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Interviewing secrets (and handling silly questions)

I’ve now recruited for a few hundred positions, and have done 5-10 interviews per position… which adds up to something between 1000 and 2000 interviews in my career.

I do tend to approach interviewing quite differently now than when I first started – to make it more of a conversation, by providing context about the position at the beginning, and inviting the candidate to ask their questions up front, before we transition into the questions I want to ask. (Hiring is an assessment process that goes in both directions, after all.)

But I remember how many interviews I used to do on a daily basis (probably five on average), with maybe a 30 minute break in between, and feeling the pressure to fill all the roles I was working on… yesterday. That created a situation where I felt the need to control the conversation as much as possible, with less room for real dialogue, and more focus on sticking to my questions.

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That’s where a lot of recruiters and HR people will be coming from – so it can help to have some empathy for what they’re facing. And, it’s worth noting that a lot of people doing recruiting have come through the school of thought about HR that is very focused on following the rules – for example, asking the exact same interview questions of every candidate.

There isn’t actually a law requiring them to do this – but rather a fear that if they stray from the script, they will get sued because they treated candidates differently.

And, underlying all of this, the recruiter still needs to know who you are and what you bring to the table, so they can effectively evaluate you for the position.

While you as the candidate can’t be in control of the flow of the conversation (definitely don’t try to do that!), there are things you can do to get across what’s important about you.

Interview Tips

  • Find a list of typical interview questions online, and write out or practice your answers to each. Look for the ways you can turn these basic questions around to get at what they really want to know. For each question, find a way to communicate one related nugget about an accomplishment, a similar situation, a summary of how you think about things. You can still answer their questions, but make sure you are also clearly communicating something you bring.
  • Brainstorm some clarifying questions. If they ask you something that seems too vague to answer well, or something you’re not sure about, just ask a question or two back – “I want to make sure I understand your question. Could you rephrase that?” (Sometimes my questions meander and are too long to be clear! I’m always happy to clarify what I’m really asking.)
  • Prepare with elements from your résumé – including those that may not have made the final cut, so you have a whole set of possible answers. Be able to talk in-depth about each bullet point you listed, with specific examples to back them up.
  • When you are asked about your strengths, don’t just list a few adjectives, but think about a specific story that demonstrates several of your strengths. Give context to what you’ve done – that way, you won’t just be sharing empty words.
  • When you are asked about weaknesses, or a time you made a mistake, the most important things they’ll be looking for are: 1) do you have genuine self-awareness?; and 2) do you learn from mistakes or challenges and improve? Again, use a story as a way to get these things across.

In an ideal world, recruiters and candidates would always have authentic conversations. At this point in the process, it may feel more one-sided, especially as you share more than just a basic answer to these questions.

Remember that this is part of the process of finding the right fit. If authenticity is one of your values, for example, and the organization’s recruitment process is really dry and superficial, that tells you something important about whether there’s a cultural fit.

Marketing yourself, using the cover letter

It’s entirely possible that cover letters are old-fashioned. I don’t honestly have a great idea how many recruiters actually take the time to read them. And – you never know what might make the difference for your candidacy, so it’s worth having a few versions of your cover letter that serve as an additional way of marketing yourself.

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Why? Because just as the résumé is a supporting document to help people understand what you bring to the table, the cover letter is a way to make it easy for people to understand why you want this particular job – and to work at this particular organization.

What I find in my recruiting work is that despite requesting cover letters that speak to these things, I most often receive truly generic pieces of writing, full of standard phrases like “I’m confident that my skills, abilities, and experience make me an outstanding candidate for this position.” (They don’t even bother to put the actual job title they’re applying for in the letter.)

And then other people don’t send a letter of any kind, even in the body of an email.

Take 10 minutes to customize your (1 page, max) letter to the position you’re applying for, and you will stand out in the pool of candidates.

This customization is simple:

1. Why this job? Write a few sentences about why this position is the next logical step in your career, and what you bring to this position from your previous career or role. Write in your own voice, not standard cover-letter-speak! What are you ready for? What specific example can you share about what you’ve done that applies to this job?

