To Quit or Not to Quit…

Many times, when people begin coaching, it’s because they’re secretly longing for a transformation. Or for someone to notice that what they’ve been doing for so long just isn’t working anymore.

In coaching jargon, this is called an “opening” – when the client is ready for some sort of change in their life, and seeks the perspective and support of a coach to help them figure their way through that change.

In my career coaching work, it’s probably not a surprise that my clients usually show up with a desire to be coached toward a different career, or a different way of integrating their career in their broader life goals. 

So it follows that during the course of coaching, many of my clients who are unhappy decide to quit their jobs – often without the next job lined up. It may be more surprising that other clients decide not to quit. 

What happens in our coaching work that helps them process what can be a scary decision?

First, we work to sort through their feelings, their wants and desires, their needs, and their realities:

  • Assessing what they really LOVE to do – and whether their current role or career path has room for that.
  • Looking at where, and how, they may have gotten stuck within the organization’s hierarchy – and whether there are options to get around that.
  • Understanding how they’d like to grow, and whether there are opportunities for that in their current company.
  • Digging into the politics, the dysfunctional team, the way their boss might not support them, or the way they’re not really set up for success – whether those are solvable problems, or dealbreakers.
  • Checking in on their overall priorities in life (including how those may have shifted since they jumped on this career path), and how their current job is (or is not) supporting those priorities. 
  • Noticing their stress level about work, as well as their level of ambition, and their willingness to put up with the hard stuff.

I help them see what I see, noticing the patterns, what’s normal and abnormal in work settings, and what I hear beneath what they’re sharing. 

And, I withhold my own advice about the “right” decision. Because each person’s path, and each person’s realities are different. My job is to support them through the decision that they make – and on to the other side of creating a strategy to get them where they want to go.

What do my clients decide?

Through our work, some of my clients come to terms with how unhappy they’ve been for a long time, and reach a breaking point where they just have to quit.

Other clients realize the career path they’ve been on was the default, safe option, rather than one they had intentionally pursued around their strengths and interests. And then, mid-way into their career, they find themselves, for the first time, thinking about how they would really like to be spending their work time.

Some clients need a kick in the pants to be stronger self-advocates for a promotion or a different opportunity within their current company, to see the value that they bring (and get comfortable talking about their contributions).

And still others find that what they really want is to maintain their current job, so they can pursue some more meaningful things on the side, whether just for now, or long-term. This can be a great option for those who want to see their career through to some milestone, or for those who have financial commitments they need to meet.

When we work to get clarity on what’s most important to you, and train a spotlight on your current situation, that can make the decision of whether to quit more straightforward. And then, we can build a roadmap to the future, where you can start to see a different possibility, a realistic goal to work toward. 

It’s no longer a nebulous, scary, dark future where you didn’t see any possibilities beyond your current situation (since our imaginations are often the first thing compromised under stress!).

And when the future looks brighter, and the roadmap not actually that long – well, that can make it feel safer to quit – or recommit to a sometimes challenging situation. Because you’re not actually that far away from taking some meaningful action on your career. 

My hope is that through coaching, each of my clients can get the clarity they need, and find confidence in whatever decision is right for them, right now. 

What if Gen Xers aren’t ambitious anymore?

I ran across a Harvard Business Review article this week about how Gen Xers aren’t getting promoted at the same rates as Millennials and Baby Boomers – and companies are going to face big retention challenges as a result. While I tend to be skeptical of overarching statements of entire generations, I was interested to read about the data behind these conclusions.

The first thing that struck me is how often my career coaching clients express a similar concern of feeling overlooked, that their previous success with putting their heads down and working hard is not being noticed or rewarded anymore. The data support this feeling:

Currently, only 58% of Gen X feels that they are advancing within their organization at an acceptable rate, as compared with 65% of Millennials. While Gen X has been loyal up until now, this frustration is approaching a breaking point for Gen X leaders who have advanced to higher-level management roles.

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While I think many Gen Xers have been comfortable with working hard at the same place for a while because they have responsibilities to fulfill to support their families and other commitments, so many of them are reaching a point of questioning what all this work is for. If they’re not appreciated or contributing to something that gets them excited – what’s the point?

