he wrote these letters to his son as a way of imparting the worldly wisdom that he had gathered throughout his political career to his, in this case, a legitimate son. And in one of these letters, he advises his son, and I'll quote him now, remember that to succeed in great things, one must first learn to please in little ones. And then I was reflecting on what you had been advising clients and what he had said, and I wondered, is what we're talking about here a little bit of flattery? And if it is, is there anything wrong with using it when you're trying to procure your next role?
- Jennifer Speciale:
- It's absolutely flattery and there's nothing wrong with it. There's nothing wrong with making somebody feel good about themselves even for 10 seconds that they read your short LinkedIn message. People want to feel good about themselves. I don't have to say that the world is kind of in a dark place right now. I think that's redundant, but it's an opportunity to connect with somebody. And I definitely implore my clients to be authentic in what they write to that person. And part of that process, part of finding something authentic to mention is that it will also have the effect of giving them their own butterflies and helping them to realise that they are indeed in this search of finding their tribe, finding their people. And so if they're looking through somebody's profile and it's at a company that they never thought would be interesting, that's great. And if they find something in somebody's profile that's actually like, oh my God, they went to my undergraduate.
- Nobody ever knows this undergraduate. I can't believe that that gives you butterflies. So you complimenting somebody, paying somebody a moment of flattery has this reciprocal effect, which yes, it's strategic, and yes, it's to your advantage. And yes, it's a good business strategy, but by the way, it actually makes life more fulfilling. And when you're in a job search and if you've been impacted by a layoff, you need anything that is fulfilling any kind of good F word because there's so much that's so hard and so difficult. So it's really hard reaching out to people that you don't know. It's really hard putting yourself out there. And so the other facet of one moment of flattery, it's not that it's just gratuitous, oh, that looks nice on you, which you could say to anybody, it's something very focused, very specific. LinkedIn is a business application. You are seeking something for business. That moment of flattery is something that is also sparking something that makes you feel positive. So you're seeking a connection. Sure, it's complimentary to the receiver, but nobody ever feels bad when they're paying a compliment. It's a moment of connection, and it's really powerful and effective.
- Brendan Jarvis:
- It's so true that nobody ever feels bad when they're giving a compliment. I think the only caveat there is if you know that you are giving a compliment, that's not genuine. But what you are talking about here is not that you've talked about zeroing in on something that maybe you share in common or something that does genuinely impress you, that you want to share with that other person as a way of opening and warming that. And something that I've noticed about you, Jennifer, is you are someone who's really good at putting other people at ease in conversation. And no doubt that's something that served you very well in your career as a recruiter and also now as a coach. It's certainly something that I'm sure you've refined over time and one of those situations that your clients will find themselves in, and also the people that are listening to this, all of us will find ourselves in is in the interview. And I know that interviews can be very high stakes and can be quite stressful, almost interrogations when you're on the other side or on the
- Jennifer Speciale:
- Candidate
- Brendan Jarvis:
- Side, right? Yeah. So from your experience on the other side of that, on the recruitment side of it, how do you help people in interviews to relax, to open up, to help join the dots between the relevant things in their career career, and what advice based on what you do, would you impart to candidates that they could use to flip interviews from interrogations into something that's more like a conversation?
- Jennifer Speciale:
- Yeah, absolutely. We spend a lot of time talking about this because it's so important and I care so deeply about my clients having a sense of control. It's one of the reasons I started my practise and I tell my clients like, look, we're not bound to our meeting every week. If you've got an interview coming up, we drop everything and we focus on preparing for that. It's not just something like, I'm there to give you a pep talk. It is absolutely paramount that you're prepared for that. And I care so deeply about my clients feeling empowered as a candidate and not at the whim of bad interviewers or an unprepared recruiter or a frenzied hiring manager or all of the above. I want them to feel focused and strategic and grounded. And the way that I tell people to do that is by taking control of the interview from the moment go, it will be repetitive.
