Developmental Career Strategy

18 minutes, 6 links


Updated September 25, 2023
Ask Me This Instead

You’re reading an excerpt of Ask Me This Instead: Flip the Interview to Land Your Dream Job, a book by Kendra Haberkorn. This powerful work is written by a veteran recruiter for job-seekers who want to find their dream job—not just the next job. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, worksheets and a question database, commentary and future updates, and a high-quality PDF download.

By this point, you’ve put in a tremendous amount of thought and preparation into getting the best outcome from the interview process, which gives you a meaningful advantage relative to other candidates. You have done more in that effort than the large majority of candidates ever will, and you’ll be better off in your next job and throughout your career because of it.

Hiring is hard and companies have an advantage. They know the pool of candidates they are working with, they can click through resumes, peruse LinkedIn, and control the flow of the process while they decide who is the “best.” They have the chance to test, compare, and see how everything settles. Hiring teams get to ask, ask, and ask some more. Then, at some point, they make a decision. If it’s an offer, they push, nudge, and smile to get you to accept and join on their timeline, and with their terms.

Companies often talk about hiring the “best people.” Realistically, teams hire the right person to do the work well enough, and who is also interested, available, and known to the company. I realize this is less impressive from an ego perspective and less punchy as an employment brand headline, but it’s closer to the truth. Someone can be the right hire in one environment—succeeding, thriving, and delivering impact all day, every day—and fail in another environment. It’s the mutual match that matters.

importantIf you put the practices outlined in this book to use continually, you’ll have an even greater advantage. You will:

  • Find and evaluate career opportunities as they arise.

  • Learn about different companies and industries, meet people from various teams, and match roles with your priorities with more confidence.

  • Be ready to tell your story, advocate for what matters, and succeed in navigating the hiring process.

  • Be empowered to choose the job you want, not just the job you need.

Take Power in the Process

Now, I want to remind you of your power in this process so you can seize your potential.

  • When you know and commit to your priorities, you have power. With reflection and preparation, you’re going to hone in on what is most important to you as you go through the job search and interview process. Then, when you’re in the interview room, you can focus on being authentically you. If you feel yourself putting on an act, projecting something that is not naturally you, or compromising on one of your priorities, beware! Think of the effort it’ll take to sustain and maintain energy, engagement, and commitment to the work if you’ve made compromises on the things that matter most.

  • When you have a plan, you have power. You might have wondered while reading why you should take all these steps to prepare for your interviews and might still be doubtful about your intent to follow through. Having a plan gives you power; you aren’t only subject to the company’s process but can take steps to ensure that your priorities are covered as well. When you walk in with a plan, you can maximize the limited amount of time you have with each interviewer and target your follow-up on the most important items. Getting to interview for a job you’re really excited about is hard enough. If you don’t know what you want out of the process, you’ll miss the opportunity to get the job that could be right for you.

  • When you are proactive, you have power. Knowing what is most important to you, asserting your preferences, and collaborating throughout the process (interviews are a mutual exercise!) is empowering. By asking targeted questions, you’ll demonstrate your capabilities and confidence far more effectively than providing polite, respectful, diplomatic answers. Both the company and you want the best outcome—a strong mutual match based on known strengths and acceptable tradeoffs. If someone pushes back when you ask questions to get the answers you need, think about whether this is the kind of place you’d be inspired to do your best work.

Nurture Your Network

You should start looking for a job long before you’re ready to apply or make the move. This is the interviewing equivalent of “always be closing.” You should “always be looking.” To do this successfully, you need to find credible websites that focus on the roles and companies that are most in line with your interests (for example, B Work for mission-driven job seekers, Jopwell for Black, Latinx, and Native American students and professionals, or FlexJobs for remote or work-from-home roles). To find these niche boards, pair a role or function, for example “design” with the words “job board” and you’ll quickly discover sites like Dribbble or Behance. These are not the big job search engine sites. Those sites, including LinkedIn or Indeed, can be helpful when you know precisely what you’re searching for and want to see what openings might be available within your geographic area or search criteria. Next, you should subscribe to newsletters or updates that you can consume on your own timeline (or when an interesting subject line catches your eye) and that include reliable highlights about leaders challenging the status quo, companies making a difference, or products that are changing the way people perceive, experience, or spend their money within a particular space.

Even if you do not want to have a prolific voice on social media, establishing a presence by following interesting people who comment on relevant topics, have roles that you’d aspire to have or who surface articles, podcasts, or posts that intrigue you is beneficial. “Using Twitter,” by Fadeke Adegbuyi provides expert advice on how to use Twitter to find a job (including those that are never posted!), build your network, and advance your career. This is important to start and sustain before you need a job, you never know when you might hear or find something worth pursuing!

important You should also cultivate and invest in your network on an ongoing basis. Your LinkedIn connections are only valuable if you can activate them (i.e. get a response when you reach out)! One strategy is to organize your connections into three groups.

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  1. Connections you need to stay in touch with—these are the individuals who have made a difference in your career, with whom you’d gladly work again, people you could ask to be a reference, or who you believe will play an important ongoing role in your career. This group is probably 15–20% of your network.

    • Make a plan to reach out to these individuals 2–3 times a year if you’re not actively working with them. I block time at a couple intervals throughout the year to actively touch base with this group within my network. One of my touchpoints is a personal email or LinkedIn message and then I try to text, comment on a milestone post, or get together in person (outside of a pandemic) for another touchpoint.
  2. Connections you want to stay in touch with or build a relationship with—these are individuals who are not as close as those in the group above but who might work in a similar role or field or at a company you find interesting, or individuals who you’d feel comfortable reaching out to if you were looking for advice or a new role. This group likely represents about 25% of your network.