The assertion in the article I take issue with is this:

But [Gen Xers’] unambitious reputation may be holding them back in the workplace, as new data reveals Gen X to be the “leapfrog” generation, overlooked for promotions at higher rates than their counterparts in other generations.

What I wonder about is whether many Gen Xers really want to be ambitious – especially when so many of them question the moral compass or ethics of the companies they’ve been loyal to for years. If many Gen Xers have realized these companies are making questionable decisions – while also contributing to problems like climate change and economic disparities – then why be ambitious? Why bother climbing the ladder of leadership only to be saddled with decisions that might have a negative impact on the world their children are growing up in? 

I suspect a lot of Gen Xers feel stuck. They have financial obligations to fulfill, between houses and kids and retirement funds. They’ve invested time building careers. They’re getting older, and are afraid they won’t be attractive candidates for other opportunities as a result. They know their careers aren’t going to end as their parents’ have. 

And they feel a pull from within to chart a different course for themselves. 

This place of feeling stuck is overwhelming. The risk of leaving feels too great. And they don’t have clarity on what this new path looks like, or even how to find it.

My role as a coach is to help my clients find that new path – or set of paths. To help them get clarity on what really matters to them, and then build a career search around those priorities. 

As a generation, Gen Xers might be charting a new path on what work can look like in the future.

What a kid’s movie has to say about “real” men

I have two young kids, and a house full of LEGO, so a natural movie for us to see together this summer was The Lego Movie 2. (We have now seen it at least three times.)

I often appreciate well-done kids’ movies for the layer of nuance that parents can find underneath the silliness. While Lego Movie 2 may not have reached the pantheon of Pixar movies, I loved the messages that were underlying the plot – in part because I hope they’ll stick with my kids as they grow up.

You see, I’m raising two boys. In an interesting time, when there are lots of competing messages out there about how they should be, what’s cool, what’s “appropriate” for boys, and what “real” men look like and do. While girls have encountered negative messaging forever, it feels like there has been a shift more recently toward a more inclusive way of being a girl – smart, strong, silly, and sweet.

For boys, what I’m noticing is that there aren’t a lot of spaces where they can see role models who are in touch with their emotions, who aren’t just putting up a tough front, who are willing to go out on a limb to declare what they love to do if it’s outside the norm. 

Emmet, one of the main characters, is one of those role models. He is motivated to help others, and be kind to people. He is honest about not feeling as confident in his skills and abilities to build things (what everyone does in that world). Even in the midst of a stressful, negative-leaning world, he just wants to create a place of joy and awesomeness, and help people work together. 

When we look at how men are supposed to be, Emmet is extremely unusual. Men are expected to look out for #1, to get ahead, no matter who they have to step on. Men have to cover up what they’re not good at, and can’t be vulnerable about what’s hard for them. Men have to overcome obstacles and focus on results, success, achievement.

And in fact, in the beginning of the movie, Emmet gets a bunch of crap for who he is, for his authentic way of showing up in the world. And after enough of that relentless criticism and feedback, Emmet questions his gifts and himself, and starts to toughen up, thanks to the role model he’s inspired by, Rex Dangervest – who lives up to all the things I described in the last paragraph.

I often find my male clients are in this space – having sublimated their true gifts, leadership style, or desires for their career, and gone along with whatever the world told them they were supposed to do, or how they were supposed to be. (This happens for many of my female clients too – the ones who’ve had to put on “masculine” traits to succeed.)

After a decade or two of trying to meet those societal expectations, these men are tired. Tired of showing up with a mask on every day. Tired of doing work they don’t really care about. Tired of playing the game, engaging in politics and tearing others down just to succeed.

When ultimately, what they really want is to feel excited to show up to work every day. Or to spend more time with their families, tapping into their loving and silly sides a whole lot more.

Though my clients typically show up wanting to figure out what their new career path should be, we have to start from a deeper place.

The journey starts with understanding what matters most to them. What their priorities in life are right now, and what might need to shift to focus on those things. What they get excited about, and what they bring to the table. What kind of culture supports the gifts they have to offer.

Then, we can work through a process to find them the place where they can shine without a mask on, where they can make time for what matters most.