- I've said it, but I can't impress upon it enough, which is thank them for investing time to meet with you. It's always an investment, not spending time. I care very deeply about using the word invest, not spend. And then the very next thing out of your mouth is to understand deeply what that person is looking for or the organisation, what's really needed. Try to illuminate what you can in this person's motivations because so often is the most dreaded question on the planet, which is tell me about yourself. I think that is just the most awful question ever that how can you garner anything about a person? I mean, some people think that it's good to know what they do in their free time, be specific about it. Anyway, I could go on and on about bad interview questions, but you have to be prepared for those things.
- And the way that you'll be prepared for those things is by asking the first question, taking control of that conversation, which doesn't mean be aggressive, come onto the zoom screen, ready to rumble. No, it just means you're calm, you're focused, and you have your plan, you have your strategy. The first question you're going to ask so that you can then answer actually appropriately and accurately. And you don't allow yourself to get nervous or spiral or wonder about the failed interview from last week or all the rejection you've experienced or all the things that are happening at home. You have three kids, you have a mortgage, you're the breadwinner. All of those things can be compartmentalised away because in that one hour you are actually in control. You're focused, you've asked the first question, you're waiting for the answer, and you will respond precisely to how they've answered.
- Because I know so many hiring managers that have logged in with my candidates, I've coached my candidates to start that way because I want my candidate and my hiring manager to connect on a different level. And I forced that connection by coaching my candidate, and my candidates will come back and say, boy, that was great. Thank you for telling me. Because the hiring manager said, I don't even know what the job description says. What I'm going to tell you is my life is a disaster. I need a clone of me. I need X, Y, and Z, and this role will be reporting to me, but I can tell you the roles and responsibilities will be blah, blah, blah, whatever it is. Or maybe the hiring manager says, thank you for asking. Nobody ever asked me that. Everybody just starts spewing off about all of their accomplishments and I don't get a word in, I don't get a question in. It just changes things. It starts a relationship. And I think that that's at the root of everything.
- Brendan Jarvis:
- Yeah, certainly highlights the importance of not just the preparation, which is obviously quite key, but also that initial starting point and using the question as a way of levelling the playing field. Now, I dunno if my framing here is going to be too sort of masculine perhaps or too aggressive, but do you get a sense that the candidates who are both prepared, composed but also believe that they are the prize and not an arrogant way, but a confident way, are the ones that are able to carry interviews to more successful outcomes? Or is there a different mix of objectives that you'd use to describe the type of presence people need to have in order to get the most out of those precious moments that they have in an interview?
- Jennifer Speciale:
- Such a good question. I love that question. It is a difference. My dream is that all candidates believe that they are the prize. Whether or not they are the prize for X role that they're interviewing for or not is the subjectivity. And the important nuance there is as a candidate to present yourself in a way that makes obvious that you are the right fit. However, if you are not the right fit, it is to everyone's advantage that you not get the job. And so clients that don't get an offer or don't get that job, I tell them, that's a gift, that's a save. They know something that you don't and you have to trust that they didn't see something in you that would've been a fit for them or that role. And that's a gift. That's a save. There were so many times in my career, not so many times, but there were definitely times and my career that I counselled candidates, look, I know you want this job badly.
- You want to be in this role, you want to have this experience, but I'm telling you, you won't be happy here. This is not the place for you. And I had, I'll never forget one woman push back like, you don't understand. I've wanted this company my whole life. This is isn't my dream job. And I said, I know you think that based on whatever you certain criteria, but I'm telling you, it is not actually your dream job. This is not actually your dream place. And I try to be specific about why it isn't. It's really hard to talk somebody down from that. But essentially I had to tell her, you just have to trust me. I know more about the organisation than you do, and I know you won't be an exact fit. You won't be happy and so aggressive or otherwise that doesn't matter.