Especially for career-changers, your cover letter is the opportunity to explain why you’re changing careers, and how you’ve landed on this particular career path as a next step. It’s a chance to clarify why your background is valuable to what they do, and to this position.

2. Why this organization? Don’t just say “Your mission is inspiring.” Take the time to do a little research about who they are and what they do, what big things have been happening lately – and then write 2-3 sentences about why this is exciting to you. Connect it to your interests, your background, whatever is relevant – but make an authentic connection, not just pasting a sentence you found online.

From these steps, you can form a template cover letter that you can use for other job opportunities – as long as you make sure to write new content for those two key questions.

Take the time to write a letter that stands out – because the worst thing as a recruiter is getting a cover letter that literally has another organization’s name on it (and I’m guilty of sending one or two of those myself).

Slow down, and do it right. You will stand out.

(And as an added bonus, this thinking will help you prepare for an interview.)

Résumé tips for career changers

When changing careers, people tend to start with two things: searching through job postings, and updating their résumé. While those are two components of the process, I see each of those as supporting tools, rather than starting points or essential steps.

Once you’ve done the work to inventory your values, what you bring, and what you’re looking for, it’s easier and faster to look through existing job postings and know whether there’s a fit, or whether they’re worth exploring before you apply through an informational interview.

Similarly, your application materials – a résumé and cover letter – are best used to effectively communicate what you’ve already figured out about yourself, and to market yourself for a specific kind of opportunity.

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Ideally, résumés should not be used as leading documents – especially if you’re making a big career change.

Why is that? Because your résumé, as it currently outlines your previous career path, will not make sense to the person reading it in your new career path. And as I’ve mentioned, recruiters have a lot of applications to sort through, so anything that’s unfamiliar will get tossed.

You have to make it easy for them to understand:

  1. What you bring to the table, and how it translates to this job (the résumé)
  2. Why you want this particular job (the cover letter)

Marketing materials are designed to sell you something. Your job application is the supporting player (after networking) in selling you as the right fit for their open job. After reading thousands of résumés over my career, I know what actually works to grab people’s attention – and keep it.

Résumé Tips

  • Keep it short – 1-2 pages at most! In a simple font – not fancy, and not tiny.
  • It can be organized chronologically (most recent job first), or functionally (by summarizing the common threads of your career in categories, such as “sales” and “management”). If you go the functional route, you just need to include a short list of your work history (with dates) at the end.
  • Focus on communicating the top 3-4 accomplishments from each position, rather than bullet points from your job description, which are rarely effective at conveying what you actually did. Use data, results, numbers wherever possible to help translate what you did (e.g., Increased sales results from $1M to $2.5M over two years).
  • Take out any jargon specific to your previous industry – acronyms are useless unless you’re staying put! Have someone outside that industry read your résumé to point out all the questions they have about what things mean.
  • Use a summary at the top: especially for career changers, it’s critical to explain on your résumé exactly why you’re looking to switch careers, what skills and experience you have to offer, and how they apply to this general job category.
  • You should not, however, state in your summary or objective that you want this specific job. That’s a) too easy to forget to change before sending your résumé elsewhere, and b) not really true as you’re looking for the right fit, not one exact title.
  • It doesn’t need to have a creative design component to it – unless you’re a graphic designer or artist, in which case that should be your primary focus! For everyone else, keep it simple.
  • Add the same résumé on LinkedIn – it’s important to have an online home for your résumé, so you can quickly share a link in your networking. And frankly, when people don’t have a basic online presence, I wonder about their technology skills.

You’ll notice I haven’t talked about using keywords hidden in your résumé, or other tricks to get an application system to put you at the top of the pile.

This approach is all about making use of the human connections first, so you don’t have to worry about how a bot is going to scan your résumé. Even big companies hiding behind solid fortresses of application software still have humans who work there!

What are some résumé tips you’ve learned?

Preparing for Informational Interviews

Spending time to hash out the specifics of what you are looking for in a new career (and why!) is critical to your job search process. When you reach the informational interviewing stage, all the people you’ll come in contact with have a million other things going on in their lives, and while they most likely want to be helpful, your job search won’t be top of mind for them.