    • Check in with this group at least once a year via a personal email, LinkedIn message, text, or a coffee meetup. This group has the potential to point you toward interesting opportunities you would otherwise not hear about!
  3. Other connections—these are individuals who you may have crossed paths with directly or who are in your network due to common connections, interesting posts, or quite possibly for some unknown reason! You may or may not have ever had a direct interaction. While it’s possible that these individuals could play an active role in your career, it’s unlikely. This group could represent 50% or more of your network.

    • Respond to requests that seem viable or interesting and comment, share, or like their posts if it makes sense.

Keep a pulse on what or who piques your interest consistently from the activities above. It’s possible that you will find a single, amazing opportunity that you’ll be able to pursue and everything will come together. Those rare instances where serendipity and the forces of the world converge can happen, and it’s exciting when they do. More often, it’s a process. You’ll follow people and companies or search for a category or two of roles and start to get a feeling for how particular companies and teams represent their opportunities. When you first start searching, you might have a pretty narrow set of criteria that you’re focusing on. As you progress, it will likely expand, and then, with many examples as a reference, you can begin to calibrate, see through the marketing (and occasional false advertising), to refine your efforts again in a more targeted direction.

Interview, Interview, Interview

You build on your power and seize your potential when you interview every chance you get. To the job of your dreams, you have to show up at your best. You don’t show up at your best without practicing. I want you to interview every chance you get, or at least every year.

important Why should you look elsewhere when you have a job you like? It’s the best way to make sure you are there for the right reasons—engaged, enthusiastic, and all-in. Thinking clearly about your career path and preparing to succeed in interviews is more easily approached when you’re not under the pressure of needing a new paycheck, and when you have the chance to weigh your current role’s pros and cons relative to any move you’d consider making. This provocative approach to interviewing opens the door for honest reflection throughout your career. It gives you the freedom to see what else is out there and determine if what you have is better than other options available. You can explore and have conversations to learn more about yourself and how a role and company can support your interests and priorities. It also helps you understand how your experience and skills are valued in the marketplace, which can help you negotiate an offer or go back to your company and ask for a raise. These realizations unlock something powerful—you have options.

If you keep your skills fresh, do your best in the role and cultivate relationships with current, former, and prospective colleagues, you won’t be stuck. So, even when you love your job, answer recruiters’ emails and apply for jobs that look amazing. Sometimes these efforts will go nowhere. Other times, they’ll yield worthwhile conversations and new insights. And maybe, they’ll end up pointing you to the next best opportunity for you—one that you wouldn’t have found without looking at your career as a journey with multiple destinations and a variety of ways to get from here to there.

You will learn every time you go through the interview process as you reflect on the work you’ve done and what you’ve achieved or messed up. You get to articulate your story, refine your value proposition, and learn about yourself and a bit of the world beyond. Maybe the conversations you have this year aren’t the ones that lead you to make a shift, but they help ensure you’re ready and prepared if and when that right role comes becomes a real possibility.

Get Ready to Run

So how do you know if you’ve found the “one”—the job that’s right for you, right now? You should answer one of my favorite questions to ask candidates for yourself. I like to close final round interviews by asking, “What would make you run toward this opportunity with enthusiasm and what would make you run away?

I give this advice because, though I have asked this exact question dozens of times to others, I didn’t ask it to myself a few years ago. While working long hours in a demanding job, I found myself daydreaming about quitting during the day and casually scrolling through job postings or venting about my job to friends in the evenings. Though I couldn’t see it and truly didn’t realize it, I was already running away. So, when a compelling opportunity with awesome people came up, I took it. It was, objectively, a great job, but it wasn’t the right job for me. Had I taken the time to evaluate my priorities, explore what options were out there—and crucially, had I asked better questions of my interviewers—I could have saved myself and a team I cared about a lot of time, effort and … emotional turmoil. Look, this type of thing happens, and it’s not necessarily anyone’s fault, but the work and approach outlined in this book can save you and others from having to have the same experience I had.

It is best to intentionally move toward a new role rather than leave a job for any role other than your current position. As an interviewer, the “run toward” question gave me some of the best clues and cues about what mattered to the candidate, where their mind was, and what our risks were if we wanted to hire them and bring them onto the team. I knew it was getting at something when I started to see how people reacted to the question. It often made them sit back, smile, and genuinely reflect before they answered.

So think about a job you are interviewing for.

Are you running toward this role? Here are some of the most telling signals:

  • You start telling everyone about the company, the role, the people.

  • You start using “we” as if you’re already part of the team.

  • You think about it non-stop, ideas or reflections pop into your mind at unexpected times.

  • You start to “do” the work—the questions and problems you’ve learned about are so interesting that, in your spare time, you begin to research and dig into them to try to solve them.

  • Your gut is telling you that these are your people, this company represents your purpose and this product is the one you want to support.

  • You realize that if you were to sit down and craft your dream job, it’d look a lot like this one.

Or, are you running away? These might be indicators that you should explore other paths:

  • Your conversations leave you with more questions than answers.

  • You get an odd feeling about interactions with members of the team—nothing specific but something’s still off.

  • You get the impression that what the job description or careers site promised is more fiction than truth.

  • You are experiencing stress or anxiety even if the process has positive momentum.

  • You cry ugly, not happy, tears when you get an offer and don’t know what to do (not that this has ever happened to me …)

  • You are bored and uninspired during interviews and forget about them the minute you walk out the door.

  • You’d be “OK” if it didn’t work out.

Finding your place is as much about eliminating the options that won’t fulfill your expectations and aspirations as it is about locking in on the ones with the most potential. Going into such a major decision with eyes wide open provides the greatest odds of a beneficial experience and outcome for everyone involved, especially you!

This book is for you. Where are you running to?

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