In the Lego Movie 2, Emmet goes on a journey, too. He tries to hide who he really is, and to be as tough as others want him to be. He tries to prove himself as a “real” man. But in the process, he alienates those he cares about most. And (spoiler alert), ultimately, he finds a different kind of strength within himself – the belief that he already was a real man, and that his kind of leadership is needed in the world.

My goal is for each of my clients to reach that strong sense of knowing who they are and what they have to offer. And that in the coming decades there will be even more Emmet-like role models (especially in real life) for all the kids like mine who are watching closely to see if their gifts will be fully appreciated.

Why does meaning matter at work?

There are plenty of opinions out there about why we work. About how our society has now shifted from work as a means to an end, to trying to get everything we could possibly want from our work. This article in The Atlantic had a field day talking about how we put too much pressure on our work to be the end-all, be-all – the new religion.

While there may be some truth in how far that train has traveled, how much we may have come to worship work, there is still truth in the midst of our desire to feel like we’re having some impact, making some difference at the end of the day.

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Some yearning that our commutes, our full inboxes, our days of meetings aren’t completely pointless.

As a Gen-Xer, I’ve found we have a unique window into the world of work. We’ve seen our parents give their entire careers to one institution – mostly getting rewarded for that with moves up the corporate ladder, fully-funded pension plans, and deep relationships and impact at one place. (Sure, there were also zeitgeist-setting examples of mid-life crises, toxic leadership that never got questioned, and so on.)

As our generation has reached that mid-career point, our experience has been quite different. We aren’t willing to put up with poor leadership, or the same old status quo. We don’t necessarily want to repeat the “having it all” desire that our mothers may have fought hard for. We question whether it’s really worth it to put in all these hours, knowing the sacrifice to our families or community or things we love doing.

We are fueled, in part, by wanting some meaning, some substance behind what we do to earn money. We are perhaps more practical, too – already committed to mortgages and college savings and retirement plans and school districts – and less able to just quit and join the Peace Corps. 

So, it’s important – especially in this mid-career period – to know that we don’t just have to grind away for the next several decades. To feel confident that the hours we spend working give us a sense of satisfaction, purpose, joy, or impact.

And sometimes, it’s important to know that there really are other options out there.

There are different ways of seeking out that meaning, too. I often work with my coaching clients to tap into their curiosity to uncover what that looks like for them. A few questions we explore are:

  • What challenges do you enjoy taking on (at work, or elsewhere)? How could you find or create more of those opportunities?
  • How do you spend your free time? What would you spend more time doing, thinking about, learning, playing with, if you could?
  • What lights you up? How can you create more time for those things in your day or week? How can you build some routines or habits that incorporate joy?
  • What’s taking up your time that isn’t truly essential – either to your work, or your life? What can you say no to, or delegate, or outsource, so you can do more of what you love?
  • What do you get fired up about? What problems in the world make you mad? How could you get involved, explore new career paths, or other opportunities?

We all know that work is essential in providing for our needs. So, why not figure out how to make time for meaning, whether directly through your work, or in creating a different kind of “work” outside the office?

Persisting through the job search process

Searching for the next right job opportunity isn’t likely to be completely smooth. There is so much of the process that’s out of your control, whether it’s submitting your application into the abyss of internet job application sites, rounds of interviews that keep dragging on, lack of communication, or not quite getting to make your case in an interview.

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Resilience and Feedback

There is a certain amount of resilience you need to keep pushing through a process that can at times feel depressing or dehumanizing. What will fuel that resilience is taking time to step back and assess how your pursuit is going, what you’re learning along the way, and how to adjust your search based on the feedback or data you get.

You might get specific feedback about why you’re not being considered more seriously – you have too much experience, or not enough; they are looking for just the right fit for the team’s chemistry; you wanted too high a salary.

Each of these are data points to reflect on – to evaluate with your strengths and how you’re presenting yourself, and whether you need to emphasize some elements differently. Sometimes these data require a check-in with your values and priorities, to consider whether this information from the marketplace changes anything that you were prioritizing.

If you haven’t been able to get much feedback, and are getting a brick wall impeding your progress with no concrete information why you can’t get through – that can be an opportunity to reach back out to the places you’ve applied to ask for some feedback. It might be a sort of reverse informational interview, or an excuse to schedule one, to understand how to present yourself more effectively, or what they’re actually looking for compared to the job description, and your experience in applying for it.