- I want all candidates to think that they are a prize. They are a prize. They are the prize. Whether they're the right fit for a certain role is a different nuance, and I want them to be cognizant of that. Yes, you put your best foot forward, you create your portfolio and your case studies to highlight your best work. You can have a terrible interview and you can still get a job offer. It happens. There are those stories, how I bombed the interview, but thankfully the hiring manager and I had some unspoken bond. I can't believe I even got that. It happens. So that's not the only thing. There is something about being the right fit, really believing you're the right fit and that being the case.
- Brendan Jarvis:
- And also it sounds like there's something in there around as long as you can be sure that you brought your best. Don't judge yourself on the outcome. The decision was to turn up and present yourself the best way you could as the prize that you can be. But it's not a guarantee that every company's going to want to hire you. And I think that collectively, if we could shape more of our thinking around our decisions and the quality of those rather than on the outcomes which often are wildly out of our control, that would certainly help people bounce back and spring into the next interview better.
- Jennifer Speciale:
- I always tell my clients, and I told my candidates for years, don't forget you're looking for a match just as well as we are. And so if we've determined you're not the right fit, then you have to know that you're not the right fit and you are looking for the right fit. It's not only that you are at the whim in the control of the company, you have to find the right thing to. So I just wanted to say that.
- Brendan Jarvis:
- Yeah, 100%. Jennifer, you mentioned this a little earlier. You mentioned, and this is where I want to finish with you, is that women generally speaking have a behaviour that doesn't serve them particularly well, which is apologising too often. And just to finish up today, in your experience, what's a more empowering approach that you could recommend or in part to women who find themselves saying, sorry, too frequently.
- Jennifer Speciale:
- I have a decent number of male clients as well who have this. So all of the research I've done made me think it was more a female trait than male, and maybe the research proves that, but thankfully, my body of work is I have a nice balance of people who apologise too often. And the way to buttress yourself from this is to ask questions. Try to get in front of that interview first so that you are, if you have to answer an interviewer's question with a question, you should do so. That doesn't mean be obnoxious about it. At some point you have to answer questions, but if you can get enough information, get enough clarity on what the interviewer is really asking you will be answering questions in the right way. And don't apologise for asking a question. Don't say, sorry, I just want to clarify. No, pause and say, I have so many different stories I could share with you. I want to make sure I give you the right information that will help you understand me. So I want to clarify and then ask your clarifying question and then give the right answer. There's no apology necessary. If somebody asked you for directions and then they asked a clarifying question, you wouldn't expect that they apologised for asking a clarifying question on how to get there. You would want them to get there.
- Brendan Jarvis:
- That's a really important point to finish on. Jennifer, I've really enjoyed today's conversation. You've certainly shared many important insights that are valuable to people today. Thank you for so generously sharing your stories and insights with me.
- Jennifer Speciale:
- Thank you. I've really enjoyed this. You've asked such amazing questions. It's been really fun.
- Brendan Jarvis:
- It's been my pleasure. And Jennifer, if people want to connect with you, they're interested in the type of executive leadership coaching that you're providing, something that they heard today really resonated with them. What's the best way for them to reach out to you?
- Jennifer Speciale:
- They can reach out to me on LinkedIn and send a message there, send a connection request with a message. They can also go to my website and have a message sent. I have an amazing EA that helps me keep organised and respond. So definitely reach out. I'm here to help.
- Brendan Jarvis:
- Wonderful. Thanks, Jennifer. And to everyone that's tuned in, everything will be in the show notes, including where you can find Jennifer and all the things that we've spoken about. Thank you for lending us your ears and your eyes.
- If you've enjoyed the show and you want to hear more great conversations like this with world-class leaders in UX research, product management and design, and things that are adjacent to design, like leadership coaching, don't forget to leave a review, subscribe so that the podcast turns up every two weeks in your feed. And also tell perhaps just one other person about the show that might find value in the things that we discuss here.
- If you want to reach out to me, you can find me on LinkedIn. There's a link to my profile at the bottom of the show notes as well. Or you can head on over to my website, which is thespaceinbetween.co.nz. That's thespaceinbetween.co.nz. And until next time, keep being brave.