You have to make it easy for them to help you.

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Prepare Your Request

The first element is crafting a few versions of the request for an informational interview, which you can develop as you do your outreach and adapt it for different people, and especially for those who might not know you as well.

“I’m looking to transition my skills in business development into fundraising, and would appreciate spending 30 minutes with you to understand more about what your day-to-day work looks like.”

“As part of my career change process, I’m interested in connecting with people who work in marketing positions at start-up organizations, and was hoping you could think of three people to connect me with.”

“Jane Smith suggested I reach out to you. I want to move to an organization working in the international development space, and she spoke highly of your work and what XYZ is doing. Could I treat you to coffee in the next few weeks?”

“I understand your career path aligns well with what I’m looking to do. Though we’re not in the same city, would you have time for a 20-minute video call to share your experiences?”

Prepare Your Pitch

Next, you need to have a brief description of what you’ve been doing, what you want to do, and how your skills and experiences translate to this new environment. Do the work for them, so they know what direction to point you in! And, be prepared to answer questions like these at some level of depth.

  • What kind of organization, culture, values are important to you? (You may not talk about this directly in your conversation, unless there is alignment – otherwise, it may just inform the questions you ask them.)
  • What is the kind of work you want to be doing?
  • Describe what you want an average day or week to look like.
  • What level of responsibility do you want? In what kind of organization?
  • What kinds of challenges are you looking to tackle?
  • What are you bringing to the table that might meet their needs?

Do Your Research

Find out about their background to inform questions you might ask. Look into what positions are currently open at their organization, to see if there might be a potential fit, even a partial one, to explore. Understand what’s been happening lately with the company – big news, growth, issues.

Come up with your list of questions for them – remember, people like to talk about themselves! A few of my favorites are:

  • Tell me how you got into this work.
  • What skills/experience/training have you found essential to the work you do?
  • What are the challenges/problems you’re trying to solve?
  • What does your typical week look like?
  • What do you look for when you hire someone for your team?
  • What is the culture like here? How do people work together?
  • What do you enjoy about working here? What are some of the challenges of working here?
  • How does your recruiting process work? How can I best position myself?
  • What are the intangibles that make someone succeed in this role?

Preparation is a key part to having a great informational interview – when you show you’re prepared and thoughtful, those are some of the qualities they’ll remember about you.

And, doing all this preparation can turn a situation that’s nerve-wracking (or awkward) into one that’s less scary, where you can just have a real conversation with another human being, knowing you’re ready to share what you care about, and to engage them in a way that shows you care about them.

Brainstorm 3-5 questions you’d like to ask in your next informational interview – then try them out!

Building your networking muscles

Fairly often, I get requests for informational interviews, and I’m usually happy to squeeze those in (after all, these were the foundation of my initial career search!). While I’m honest about the fact that I may not have a specific opportunity for them, these conversations help me learn whether I might want to recommend them for something in the future.

Everyone I meet with goes on a list of potential hires, because there are organizations reaching out to me all the time with hiring needs, and whenever I get one of those, I go back to my list to see if there’s a potential connection to make.

And that’s what informational interviewing produces – potential opportunities, which may take a little longer to come to fruition. But because you were able to get in front of a real, live person, and explain all the great things you bring to the table, you’ll be top of mind for them.

There are a few things to keep in mind as you build your networking muscles.

Dedicate Time to Networking

You need to block out time each week to focus on this part of the process – time to comb your networks, to reach out with requests, to meet with people, to do the follow-up needed (even just a quick thank-you!). It doesn’t need to be incredibly time-consuming, but focusing 2-3 hours per week is one thing that will yield results. The more people you can get in front of, the more potential opportunities will surface.

Informational Interviews Are Not Job Interviews!

In the beginning of your job search process, you’re looking to set up informational interviews – not actual job interviews. This may sound a little disingenuous, but it’s a way to help people feel comfortable giving you some time on their calendars – especially when you don’t know each other.