Take a Vacation (Really)

And if you hit a point in your job search or career change where you feel depleted and frustrated, that’s a signal to step back for a little bit. Give yourself a vacation from fixing your résumé, meeting with more people, submitting more applications – and I mean that literally. Even if things are getting tight financially, take a full week off from these activities to do something else, to have some fun, to do things that feed your soul.

That’s critical to do in a process that’s really about selling what you bring to the table, and being authentic. You can’t do those things well if you’re exhausted (and the organizations can tell you’re just going through the motions).

Letting Go and Moving Forward

Finally, we all know that sometimes, the opportunity you had grown attached to – the one that really does feel like the perfect fit – isn’t yours after all. (I’ve certainly had that experience.)

Give yourself some time to grieve that, so that you can work toward letting go of all that you were imagining. That way, you will avoid comparing everything else to them, or bringing bitterness along with you in the next phase of your search.

Be kind to yourself in this process. Get the support you need to keep going. Do things that fill you up, so you have the energy you need to put yourself out there.

By sticking to what’s most important to you, it will work out.

Deciding on the right fit

What I wish for everyone is the time to figure out if the next career opportunity is the right fit. At a high level, it can help to let go of the idea that there is one perfect job out there for you.

The reality is that there are multiple paths that you could take, and each one will take you in a slightly different direction. You never know who you might meet, what challenges you will end up taking on, or how you will grow.

You can come back to a few elements to help you evaluate the opportunities you’re exploring, and the offers that come your way.

Values & Priorities

Check in with your list of what matters to you as you go deeper in exploring different jobs or organizations. Listen to your heart, your gut, or whatever speaks to you when something feels right, or feels off. Use those feelings to ask yourself what else you need to learn about in order to feel confident in your choice.

For example, you’ve placed a high priority on finding a manager who will help you grow. Your potential boss seems promising and has good answers to your questions about management style, but it’s hard to know after a handful of conversations if it really is a good fit. That provides a nudge to get more specific information from them:

  • Ask the hiring manager some follow-up questions such as: Can you tell me about a team member you’ve helped to grow, how you helped them improve, how you supported them? (Just like in interviews, asking these kinds of situational questions will get better answers than theoretical ones.)
  • If you haven’t met anyone else from your potential team through the interview process, ask who you can talk with to get a sense of what the boss’s management style is like. (It would be even more ideal if you can talk with the person they gave as an example to the question above!)

Investigating the Culture

Interviews usually give us a distorted sense of what it’s really like to work in an organization. There’s no perfect place to work, and each place has its issues – the question is whether they’re issues that you’re comfortable dealing with. Are they just quirks, or big red flags? Here are a few strategies to go deeper:

  • Use your network – LinkedIn or otherwise – to connect with other people who work there, to pick their brains about their experiences, good and bad. You can also reach out to former staff – just be sure to take their negative feedback with a grain of salt.
  • Rating sites like Glassdoor can also give you a sense of some of the warts – but again, keep in mind that the people who comment here (anonymously) are the ones who feel strongly enough to do so, usually in the negative, so the reviews and comments will be skewed and not fully representative of the reality.
  • Keep coming to each round of the process with questions to go deeper about what the opportunity is like, what the daily life is like: What are the challenges they’re facing in the marketplace? What has been the most difficult thing they’ve experienced in the last year? What is their vision or strategy for the next year – for the organization, and this team, and this role?
  • See how you can connect with other members of the team, or the HR department. While the organization will have a particular structure for their interviewing process, it never hurts to ask for another conversation – particularly if they’ve made you an offer.

At the end of the day, you’ll know if it’s a good next step for you. Thinking of this as a next step can be liberating as well – especially for career changers. You might not find exactly what you were imagining in your career transition, but what you have in front of you might be a great stepping stone to that ideal as you adjust to a new sector or function.

And if there are some lingering doubts, that’s normal, too – it’s impossible to be 100% sure about everything based on a few conversations. There’s always some degree of risk that comes from making a decision.

But since your goal is to find a career that’s meaningful to you, the risk is worth it.

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!