Setting yourself up as someone who wants to learn more about a particular kind of role, or about the culture of a certain organization, can take the pressure off (especially if there are strict HR processes that would get in the way).

People like talking about themselves, and giving advice! They like sharing their stories of how they got where they are, what the career path is, what they’d recommend you do. This should be the main focus of your time together.

Make a Clear Ask

People respond better to requests that are specific, rather than vague.

For example: “I’m looking to transition my skills in business development into fundraising, and would appreciate spending 30 minutes with you to understand more about what your day-to-day work looks like.”

Or, “As part of my career change process, I’m interested in connecting with people who work in marketing positions at start-up organizations, and was hoping you could think of three people to connect me with.”

Follow-up Is Key

You are the only one who cares deeply about your career change, so don’t be afraid to follow up on your requests. If a contact hasn’t responded after a week or two, try again once or twice more before moving on. Or, try another mode of communication if you have options – not everyone is checking LinkedIn as often as you!

And once you’ve met with someone, send a quick thank-you note within 24 hours of your meeting. It doesn’t need to be complicated or perfect – just be polite and grateful that they took some of their precious time with you.

What’s one simple thing you can do this week to build your networking muscles?

Is anyone reading my application?

The way most of us are used to finding a new job is by looking through advertised positions, submitting applications, and then waiting with our fingers crossed. While that’s certainly logical, there are a lot of disadvantages to approaching a career change this way.

When you’re looking to move from one industry to another, or one sector to another, or to shift to a different function than the one you’ve spent decades in, just hitting “submit” on job postings will get you lots of crickets – and frustration at the black hole of application sites.

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If the recipient of your application is a sophisticated online system with algorithms scanning for key words that match the job posting, chances are they only have a superficial understanding of the potential fit (so far, anyway). There’s very little human possibility in this approach, which makes it difficult for an atypical application to get through the filters.

On the human end of things, it can be just as much of a challenge breaking through. Sometimes, the recruiter who is scanning resumes is very black-and-white in their thinking, acting more like the algorithms – how many boxes did this candidate check? – rather than bringing creative, critical thinking to the search.

Other times, the person reading applications is newer to recruiting, or hasn’t really been trained, or wears many different hats – and is going so much on instinct that they might get triggered by a certain university, or reminded of someone they used to work with, rather than making a logical decision on whom to move forward.

For applications that come from career changers, neither the algorithms, nor these kinds of recruiters really know what to do with a resume that is different from what they were expecting, one that raises issues such as:

  • This person is going to want a lot more money than we have.
  • How are they going to fit in to this culture when all they’ve done is ____?
  • This resume is nothing like the others – it doesn’t make sense to me.
  • How does what they’ve been doing relate at all to this job? I don’t see the connection.

Even one of these questions is enough to prompt them to pass on you without getting curious about the possibilities.

Pretty frustrating, isn’t it?

The best way to get your foot in the door to industries you’re interested in, for jobs you might be interested in, is still by connecting with actual people.

In order to do that well, first you need to spend time learning what’s important to you, and what you’re great at – so you can clearly communicate some ideas of where you might fit.

Then, it’s time to build a list of who you can connect with – who in your own network might have ideas, whether for positions that might be a fit, or for people in their networks they can introduce you to. You can certainly use a tool like LinkedIn to help facilitate this process, especially to see who your contacts are connected with, so you can make specific requests of them.

Building your network is your primary tool to make this a much more effective, and lifegiving, process – to remember that it really is about connecting with other humans.

Who are three people you can reach out to this week to move your job search in a new, fresh direction?

Exploring possibilities, not job postings

When most people consider making a career change, they often start by looking at what other job postings are out there, reviewing the lists of qualifications, and seeing if they meet enough of those to apply.

Unfortunately, that’s not a very holistic – or even optimistic – way of going about such a transition.

Comparing yourself to a long list of requirements makes you feel less-than from the beginning. So, you can imagine how that attitude will affect the rest of your job search, and your hopes for finding something better.

The reality is, most companies outline these requirements as a quick way of disqualifying people, because the recruiters on the other end are overwhelmed by applications they often don’t know how to process.

And the reality under that is most organizations over-rely on these sets of qualifications, as if checking all those boxes means they’ll have the right person in front of them. Instead, the process of hiring is really more art than science – sure, there may be some skills or experiences that ARE required to do a certain job. But not 20 of them.


Create Possibilities

When I spend time with my coaching clients to identify their values, their deal-breakers, and their strengths, these pieces start coming together to reveal possibilities for roles and industries that are worth exploring.

For some people, it can feel overwhelming to start from a blank page, so it can help to have ideas to try on, to see if they might fit, or if they bring up other ideas. A career inventory is one way to help you think beyond what you are already familiar with.

The goal at this stage in the process is to find a way – whether through online assessments or by working with a coach – to generate a list of possible ideas. These are potential jobs or career paths that seem to match up with the values you hold, and the strengths and experiences you have. (And at this stage, there’s no such thing as too many possibilities!)


Explore and Research

Once you have this list of possible ideas, it becomes more feasible to begin researching real-life opportunities. You can start by reviewing job postings with similar titles, understanding more about some industries you don’t know as well, and even beginning to do some networking to get a realistic picture of what people in these jobs do all day.

As you do this research, remember it is still exploration – some things will clearly feel they are not the right fit, and that is as valuable to know as what does feel like a fit. Since you’ll be starting with a fairly long list to begin with, the process will lead you to a narrower set of opportunities to pursue.

And, it’s important to remember: don’t disqualify yourself as you go through this exploration. You’re just learning and understanding – and later on, you can get a more grounded sense of how your strengths and skills match up, or what other steps to take before pursuing your longer-term goals.

What are three exciting new avenues you could explore in your career change – even if they seem scary or unknown?

Uncovering your strengths

Once you have a more global view of how you tend to work and see the world, it’s important to get specific about what you are bringing to the table. Rather than approaching this through a resume, I find it more helpful to reflect on questions that will connect the dots beyond what you’ve done in previous jobs, especially if the goal is to make a bigger career shift.

This higher-level process can illuminate some surprising things. Remember to think outside your set of traditional work experience, and include other kinds of work you’ve engaged in – side hustles, early jobs as a teenager, staying home with kids or as a caregiver, volunteer work, community projects, hobbies, and more!

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Be generous with yourself: this part of the process focuses on collecting the dots of your strengths and experiences, and later on, you can work to connect these dots. Use the questions that most resonate with you – we are sparking ideas here, not trying to nail down one life purpose (which doesn’t really exist, anyway!).

  • What are you known for?
  • How do other people describe you, and the role you play on a team?
  • What are you great at?
  • What’s a time you felt most alive in what you were doing? Describe the details of that experience – what you were doing, why, how you were working, with whom… (Now that you’ve thought of one example – what others come to mind?)
  • Where have you felt at your best? (Ideally, where you also felt filled with energy, rather than drained of energy.)
  • What value do you know you have to offer?
  • What do you feel called, or nudged, to do?
  • If you could create your ideal job, what would you be doing? What would your day (or week) look like?
  • What have you learned that you want to apply, or work with?
  • What are some of the common threads that run through the work (of whatever kind) you’ve done – the skills you’ve built, the places that have been a fit, the problems you’ve solved, the people you’ve engaged…?

These can be some heavy questions, and it may seem counterintuitive to a job search not to jump right to resume updates and applications.

Why is it worth taking the time up-front to build some clarity and certainty about your strengths?

It makes your career change or job search that much more effective and efficient:  you will be better able to find roles that match up with how you want to work, and you will be better equipped to communicate clearly in applications and interviews how your strengths will contribute to the goals of the organization.

Plus, you won’t waste your time on opportunities that aren’t actually a match for what you love doing!

Bottom line: This kind of introspection is one of the best ways to set you up as a much stronger candidate, with real clarity on what you want to do.

Finding your center of gravity

Uncovering your values – what matters most to you – is how to start building your roadmap to a career change. And, that list is probably too vague to give you a practical sense of exactly where to go on that map!

The next level of self-reflection is developing more awareness about how you show up in the world and how you engage with others. This kind of information is an important foundation of how you will present yourself in applications – and especially in interviews.

There are a number personality assessments out there which can help you understand your center of gravity in terms of how you work, how you process information, how you work with others, how you stay motivated. They can provide a good place to start – and later, an effective way to know whether the opportunities in front of you will be a good fit. Here are a few of my favorites:

  • Enneagram – a more holistic description of how you approach the world, which can provide some incredible self-understanding (if you’re ready for that kind of work!).
  • DISC – more commonly used in work settings, it helps you understand if you lean toward driving for results, enthusiastically building relationships, providing stability, or conscientiously following process.
  • Four Tendencies – this one zeroes in on how you respond to internal and external expectations, and how those help you get things done (or don’t!).

I like to think of these as helpful information, which might confirm some gut feelings you have – rather than something that scientifically labels who you are for all time. Each of us adapts and evolves with each new environment we work or live in, and we are all capable of broadening our way of being in the world.

Where these kinds of self-assessments come in handy is in reminding you how you tend to operate – and providing you with the opportunity to better explain yourself and what you bring to the table.

A few questions to reflect on:

  • How has it served you to work from this center of gravity? What accomplishments have come about as a result? What are you proud of?
  • How has your center of gravity limited what you could do or accomplish? What examples can you think of where you missed out on an opportunity?
  • How can you use the knowledge of your center of gravity to inform your career move? What past jobs or companies have been a good fit for you, and which ones haven’t been?
  • Knowing what you know now, how can you use your center of gravity in a positive way? What will you do differently in your next job?

What are you willing to shift?

The tricky part about figuring out your values is that you can’t un-know them once you’ve gotten that clarity. Your values will become a north star as you explore opportunities and evaluate them – and, will sometimes feel like a nag.

They will be that voice that says, “I don’t have a good feeling about this,” or “This job is missing a big piece of what you’re looking for.” They might even burst your bubble about a job you were feeling excited about… or make you realize it’s time to move on from the place you’ve been forever.

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The good news is that by leading with your values, it becomes easier and faster to navigate the process of job searching, because you can quickly rule out things that won’t fit.

The bad news is that sometimes it can feel like you’re letting perfectly good opportunities go, and the more time that goes by in your search, the more stressful that can become. And those opportunities might be perfectly good – for someone else.

When you make decisions based on what’s important to you, it means bringing to life a more holistic and inclusive version of yourself, without compromising the essentials.

This isn’t about being an irrational perfectionist, though. It’s unlikely that there’s one job that is 100% perfectly aligned with everything – the right position, the right culture, the right boss, the right salary, the right location, the right office space…

This process does require making some decisions about what elements are NOT a priority for you, or where you are more flexible.

Look at where you can create some wiggle room, so you can get more of what you do want.

  • What are your true needs for salary and benefits? If you are changing industries or sectors, find out how your needs match up with the reality of where you want to be. This is not about compromising on the value that you bring, but about having specific information that will help you know what to expect.
  • What locations are you open to? Especially if you’ve tried for a while to find a job where you are – think about what you love, and what you don’t love about your current location. And do some research on places that might offer more of what you love, and less of what you don’t. (For example – we moved from Boston to Colorado Springs a number of years ago. While I still miss my hometown (and the ocean), living in a smaller city has brought opportunities to plug into the community in ways I never could have back home – and without the traffic I hate!)
  • How might you think about commuting differently? If the best options for positions involve a two-hour round-trip commute in awful traffic, what if you moved closer? There can be some big savings in expenses from thinking like that (here is a blog post that might take you down a rabbit-hole about saving money from commuting).
  • What physical space is important to you? Would you be open to working virtually? From a cubicle? An open office environment?

Understanding your values and your dealbreakers is a key step in your process, and some of these elements will require engaging with your partner or family to explore some of these possibilities together.

The end goal is to have a clear sense of what matters most to you – whether concepts like values or details like desk location – and then you can move through the next steps with the confidence that you’re being thoughtful about finding the fit that is truly the right next step.